"How can anyone, even skilled conspirators, predict with perfect accuracy the outcome of a car crash? How can they know in advance that a man will go to a certain pay phone at a certain time, so that he can see a particular truck he needs to see? How can the actions of security guards be accurately anticipated? Isn't it risky to hinge an entire plan of action on the hope that the police won't stop a car speeding recklessly through a downtown area?"
A convoluted plan that relies on events completely within the realm of chance yet comes off without a hitch. If your first reaction to seeing The Plan unfold is "There is no way that you planned that!", then it's roulette.
Gambit roulette tries to make a character seem impressive but can break Willing Suspension of Disbelief. You really have to establish a character as The Chessmaster for them to be able to pull it off without arousing your audience's skepticism. If the character pulling the roulette is a god, a person with precognition, a hyper-advanced AI, or someone else with similar abilities interacting with mortals, it becomes somewhat more believable, but even then the suspension of disbelief can be tenuous at best.
If, as part of retconning in a new villain, everything up to then (including the supposed successes of the heroes against the old villains) is all part of a new Evil Plan, it's Arc Welding. Also often the justification of the Omniscient Morality License; their control over events is supposedly total.
May be parodied by having events obviously (and blatantly) be out of the character's control, and yet still have them take credit for it.
Note that complexity alone does not make a plan into roulette. A few separate plans may combine while individually making logical sense. When a dozen things are going on but the actual details of the plan aren't reliant on each item fortuitously fitting into place, then it is just a regular Gambit Pileup. If the character has plans for either outcome not just the improbable one, it's Xanatos Gambit. If they admit that they hadn't planned for certain occurrences, but took advantage of them as they came up, that's Xanatos Speed Chess. Contrast Batman Gambit which is based on the most likely outcome, based on the planner's knowledge of the people involved, rather then a improbable one. A roulette requires the planner to say that events that were literally impossible to predict were All According to Plan.
This is a Spoilered Rotten trope. Expect spoilers and avoid using spoiler tags unnecessarily.
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Death Note is filled with thesenote at one time, this trope was called the Light Yagami Gambit. The most impressive is the plan that changes the course of the entire series — Light arranging L's death while coming off completely above suspicion. This involves an extended Memory Gambit, at the end of which every element needed to be exactly in the place they were in order to work. Such utterly unpredictable elements include: a cop Light didn't know prior to the Memory Gambit missing when he shot at the temporary owner of the Death Note and Light killing Higuchi while holding the Death Note, so that he could reclaim ownership of it and make the memory restoration permanent. Note that he was handcuffed to L at that point. Had the bullet been just an inch to the left, Higuchi would've died too soon and whoever picked up the Death Note first (most likely the cop who shot him) would become its official owner and Light's memory of being Kira would be gone forever. note However, this also makes it a Xanatos Gambit, since the Kira case would have ended with Higuchi's death, Light would have been beyond further suspicion and return to his pre-Kira life without any regrets at losing (since he wouldn't have known he had lost). Not to mention that having worked as L's right hand is a serious benefit in his stated career.
In Bleach, most of Sosuke Aizen's longwinded plans rely on this, which is odd given that he's easily powerful enough to get what he wants via brute force. Later on, this gets brought to its logical conclusion: Aizen claims the entire plot (or at least Ichigo's role) has been exactly as planned. It's never fully expanded on, so it's possible he was just lying to mess with Ichigo. Also, Kisuke Urahara engages in Gambit Roulettes as well, to the point where the first 2/3 of the series can be reduced to these two Chessmasters dueling one another in a case of Aizen's "Just as Planned" attitude versus Urahara's "just as expected" attitude.
It's finally expanded on years later, both in real life and in-universe. Aizen was telling the truth when he claimed to be responsible for Ichigo's birth. It wasn't actually planned, or at least not his original plan; one of his modified-Hollow experiments was derailed by the unexpected presence of both Captain Isshin Shiba and a Quincy, Masaki Kurosaki. But Aizen finds it fascinating when one of his experiments doesn't go as planned, and being a big fan of Xanatos Speed Chess he immediately incorporates this event and its inevitable consequence (the birth of Ichigo as a Shinigami/Quincy/Hollow hybrid) into his plan. Urahara was around to witness this as well, explaining how he was able to guess that Aizen's plans would involve manipulating Ichigo. Despite this, it's still unclear—and debated by the fandom—whether he really planned for all of Ichigo's fights—which lead to him getting killed, twice,—or if he was just screwing with Ichigo's head.
Warning, this entry spoils the entire climax of the first season of Tower of God and a lot more. Every sentence is made of spoilers, you have been warned again. Test Administrator Yu Hansung from had a great masterplan in which Baam was supposed to be declared Legally Dead without anybody noticing that he was just in hiding, so that he could be trained as King Slayer in secret. For that end, he needed to have the person Baam was looking for (Rachel) in somewhat close proximity without the two interacting, which wasn't that hard since Rachel obeyed Yu Hansung already. He also had to manipulate Ho into trying to get rid of Baam by telling him that he would stop climbing if Rachel died. At the same time, he had to manipulate Koon into discovering that Ho was being manipulated by Yu Hansung and was trying to get rid of Rachel and Baam, so that he would set up protective measures for both of them in the next test. Yu Hansung had to rely on Koon's deductive and manipulative abilities, which Koon used to make Quant try and protect Rachel during said test while figuring a way out to make Rachel participate in the final test, since she could not participate anymore after she got rendered ostensibly paraplegic by Ho. This means that Yu Hansung's plan relied on Koon's plan partially failing and Koon looking for alternatives. Here Koon's detective work comes into play. Koon went with his results to Lero-ro, who told him of a secret way of testing outside of the rules which only Irregular's like Baam could use, because the test had clearly been meddled with. So Baam got a tailor-made test in which Rachel could participate and which just so happened to happen inside a lake where the two where alone and unobserved. Rachel simply pushed Baam off their vehicle so that he was left to drown and she alone completed the test. Then Baam just had to be removed from the lake so that they could not findthe body and declare him dead, so that the Government of Zahard would not follow the development of Baam, the Irregular into Viole, the Slayer, which was now made easy, since all of these events took quite a chunk out of Baam's sanity. And the greatest part of it all: Yu Hansung made it seem like he was helping the Zahard Government with underhanded methods while he actually plotted against it in secret. He is a true Magnificent Bastard.
Yuuko of Xxx HO Li C and Tsubasa Reservoir Chronicle seems to be aware of all "effects" to all "costs" via Wishes and manipulates them together to affect the future in ways mere mortals can't possibly predict. Yuuko's one limitation is that only other people can initiate Wishes, and she has to be a Literal Genie to get the result she wants. Things get complicated when the villain of Tsubasa Reservoir Chronicle uses his ability to see the future through dreams to manipulate fate this way too, often with the same costs and effects. There are other dreamseers in the series pulling strings as well, but most of them are allied with either Yuuko or Fei Wong and incorporated into their plans. Also, every member of the initial party is somehow working for Yuuko or Fei Wong. All of them had been previously manipulated by the two chessmasters into the circumstances which led them to Yuuko's shop. Only one of them knows which side he's playing for from the beginning, but even his memories were changed to better serve the Big Bad. Topping it off, everything both of them planned was secretly part of Clow Reed's plan, which also incorporated the entire plot of Cardcaptor Sakura. Clow has been dead for centuries.
Dartz, The Leader of the Doma Organization, used this to recruit his followers; except for Mai, Haga, and Ryuzaki, all of his servants' past troubles that eventually lead to their joining the Organization were orchestrated by Dartz himself just so he could inflict a rage against humanity in them and use More Than Mind Control to cajole them into signing up.
Furthermore, in every duel in the series, the opposing duelist is always thought to be a Chessmaster, no matter how competent (or not) the duelist actually is. The Magic Poker Equation is responsible by no small measure.
Yubel, Judai's Stalker with a Crush from Yu-Gi-Oh! GX gives a prime example of this trope. During Season 3 of the show, she completes and executes one of the most intricate and chancy plans of the genre by manipulating everyone and everything with mind-control, possession and, most unthinkably, losing a match on purpose.
Digimon Adventure 02: Each villain appeared (and sometimes believed himself/herself) to be the Big Bad, only for it to turn out that another, higher villain had orchestrated everything from behind the scenes. It all leads to one final Big Bad, MaloMyotismon, having used people to use other people to use still others, with no one Disc One Final Boss aware of the next one's influence. The aspect of this that most blatantly puts the lie into "I totally planned all that" was Arukenimon, the one villain who did know she wasn't the top dog: her arc was about her plan to destroy seven Cosmic Keystones and cause The End of the World as We Know It, which would have made it impossible for her boss to get what it turns out he wanted (and leaving him dead.) Somehow it's doubtful that this is what he had in mind, and the same goes for his boss, the aforementioned MaloMyotismon, who wanted the world(s) intact and accordingly conquerable.
In the anime and manga Spiral: Suiri no Kizuna, the ability to ravel and unravel Plans and Roulettes is, although it's not stated quite so baldly, a superpower many characters possess. Most of them assert that everything in the plot is a giant Roulette planned by the protagonist's older brother.
In an episode of Galaxy Angel, one (fake) debt leads to the faking of a kidnapping plot by Ranpha and Mint - which leads to another fake kidnapping plot by Volcott - which leads to another fake kidnapping plot by his commander - which leads to that victim's family landing another fake plot - which somehow results in some random little girl and bear faking one... Which results in the original perpetrator falling ploy to the plot, leading him to increase the random on his plot. The story ends on an infinite loop.
The titular character in the manga/anime Akagi used a Gambit Roulette on the blind player Ishikawa that came out of nowhere so fast, that despite everything adding up, it is still hard to believe that everything was on purpose, especially considering his inner thoughts seemed rather random during the match.
Kyo Kara Maoh!: Shinou and Daikenja/Ken Murata had a Roulette in play for four thousand years aimed at defeating the Soushou.
In Fairy Tail, Jellal reveals his Gambit Roulette after the Magic Council fires a magic laser for the purpose of destroying his aim to resurrect an evil mage. When the dust clears, it's found that it had been his plan to do so all along, as some special crystals have absorbed all the magic fired, giving him the power source to resurrect him. One could say that it was more of a Batman Gambit considering he planted an astral projection of himself in the council in order to guide them to that point, but there was no guarantee they would use the magic laser, hit the tower straight on, and the crystals would absorb all the magic, and that he wouldn't be found out...etc.
A frighteningly good Roulette is used in, of all the Gundam series, the much-less-serious-than-usualG Gundam. Neo-Japan's previous Gundam-Fighter and now military advisor was behind the intrigue to claim the Devil Gundam in order to use it to rule the world. Therefore he blamed Kyouji and removed Domon's father from the scene. He even used Domon to get his hands on his toy of destruction. In the end he can foil Neo-Hong Kong's prime minister to get his hands on the Devil but it is of no use to him.
Then we have Gundam Wing, where Milliardo Peacecraft takes over leadership of White Fang and says that in order to bring peace, he's going to destroy the source of all conflicts - the Earth. Cue his former best friend Treize Khushrenada, who assumes command of the World Nation and vows to fight Milliardo to the last man. It's subtly hinted in the anime, and outright stated in the manga, that they're faking it, and their real intention is to scare the world towards peace by showing them a horrible and pointless war - so subtly that, unfortunately, many dismiss Milliardo's actions as a hamhanded retread of Char's Counterattack. This is because Milliardo either needed to act convincing enough to seem realistically motivated (thus fooling the audience as well as his cohorts) or he actually believed in destroying the Earth like Char. Milliardo goaded Treize into retaking leadership of the Romafeller Foundation as a means to ensure that someone would play off him, since he knew Relena wouldn't be able to. However the whole battle feels more like an elaborate abstraction of chess ala Morton's Fork. This is best hinted at during the scene in which Treize almost sacrifices himself charging Libra in a Thanatos Gambit, where immediately afterwards, White Fang realizes the whole incident was a farce to get them distracted from Treize's commando troops.
In Gundam 00, Aeolia Schoenberg, a scientist who passed away 200 years before the setting, invented every essential technology required till the present to obtain his supposed ideal of humanity traveling to the stars. Therefore he initiates the creation of Celestial Being and probably the Innovators as well, and possibly foresaw all the important events of the series, e.g. the failure of the first CB actions, the birth of the federation which would turn corrupt and then be beaten by CB again. Though, it's unclear how much of Ribbons behaviour was in unison with his plans. Ribbons claims his rule was the final goal, but that's highly doubtful. It's more likely that Aeolia anticipated Ribbons' betrayal, or perhaps even considered in a necessary part of the plan.
Shoenberg's case makes a bit more sense when you consider he put the quantum supercomputer VEDA in charge of running the plan after his death. It's not so much him anticipating things that would happen centuries after his death as VEDA (through Celestial Being) playing Gambit Speed Chess with the world.
InuYasha's father, who died before the series began, is to the driving force behind many events in the series, having set it themup so that his sons would get stronger and get along before they killed each other (or someone else killed them).
In Houshin Engi it turns out that the entire houshin project was really there to destroy an omnipotent being, who was in turn manipulating history. The main character turns out to be the same person as a major villain, the person whom they were, was a member of the same race as the first omnipotent being, and he had predicted the whole series of events hundreds of years earlier.
In JoJo's Bizarre Adventure when Dio received brain damage and could barely move, he tried to run away only to be stopped and beaten by Jotaro. Then it was revealed he really wanted to get near Joseph Joestar's body to drain his blood and heal himself, manipulating Jotaro into throwing him right there.
In Project Arms, the ultimate plan of Keith White ends up being this.
Hiruma, the quarterback of the Deimon Devilbats, of Eyeshield 21. Most of the quarterbacks, actually. Takami of Ojou White Knights and Hiruma once had a "Is that what you thought I'd say?" battle in the middle of an intense play.
Near the end of the Blue Dragon anime, Zola reveals that she had managed to use events since she was a child to ensure that she could release darkness upon the world, managing to find all seven Soldiers of Light required to free it, recruit five of them, kill off Nene so that Deathroy would choose a weaker partner in Delphinium who couldn't oppose her alone, and lure both Delphinium and Logi, the last Soldier, to the Sealed Grounds, unleashing the darkness. She almost succeeded in consuming the world as a result too.
Evangelion is, ultimately, a subversion: the convoluted plans of nearly all factions have as their crux being able to control Rei Ayanami, which, right at the last minute, turns out to be untrue thanks to The Power of Love.
Evangelion 3.0 on the other hand, plays this trope completely straight with Gendo's convoluted scheme to start Fourth Impact.
Oto x Maho has Konata, Kanata's mother, having in the first chapter, what appears to be a legitimate plan. Later, in a flashback scene, we find out that it was only the last stage of a Gambit Roulette years in the making, which included nothing happening to her and her son, her finding a "supervisor" (a sort of messenger for a Magical Girl), a bad guy showing up at PRECISELY the right time, her being physically stronger than her son when it ends, and everything else that is purely in the realm of chance. Because of Unspoken Plan Guarantee, it goes off without a hitch.
Justified in Darker Than Black. The reason Amber's plans are always so ridiculously convoluted is because she can control time. It's implied that she's had to live through the same events many, many times to get everything to work correctly.
The plot of Berserk relies on a certain series of events that would be otherwise meaningless without each other. Griffth's fall from grace, for instance, requires four things to happen in sequence or it's for nothing. Justified by events being orchestrated by an Eldritch Abomination.
Though most of Kurama's gambits in YuYu Hakusho are justified, the one he used in his fight against Shigure counts. Just how many seeds does Kurama have to plant in demon world? What are the chances such an important fight would take place in one of the few places he could have planted it?
Detective Conan once figured out a case just in time by subverting this trope. He had several suspects as to who was unknowingly given a bomb, narrowing them down by whether they had something that could hide a bomb and an electronic device that could set it off. He eventually deducted the only person it could be was the woman with the cell phone, as all other people's devices were unpredictable and accidentally pressing a button could set the bomb off too early.
The overarching plan Blackbeard concocts in One Piece borders between this and Xanatos Speed Chess. While there are a number of elements to his plan that rely largely on chance, they're mitigated by how either Blackbeard put himself in the best position to succeed, or the chance occurrence simply made things easier rather than being absolutely critical. For example, the start of his plot hinges on Blackbeard finding a very specificDevil Fruit, when finding any Devil Fruit at all is an exceedingly rare occurrence; to deal with this, Blackbeard joins Whitebeard's pirate crew, realizing that he stood the best chance of finding the single fruit he wanted there. Later on, Blackbeard plans on breaking out several of the most dangerous criminals of Impel Down. He happens to arrive just as Luffy, who had broken into the same prison earlier in order to rescue his brother, has begun his efforts to break back out alongside several allies he had made along the way, which makes things much easier for Blackbeard. This is lampshaded by how Blackbeard and his crew often talk about the role of fate in their plans, as if recognizing that the plot will allow their plans to succeed eventually.
Christopher Priest's portrayal of the Marvel Universe superhero T'Challa the Black Panther resorted to this trope several times during the course of his solo series.
In the series Daredevil, Vanessa Fisk was the Chessmaster behind the sinister events that transpired within the first two arcs of writer Ed Brubaker's current run on the title. Every player acted and every scenario unfolded with near-perfect precision, the one hitch being the confrontation with Matt Murdock occurring earlier than planned.
In the original V for Vendetta, the hero seems to imply that he killed a man knowing that this would drive the man's wife to assassinate Mr. Susan. On top of that, it was a fight V could not possibly have foreseen that he would have the upper hand in. Made bearable by the fact that V never brags about doing this explicitly, but rather only hints at it. Discussion here
The creation of Preacher's Saint of Killers as orchestrated by God Himself, who through a mere blizzard he generated and a reliance on every single pawn acting accordingly, managed to have the overall chain of events unfold flawlessly according to plan (if we disregard getting Hoist by His Own Petard in the series's ending).
In Volume 9 of The Sandman, it is revealed that everything that happened, not only in that volume, but everything that came before to bring everyone to that point, was all Dream's doing. The reason for doing this is revealed shortly after, but that's not even the strangest part. It is implied that he was doing it without even knowing it.
In Superman: Red Son, Lex Luthor evokes this trope when, after a epic battle between the Superman-controlled communist world and his country, the USA, they are forced to join skills against a Brainiac that reveals itself to be evil, which results in Superman's apparent death. He says "One can almost be forgiven for thinking that this had all been worked out to the tenth decimal point forty years ago, eh?"
Some of the plots that Jack Chick imputes to the Vatican fall squarely into this.
As pointed out by Linkara, the master plan of Prometheus in Justice League: Cry for Justice, in addition to being random in and of itself, requires coincidence after coincidence and perfect prediction of the actions of both heroes and villains. Prometheus may be Crazy-Prepared for combat and a genius to boot, but he can't predict the future and the characters in the story point out that he doesn't have villains in his database of combat tactics.
Illyana's plan in the latest volume of New Mutants. Going back in time, she rescues Legion from another dimension and brings him back to earth. She then appears on Utopia, and warns them about Legion's plan to kill Dani and Karma. This causes the reforming of the old New Mutants team and the capture of Legion. Eventually, Project Purgatory arrives back on earth and kickstarts the events leading up to her return to the past. The team is defeated and captured, allowing the summoning of the Elder Gods. But this is all according to plan, as Illyana has Karma release the REAL Legion and he uses his full powers to destroy the Elder Gods. As part of a still-unrevealed bargain, he then returns Illyana's bloodstones to her and completes her revenge plot against the Elder Gods. All according to plan. And all set up with only a dying warning from Magma to let Illyana knew what was coming.
In X-Men Noir: Mark of Cain, Professor Xavier's plan to lure Thomas Halloway out of hiding so he can study his Chronic Hero Syndrome ultimately hinged on whether or not Halloway was willing to go to the extreme lengths necessary to investigate the death of his father figure Cain Marko. The last time they saw each other, Marko conned Halloway out of a payday, and Marko died on Genosha Bay, a brutal prison situated next to a military base — if Halloway wasn't in the mood to incriminate himself and get sent to Genosha Bay for a guy who ripped him off, the plan would have been a complete bust. Though, granted, this may have been the point all along, to see how far Halloway is willing to take his heroism.
How about Lex Luthor's plan in Superman & Batman: Generations? He uses Gold Kryptonite on Superman's unborn son Joel, forever robbing him of super powers. Then several years later, he goes to Joel and plays off his inferiority complex to turn him against his family, all of which hinged entirely upon Clark and Lois having another child, one who would have powers and take up the Superman mantle. Then he posed as Lois' doctor and helped fight her cancer so she could see her daughter's wedding day - at which point Joel, who has powers thanks to Luthor, kills his sister while Lex snaps Lois' neck. Then, back at his base, Lex tells Joel about all his lies while admitting that his powers are killing him, meaning Superman's immediate family is all dead now. And the plan's still not done yet...
In Aeon Natum Engel Gendo admits this is what his plans amount to. Although, considering the setting, all plans are at risk of becoming like this. Why? Well, because Nyarlathotep is a dick.
In Harry Potter and the Methods of Rationality, Draco remembers a tragedy play his father brought him to see (an expy of Death Note), and at the end, Lucius asked him what the meaning of the play was. Draco mistook it to be as clever as the characters. His father chastised him, saying that any plan that requires more than three steps to succeed is unlikely to the point of worthless and because only a fool goes with a plan that is barely possible, you really should never plan more than two steps.
At the end of the HeroHighSeries. The main villain Pharaoh Alexander Sovereign nee Tempus reveals that his entire plan that he has practically set up throughout the series, was to stop his mother's crazy plan, revealing her to be the true villain. Or at least the eviler of two evils. He was also known to being infamous for his plans within plans, as well as fully understanding what a person is likely to do in the situation he presents them.
My Little Avengers: It's eventually revealed that the entire plot was engineered by Loki in order to create a scenario wherein Big Mac is forced to willingly surrender Thor's power, allowing Loki to take over Equestria. It temporarily works and was only undone due to Pinkie Pie being a bigger Spanner in the Works than Loki anticipated.
Jigsaw, the main villain of Saw, is the textbook writer on this. Not only does he manage to contrive up elaborate traps (some of which can easily be thwarted in the end), but he also can somehow pick out the best people to inflict these on, and figure out exactly how they're going to reach to further his aims. And he does this all while being bedridden. And later, dead, and still able to accurately predict everything that will happen in the world several years after his death, down to the tiniest of details.
Parodied in an episode of X-Play. Adam and Morgan are locked in a cell; which leads Adam to discover a cassette player; which he uses to describe how they are trapped in a madman's game. Morgan, realizing that the player might've had a clue to help them escape, slaps it out of Adam's hand. It turns out the player had a key inside it, which unlocks a cabinet with a TV that the killer broadcasts his messages (his first being that he knew Adam would tape over his recording, Morgan would break the player, and they would find the key).
The Collector rigs up a normal house with pinpoint, gruesome traps so quickly and effectively that it seems more likely that he has magic reality-warping powers like Dr. Manhattan than anything human.
In particular, the heist in Ocean's Thirteen relies on a Gambit Roulette within a Gambit Roulette, with a third Gambit Roulette thrown in for good measure. By the end of the film, the plan becomes so circuitous that it crosses some kind of gambit event horizon.
In the original all of their gambits pa off but a small oversight results in them losing the money in the end.
In Wild Things, Suzie plots to kill the dirty cop who killed her ex-boyfriend and get rich in the process. The full plot is too complicated to explain, but involves relying on everyone being willing to betray everyone else, before then discovering that they've been betrayed themselves. As if that's not enough, in the final scene, the defense lawyer from the rape trial, chosen from the phonebook, implies that he was somehow in on it all along. Most of it does rely on people behaving in character-predictable ways rather than sheer insane chance, especially as the plan meant that anything that looked coincidental was usually a result of then-unrevealed plotters working the other side and delivering the right evidence exactly on cue. It's still ludicrously complicated.
The Game. Although it's implied at the end that they had backup plans here and there, and a detailed psych profile on Nicholas to figure out exactly how he'd react, it's hard to believe that CRS could control every detail so completely.
The terrorist plot in Die Hard 2 depends on a conveniently-timed severe (but not too severe!) snow storm on the day their leader was being transported. Perhaps there was a deleted scene featuring a weather machine.
Eisenheim's plan in The Illusionist to fake his love's death and blame it on the Crown Prince of Austria has too many elements to have been coordinated and pulled off as masterfully as it was.
The main villain, whatever his real name may have been, in Swordfish. More identities, schemes and deceptions than you can shake a stick at; neither the characters or the viewer are informed much regarding his real plans.
The movie The Adjustment Bureau has human agents of Fate who are running one of these with every person on the planet. They are aided by magic fedoras which allow Portal travel and a magic people tracker which shows their people's planned path. The Chairman (who is apparently God) says the eventual goal is not to need them anymore.
The plot of Fracture requires that the correct cop be called into the scene of a murder, recognize the victim as the woman he was having an affair with, and then attack her husband. Furthermore, it required that he not kill her husband, but be sufficiently angry to not notice that the husband was switching their guns. In spite of his otherwise brilliant planning, the husband failed to even realize that shooting someone, being found innocent of attempted murder, and then having life support withdrawn, constitutes a count of murder separate from the initial crime.
Down with Love. The plot turns out to be one of these by Renee Zellwegger's Doris Day-esque heroine to get Ewan McGregor's Rock Hudson-esque guy to fall in love with her, as Zellwegger explains in one really long, fast-spoken monologue. It works perfectly, but subverted in that the side-effects of her campaign lead her to (temporarily) lose interest in him.
While the movie itself wouldn't necessarily be one, the backstory of the film-version of Speed Racer might qualify. Apparently a bunch of industries have been controlling the winner of every important race for decades. Apparently all the sponsors agreed on who won ahead of time, were always able to get the drivers to cooperate with them, and (most insanely) no designated "winner" ever crashed, leaving the race open. Let's not even go into the idea that sponsoring a winning car could double your stock price instantly.
In Wicker Park, one character, Alex, is single-handedly manipulating the three other main characters in a desperate attempt to be with Matthew. She convinces Lisa that Matthew is cheating on her and leads Matthew to believe that Lisa has abandoned him. Also, she dates Luke for the purpose of pumping him for information on Matthew and Lisa.... among other things. Although it appears that most of her plans are made up on the spot, her schemes do seem to generally work masterfully in her favor. That is, until Matthew discovers enough information to force her to admit everything she did.
J.R. Ewing claims to have planned every frickin' little thing in the Dallas movie.
The person running the tables in Eagle Eye at first appears to be damn near omniscient and prescient - creepily anticipating everything except Jerry being alive - to the point of (as just the most "damn"-worthy example) calling the cell phones of every single person on a train within seconds of needing to do so. It becomes slightly more believable when it's revealed "she's" a government supercomputer... until the Fridge Logic sets in.
Lucky Number Slevin, in which the main character suffers a case of mistaken identity, and is brought in by two separate mob bosses to get revenge upon each other. Long story short, it turns out that he and his mentor - the assassin the mob bosses both hired to take out the MC once he'd done what they wanted - planned the whole thing in order to get revenge on both of them for the murder of his parents.
The aggregate actions of the Joker in The Dark Knight: for an agent of chaos with a stated disdain for Chessmasters, he effortlessly pulls together seemingly random and improbable events into a single overall scheme.
Total Recall (1990) (1990): For his scheme to work, Mars Administrator Cohaagen has to eventually get Quaid back to Mars (but he blows his memory cap early so he ends up becoming a Loose Cannon Cop), he has to get in contact with the Mars Resistance so that Cohaagen can find Resistance Leader Quaato. When this actually happens, Cohaagen admits that the possibility was nearly unbelievable, and Lampshades it, rattling off a list of all the ways in which the plan actually went wrong. This is one of the many reasons behind the All Just a Dream interpretation of the movie.
The Antivillains' scheme in Inside Man. It hinges on ensuring that Everybody Lives (hence their Anti-Villain status) while simultaneously keeping the cops thinking they're deadly dangerous. While the movie presents this as Gambit Speed Chess, it falls apart when you consider that it relies on the cops not making any mistakes like accidentally shooting a hostage.
While Chaos is a good movie, it suffers for being completely made up of hundreds of Gambit Roulettes in order to advance the plot. 1: The banker pressing the alarm, thus sending in the police. 2: Conners being made the negotiator, thus shutting down the power. 3: Conners shutting down the power, thus giving the virus free game. 4: Conners failing to stop SWAT from entering the bank, thus making the mooks escaping the bank. 5: The mooks not being caught on camera while escaping the bank with the hostages (granted, this one was admitted failed in movie). 6: The female cop's phone going off, thus making the cops entering that building. 7: The fact that the whole idea of letting Conners pretend to be dead was based on the idea that out of 2 guys, 1 body is found, and just because it has Conners badge on it makes the cops take for granted that it's Conners body, while not bothering to look for the MISSING SECOND BODY!)
In Push, Nick's plan to save Kira relied on knowing exactly what lie Agent Carver would tell her. That's just the most obvious sneak in the plan; the whole thing was so convoluted that psychics couldn't tell what was going on. Ultimately, the entire movie was planned, predicted, and orchestrated by Cassie's mother. There's a reason why she's known as the best Watcher in the world.
Subverted in the Danish Olsen Banden films (and the Norwegian and Swedish remakes thereof) by having Egon Olsen's elaborate schemes go off almost without a hitch, only to have the gang deprived of their rewards later by some amazing coincidence. Egon (the only competent member of the gang) is caught by the police and goes to prison (sometimes even for something he's actually done). Though, sometimes he's playing Gambit Speed Chess while the Roulette is spinning.
The remake of The Wicker Man: every ten years or so, a woman is sent from her isolated island community for the mainland, to find a man, make him fall in love with her, get impregnated, and then take off back to the island. Then, ten years later, they will contact the man, betting on the off-chance that he's still in love with her, and ask him to come to the island in order to search for her missing child (that she only later informs him is his own child). Why do these women participate in this rather odd sequence of events? Well, it turns out the honey-bees aren't doing their job properly, and they need a human sacrifice with a blood connection to offer up to the fertility gods.
The original Wicker Man had shades of this as well. Lord Summerisle explained at the end of the film they needed a person from the mainland who wouldn't stop looking for the girl, and assume he has command over the islanders, and who also would resist even the most blatant of sexual advances. Aside from knowing all that about Howie personally (he mentions "painstaking research"), or that Howie would be sent to the island to investigate, he was able to jerk Howie around, assumingly with the cooperation of the entire island. There was certainly no way of knowing Howie was going to dress up as The Fool by stealing someone else's costume. The only really direct way he kept Howie in line was sabotaging his plane so he couldn't leave.
In Flightplan an elaborate plot required Jodie Foster's character to take the correct flight on the right day and time, to bring a coffin of her dead husband with her, sit in the correct seat and for no other passenger to notice her daughter. She would then have to fall asleep during the flight and her daughter would need to be kidnapped during the flight while she slept, without anyone noticing the daughter was ever there. Then she would need to act crazy so that no one would believe her story, and go crazy enough to want to see her dead husband, be savvy enough to pull off a successful Indy Ploy to get into the cargo bay, and be forgetful enough to leave his coffin unlocked.
Arlington Road: the general convolutions of the plot supply Roger Ebert's page quote. It has since changes now, but to quote the opening paragraph of his review: "Later, thinking back through the film, we realize it's not just the ending that's cuckoo. Given the logic of the ending, the entire film has to be rethought; this is one of those movies where the characters only seem to be living their own lives, when in fact they're strapped to the wheels of a labyrinthine hidden plot." It is definitely a Batman ploy taken to Roulette levels to the point of being a Shoot the Shaggy Dog story.
The best part of this is that Lang actually says to Faraday in the middle of the plan unfurling "Did you really think I would leave anything to chance?" even though his ENTIRE plot relies on several unlikely scenarios to all have to happen one after the other.
The plot of Oldboy has a Big Bad whose elaborate plan can completely break the Willing Suspension of Disbelief at his scheme to get revenge on his high school nemesis. Specifically, the big bad's plot depends on the protagonist having a relationship with a specific woman, who turns out to be his own daughter, whom he hasn't seen since she was a baby. This is handwaved by having the villain explain that he used post-hypnotic suggestions on both of them to ensure they would fall in love.
in which John Doe's master plan hinges on Mills deciding to just shoot him, though he did take measures to increase the likelihood of it happening. John Doe explained in his phone call to Mills that he was "stepping up" his agenda. His final two kills (Wrath and Envy) were originally planned for somebody else, but Mills provided a better opportunity. It is impressive that he was able to pull it together in time.
Another Roulette would be orchestrating how the cops find Victor, the "Sloth" victim exactly one year to the day after John first captured him. He had to kill the attorney (Greed), plant Victor's fingerprints behind the painting, assume the cops would get the clue to the lawyer's wife, know that the cops would ask the wife about it at the right moment, and know exactly how long it would take them to match the prints with Victor in order to bust into the apartment at the right moment.
Face/Off: In a prison break sequence for Sean Archer, who is actually in Castor Troy's skin, his plan of escape involves removing the metallic shoes from his feet which inhibit his movement. The only way to do that is to be strapped to an electric chair that fries his brain and presumably kills him. He gets into a fight with a guy Troy screwed over in the past and the guy needed to be put to the chair at just the moment before he was, and have his brain fried but also he needed to barely survive it. Archer (as Troy) would then be strapped himself and have his boots removed, but would quickly have to convince the guy who hates his guts to help him and save him from the guards before they can electrocute him. It didn't take many words to convince him to die to save Archer.
The antagonists' plans in the original House on Haunted Hill (1959) are not only extremely complicated and based on a large amount of chance, they also require an improbable level of footwork on the part of the antagonists, almost requiring them to be in two places at once.
Children of Men contains a pretty major spin of the wheel in the bandit attack: it turns out that Theo is travelling with a terrorist group that's decided on a bit of regime change. Julian's death during the attack was part of the plan to bring Luke to the leadership of The Fishes. But that means the plan involved a perfect pistol shot, taken from the back of a speeding motorcycle, into a very small car containing not only the pregnant girl who could be the last hope of humanity, but the would-be leader as well. In a realistic film like this it's hard to imagine a plan so dangerous even being considered.
In Speed, the main villain of the film puts a bomb on a bus to take revenge on a police officer that ruined his last scheme and ransom them for $3.7 million. The rules are that once the bus reaches 50 mph, the bomb is armed, and if it drops below 50, then the bomb goes off. The villain then tells said police officer, conveniently the protagonist, all about this. The problem is, the film makes it quite clear that had our protagonist been just a second sooner, he would have caught the bus before arming the bomb, showing that there may have been time to do so. In this sense, the villain relied on the chance that the protagonist wouldn't make it to the bus in time, else the bomb would never arm and there would be nobody to hold hostage.
The antagonist did have a remote trigger for the bomb, so he could have just ordered the bus to speed. Maybe...
Note that the villain is also doing this, again, for money. The revenge part is just an added bonus. And that his leverage (the hostages) hinges upon the bus (who is constantly speeding through LA, burning through red lights, and driving at high speed unable to slow down through traffic) never crashing before he gets his ransom (which almost happens several times, and in fact does end up happening). Because the moment the bus blows, the cops have no reason to give him the money he so eagerly desires. Made even worst by the fact he was previously thwarted by losing his hostage (when the hero decided to Shoot the Hostage) so he knows the value of making sure one can hold on to one's hostages.
The end of Ninja Champion is especially (in)famous for this.
In The A-Team every military action is needlessly dangerous and complex, often relying heavily on the enemy doing some very exact and unlikely actions, like shooting someone directly in the head.
Reindeer Games would be completely forgotten if it wasn't for the twist ending that's so insane that it defies all logic.
Alexander Pearce's plan in The Tourist. He tells his wife to board a particular train at a a particular time and randomly select a passenger of his height and build, whom she will then pretend is him in disguise. It turns out that the guy she picked really is him in disguise. But, wait, go back and read that again: she's to pick a guy at random. Well, what if she had picked a different guy? It's not like there's only one man of his height and build on that train. In fact, she almost does pick someone else, but it turns out he's traveling with someone. Could have gotten a bit sticky if he'd been alone, no?
The traps in some of the Home Alone movies require knowing what the thieves will do precisely, far beyond "try to steal X object." This is particularly bad since the maker of the traps is a child. Of course, if it was more realistic, the villains would only have to get caught in one or two of the many traps to be either killed or crippled horribly.
The last car chase of The Skulls sees the heroes Luke and Will being chased at high speed along a train track before it finally comes to a stop with them crashing full speed into a dirt berm at the end of the tracks and the bad guy about the shoot Luke. But a split second before he pulls the trigger, he is shot (at long range) by the cop who then tells them that it was his plan all along to have this happen, thus showing that even the good guys can have convoluted plans. At any time during the car chase, Luke and Will could have crashed and been killed. Or the cop could have missed his long range shot with a pistol, allowing the bad guy to shoot Luke. But I guess that was part of the plan as well.
Angels and Demons has a villain fake the involvement of an old secret society called the Illuminati to take the blame for his actions of trying to destroy the Vatican. Except, the clues he was using were obscure and there was no certainty anyone would have otherwise found the clues and discovered the murdered cardinals had Tom Hank's character not been there. Even with his involvement, they barely discover some of them. In addition, there's no public discussion of the Illuminati, and The Plan is for the entire city to be vaporized in a short time frame. So, there was a very high chance that the entire city would have been destroyed with none of the outside world being the wiser, which might have also complicated the villain's plans. As it was, with Tom Hank's help they discover the "bomb" mere minutes before it's supposed to go of, and then the villain decides to change his mind and take the device safely out of harm's way at the last second. Just think how the movie would have unfolded if Tom Hanks had not been invited to help or if he had been a slight bit slower at solving the clues. In fact, a random event of electricity being shut off almost kills him.
Silva's escape/assassination plan in Skyfall hinges on, among other things, his being captured and held at MI6 on the day of M's hearing, Q springing his computer trap at exactly the right time, perfect choreography and timing between numerous teams of henchmen in the London Underground during rush hour, and Bond chasing him into one particular room at exactly the time that a train is passing overhead (and not deciding to Just Shoot Him).
Admiral Pike accuses Kirk of making reckless command decisions and relying on blind luck to ensure his missions go according to plan without harming his crew.
Harrison guessing that Kirk would decide to capture him instead of just bombarding him from afar, and also guessing that Marcus would come personally to finish him (and all witnesses) off. Which leads to a Xanatos Speed Chessonce the USS Vengeance, which Khan possibly designed to be manned by one person in the event that he could get his hands on it, comes into play.
The only part of Marcus' plan prepared ahead of time were the torpedoes and the USS Vengeance. He did not know that Harrison went to Qo'noS, or that Pike would die during Harrison's attempt on his life, or that Kirk would be agreeable to assassinating Harrison. Meaning that his plan to use the Enterprise to kill Khan and his crew while at the same time provoking the Klingons to war was made up on the spot in less than a minute after Kirk told Marcus of his intentions and Harrison's location.
"So his plan was... herd a bunch of working class Brits into, breeding someone genetically able to think on the Eternals level; lead him to a library. Hope, that he taught himself how to read properly. Hope, that he came across the one specific book that inspired the whole Zardoz shtick. Hope, that he would stow-away on the Zardoz head and shoot him. Then hope, that the head would crash back inside the vortex. Hope, that the other Eternals didn't kill him immediately, and teach them all that they know; in the hopes that he would figure out how to destroy the tabernacle and therefore all the Eternals. In other words, the exact kind of plan you expect for a man who draws on his goatee."
In Now You See Me, the Horsemen's scheme is planned down to the last detail all so that Dylan can get revenge on the people he holds responsible for his father's death.
One specific example is the "quarterback" hypnosis in the Horsemen's second show, which involved predicting the exact word to come out of Dylan's mouth (though "freeze" is a reasonable thing to expect a cop to shout at a fleeing suspect). Further justified and subverted when you realize Dylan was the one who planned the stunt in the first place.
Gunslinger: Erica Paige buys up all the cheap land around town believing that she'll make a fortune when a railroad is built through town. It all goes to hell when the railroad is built along a different route.
In Sherlock Holmes, Lord Blackwood's plan to kill Ambassador Standish would have failed if it hadn't been raining that day (since it required that Standish be doused in oil without realizing it).
North by Northwest has Roger being abducted and nearly killed by someone pretending to be Thornhill, whom Roger later learns is a UN diplomat. After narrowly surviving the attempt on his life, Roger visits the UN General Assembly building to confront Thornhill. Thornhill turns out to be someone he has never seen before, and shortly after Roger arrives, is killed by one of the men who tried to kill Roger. Roger was manipulated into meeting Thornhill so that Thornhill's enemies could kill him in a way that would look like Roger was responsible. But how did they know Roger would seek Thornhill out? And if they needed Roger as a patsy, why try to kill him? And how did they know the attempt to kill Roger would fail?
In The Brothers Karamazov, many of the elements of Smerdyakov's plan to kill Fyodor Karamazov were obviously beyond his control. The book offers a good example of a Chessmaster attempting to manipulate events and people he realistically doesn't understand fully. The kicker though? He still pulls it off with a bit of improvisation.
In The Possessed, Petr Stepanovic's labyrinthine plan, involving dozens of different characters, is mostly successful - he manages to manipulate people left and right, even if he is shown to completely misunderstand the motivations of some of them, like Stavrogin and Kirillov. Another interesting subversion of the trope is that the more complex parts of the plan (like persuading several persons to kill another man with a flimsy reason) go off like clockwork, and the apparently simpler details (like persuading a suicidal nut to... kill himself) almost fall apart on several occasions.
The Count of Monte Cristo has the Count executing a plan for revenge that's unspeakably convoluted and relies on manipulating people in ridiculously subtle and complex ways—for example, he somehow manipulates Madame de Villefort into poisoning half her family by casually conversing with her about chemistry.
Deconstructed in Evil Genius, a young adult novel by Catherine Jinks. Although the hero, Cadel, is very good at manipulating people, when he attempts a Gambit Roulette, it gets out of his control very quickly, leading to the death of several characters.
The Shadow Lord in the Deltora books made it clear: "I have many plans. Plans within plans..." And indeed, by the beginning of the series, he had them set in place so that he was prepared for any conceivable contingency. Except dragons.
In Harry Potter and the Deathly Hallows, Dumbledore had orchestrated or manipulated almost every major event that had taken place in Harry's life since about the halfway point of The Half-Blood Prince, with the ultimate purpose of Voldemort's destruction.
Also in Deathly Hallows, Dumbledore's method of getting Harry to find the Hallows relies on random encounters - for example, Hermione only recognised the symbol in her book because she happened to meet Luna's dad at Fleur and Bill's wedding. The same goes for Harry finding out he is a Horcrux; if he hadn't been there when Snape died he would never have made his Heroic Sacrifice and Voldemort would've stayed immortal. To be fair, Snape was supposed to tell Harry - that's why he asks that Voldemort send him into Hogwarts during the Battle - but didn't do so in time. That is why he is scared when Voldemort tells him that he is going to kill him - he thinks he has failed. No excuse for the symbol, though Dumbeldore handwaves it by mentioning that Hermione wouldn't rest until she knew what it meant, so he assumed she would work it out somehow, just not necessarily from Xeno Lovegood.
Even if Xeno hadn't been wearing the symbol, they would have found it on Peverell's grave in Godric's Hollow, which everyone and their goldfish knew Harry would go back to. And remember that Dumbledore didn't want Harry to find the Hallows; he feared that Harry would fall into the same temptation that he had, so he gave Hermione the book that warns about their dangers in the hope that she would "slow Harry up" if he did decide to chase them down.
In the Young Bond book Double or Die, a teacher at Eton is kidnapped and only has enough time to send a letter confirming his resignation and send his last crossword to The Times. In this, he manages to get clues to Bond and his friends about what's really happened to him, where they can go to find more information and that a friend of his is coming to Eton. This teacher probably attended a school where Light was the headmaster and Jigsaw was the art teacher.
Avrell Torrent, the Big Bad of Orson Scott Card's Empire, has been setting up a massive Gambit Roulette that would make Palpatine envious for decades.
The Dune series by Frank Herbert contains some of the most elaborately justified Gambit Roulettes ever committed to paper, due primarily to the fact that the protagonists and many of the antagonists are genuinely prescient.
Leto Atreides II in Children of Dune becomes Emperor on the strength of a plot that pits him against his father, aunt, and grandmother, all of whom are or were operating their own Plans. The prize is absolute domination of humanity's future. The plot involves Leto faking his death, which was anticipated by both Jessica and Alia. Jessica sets up a test to see if Leto is possessed, which Alia knows about and infiltrates with her own instructions to have Leto killed no matter what. The method of their testing: overdosing him with spice, awakens Leto's prescient memories and forces him to choose his vision of the Golden Path without which humanity is doomed. Leto then confronts his father, Paul, who had earlier faked his own death in order to escape the curse of prescience, and wrests control of the vision from him, then proceeds to take the throne, killing Alia and utterly humiliating every other participant in the Gambit Pileup.
Leto II then continues the trend in the next book, which picks up at the end of his 3,500 year reign as God Emperor and details an incredibly complicated plan whose final goals are to produce a breed of human who is immune to prescience and to wean humanity off of its dependence on oracles. Furthermore, the product of this breeding program is intended to kill him in such a manner as to guarantee the continuation of the sandworms and the spice. Further furthermore, he manipulates human culture and society for 3,500 years to push humans to invent synthetic spice and no-ships (ships which shield the occupants from all prescience), to scatter to other parts of the galaxy upon his death, ensuring the survival of the species and ending their total dependence on the planet Arrakis (spice was previously only available from Arrakian sandworms, and necessary for all space travel). He succeeds on all counts.
The gambits of Miles Teg and the Bene Gesserit in Heretics of Dune and Chapterhouse: Dune take on a similar flavor, resulting in yet another Gambit Pileup.
And Then There Were None by Agatha Christie involves a person who not only wants to kill 10 people who got away with a crime, but to do it in a certain order (from least horrible crimes to most horrible), and to make the deaths fit a nursery rhyme that he/she happened to like. So many things had to go right: if a certain victim had not died last or had shot rather than hung himself/herself under psychological stress, or if someone had seen the killer after his/her "death," or if the doctor had been less gullible, or if a sea storm had not sprung up, preventing any rescuer from reaching Indian Island, or if the killer's body had not rotted enough for the time of death to be uncertain, etc.), that it was almost impossible for everything to work out perfectly in the end. Yet it did. With the occasional Plot Hole added into it, such as the gun having only the fingerprints of the last person to touch it, despite its owner also having handled it.
The Film of the Book does away with the silliness with the result that the killer's plan ultimately fails, and the last two intended victims survive.
There is another The Film of the Book (USSR, 1988) which repeats the book with one exception: in the end the killer, instead of wiping away all clues, just shoots himself/herself.
After the Funeral is much in the same vein. Miss Gilchrist's entire plot hinged on every single member of the family not recognizing their own aunt at Richard Abernethie's funeral and believing that Richard had indeed been murdered. Even when one takes into account that none of the family members had seen their aunt in a long time, it still doesn't explain why they didn't notice that Miss Gilchrist - with whom they spent several days in the same house - looked almost exactly like the 'Aunt Cora' they had recently seen at the funeral. It also stands to reason that after the real Cora's death, a family member would have to identify the body, thus exposing the deception. Miss Gilchrist's plan to poison herself so as to appear innocent could also have colossally backfired.
The plot in Evil Under the Sun is another example. The murderer/s not only rely on synchronizing their movements according to a very precise schedule, but also arrange for the body to be "discovered" before the actual murder takes place, while the unsuspecting intended victim is hiding nearby. There are a number of ways that could have gone wrong...
A lot of early detective fiction relies on Gambit Roulettes to the point where Raymond Chandler discusses it as a failing of the genre in his essay "The Simple Art of Murder".
Jake's plan to infiltrate and capture the Yeerk pool ship is a complex Batman Gambit that includes the manipulation of no less than eight separate factions, brilliantly executed by a sixteen-year-old kid of average intelligence.
The true Chessmasters in the series are the Ellimist and Crayak. The Ellimist's backstory begins with his favourite game being to achieve world/system domination by proxy in a simulation by changing just one factor. In the game he decides to have the clouds on a moon part to give the inhabitants the urge to travel (he loses the game though). Everything that happens in the series (including the creation of at least two highly advanced races) is implied or outright stated to be the result of his subtle moves in his overall game against Crayak.
The Ellimist is a subversion however, since he loses. He loses a lot. He was called "the greatest loser" more than once. It's not until he meets the Andalites that he starts to truly reverse that trend, and then he becomes a god and is kinda exempt from this trope.
Cassie's surrender of the blue box.
The book Small Favor from The Dresden Files features a subversion. Harry considers the enemy's plot to be so complex it simply should not be possible, until Murphy points out that Harry really IS that predictable, and that the villains stood to gain by doing what they are doing, whether or not Harry acted as planned.
On the other hand, Martin's actions in Changes are precisely this trope. He engineered an incredibly complex plot, betrayed his entire organization and his closest allies, and became a triple agent in the hope of a grand masterstroke that would destroy his enemies. It ended up working, but if Harry hadn't been able to take on the entire Red Court, or if the Red King had stopped grandstanding for just ten seconds, it would have failed completely.
In Outbound Flight, an agent of Sidious states that his plans to take control are to prepare for the Yuuzhan Vong invasion (though they're only known as distant invaders at that point). The book cleverly leaves it unmentioned whether Sidious really knew they were coming, and whether this was truly part of his justification for a power grab. Several characters comment that the threat of unknown invaders is a convenient excuse. Then again, he is a Magnificent Bastard with insight bordering on omniscience.
Thrawn's actions in the Hand of Thrawn Duology were retroactively made part of this conspiracy when the New Jedi Order era rolled around. Carefully cloning entire families worth of an extremely talented pilot with a bit of Thrawn's own brilliant mind, then ingraining in them an attachment to the worlds to which they were dispatched, all for the purpose of having a grass roots sleeper cell on numerous worlds, ideally positioned to help drive back the Yuuzhan Vong if the central military organization of the galaxy (regardless of whether it was the Empire, made strong by Thrawn or the New Republic, forced to become strong because of him) were disabled.
A similar plot was hatched in Knights of the Old Republic. More accurately, its sequel, which proposed that Revan's "fall" to the Dark Side and his subsequent conquering of the Republic (carefully leaving intact key positions and structures) was just to prepare for the coming of the "true Sith" lurking outside the galaxy, making Revan a Well-Intentioned Extremist. This was all from the perspective of Revan's teacher, so take it with a grain of salt. Though even if you think Revan was just flat-out evil, this theory has some merit: you can't exactly conquer the galaxy if a bunch of crazy "true sith" destroy it.
Subverted in the Belisarius Series where Belisarius's answer to a Gambit Roulette is to keep adding pieces and confusion to the board until Link doesn't know whether it's coming or going. Also subverted (although not entirely successfully) in that Belisarius claims not to calculate in depth but instead to cause confusion and take advantage of the opportunities that arise from this.
In the Legacy of the Drow Series by R.A. Salvatore, Jarlaxle at first appears to be a Manipulative Bastard. In the later books, Jarlaxle muses that most of his plans are in fact Gambit Roulettes. Whenever he stirs up chaos, he always seems to come out on top. It's also hinted in later books he is the chosen of a god of chaos.
In Second Apocalypse, everything seen thus far has been a complicated roulette by Moenghus. There is some fan disagreement on whether the roulette paid out or not. Things get complicated at that level of misdirection.
Kellhus engages in a calculated Gambit roulette a few times too, hoping to win big.
Subverted in Arturo Perez-Reverte's novel The Club Dumas (which was made into The Ninth Gate). Corso spends most of the novel dodging two antagonists attempting to steal a rare manuscript and inconveniently discovering corpses along the way. Corso reasonably suspects a massive and powerful conspiracy is dogging his every move. Corso is just being paranoid, as the narrating character explicitly tells him, and there is no relation between the murders and the two manuscripts. The Film assumed that Viewers Are Morons, and so let the plot progress as expected.
In Isaac Asimov's Foundation series, Hari Seldon plans 1000 years of history culminating in a new galactic empire and sets it in motion by creating an encyclopedia. He does this by using a fictional science called psychohistory which is calculating the probability of a specific development of the happenings based on how large masses of people reacts. The psychohistory is not exact and can fail to give an accurate prediction (ultimately it does, but Sheldon created a second foundation in the case of anything not going along the plan) with only add more to the Roulette part of the trope.
This 7 book series is part of a much bigger plan by the psychic robot that lives in the Moon.
There are something like 3 different factions of psychic telepathic people (or robots) capable of predicting the future and manipulating it by subtly twisting people's minds and by carefully manipulating certain key individuals into situations where they'll behave in predictable ways, and all of them believe that they are the ones who are secretly controlling everything. The Second Foundation that's using the First Foundation as puppets to create their ideal future, the Gaia-like hivemind that is using the Second Foundation itself as their puppets to create it's ideal future, and the robots themselves.
Tad Williams's fantasy trilogy Memory, Sorrow, and Thorn uses this to good effect. The nebbish protagonist gets embroiled in a standard fantasy plot, complete with magical swords and ancient prophecies about what to do with them. However, the Big Bad, who's been around since forever, made the prophecies to trick the heroes into bringing the swords right to him. He doesn't do a single thing throughout the book until the end.
Apparently, everything Saint Dane does is part of his grand plan for Halla. A lot of which is manipulating Bobby (and Mark and Courtney) to do exactly what he wants them to do without realizing it. And then stepping in to show Bobby how horribly he's been defeated just after he thought he won.
Fortune Teller Shalice of The Pilo Family Circus demonstrates her understanding of the trope in this statement:
Man raises his middle finger at a passing car; the driver ponders it, wondering what he'd done to offend the stranger, misses his route home while distracted, and collides with a van, killing the driver who was the real target of the exercise. The simplest of scenarios, but the setups could be so elaborate and huge they shaped the course of history.
One of her simplest manipulations involves watering the lawn in front of the Acrobats' tent; when one of them left the tent, he slips on the wet grass, and angrily blames the pranksters in the Clown Division. He then steals a crate of fireworks to take revenge on the clowns, only to leave it by the Circus Funhouse, where one of the local dwarfs uses it as a target in a cigar-flicking game: the resulting explosion takes out half the funhouse, and forces the management to start relying on Shalice for help again. Or at least, it should have.
Revealed to be the entire point of the first two books in Sergei Lukyanenko's Night Watch series (Nightwatch and Daywatch respectively).
In the first, everything is set up by Gesar in order to rewrite Olga's fate in order to reinstate her connection to the Twilight and give her back her magical powers so that he and she can be equal. Some of this may be justified in that they are magicians of great power who have been alive for thousands of years and have the ability to peer into the possibilities of the future, but there are still moments when the reader (and the characters) is left wondering what is a planned Roulette and what is just taking advantage of the situations as they arise (Gambit Speed Chess).
In Michael Crichton's novel Rising Sun, the Japanese nation is portrayed as Gambit Roulettists in garish contrast to stupid Americans who don't seem to know their noses are actually on their faces, much less than they're being led around by them. The implication is that the murder of the girl in the novel was set up right from the beginning simply to embarrass another Japanese family, right down to knowing which officer was on duty that night, that John Conner would become involved as a result, and that events would go very much as planned.
From Encyclopedia Brown, we have a robber planning to strike as the victim does his grocery shopping, but calculates he won't have enough time. No problem, just ask him to pick up four tubes of toothpaste, extending his grocery list from 7 to 11 items and thus forcing him to take a non-express lane. So the plan is: Our victim won't question why the man wants four tubes of toothpaste and will proceed to buy them all. Our victim will be honorable and take a non-express lane for being one item over (since that fourth tube of toothpaste was so important). This will slow our victim down significantly enough to finish robbing his house. (This one, at least, was given a Hand Wave— apparently the supermarket in question is notorious for all of its non-express lanes being glacially slow... all the more reason why our victim might choose to take the express lane despite that 11th item.)
In Fred Saberhagan's Book of Swords, and companion series Book of Lost Swords, the character of The Emperor is shown to be very nearly omniscient in his plans, including fathering several children to various otherwise unimportant women around the known world, some 10 years before the events of the first book. Justified since the Emperor is G-d.
In Daemon, by Daniel Suarez, Matthew Sobol, through his Daemon AI, manages to accurately predict and control events throughout the book, even after Sobol's death. While there are humans in the Daemon apparatus, they are not depicted as being in controlling positions. Either Sobol was a master at the Gambit Roulette, or his AI was a master at Speed Chess.
By the time the sequel rolls around, the AI proves to have the ability to predict The Future well enough to know exactly where plot critical events will occur. Even with this level of prescience, The Cavalry has to roll in several times to avoid the entire gambit falling apart.
A very common occurrence in Iain M. Banks's Culture novels. The Mind AIs are frequently do this, especially when it comes to the activities of the Culture's two interventionary groups, Contact and Special Circumstances. May potentially be a subversion because Minds can think in Hyperspace and are so ridiculously intelligent and powerful that they can pull off such a plan easily.
In Niven and Barnes's The California Voodoo Game, Dream Park's security team catches on that one of the Game's tournament participants isn't playing fair, and theorize that he's attempting a Batman Gambit to throw the win to Army. However, the suspect can't realistically expect to do this, given the sheer number of variables involved, which would make it this trope instead. As it turns out, the suspect is plotting another crime entirely, and only set things up to look like an attempt to fix the Game in order to deceive an accomplice.
The Demon King in Kylie Chan's Dark Heavens trilogy has one of these running from when he first meets Emma, although since a) it's implied that he was planning One Two Two's downfall even before Emma unexpectedly showed up, and b) he didn't expect her to outsmart him the first time he tried to manipulate her, it could also be considered that he starts off playing Gambit Speed Chess which develops into a Roulette.
Used and lampshaded in the Bad Blood chapter of the Trainspotting novel, where the HIV-positive character Davie pulls this on Alan Venters, the man who gave the HIV to the former's girlfriend by raping her, thus leading to Davie's own contraction of the virus. His plan is to make friends with a dying Venters, so that he is allowed to visit him in hospital, and also with the mother of the rapist's only son so that one day she may trust him enough to let him babysit for her. When this happens Davie drugs the child with a sleep-inducing substance and takes pictures of him, making it look like he violently raped and murdered the boy. Then he shows the pictures to Venters on his deathbed and suffocates him with a pillow, thus filling his last moments in life with immeasurable suffering. This plan depended greatly on random chance (most significantly on Venters staying alive long enough for all the pieces to fall into place), a fact that Davie is well aware of.
In The Saga of Darren Shan — in the last book Darren and Steve find out that they are sons of Desmond Tiny (Destiny) and that their entire life, the wars they fought in, the losses they suffered... it was all planned by Mr.Tiny. It was all a game for Tiny that in the end would in the end come down to only Steve Vs.Darren- which would then proceed to get rid of the weaker of the two.
At the end of Good Omens, the characters begin to suspect (though they certainly can't confirm it) that the whole plot was a Gambit Roulette by God. Could be a justified example for once...
Kronos in Percy Jackson and the Olympians earned his nickname, the Crooked One, for excelling at this. Whenever his plans are thwarted, he or one of his minions says something along the lines of "we planned it that way". While he's still rotting away in Tartarus, he assembles an army, brings a dead girl back to life, kidnaps a goddess, and plans an invasion. After finding a way to possess Luke's body, he becomes almost unstoppable and is barely defeated in the end. Apparently the one thing he didn't plan for was Luke regaining control of his body just in time, resulting in Redemption Equals Death for Luke And I Must Scream for Kronos.
A heroic version of Gambit Roulette is found in Master of the Five Magics, by Lyndon Hardy. The fate of the world depends on a thaumaturge solving the puzzle of a castle in order to find an alchemical solution which will lead to a magical sphere which, when completed, will lead to the study of sorcery. After that, he has to come close enough to the chamber of a wizard in suspended animation to recognize the location, then awaken the wizard. Among the things that make this truly roulette: alchemy is a magical gamble, where one thousand starts can end in two successful potions, or none; getting the magical sphere correct depends on recognizing a faint difference, correcting the ritual for it, and finishing the crafting before the sphere explodes; the only reason Alodar is anywhere the tomb is because the ship he's on sinks nearby; and the plan finishes with what amounts to, "Hopefully, this person can save the world."
Sharon Lee and Steve Miller's Liaden Universe: aware of the Department of the Interior's machinations, Liaden's Scouts hatch a cunning plan: they will destroy the DoI from within by feeding Val Con yos'Phelium to it without giving him any forewarning or preparation, counting on his line's Weirdness Magnet nature to throw a monkeywrench into its schemes. Given the way There Are No Coincidences in the Liaden Universe, this effectively turns a Roulette Gambit into a Batman Gambit.
Clonak stared at him as if he’d taken leave of his wits. “Well, of course we gave you to them, Shadow! Who else did we have more likely to trump them than a first-in, pure-blood yos’Phelium scout commander? Concentrated random action. Would we waste such a weapon? Would you? I didn’t think so.[...]"
At the end of the Discworld novel Jingo, Lord Vetinari discusses his Batman Gambit with Vimes, making a big deal out of the fact that he managed to stop the war before too many people were killed ("Bought and sold? Perhaps. But not, I think, needlessly spent"). Except that we already know that there's a parallel universe where the Klatchians took Ankh-Morpork and the entire Watch was killed before he unleashed his Gambit, and the difference was a decision by Vimes that could have gone either way and that Lord V wasn't in a position to know anything about.
Jared from The Host initially believes everything Wanderer does is proof that she's secretly a Seeker trying to infiltrate the group. This starts to annoy the others since he keeps it up way too long and even Jared starts to realize how ridiculous he's being.
Several of Petyr's plots in A Song of Ice and Fire, most notably the plot to have Joffrey killed via poison conveniently taken from Sansa's hairnet.
To be fair though, Varys is built up as an elite Chessmaster from basically Book One Page One, and Petyr is revealed pretty early on to be his equal. None of the things they orchestrate rely on too much luck (other than the bits involving Daenerys doing, or rather NOT doing, certain things), when you learn how it was done.
In Lee Child's Jack Reacher novels, basically everything the main character does in action sequences is one of these, often relying on flimsy guesswork to construct a plausible scenario, which just so happens to be exactly right. The most vivid example so far being when he - given a vague description of a character's height, weight and handedness, manages to hit him in the arm with a sniper rifle from a huge distance while the target was INSIDE A (wooden) BUILDING (he was aiming for the arm to disarm his weapon). Reacher had no reason to know where in the building the guy was standing, he just 'assumed' he would be standing behind the door waiting for Reacher to enter. The entire series is based on such coincidences and vague assumptions.
Live Action TV
In japanese drama Uramiya Honpo, almost every plan Uramiya uses to punish her victims is a Gambit Roulette. The most blatant exemple being the second movie special, 'Mind Control No Wana'. In the last episode of the first season, we were introduced to Kiyomi, a woman who looked exactly like Uramiya and has been institutionalized since her family was murdered before her eyes when she was a child. In 'Mind Control No Wana', it is revealed that the murderer is Sunstone, an insane guru who is also her real father (he raped her mother) and intends to marry her on his 55 birthday. After discovering the truth, Kiyomi hired Uramiya to help her avenge her family's death. Uramiya's plan was to disfigure Kiyomi with acid so her face could be rebuilt into an exact replica of Uramiya, so years later, Sunstone will kill Kiyomi, mistaking her for Uramiya. And it worked!
In the series Lie to Me, this is Cal Lightman's favorite strategy, calling it the Long Con. This to the point of even tricking his own employees into actions he knew they would do to help.
On 24 many terrorist plans are of this nature. For example, one plan in the fourth season involves kidnapping the Secretary of Defense, and threatening to execute him live on the Internet; using the traffic that generates as a mask for them hacking into every nuclear power plant in America; using that as a diversion for hijacking a fighter plane to shoot down Air Force One, then stealing the nuclear "football" from the wreckage; using the data in the football to intercept a nuclear missile being transported through Iowa; and finally, firing the missile at Los Angeles. The villains have no explicable way of knowing that the football would survive the impact, that the plane would crash close enough to their location for them to reach it before emergency crews, or that a nuclear missile would be on the road in the vicinity of their secondary team.
The football codes are worthless unless you are the President and he can't launch alone unless we are already at DEFCON 1. It takes 2 people, the President and the Secretary of Defense (if he is kidnapped or compromised, another approved official) to launch unless at DEFCON 1. Also, the President's nuclear codes are to activate the Single Integrated Operational Plan (now known as OPLAN or CONPLAN), not any single missile.
To be clear, the terrorists would have wanted the code to the Permissive Action Link (PAL) mechanism on the warhead, which is not known by the President, but would only be accessible to a senior officer (at least O-6) responsible for those weapons. PAL code lists (usually six digits) are (supposedly) split between commands, so any one person or one location will only have half of any particular PAL code until the code is relayed in a nuclear release order.
On the other hand, Habib Marwan's plan is a little more flexible than many Gambit Roulettes, in that overall success or failure did not require every single sub-plan to succeed. Sure, Bauer and CTU foiled a lot of his plans, but he accomplishes quite a bit - destroying a train, kidnapping the Secretary of Defense, shooting down Air Force One and apparently killing the President of the United States, or at least forcing him out of office., causing massive fear and terror, and all in one day. The guy's at least the most successful terrorist since Osama bin Laden, and no doubt a revered martyr among the Islamist radical community.
The heroes had to make some staggeringly stupid decisions for the plot even to advance as far as it did: Federal Agents arrive to arrest Jack in the middle of trying to arrest Marwan and refuse to let him finish, allowing Marwan to escape. A defense contractor worries that that the Secretary of Defense's future son-in-law might find incriminating information, so they start torturing him to find out what he knows. When Jack threatens to get away anyway, they set off an EMP in downtown Los Angeles and fly in a team of mercenaries they apparently had on standby for murdering CIA agents. Many other examples.
Subverted in Heroes: it appears the mysterious organization seems to be manipulating a ridiculous number of variables to come out at a dark future, but we eventually discover that things didn't turn out quite as they planned either...
They specifically have: 1) a guy who can see the future; 2) a little girl who can tell them exactly where any human being in the world is at all times; 3) a telepath capable of reading people's minds over long distances and probing their deepest memories. And, initially, 4) an agent capable of total mind control, being able to order anyone she can talk to to do anything and then make them forget about it. All this makes the villains' prescience at least a bit more plausible. Really, the dizzying array of assets the Company has at the outset of the series tends to make their failures less believable than their successes. As is frequently said about the RPG Exalted, with characters this powerful, if they haven't remade the world in their image by the end of the campaign, you must be doing something wrong.
Used straight on a smaller scale, when Nathan's crusade is about to be shut down by an appalled Homeland Security agent (and acquaintance of the currently imprisoned Tracy), Nate's Psycho for Hiresecond-in-command manages to rig Tracy's restraints, so she'd break free, try to escape, and show just how dangerous she really is... just in time for the agent (who'd just returned with an armful of Cease And Desist orders) to see her freak out and kill someone (something Tracy hadn't done in a while because she had actual control of her powers now). This whole scenario only works if Tracy panics and kills - something she hadn't done in months. Plus the chance that the agent shuts the place down anyway and insists Tracy be tried for murder, publicly.
In a similar vein, Danko strongly suspects that Nathan is a super, and decides after he is let go to expose him...by shoving him out a window. At that point, Danko had no strong idea what Nathan's power was, and if it hadn't have been flight - Oops, you just murdered a US Senator.
An episode of NUMB3RS centers around a dirty bomb threat somewhere in LA, which turns out to be fake; the actual point of the threat was to trigger the evacuation of the immediate area, so the crooks could break into a vault without interference. However, the plan requires that the FBI evacuate the right area, which was not revealed by the "terrorists" and which is only determined at the last minute through extreme deductive skill (and nearly incorrectly anyway). Had the FBI guessed wrong, the plan would have failed.
This is actually similar to the plot of Die Hard With A Vengeance, with the Roulette-averting caveat being that the terrorist there said the bomb was in a school, making sure the NYPD and FBI were busy searching schools instead of patrolling Wall Street and the Federal Reserve (as there are no schools in that vicinity).
This is a common problem on this show in that it relies on mathematics far more than real investigations ever would. While statistical analysis and some other techniques are used in law enforcement they are not used in individual cases to the same degree as in the show.
Parodied neatly in the Doctor WhoComic Relief spoof, The Curse of Fatal Death. The joke here is that the unexpected roulettes become so expected that it is funny when they stop happening. The basic idea is that each is using his time machine to bribe an architect to set a trap, or UNSET a trap. It is up on YouTube, but unfortunately a direct link would result in them taking it down.
Doctor Who also inverts this one - kind of - throughout the Seventh Doctor's tenure. The Seventh Doctor seems to sashay through story after story knowing exactly how to tweak every adversary's nose to ensure their destruction, often by their own hands, and never bothers to explain himself, either to poor Ace or the audience. What complicates matters further is that Fenric, one of the last adversaries he faces, claims to have been pulling a similar Roulette on the Doctor ever since he met Ace...
Furthermore, many of the Seventh Doctor's Roulettes tend to come perilously close to crashing down around him as one of his adversaries complicates things by doing something he never expected, resulting in a fair bit of frantic running around trying to get everything back on track.
Supposedly the reveal would have been that the Seventh Doctor was playing the Bill and Ted's Excellent Adventure game. His future self was setting things up so his past self would succeed ... which meant that he couldn't cheat his way out of having to play Gambit Speed Chess, since his future self would remember his past self's difficulties and be unable to prevent them. It's hinted at vaguely in "Survival" and blatantly in "Battlefield," but the series ended before it became explicit.
Though we haven't quite seen all of it yet, the plan of the Silence over series 5 and 6 of the new Doctor Who is very much turning out to be a case of this. Much of the plan is coherent. YMMV if this is a gambit rather than a roulette.
In Angel, Jasmine claims that virtually everything that's happened in the series up to the point of her arrival on Earth was the result of her manipulation. She may have just been trying to be impressive, though.
The odd thing is of how little importance to her actual plan was the stuff that she was obviously directly responsible for. It's revealed that she is the master of the Beast, the demon that came to LA to slaughter a group of mystical beings in order to black out the sun and cause LA to become a haven for vampires and force the gang to release Angelus to deal with the Beast, only to have to deal with the trouble of re-ensouling Angelus after the whole ordeal. And this is all AFTER she has possessed Cordelia and has a vessel to release herself to Earth. The excuse given is that this is all a distraction so no one notices that she has possessed Cordelia, when in fact she could've just ran off somewhere for the time being before giving "birth".
They do mention that she claims all the disasters she had caused where in fact "a higher being's birth pains", and the people claiming that this was "all part of the plan" were either working for her, or came out of her mouth. In other words, Unreliable Expositor.
Benjamin Linus from LOST may be one of the all-time greatest chessmasters. The leader of the "Others" is able to manipulate the show's castaways into thinking his group are primitive savages (in truth they are a bunch of modern savages/guardians of the island) AND arranges for his own capture by the castaways, in a net of the crazy Frenchwoman whose child he abducted and raised as his own, while claiming to be a castaway whose balloon crashed on the island, killing his "wife" in the process. In spite of having his lie exposed, he succeeds in getting the father of a child his minions have already kidnapped to free him, resulting in the deaths of two of the dad's fellow castaways in the process, at the hands of the father. He then uses this as leverage to get three of the castaways to surrender themselves to him. In season 3, he steps it up a notch by somehow managing to force Jack to perform an operation on his spinal column. This may be one of the only times where Ben's plans don't work too well, as Jack slits his kidney as a level to force the Others to allow Kate and Sawyer to go free. Ben survives, and seemingly without doing anything at all manages to destroy several chances for survivors to escape the island, thanks to John Locke. He is also revealed to have orchestrated the murder of the village the Others now live in, the hippie commune/big secret science project thingy known as the Dharma Initiative, including his evil father. By season 4, Ben has successfully manipulated Sayid (who tortured Ben) into working for him as his personal assassin and in season five, it's revealed that Ben murdered John Locke in order to make the rest of the castaways who did escape the island, go back to the island.
It has been hinted by the writers that many of the things that have happened were not actually expected in his plan for example, getting caught in the net, his daughter being brutally killed, making his true genius his ability to adapt his plans very quickly.
And yet, in the season 5 finale, we discover that the entire frakkin' show, including Ben with all his Gambitian schemes and Magnificent Bastardry, have all been part of the plan devised by Jacob's nemesis, as many as 200 years ago, with the sole aim of killing Jacob without breaking these rules they both must follow. The real kicker? His Unwitting Pawn is Ben.
The most recent episode has Flocke predicting that Widmore would rig the plane to explode so he could take the explosives and put them in Jack's bag, and that Sawyer would prevent Flocke from getting on the submarine, AND that the people trapped on the submarine would attempt to disarm the bomb (since Flocke himself apparently can't directly kill these particular characters). The plan did not end up panning out perfectly, though.
Many of the schemes in Veronica Mars verge into this territory, most notably the plan to kidnap her boyfriend's baby, which had as linchpins one character opening a letter addressed to someone else, her phone being tapped, and the sheriff driving all the way to Mexico without looking in his trunk.
The Tales from the Crypt episode "The Pit" relied entirely on this. Not only were two men able to predict exactly how their wives would react in a certain situation, they were also able to reschedule a major international fighting event, change the designated fighters, AND apparently hype this last-minute change to the point that no ratings were lost, all without their wives finding out. Even more bizarrely, they seemed fairly confident that their wives would kill each other in the match (although, assuming one survived, her husband could have filed for divorce).
An episode of Fringe had an FBI agent who was infected with a life-threatening parasite which was cured at the very last second. Turns out he apparently infected himself, and the entire episode was a plan to get his wife to overhear a secret discovered by other FBI agents while they were trying to save him. But if even a single thing in the episode had gone differently - including the fact that an attempt to catch a suspect had been botched - then the plan would not have worked. If the heroes were even five minutes too late, the plotter would have been dead, and if they had gotten the necessary information just a few minutes prior, the wife would not have been in the room.
Fringe writers seem to enjoy justifying this trope. in the episode Plateau, the villain Milo gained super plan making powers by taking a drug. He orchestrated peoples deaths by setting a pen on the ground and creating a chain reaction ending in a traffic accident. In the most recent episode its been revealed that the observers are crazy good at these, but that's justified by time travel or by the fact that time isn't even linear for them. They can see all points of time at once.
In the case of Milo, it was subverted by the episode's end. Olivia managed to avoid the subtle death trap Milo planned, because she ignored the "air quality" warning that was crucial to her getting distracted for a split second, like all the other victims. The reason? This took place when Olivia in our universe was manipulated into believing she was the "other" Olivia in the alternate universe. Fortunately for her, minor details didn't quite get through to her, so she wouldn't have recognized the "air quality" warning everyone else did. Needless to say, Milo was quite surprised when Olivia didn't fall for the trap.
In the Grand Finale of Star Trek: Voyager the evil Borg Queen suggests that the reason Voyager always miraculously escapes the Borg is because she's been protecting them all along, as Seven of Nine is her "favourite." This is somewhat implausible, but the audience may not have noticed due to the distracting sight of the Borg Queen's blatant Les Yay with Ms. Fanservice of Voyager.
It precedes this, as Dark Frontier has the Borg Queen essentially say that she orchestrated 7 of 9 being taken in by Voyager and integrated into the crew, so that she could later coerce her into returning to the Collective. This required the following - Voyager to attempt to ally themselves with the Borg, then ask for a representative, then for the cube to be destroyed allowing 7 to get onto Voyager and then, despite the Borg stabbing Voyager in the back, 7 surviving and being taken into the Voyager crew.
In Red Dwarf season 8, Holly claims that everything that has happened since Lister woke up from stasis back on Red Dwarf has been orchestrated by Holly to keep Lister distracted. Resurrecting the crew was just his latest scheme.
Holly being Holly, it's most likely just made up to make himself sound smart. Or because he felt like saying it, said it, then realised it would make him sound smart, so stuck with that story. So maybe not an actual Gambit anything.
In an earlier episode, Holly impersonates another AI and leads the cast through a complete adventure where Holly Dies at the end. It's actually completely possible that Holly is orchestrating the entire series to keep Lister distracted and that pretending to be computer senile is part of it.
On of the villains in Wizards of Waverly Place was a shopkeeper who sold the kids a pet dragon. For some reason, Alex can't tell her parents about it. So she pretends it's a lost dog that they found, and they post lost & found posters. Suddenly the shopkeeper apparently responds to the posters and takes it back, claiming to have done this several times before. This way, he can sell the dragon several times to different people while getting it back each time. So the guy apparently planned for Alex, and everyone he sells it to ever, to do something stupid like that. Either the guy was just a really devious shopkeeper, or you could just blame this on bad writing.
Wonderfalls has the same overarching theme, with God's big Rube Goldberg device.
Lampshaded in an episode of the (surprisingly good fun) 2000 series The Invisible Man with a speech given by the hero to the recurring villain, at whose mercy he is. Having asked the villain to Just Shoot Him or at least knock him out and get on with whatever he wants to do, he launches into:
What is it with all these complex plots, huh? What is it? Is it a Swiss thing, is that what it is? (...) No, no, don't defend it, please. (...) Please, will you just admit it? (...) You're ridiculous. You are! I mean, you join the Q gland design team just so you can steal the design. You... you make me think Kevin's alive so I can lead you to some files that, hey, Buddy? You could have found on your own with a little research. Then you give me the flu so I can what? Wind up in some hospital room and you can take the gland out of me? Douche. Rube Goldberg has got nothing on you, pal.
Lampshaded by the National Security Advisor in the Season 4 finale of The West Wing: the terrorists' entire plan to kidnap the daughter of the President of the United States hinged, first, on her taking some of her boyfriend's Ecstasy (which had been laced with GHB) and, second, on her deciding to use the bathroom in the club before leaving.
Her point was actually that the crime, since it relied on those variables, probably wasn't the work of a master criminal or terrorist cell, but probably some opportunistic idiots. That made a lot more sense than the eventual resolution, and since Aaron Sorkin left the show before the cliffhanger was wrapped up, that might have been its intended conclusion.
Boyd Langton's plan in Dollhouse. The goal is to have Echo repeatedly imprinted, so that her resistance to imprinting will leave chemical markers in her spinal fluid, which he can then harvest and use to create a vaccine against imprinting. To this end, he installs himself as Echo's handler on a long-term basis, without anyone else in the Dollhouse knowing who he really is. During this time, Echo is sent on several engagements that nearly get her killed, as well as one or two that nearly get him killed, and he really has no reason to be so sure that she will survive. Not only that, but he's simultaneously testing Topher and Adelle to see whether or not they're worthy to be among his 'family' that will survive after the mind-wipe apocalypse.
He didn't just want Echo for that—-he admitted he really did love her and wanted her as part of his "family" too. He mentions that he had wanted all of them to "grow" through the challenges he presented. As Adelle commented: he is spectacularly insane.
On the Reunion episode that aired immediately after the final episode of Survivor: China, season winner Todd implied that everything that had happened during the show, up to and including who was selected to be on the show, was all somehow part of his master plan.
D. Gibbons on Flash Forward is running a massive Gambit Roulette. It becomes particularly obvious when the heroes find a hidden base in Somalia and discover a 17-year-old videocassette of D. Gibbons where he addresses them by name. Then again, he's a literal Chessmaster, and he has a lot of experience with seeing flashforwards of the future.
Potentially a subversion. At first glance, the Scuba Diver does seem to rely on an uncontrollable event and a second person performing a plan of their own, but neither are really required. Barney did not specifically need to steal that particular girl, Lily regularly has set up Ted on dates, and any one of them could have started his plan. Lily's plan wasn't actually required, she could have just grabbed the book out of his hands and ran and Barney's plan still would have worked. Barney baited her to launch the gambit, but he didn't actually need it. Although it still seems to require that all 4 of his closest friends will fail to see his insincerity.
In the eighth season, Barney takes this same premise and turns the dial way up for his final play: the proposal. Likewise, some of the steps weren't really necessary, such as the intervention, but for other steps the roulette was even justified. At one point he says that Ted's actions would reveal his true feelings on the matter and allow the play to continue or fall apart accordingly. It's probable that he intentionally set it up so the same was true for Robin as well.
An interesting justified version happened in the first episode of Sherlock, where the murder victim used Gambit Roulette to lay out a trail of clues to help the police identify her killer. Yes, it was a roulette, but considering that she had to concoct and execute this plan within the last hour or so of her life while under the watchful eyes of her killer, it makes sense that it wasn't planned out better.
Also, a lot of Moriarty's plans depend on this. The second series finale is the best example, with many elements apparently coming down to luck, and absolutely hinging on the police being incredibly stupid.
Happens in Star Trek: The Next Generation episode "The Most Toys". Collector Kivas Fajo wants to add Lt. Data to his collection. To succesfully kidnap Data and fake his accidental death, he poisons the water supply of a Federation colony with Tricyanate, making it look like a natural disaster. Because the only antidote, Hitridium, is extremely unstable, he's the only merchant in the region selling the Green Rocks needed to solve this catastrophe. Said green rocks cannot be beamed, thus they must be be shuttled over because they are highly volatile, resulting in a good cover-up for any accidental explosion of the shuttle. His plan, however, hinged on the fact that Picard would send Data on the simple job of ferrying things back and forth, and this is nothing the collector has any control over. Furthermore, Data is not even the crew's best pilot (that honor goes to Riker), and being a high ranking member of the crew, he could very well not have been available to do this ferrying job. Furthermore, the Enterprise has HUNDREDS of crewmembers Picard can choose from. Thankfully, it seems fate threw him a bone and Picard decided to pick Data for the job that day.
It leaned heavily on the Enterprise being the closest ship in the sector to respond to the distress call from the colony.
The fact that Data is the only android crew member might be part of why he was picked for this mission. He's a stickler for procedure, thus eliminating the possibility of "pilot error" that might result in a Hitridium explosion.
This was not the only episode showing Data's penchant for shuttling dangerous materials, such as the episode in which a shuttle crash wiped his memory and he strode into a pre-feudal town with a radioactive briefcase.
In fact it is this precise detail (that Data, as an android, is incapable of blowing the ship up by accidentally pressing the wrong button) that sparks Geordi's suspicions about the "accident" in the first place and eventually leads to Fajo's plan being uncovered then ruined.
Not even. What actually lights the first spark is that Data never reported the shuttle clearing the cargo bay. Which was completely unnecessary in a practical sense but the idea of Data not following standard procedure is inconceivable.
Revenge, on occasion. For example, Tyler's plan to break up Emily and Daniel would not have worked if Jack hadn't shown up or if Emily hadn't invited him in, things Tyler hadn't no control over. In fact, if that hadn't happened, the conversation would have gone like this:
Emily: You are extremely late. I hope you have a good excuse. Why didn't you call?
Daniel: What? Tyler told me you cancelled. I came to ask why.
Emily: Well, he lied.
Tyler: *dead man walking*
The plan to frame David Clarke as a money launderer for terrorists relied on a large number of people being willing to perjure themselves in court and the prosecutor suppressing evidence. If any of these people were honest, the case against Emily's father might have fallen apart. It is likely that the initial plan did not require the frameup but Conrad screwed up and then had to play Xanatos Speed Chess so someone else would take the blame.
Babylon 5: In the fourth season, Psi Cop Alfred Bester used subtle mind manipulation to make Michael Garibaldi his unwitting agent. Over time he subtly "nudged" Garibaldi's personality in the ways he wanted, heightening Garibaldi's natural suspicion, and turning him into a Manchurian Agent of a sort. As this happened, and (in many cases) as a result of the manipulation, Garibaldi took several steps that Bester himself admitted he hadn't--and couldn't have--anticipated, such as Garibaldi's resignation from the command crew of Babylon 5. All of which played straight into Bester's hand. Making the entire "plan" of Bester's a hybrid of Gambit Roulette and Xanatos Speed Chess.
Spoofed in an episode of the Frantics' sketch comedy show Four on the Floor. Burglars are breaking into an office building. As they close in on the safe that is their target, the ringleader accurately predicts a series of improbable events including the night watchman having a fatal heart attack, a flying priest passing the office window, and a door-to-door dynamite salesman happening to be in the area. Each time, the leader smirks and tells his cohort, "Just like I planned it!"
In LEGO's BIONICLE universe, the main villain of every story year so far, Makuta Teridax, has been defeated several times, but has revealed that he has, in fact, planned for every possible setback ahead of time. The Gambit Roulette is still turning, in fact, as he planned for all of the following to happen: the destruction of his own body, the death of the benevolent Great Spirit Mata Nui, the subsequent resurrection of said spirit, the rest of the world believing him dead... And the odd thing is, he seems to be the only one. There seems to be no Gambit Pileup coming, no (glaringly obvious) Deus ex Machina, just a slow slide towards his victory, trying to keep him from winning as long as possible. Quite dark for a Merchandise-Driven children's story. It went exactly as planned. Makuta committed Grand Theft Me on Mata Nui just as his soul was about to return to his body, becoming the universe as a result and banishing Mata Nui into a Soul Jar and out of the Matoran Universe
Indirectly lampshaded when he discussed the matter with Vakama: "Little Toa, you have not yet begun to see even the barest outlines of my plans. I have schemes within schemes that would boggle your feeble mind. You may counter one, but there are a thousand more of which you know nothing. Even my ... setbacks ... are planned for, and so I shall win in the end."
Well, he hasn't planned for every possible setback, but instead tended to adapt to the situation. Throwing the fight against Takanuva was likely improvised as a way to get the heroes off his back. Getting crushed by a huge gate at the end of that confrontation was definitely not part of The Plan, according to Word of God but it didn't hurt too much as he was going to abandon his body in the end anyway.
Piraka Zaktan has seen the full plan, and keeps it in mind. This has allowed the heroes to actually work towards foiling it, as when Zaktan became their captive, he guided them to Teridax's then-supposed location. There was some ambiguity whether he was telling the truth or just wanted to play a roulette of his own, but we'll probably never find out, since that story-arc was abandoned quickly.
In The Iliad, Zeus launches an incredibly complicated plan that involves manipulating gods and mortals alike to set off a war between Troy and the cities of Greece that kills thousands upon thousands of mortals. One of his two ultimate goals is to whittle down the surplus population of Earth so the earth goddess Gaia wouldn't send another monster after him, as she had done previously with Typhon and the Giants, and more particularly to destroy the many demigods he had fathered with various mortal women on all those occasions he had cuckolded Hera, to keep them from threatening his power.
The story of Oedipus, in which everything that has happened to Oedipus has been one of several possible outcomes all to the benefit of Apollo, who is implied to have orchestrated the events of the play from at least as far back as Laius's rule before Oedipus was born, and possibly as far back as Cadmus' searching for his sister Io and founding Thebes in the first place. Then again, Apollo is not only a god, but specifically the god of prophecy. Oedipus and his family were part of a plan to make another war (with Thebes as the main participant) to finish what the Trojan War started.
In the retcon type, it has been revealed that WWE's Kane has been working a plan that's equal parts this and Indy Ploy since he debuted fourteen years ago, the overall goal to be to exact vengeance against his kayfabe brother The Undertaker by overcoming him and taking his place as the dominant force in the WWE. One thing that really puts this one over the top - Kane's ultimate success came in the form of burying Undertaker alive. This fourteen year plan involved doing so twice before that.
In TNA, the recent Eric Bischoff / Hulk Hogan angle paints the both as cunning schemers of Machiavellian levels though many elements of their scheme (Jeff Hardy being able to make it to the World Title Tournament finals & Dixie Carter foolishly signing a contract without even looking at it) would completely unravel the scheme if it had not gone precisely in their favor, requiring the conspirators to either be insanely lucky or nigh-omniscient.
There is also the fact that they had plenty of opportunities to get the World title on either Jeff Hardy or Abyss that were much more convenient than the Triple Threat match at Bound for Glory. For example, at Victory Road 2010, there was a Fatal Four Way match involving Jeff Hardy vs. Abyss vs. Mr. Anderson vs. Rob Van Dam, or at The Whole F'n Show where they had Abyss vs. Rob Van Dam with Eric Bischoff as the guest referee.
That's not even mentioning the fact that Kevin Nash, Sting, and The Pope had figured out the plot (or at least a general idea of what would happen), but instead of politely informing Dixie Carter or the TNA fans of what would happen, they started talking in riddles and attacking people without any given reason to the point where they became heels in the storyline. They even challenged Hulk Hogan to be a part of a match against him on the date of the reveal, even though he was recovering from major back surgery. Had Nash, Sting, and Pope acted like mature adults in the storyline, the Gambit Roulette would have probably failed.
What's particularly strange is that, unlike what you might think, they actually did nothing to help Jeff Hardy win the title. When it comes to something that your plan hinges on this way, you'd think they would actually do something to make sure it happened.
The Higher Power plot involving the Ministry Of Darkness was started MONTHS before their slated goal was even needed, depended on their target acting very much out of character, and disregarded simpler, much more assured ways to accompllish their purpose.
The chaos god Tzeentch, also known as the Architect of Fates and the Great Schemer, is the Warhammer and Warhammer 40,000 god of Gambit roulettes and lives for pulling the strings of reality in increasingly implausible and intricate ways - in fact, because such scheming is such an intricate part of its being, Tzeentch is virtually incapable of doing things straight. Even the other gods step carefully around Tzeentch because of this, which is probably just what it planned anyhow. Tzeentch's C'tan counterpart the Deceiver has been pulling some pretty twisty stuff too and it is not very clear how far each is playing the other. To a much lesser extent, the Eldar Seers have pulled off less ambitious ones - like engineering Ghazghkull Mag Uruk Thraka's rise to Warboss and indirectly causing the last two wars for Armageddon, with billions of human lives lost, just to avoid an Ork attack on a Craftworld many years down the line.
Some fans theorize the God Emperor of Mankind planned out his necessity for life support, to better make the Imperium worship him, which helps humanity weaken Chaos (as faith weakens them).
Reinforced with the presence of tarot cards being used by Inquisitors to help determine the Emperor's will with a great deal of implication towards this being the case as the emperor's mind had to fracture to cope with ruling the Imperium as his body lays dieing. Some of the books even show aspects of the emperor's mind(s) even disagreeing showing that not all of them are in communion with eachother. Or are they? Meaning no one is really sure what the Emperor's plans and thoughts could be. Probably not even Tzeentch. This has led to a running joke in 4chan's /tg/ boards of the Emperor, Tzeentch and the Deceiver getting together every saturday and having Gambit poker.
Tzeentch has a bit of an advantage here in that he can make sure all the little chances come up, since he's sort of in charge of the time stream. Equally, the Eldar Seers are planning convoluted, chance-driven plans- but what they're actually doing is looking at the various paths the future could take and pushing it onto the one that's best for them with the minimum of effort (hence a little reliance on random events- they know it'll happen in advance if they set up for it).
The extent of the deceptions of Tzeentch and the Deceiver are so convoluted, one might think that they're one in the same. Or not.
There's also a third one, the Eldar's Laughing God. Some of the stories of it's deeds are identical to stories about the Deceiver, specifically starting the C'tan fighting amongst themselves. This has actually been noticed in-universe a few times, so it's unlikely to have a "word of god" explanation anytime soon.
A throw-away line in the new in the new Warhammer Daemons army book suggests he might not actually have an end goal at all, he just likes setting these things in motion and seeing what happens. He is a god of Chaos, after all.
All of Tzeentch's greater plans intentionally oppose each other. This is because, being the very concept of scheming personified, if any one grand scheme were to actually succeed, Tzeentch would write himself out of existence. So, unless his goal is suicide, he doesn't have one. Daaaaaaamn, man.
Regardless of his ultimate purpose his most famous and abysmal failures are at the hands of a bunch of intoxicated, overstuffed, oversexed, genetically engineered, battle lusting, werewolfish, space vikings. In your face biatch. HOWL.
The attack on Prospero was in itself one of his Plans. First, he lets Magnus, one of the most powerful psykers in the universe forsee a future where the Imperium is destroyed, causing Magnus to break his word, his father to turn against him and all of this before anybody even knew he existed. Second, he allows Magnus and his legion of psykers to get the crap kicked out of them so they had no choice to turn to him for aid. Third, he causes them to use the Rubric, resulting in his now faithful legion of Supersoldiers being nothing but Gambit Speed Chess playing psykers or their mindless servants.
And remember kids, in this universe, this guy is the god of Hope...
Sidereals in Exalted. As they have access to the Loom Of Fate, they have the power to observe the tiniest workings of Fate and all its potential consequences. Moreover, they can subtly alter fate more or less by filling out the right paperwork. As such, they have a bad tendency of putting forth Plans and Roulettes with disturbing frequency.
And yet they're still not as bad as their employers. The Maidens of Fate seem to order baffling orders to their servants, who just go along with it because who's going to argue?The Bureau of Oversight is just as bad, often giving Sidereals assignments like "Make sure the princess is wearing white at the ball next Thursday" or "replace a rose in a garden with a lily" or "move the chair four inches to the left."
Both of these groups, however, have the supernatural powers and influences to make sure they can see the full consequences of these gambits in advance, and/or adjust fate itself to pre-ordain them. It's a gambit roulette to outsiders, but fairly predictable daily business for them.
The Great Dragon Dunkelzahn, an important metaplot NPC in the Shadowrun universe, manages to orchestrate plans that required the ability to predict volcanic eruptions causing new islands to form, massive stock market transactions, an insane AI taking over an archology, and every major event, even those happening over a decade after his death, and still manages to influence all of them in some shape or form, even causing some of them...
This is Lampshaded many times by the Shadowtalk commenters and handwaved by others speculating Great Dragons possibly having divination powers. This is done for any of the massive plots of any of the Great Dragons... though how the immortal elves managed THEIR roulettes...
In Magic: The Gathering, the ancient Magnificent Bastard planeswalker dragon Nicol Bolas subtly pulls strings behind the scenes to unseal the Eye of Ugin and release the Eldrazi for reasons known only to himself. When his henchman Sarkhan Vol asks how he managed to set up the exact circumstances to unlock the seal, Bolas admits that he merely set up as much as he could and relied on chance for the rest.
Speaking of which, in the actual game it is possible to pull off one of your own with Genesis (not tournament-legal) and a green/white Kamigawa deck that contains among other things, Kodama of the Center Tree. Just discard Genesis, and have enough green and white lands to summon most cards. If your foe has enchantments or artifacts, cycling one of the spirit cards destroys them (there's even one to prevent damage, Kami of the False Hope). If your enemy relies on multiple attackers, you can soulshift Kodama of the Center Tree to pull them out of your grave. If you need to have a heavy hitter, you can pull Kodama out of your grave. Then you can use Genesis to put it back in your deck. There are random outcomes that can cause you to lose (the opponent has a speed deck, you don't draw Genesis or enough lands), but normally no matter what you do or is done to you, you can have some option to win.
The Quori in Eberron frequently pull off this kind of plan, and the game offers a really good explanation as to how: in addition to being super-intelligent Eldritch Abominations, the Quori frequently return to their home plane to plot, where Year Inside, Hour Outside is in effect. This essentially means that they have weeks to plan their next move while a single night passes on the Material Plane.
The Temporal Probability Agency is all about this. A sentient computer sends information back in time to itself from all possible time lines in order to best instruct their agents on how to save the world. Agents get odd little instructions, like 'Save this plane from terrorists. Also, spill a drink on the captain.'
Theatre and Stage Shows
In his fourth tour, Enigma (2009-10), British illusionist and mentalist Derren Brown pulls one off spectacularly, with the set-up lasting the entire show:
At the beginning, he gives a man in the audience an envelope containing a card and tells him not to open it.
At the interval, he asks the audience to vote for a choice of seven cards: a goose, confetti, ice-cream, a moose, an egg, a needle, and apple juice.
Near the end, he gives six men from the audience numbers from one to six and asks them to randomise themselves in front of poles A to F. At the same time, he opens two envelopes, both containing six of the cards from the interval, giving the cards from one to each person in order of their numbers, and places a third at the front of the stage.
He then calls a woman up from the audience and asks her to pick a man at random, choosing #2, standing in front of pole C, and a card from the second envelope at random. It turns out to be the ice-cream, which is the same card #2 has. He opens the third envelope, revealing it to... be the ice-cream, with the letter C on the back. All six men place the cards on hooks on the poles and leave the stage.
He calls on someone to reveal the winner of the interval poll: confetti, which is written on the card given to the man at the beginning. He then reveals how he did this exactly: with props in the wings covertly saying "choose the confetti".
Then, he shows a clip of the band Mc Fly (part of an unrelated at the beginning) singing a version of their song "Obviously", rewritten to contain the lyric "(He said) obviously, the order will be, an egg then a needle and then an ice-cream and there'll be a goose and moose and apple juice, oh yeah." Cue gasps and standing ovation #1. For the second chorus, he then flips the tops of the poles to reveal the same order. Cue gasps and standing ovation #2.
And finally, he says "But Wait, There's More!", and reveals the main reason he called the tour Enigma back in 2007: it's an acronym of all six cards in the order. Cue the final set of gasps and standing ovations.
In Shadow Of Destiny the Homunculi arranged all the events in hopes of being free of the bonds of the game put on it leading to multiple endings including Discovering Eikre is actually the Alchemist from centuries ago , discovering the girl in modern times is actually the centuries old daughter and the real daughter was trapped back in time , and other things. However after all play throughs Eikre can use the players own knowledge and choose bonus ending A. Causing a paradox by making the homuncili touch the gem and destroying it thus ending it's Gambit roulette or bonus ending b Giving the alchemist the knowlledge and means to save his dying wife Either ending ends with Eikre fading away and then in modern times a man looking like him getting hit in the back like in the beginning of the game but instead of a knife he turns to see it's a soccer ball and the boy who kicked it turns out to be a descendant of the boy who was trying to kill him but now since none of that happened everyones happy... cept the homunculi
Both 3D PS2Castlevania games have plots that sneak suspiciously close to this. Lament of Innocence more so than Curse of Darkness, as in Curse of DarknessDracula is wirepulling everything from behind the scenes, and there's perhaps only one character he has no major influence over - Julia. Anyhow, Isaac's devious and original scheme is Dracula's devious and original scheme. Hector even spells it out in the end. Lament of Innocence sees Mathias playing some serious hardcore roulette, and it's actually quite terrifying to see how much of a 'Master tactician' he is. For that plan to work, everything would have had to unfold exactly as it does in the game. Which it does. He is a scary, scary man.
City of Heroes has a Doctor Doom-esque villain named Nemesis who takes this to an extreme in almost every encounter. In a single story arc, he tricks the hero into defeating some neo-fascists that looked like they were going to take over his infrastructure, just to save himself the bother; predicts that your contact will believe Nemesis's real plan was to take over the neo-fascists' robot army and send you to prevent that, while he proceeds with a kidnapping; and wraps it all up by having you supposedly kill him - even though, as a superhero, you may have never killed anyone else before (and indeed are explicitly prevented from doing so by the game mechanics), and despite his well-known use of countless robot doubles. Your Contact actually comments on this, noting that his death should have been impossible, speculating that Nemesis's real objectives were twofold, first to throw the heroes off his trail by faking his death, giving him breathing room to implement more plots, and second and most importantly, to get ahold of the technology from the kidnapped person to enable him to create perfect mechanical duplicates of his own mind, resulting in the annoying prospect of having to deal with an endless supply of super-intelligent mechanical jackass villains. Finally, many heroes might have preferred Nemesis's power-base to be taken over by virtually anyone that wasn't quite so good with the Gambit Roulette. (This is far from Nemesis's most convoluted scheme.)
Oh, it gets better when you find out that he engineered the Rikti war.
One of the Loading Screen hints is "Everything is a Nemesis Plot." Another hint is "Not everything is a Nemesis Plot." Also he was apparently Emperor of the US after World War II (his reign was brief, however.)
More recently, following Issue 14: Architect: "If it's not already a Nemesis plot, you can use the Mission Architect to make it one."
The Metal Gear series is rife with Gambit Roulettes, but Metal Gear Solid 2 takes the cake, though, with a plot so staggeringly convoluted that the bad guys reveal they didn't really have a goal. It was a test run to see how good they were at manipulating events. Surprisingly the bad guys are still in control long after they reveal their plot. Only the previous game's player character and his dead brother's arm have any freedom. It's a symbolism thing, honest. Unless it's not.
Metal Gear Solid 4 is the pinnacle of this insanity, revealing the Liquid Snake "possession" was in fact an elaborate ruse by Revolver Ocelot (through self-hypnosis and nanomachines), who was working on bringing down the Patriots (A series of AIs) in order to free Big Boss. The kicker? From shortly after the end of MGS2 until thirty seconds before his death five years Ocelot's personality was completely dominated by Liquid's, preventing him from being able to alter any part of his plan once it was put into effect.
It's beyond that in complexity. Ocelot actually pretends that Liquid's arm took over his personality by self-suggestion in order to trick the Patriots into believing he was a similar threat as Liquid Snake in Metal Gear Solid 1, so the Patriots would pull their own plan to use Snake to defeat Ocelot, which is what he exactly planned for, as they became so focused on defeating Ocelot that they failed to realize that in the course of defeating him Snake would also end up destroying the Patriots.
Bian Zoldark from Super Robot Wars: Original Generation tried this. It was subverted by the fact that he was able to do it while still in control of his organization, but once he died as part of his master scheme, his own group fell to factional in-fighting and nearly doomed it.
In Super Paper Mario for the Nintendo Wii, Dimentio has been orchestrating events all along as part of the Quirky Miniboss Squad so that after the hero's prophesied defeat of the Big Bad Count Bleck, he could take over the power needed to destroy the universe, channel it through one of the heroes, Luigi, to destroy and recreate the universe.
Dimentio does have a prophesy to work off of, though, which lowers the roulette factor from "how could you possibly know that?" to "I can't believe you were right." It's still a gambit, it's just that he has access to pieces of vague future knowledge from a book proven to be reliable.
In Chrono Cross the entire plot is the result of multiple sides manipulating each other into doing their bidding. But it turns out, the manipulators are also being manipulated. And so are the manipulators of the manipulators. Now throw in Time Travel and Alternate Universes and you see how overcomplicated this actually gets.
The entire underlying plot behind Fire Emblem: Path of Radiance is a twenty-something year-old Gambit Roulette centered around Lehran's Medallion and channeling power into it by thrusting the entire continent into a war, so that Ashnard could release the Dark God.
And in the sequel, Radiant Dawn, it is revealed that Ashnard was but a pawn in an even larger roulette, orchestrated by none other than Lehran himself, who turned out to be Sephiran, the Prime Minister of Bengion, and a major ally in Path of Radiance. He wanted the "Dark God," Yune (who's actually rather nice, if a tad rude) to be released, only because this would also wake up her sister, Ashera, the Goddess of order, who would then cleanse the world of all life.
In Jade Empire, Master Sun Li, the Glorious Strategist, pulls off a twenty year Gambit Roulette to put himself in power by training the main character so that only he knows how to kill him/her, yet keeping him/her loyal, letting him/her kill the emperor after baiting him/her to that point, and then killing the main character and taking the throne. If you replay the game you can see all the points where he was manipulating things. Also lampshaded by the Spirit Monk while talking to the soldier in Tien's Landing when s/he comments that "he couldn't possibly have known that the flyer was going to crash here" (or something to that effect).
In the higher stages of Kirby's Avalanche, a computer will, despite all of your disruption tactics, somehow always manage to pull off an Avalanche (a chain of 9 or greater) if you don't beat them in under two minutes.
Master Albert from the Mega Man ZX series may have broken a record for the longest-running single Gambit Roulette (in video games, at least), in order to reset the world and become its god. He even threw a couple of gambits into the mix. And it all conspired over a couple of centuries. It didn't quite work out, considering he was fighting his great-great-great granddaughter/spare body, with the biometal with the same powers as he, but even then, he doesn't seem to care anyway.
ZX actually has TWO Roulette records - Master Thomas planned out his own Gambit Roulette to kill off Albert so he could do his own scheme to reset the world. It may or may not have gone on for as long as Albert's, but that's not the point. This marks the first Gambit Roulette being designed to destroy ANOTHER Gambit Roulette... And the most remarkable thing about it, is that it worked.
It may be even more complicated, actually. Dr. Weil, the Big Bad from the Mega Man Zero series, is the one who inhabited Model W, the object of each ZX villain's desire. There is a good chance that he still lives on as Model W, and has in fact manipulated EVERYONE from behind the scenes. ZX Advent seems to culminate in the total destruction of Model W, but then again, who knows?
Legacy of Kain. Possibly justified in that most of the players involved either have access to time travel, or happen to be an omniscient squid god.
Subtly lampshaded by Mobius. In Soul Reaver 2, he tells Raziel that he's stupid for thinking he can pull one over on him, as Mobius is only man who has completely unfettered access to time travel and the ability to see through time; everyone else's ability in this regard comes from Mobius (usually intentionally) leaving behind his time-traveling relics in some places and time-viewing relics in others. In Defiance, he tells Kain that he only thinks he understands the complicated nature of what's going on, and it's actually more complicated.
The justification is one of the simpler things about the series; there are no less than four sides in the conflict, all of them opposed to each other (whether they realize it or not, or if they even realize all the others even exist) but because Raziel is the only one who has true free will, all of these sides have to plot against each other with the end goal of successfully manipulating Raziel into doing their work for them while stopping him from doing it for anyone else.
Raziel lampshades this himself with this memorable quote; "What game was this, where every player on the board claimed the same pawn? "
That's just the factions with time travel. The big winners at the end of the last game were the Hylden, who don't have any access to time travel at all, are opposed by all the other factions, yet still manage to play them all.
Chzo of the titular Chzo Mythos was able to pull this off, due to being omniscient (and only on one day of the year, too) and able to see the past, present and future at the same time. He got what he wanted, but how much was exactly the way he intended is up for debate.
Lupin's scheme in Sherlock Holmes Versus Arsene Lupin. And then it turns out that the whole scheme- which took months to set up- was actually a smokescreen to ensure that the whole of London's police force would be in the wrong place while he carried out his ''actual'' theft. This required a plan of its own. And then the game has been playing Gambit with you all along, and if you fall for Lupin's ploy it gives you a really disheartening ending. While you are given a hint to the real target at the beginning of the game, it is tempting to choose the obvious option when the clue to your final destination is "It starts with 'B' and ends with 'ig Ben'." Choosing Big Ben, however, results in a cutscene of Watson, Lestrade and the Prime Minister coming up with precisely nothing, and then you are treated to a screen explaining that, due to your incorrect choice, Watson and Holmes become estranged, Holmes retires because he's crushed by his failure, and Lestrade is demoted to traffic duty.
Battalion Wars 2 provides a fine example of this.In an attempt to recover a lost superweapon, Kaiser Vlad manipulates the news to cause the Anglo Isles to attack the Solar Empire. When the Anglo Isles retreats, the Solar Empire launches a counter-attack, and asks the Tundran Territories to help them. While everyone is busy with that, Vlad launches a full scale invasion of Tundra, fights his way to the far north, locates and mines the super weapon, and tries to run away. Everything goes as planned, until that last step. The allied nations crush his armies, attack his mining spider, and in the end, Vlad and Kommandt Ubel end up trapped in a mine shaft.
What's really maddening is that Vlad Doesn't invade Tundra until After they pull out of the Isles.
Gambit Roulettes are the entire modus operandi of the Alchemists in Melty Blood, to varying degrees of success. Apparently, all the really experienced alchemists planned so far ahead that they noticed the inevitable end of the world, and set about trying to stop it. However, everything they do just makes it worse (they've developed an impressive collection of doomsday weapons designed to stop all the other doomsday weapons that they themselves have made). It's implied that saving the world would require the realization of the impossible, which is why at least one alchemist (who managed to set up a Gambit Roulette wherein the particles of his soul would not-quite-randomly come back together after being scattered into the The Lifestream and bring him back to life every so often) is seeking the 6th sorcery (sorcery being defined as that which realizes the impossible), which could save the world.
Admiral Aken Bosch does this to both the Galactic Terran-Vasudan Alliance and his own rebel organization, Neo-Terran Front. The entire rebellion is just a smokescreen to hide his true goal of obtaining old documents and schematics from the archives of Galactic Terran Alliance to build a machine called ETAK capable of translating the Shivan Starfish Language, and then plundering Vasudan archaeology sites to acquire Ancient texts and artifacts so he can activate the Knossos portal and use his ETAK device to speak to the Shivans and forge an alliance with them.]] And he actually succeeds, because he also knows that the Alliance Intelligence wants him to succeed, meaning that several attempts to intercept him "mysteriously" fail.
Gizel Godwin in Suikoden V loves this kind of trope, to the point where he often runs two or three plans at once just to see what will stick. His father actually advises him against this method, arguing that intrigue should be done decisively to minimise the risk of an unintended consquence. He is ultimately proven to be right: although one of his schemes during the Sacred Games is successful, the fallout from the failed schemes generates a great deal of ill-will towards the Godwins. This sets the tone for Gizel's haphazard conduct during the war, which slowly turns public opinion against him and allows the Prince to stage a successful coup.
In Vampire: The Masquerade – Bloodlines, Smilin' Jack runs one of these. To make a long story short, he replaces the Ancient sleeping inside the Anarkhan Sarcophagus with half a ton of C4 in an attempt to assassinate Prince LaCroix. His method of achieving this is... complicated.
It wasn't even really an ancient, he planted clues to make everyone think it was. One character even points out how the symbols and various historical hints have non-supernatural explanations, but even he gets spooked in the end. There are also plenty of clues, especially playing as a Malkavian, that he is only acting for the real manipulator: Cain, the father of all vampires.
Jack being Jack, it's quite possible he's just stirring up chaos For the Lulz. Even if LaCroix doesn't get blown up in his moment of truimph, he's still got every faction running around in a panic shooting at each other, which he likely finds hilarious.
There's no evidence that Caine had any interest other than as an observer; Los Angeles is still just a small corner of the world. Jack's Plan could have been planting the sarcophagus to answer the question whether La Croix is powerhungry enough to commit diablerie, on a Methuselah no less, and solve the problem in one go. If La Croix hadn't attempted to open the coffin, Jack could be content that while the Camarilla in general and La Croix in particular are nuisances to the anarchy status quo, at least their professed enlightened self-interest isn't a dangerous sham.
Wilhelm from Xenosaga. It wouldn't be a far stretch to say he had prepared a plan, which involves MANY other plans, that spans several millenia. And involves resetting the universe countless times, not unlike a "Groundhog Day" Loop, so that the whole plan may actually span many tens of thousands of years. And that's probably on the lower end of the scale. However, this actually has a good Justification. Wilhelm possesses something called the Compass of Order and Chaos, which allows him to see the flow of the human conscious. He has also been the head of Vector since humanity left Lost Jerusalem (Earth); the kicker is that, if Vector didn't exist, humanity would've been wiped out. Because humanity needed to rely on Vector's goods to survive, it gave Wilhelm de facto control over humanity. Additionally, being the head of Vector, a former member of politics in the world of Xenosaga, a Cardinal of Ormus by the name of Heinlein and the President of Hyams Heavy Industries, Vector's main rival]], Wilhelm has extensive knowledge of what's happening throughout the story. It helps that he's also a chessmaster extraordinaire, probably due to living for several millenia. Given all this, it really isn't a far stretch that his plan worked simply because he had that much control over events.
Wilhelm, and the Four Testaments, are based on the figures of the Demiurge and his Archons from Gnosticism. According to the Gnostics, Sophia, a female aspect of the true god that created the universe, an ancient word for wisdom, and analogous to the human soul, is an Aeon, an emanation of this god and, according to some traditions, she attempted to emanate as the true god did and failed, which caused her to fall out of what is known as the Pleroma, the Fullness or Oneness of the true god which is composed of all the aeons. During this exile, she gives birth to the Demiurge, and being ashamed of this, encloses him within a cloud and gives him a throne. The Demiurge who is sometimes called YHVH, also known as Ialdabaoth, is oblivious of Sophia but apparently knows of the true god's existence, and creates the material world, encasing the power he has from Sophia in matter. To ensure that the souls trapped in matter remain so, he resorts to the eternal recurrence which is, as was mentioned before, a universal time reset button. To go back to the Pleroma, one must learn the Gnosis, the secret knowledge, which was spread by Jesus, who is another Aeon. The seven Archons are the servants of Ialdabaoth and can be compared to the angels and demons of other religions, and represent the seven sins which further distances the human from returning to the Pleroma.
Now Xenosaga makes a lot more sense.
Star Fox Adventures has Andross's plan to revive himself. As explained at the end, he learned of the power of the Krazoa spirits on Dinosaur Planet, as well as Krystal's ability to channel their power, then had her trapped a crystal so that as Fox returned the other spirits, their power would be channeled through Krystal to revive him. So he had to manipulate General Scales into pushing Krystal into the Krazoa spirit's breath's path, which trapped her in a crystal that would channel the spirit's energy, and more importantly somehow know both that Krystal would arrive on the planet and that she had the ability to channel energy... although we have no idea how omniscient evil ape ghosts really are.
As it turns out, almost everything that happened during Starcraft 1 and Brood War was just one epic Gambit Roulette by The Overmind. The Overmind was created by the Xel'Naga to control the zerg swarms, but The Fallen One made sure it was made "with consciousness but without free will" and compelled to destroy the protoss. The Overmind (presumably by virtue of being a mountain-sized brain) had a vision of the future telling it that if it didn't do something to change the course of events then all its zerg children would become food for the menacing hybrids, so - it infested Kerrigan, the most powerful psychic it could find, to give her the potential to control the zerg, then engineered its own death so that the zerg would be released from its control and into Kerrigan's, but not before making its prophecy available for Zeratul to reach, letting Zeratul know that they needed to use the artifacts on Kerrigan so that she'd be freed from the same overriding compulsions that had ruled The Overmind, and also letting them know that they must not kill her. This would then rob the hybrids of their ability to control the zerg and use them to destroy all the other factions and bring about the end of the universe. That's a pretty epic gamble right there.
Overmind develops Kerrigan to replace him. Problem: He's still controlling her.
Solution: Make himself vulnerable. She takes over, she can defy the hybrids. Unfortunately, she's still an evil bitch....and still under the lingering influence of the Fallen One, AKA the xel'naga Amon.
After death, the spirit of the Overmind lives on...and lets Zeratul via the spirit of Tassadar know the plan, and reveals the artifact.
There's a famous video of a Pokémon player using a convoluted method to turn Magikarp into an overpowered sweeper capable of laughing off uber-tier Pokémon. This method relies extremely heavily on the actions of his opponent (opening with Kyogre and not switching, to give Magikarp rain for its Swift Swim speed boost), and some utterly random factors (the duration of the sleep status effect). The video creator mentions this.
In .hack//G.U., Ovan's plan is this. His plan relies entirely on getting Haseo to fight all of the other Avatars, something which could have been rendered impossible by any number of circumstances (What would've happened if an epitaph user simply decided to stop playing the game?). He even lampshades this near the end; when Yata asks him if everything that's happened was all part of his plan, Ovan responds that all of it was pure chance.
Although its mentioned in side materials that if an Epitaph PC is deleted by the user (ie, they quit the) the Avatar will simply find a new host. Furthermore, some of the plan requires no plotting at all. Haseo ended up fighting Endrance and Kuhn of their own volition, with no manipulation required.
In Rainbow Six Vegas, Gabriel Nowak—one of your allies—turns out to be the mastermind behind an assault on the entirety of Las Vegas by an army of mercenary terrorists, in order to distract the authorities and assault a hidden military complex under a dam suspiciously like Hoover Dam, in order to steal prototype weaponry. How does he convince the good-guys he is on their side? He participates in an operation where he is captured by terrorists. In the first game, after being captured, he is rescued by other members of Rainbow. In the middle of the escape, the team gets into a firefight, then leaves him behind, later revealing that he is the bad-guy when he manages to steal a Rainbow helicopter and is either shot down or just crashes it. In Vegas 2, he apparently was released before his "rescue" in order to masquerade as an NSA agent supporting yet another Rainbow team—two members of which were in the team that rescues him—before going back to the casino where he is "held captive", then goes back pretending to be an NSA Agent in order to fool his former mentor and fellow Rainbow member, Bishop and bump off an underling, one of the terrorist leaders. In addition to being a heist plan who's complexity surpases that of something cooked up by Danny Ocean, it requires absolutely everything to go exactly to plan. And all the while, he is simultaneously at huge risk for getting mistaken as an escaped hostage or an NSA Agent and shot by his own mooks, getting blown up in his own capture or dying in the helicopter crash (you can just shoot it down, but if you don't it seems like he did it intentionally). It's also worth mentioning that he also did the attack on Vegas to take two scientists from the WMD project hostage, knowing they would be rescued so they could be sent back to the compound under the dam...to be taken hostage again in the attack on the dam! The odds that he would not get killed trying to do this—never mind getting away with it—are astronomical. But he does...nearly. But hey, it's Vegas, baby!...*sigh* I Need a Freaking Drink after typing that...
The Ace Attorney series subverts this, in the fourth game's finale. The real killer's defense is that since he was in prison, he had no way of getting the victim to lick the poison stamp just as Wright and Brushel started to look into a certain case more deeply, and challenges Apollo to prove he had some convoluted plot to carry this out. Klavier, though, calls his bluff, and points out that he can't prove it - because the whole thing was one big coincidence anyways, and the victim should've died from the stamp years ago, but survived due to his daughter being a Spanner in the Works.
This is rightfully pointed out by Klavier to be justified on Apollo's part however, as the case he presented was simply about what did factly happen and had nothing to do with whether the real killer could have predicted it would happen and that the real killer was twisting what Apollo was presenting.
G-Senjou no Maou gives us one in the form of the devil, Maou. Every one of his plans require that everyone acts exactly how he knows them to act. A single misstep would bring down the entire scheme. This culminates in his last giant trap: creating a blockade and making it a hell on earth all to get his father out of prison. Despite this, he still manages to weasel himself out of sticky situations by playing Gambit Speed Chess with the protagonists.
At the end of the "Professor Madblood and the Doppelganger Gambit" arc in Narbonic, Helen claims the whole chaotic sequence of events was her plan. As the series goes on, it's hinted that she plans a great deal more than typically believed - Artie at one point suspects everything about him was engineered so that he could save Helen's life at one crucial, impossible-to-predict moment. Helen is a megalomaniac (albeit an extremely cute one), so some or all of this could be from her own self-aggrandizing. Indeed, in another comic in "Doppelganger Gambit", she explicitly claims a fondness for the Indy Ploy approach: "It's times like these I almost question my usual strategy of doing whatever dumb thing pops into my head." It's possible she masterplans things at a subconcious level which then tells her concious mind to do seemingly random things - in another "Doppelganger Gambit" strip Artie says her mind operates on a different level from his, making him a cog in her machine (and he's a genius himself) and Dave points out she also giggles while trying to set herself on fire. Artie then sums it up as "That's mad genius for you. It's a sort of brain potluck."
And then there's the system administrator who always has a backup plan: "You see, you never want to fake a major organ failure to hijack an ambulance to a concert where you falsify medical documents and sneak into the trunk of your friend's car in a Spider-Man costume unless you're PREPARED for the eventuality that someone might get hurt if the car slams into a deer."
Near the end of It's Walky!, a We Can Rule Together speech by Penny and (presumably correct) extrapolation by Alan reveal that Dargon founded SEMME in the seventies specifically to gather abductees and Martian technology, the former to be given just this We Can Rule Together speech, the latter in anticipation of SEMME's eventual disbandment and the resultant scattering of Martian technology to military centers around the world. The latter event, by the way, was thirty years later and contingent on an HA caper they couldn't possibly have predicted, itself following his death and resurrection. If either Dargon or Penny had lived long enough, we might have seen what, exactly, they planned to do with the world's military infrastructure destroyed.
The mindgames the Travorias play on one another throughout the series would count as Gambit Roulettes... except that they nearly always fail.
Averted in Girl Genius, where a character is able to work out that a conspiracy against The Empire won't be coming after its incapacitated ruler because his being crippled couldn't possibly have been planned by them.
A really stupid example, or even possibly a parody of this trope is Bob and George in it's entirety. The whole series just being a gigantic set up for their mom to make George stop being a too much of a pussy to fight, and kill Bob if he got out of hand. And the last few years being a bet between the Helmeted Author and Author to see if George would shoot Bob or not based on Gambit Roulettes between Bob and George themselves where George merged with the Shadowy Author and Bob was merged with the Helmeted Author, and manipulated certain aspects of their final meeting, that were in truth being manipulated by the author characters (even when the author characters WEREN'T using their "author powers" to alter fate and such, thus why it was bet.)
Homestuck: Doc Scratch and Lord English's master plan takes this to truly absurd extremes. Being omniscient time travellers in a multiverse where You Can't Fight Fate probably helps, though.
Freefall: Sam Starfall's favorite master plan is to simply imply he HAS a master plan, then let his victims make up the details....
In El Goonish Shive, Magus needs Ellen to zap Elliot with her Gender Bender ray. His plans range from the "slightly implausible" (he orchestrated the entire sequence of events that led up to Ellen's "birth") to the completely ridiculous (planning to amplify Ellen's desire for pepper in order to make her sneeze and accidentally zap Elliot).
It helps that he really doesn't have much of a choice. The only way he is able to affect the mortal plane is to slightly amplify emotions that people are already feeling. Not a lot you can do with that without having to get creative.
Chaos has more of these (and in fact was involved in some of Magus'). Justified in her case, since she's practically omniscient and bored. She wants things as random as possible because its more fun that way.
Chaos actually is more of a subversion. As mentioned above, her plans are largely reliant on coincidences and chance because she's deliberately ensuring that they have a chance to fail. If her plans succeed, it's not at all because she was just that good that predicting what seemed impossible to predict; she really did just get lucky.
Tarquin: A Gate, an abomination, a ritual, and you don't even have the ritual but a friend of a friend does? We were never in any position to realistically pull that off.
Played with in The Defrosters. In episode 9, Pixel Girl implies that she is working on a plan to stop Pixel Boy from playing World of Warcraft. She and James even mention TV Tropes as they debate the differences between a Gambit Roulette and a Xanatos Gambit.
Obscure example, but in GanXingba'sAvatar: TAS, a comment is made mocking Zhao's- and Light's (Death Note) -ability to have plans that rely on perfect timing and actions they shouldn't be able to see coming.
Zhao: (Speaking of Zhao's denial of use of the Yu Yan Archers) Well darn, it looks like I'm out of luck barring a sudden promotion, like the one arriving right now.
Colonel Shinu: What!? There's no way you could have timed this down to the second!
Zhao: Of course I can. I went to the Light Yagami School of Strategy. I can practically predict the future.
The purple and pink unicorns of the Charlie the Unicorn fame went through some pretty crazy convoluted schemes just to steal from Charlie. In Charlie the Unicorn 2, the fact that they get sucked into a strange vortex and find an amulet to return to the alleged Bo-nana King, have a somewhat Gratuitous Spanish conversation to a giant block Z, ride a giant sneaker, arrive at the Temple of the Bananas, then perform in a sing-a-long accompanied with a chorus just to discover that Charlie was the Banana King all along is a completely outrageous chain of events seeing how this was just used to distract Charlie long enough to rob him of his valuables. Then again, the pink and purple unicorns could just be using Obfuscating Stupidity... or are they?.
This webpage lets you create your own plots which can easily become Gambit Roulettes, for example: Your unstoppable plot: hone your psychic powers, easily allowing you to summon a powerful spirit, easily allowing you to kidnap a popular singer for a huge ransom, easily allowing you to force your minions to make a super battleship, so you can create an evil temple, so you can acquire an unstoppable mega-tank, which allows you to kidnap the prime minister so you can replace him/her with an imposter, so you can force your minions to make a high-tech submarine, easily allowing you to summon a demonic force, which sets the stage to seize control of a legion of golems, which sets the stage to build a clone machine, which sets the stage to pillage the hemisphere which will slake your dark need for power!
In an article on creating villains, the sample villain, the Fire King, infiltrates an elven noble's household, takes over the household, becomes the king's trusted advisor, starts a war, eliminates elements on both sides to prevent peace. The point of all this is to wipe out all the elves so that he can perform a ritual to absorb all the magical energy in the world, and conquer hell.
Futurama parodies this in its (at the time) final episode - the Robot Devil brags that his "ridiculously circuitous plan is one-quarter complete".
1) Trick Bender into accepting an air horn, 2) Hope that he deafens Leela with it, 3) Convince Leela to sign a deal with the devil with him for her hand (with a twist) 4) Use the threat of this to get his hands back from Fry. All just to get him back where he was at the start of the episode.
Even more, he somehow managed to get Bender to trade his hind plate for the air horn so as to have the perfect comeback for his Catch Phrase!
Parodied in The Aqua Teen Hunger Force Colon Movie Film For Theatres; antagonist Walter Mellon reveals that he created the Aqua Teens, Dr. Weird, and the Insanoflex, and kidnapped Neil Peart in the meanwhile, so that Frylock and Dr. Weird would ultimately become enemies and fight to their deaths, whereupon he would inherit their houses and use the land to build a gym. Frylock then informs Mellon that they all rent, and he couldn't have built gyms in residential areas anyway. Then the movie ended.
The "Winners Special" was actually an overcomplicated plot for the Total Drama Island powers that be (both in and out of universe) to use for the purpose of making the second season, in a Crowning Moment of Awesome for the whole series.
In the infamous South Park episode "Scott Tenorman Must Die", Cartman devises an extremely intricate plan to exact revenge on Scott Tenorman for cheating him out of $16.12. The plan relies on several red herrings and on Stan and Kyle's betrayal and culminates with Scott eating chili that is made of his own parents' ground-up remains and subsequently crying in front of his favorite band, Radiohead, who then mock him for being a "crybaby".
The Pixies' "thirty-seven year plan to take over Fairy World" in the Musical Episode of The Fairly Oddparents is so hilariously convoluted it defies description but let's try anyway...They are driving and comment that they need a baby to their next plan of 37 years, close by a train of the circus is approaching a broken bridge, two clowns see this and use the cannon to launch their son, Flappy Bob, to safety. He lands near HP and Sanderson, who take and raise him, in the right way so that he could take the plans to the Learn-a-Torium and make it, then the two pixies use their magic to help the children destroy the city, so that Flappy Bob could convince the adults to put all their children in the Camp Learn-a-Torium, so that HP and Sanderson could manipulate Timmy into wishing a world dominated by kids, so that the kids would not need fairies any more, so that the pixies could grant a wish to Flappy Bob with a loophole to control the fairy world... After it ultimately fails (for apparently not the first time), they wonder if they should try a six-week plan this time
Homer Simpson's mother plotted to destroy a missile silo owned by Mr. Burns. This plot relied entirely on her dying at exactly the right time, Homer finding her video will on the right day, everyone using what they left her in precisely the right way (and Lisa stealing her crystal earrings), and Mr. Burns leaving a cinder block and chain near the cell Homer was trapped in.
Also seen in the episode "Eternal Moonshine of the Simpson Mind," in which Homer pulls a Gambit Roulette on himself. Upon learning that Marge was planning a surprise party for him, he goes to Moe's and orders an amnesia-inducing drink. Before he downs it, he predicts that he will wake up to find his family missing, remember snippets that imply that he hit Marge, go to Dr. Frink for memory recovery, only remember enough to conclude that Marge was having an affair with Duffman, and then throw himself off a bridge at the exact moment in which the party ship was underneath and at the exact place in which he lands on the ship's moonbounce.
Sideshow Bob in "Funeral For A Fiend" does this. He builds a fake restaurant and broadcasts commercials for its grand opening solely for luring the Simpsons (and no one else) there. Then he purposely misquotes Shakespeare in order for Lisa to correct him so he could pretend to look it up on Wikipedia in order for the laptop to overheat and explode, leading to his capture. Then at his trial he relies on the chance that Bart will snatch away his nitroglycerine so he could fake a heart attack and allow his father to inject him with a drug that simulates death. Then he manages to undergo a funeral without an autopsy or any embalming process, and gets his family members to make Bart feel guilty enough about his death in order for Bart to enter the funeral home when no one else is around, and make peace with his "corpse" before it is cremated.
Subverted in one episode of Teamo Supremo: the main characters are stumped as to how the seemingly unrelated robberies committed by "Mr. Vague" contribute to his ingenious plan.
Mr. Vague: You fools! I have no plan! I just like to act evil and steal stuff!
An example (but certainly not the only one) where this is used for comedic effect: In the Looney Tunes cartoon "Fool Coverage", Daffy Duck (after much persuasion) sells Porky Pig an insurance policy that will pay him a million dollars if he gets a black eye. However, after Porky signs, he's informed that the policy has some fine print - the payout can only occur if the policyholder receives a black eye as a result of a stampede of wild elephants running through his house between 3:55 and 4 PM on the Fourth of July during a hailstorm. When this improbable sequence of events actually occurs (right after Porky signs up), Daffy makes up an additional clause on the spot that requires that a baby zebra be part of the stampede - and guess what runs through the house immediately thereafter.
In Justice League, after Brainiac has been revealed to have been living in Lex Luthor for years, he states that he's been manipulating Lex Luthor into manipulating everything else so that he, and not Lex, could implant his mind into a duplicate of Amazo (or rather, a "more suitable body"). Really, he just installed a backup of his program into Lex and rolled with whatever came his way. This turns into Gambit Speed Chess when Lex takes advantage of being merged with an immortal robot in order to try and become a techno-organic god.
There is never a full outline of what the plan was, or who was planning what, but the events of the third season finale and fourth season premiere of The Venture Bros. required an absurd amount of chance and relied on a Shocking Swerve for resolution. Molotov Cocktease and Hunter Gathers manipulate events so that Brock Samson kills OSI's top three assassins in a fairly straightforward plan to ensure the supremacy of their Blackhearts organization. Although not specifically stated, they may have also been responsible for Brock's car attempting to kill him, which itself relied on pure luck on several levels. It gets completely ridiculous once it turns out that the whole storyline going back to Hunter's sex change operation was an elaborate plan by Hunter Gathers, who is actually The Mole for the Blackhearts who reversed his sex change, in order to convince Brock to join Hunter's SPHINX organization. The plan is either the most convoluted and implausible plan of all time or an unbelievably well executed game of Gambit Speed Chess. It gets even crazier in the season 4 finale, when it's revealed that EVERYTHING outlined above was in fact orchestrated by General Treister to expose and eliminate Doe and Cardholder, who were actually moles for the Guild of Calamitous Intent; then install Hunter as the new head of the OSI. In other words, Treister's roulette depended on somebody else perfectly orchestrating and executing their own roulette, which quite possibly makes him the true master of this trope. Meanwhile Mol infiltrates SPHINX as "the rookie" (unsure if she's always been or just sometime before the season finale) in order to (possibly) place her Blackhearts as prostitutes that Dr. Venture orders for Hank and Dean's home school prom in order to distract Brock while she gets away with her SPHINX captured and doped up love, Monstroso (who may be a decoy or maybe the Blackhearts thing was a lie.
The episode "Metamorphosis." Xanatos plans to fake the death of his colleague Dr. Sevarius and get a mutated Derek Maza on his side requires that Derek jump in front of him to take the dart with the serum, the Gargoyles attack his lab at exactly the right moment before Derek is about to receive a "cure," for the cure to be destroyed in the struggle, and then for Sevarius to get knocked into his aquarium during the ensuing fight and somehow not receive a fatal charge from his two electric eels. Given that Sevarius was in on it and that Xanatos is otherwise a competent chessmaster they probably had other ways of making it work.
All indications are that the Illuminati was preparing for one of these in the Gargoyles comic, considering its operatives specifically told Xanatos that they wanted the Gargoyles to be accepted in society, told the leader of the Quarrymen that the organization wanted them destroyed, and told Matt Bluestone that they preferred the current status quo of uneasy distancing. Too bad it was Cut Short.
In the fifth season of Teenage Mutant Ninja Turtles (2003), it was revealed that every event in the series until then — the Shredder's rise to power, Hamato Yoshi's death, the creation of the turtles, etc. — had all been allowed to occur as part of a plan to kill the demon Shredder.
My Little Pony: Friendship Is Magic: When Princess Celestia appears at the end of the two-part pilot for the first season, she announces she'd planned for everything that happened. How she knew she'd run into just the right group of new friends and they'd each get a chance to prove themselves along the way as fit to wield the Elements, and that Twilight would recognize all of this in time for it to mean anything is anyone's guess. Celestia is certainly smart, and the true extent of her abilities is unknown, but predicting all that would have taken omniscience, thus making the plan this trope either way.
Deconstructed in Young Justice. Nightwing starts a complicated scheme to infiltrate The Light by sending in Aqualad and Artemis as moles. This plan will require the moles to commit genuinely villainous acts to maintain their cover, and most of Nightwing's team must be kept in the dark about the plan, meaning that they will be unaware that two of their greatest enemies are secretly allies. These two facets of The Plan eventually cause the situation to spin wildly out of Nightwing's control, and Kid Flash calls him out for putting his allies at risk with a plan that had too many variables.
Canaletto in Oban Star Racers Arranged for the death of the mother of the right girl i.e. Eva, so that she would be emotionally scarred and chase after her father off-world. Then he injured the main pilot to make her the only remaining pilot who would then would have to win a VERY competitive race, and relied on her prior emotional scarring so that she would reject the grand prize at the end and he could claim it for himself. Ironically, the only point at which he hits a bumb is not when any one of these chance events fails but when Sul changed the flow of destiny. The only thing that helps this go down easier is that he's implied to be able to see the future and manipulate certain events.
According to some historians, Adolf Hitler. He is supposed to have had an exact 'blueprint for aggression' before coming to power. More recent interpretations tend to portray Hitler as an often brilliant opportunist instead, who seized opportunities others provided and got by with Indy Ploys. It didn't end so well. A third common theory is that he was trying to do this trope and did so badly, which is why leaders on both sides saw him as a threat to his own plans.
Admiral Yamamoto's plan for the Battle of Midway was supposed to be a Gambit Roulette that involved splitting his forces into seven different groups across the entire Pacific to defeat the American carrier fleet. A simpler idea like "Put all my ships in one fleet, sail in to attack Midway. The Americans don't have enough ships to stop such a fleet, so if they do force a battle, I destroy their fleet. If they don't, I conquer Midway," would have been a pretty good Xanatos Gambit. Yamamoto's roulette plan ended in a spectacular failure when American codebreakers figured out key details of his plan. Because his ships were split up into many groups, they couldn't support each other, leading to many ships not even seeing action; this was especially damaging since the escort cruisers with Yamamoto's scout planes were all assigned to a battleship taskforce which was not in position to scout for the carrier taskforce. Some of the more ridiculous elements, like the "diversionary" attack on Alaska (which contradicted the entire point of the operation and served only to weaken the main force), were imposed by Yamamoto's superiors.
A certain screenwriter, presumably just to get attention, claimed that a particularly ludicrous Roulette was performed against him by 20th Century Fox. In summary, he alleged that a script of his was stolen by Fox, who then gave it to Alan Moore to be turned into a comic (The League of Extraordinary Gentlemen) specifically so it could be filmed without people guessing its true source. The resulting Frivolous Lawsuit treated Moore, who had done nothing wrong, so badly that he chose to cut all ties with the film industry.
There's an Urban Legend that on his death Walt Disney left a series of films dictating, in detail, exactly how every aspect of the Walt Disney Company was to progress for the next twenty years — films directly addressed to the various members of the staff, as if he were still in conference with all of them. (As Snopes points out, all one need do to demonstrate the fallacy of this is to look at the company's record in the 1970s: dead Walt could have done better than The Computer Wore Tennis Shoes and Now You See Him, Now You Don't.)
In the 1793 Siege of Toulon, while still a captain, he deliberately disobeyed his commanding officer's orders. Luckily, it was this disobedience that won the battle.
While a general in Italy, he once put himself on the front line of the battlefield at the Arcole Bridge. The French lost the battle and Napoleon barely escaped with his life, but the move won him huge respect and loyalty from his soldiers.
Any treasures captured on campaign were supposed to be either left alone or sent to the French government in Paris. Instead, Napoleon took a risk and disobeyed this rule, allowing his soldiers to keep their loot. This gave them a huge incentive to win battles and firmly won them to his cause.
In 1799 Napoleon was invited to be part of a coup attempt. This coup was intended to be purely parliamentary with no military involvement - Napoleon's inclusion was merely intended to win the army round. When the initial attempt looked like failing, Napoleon just marched in with his soldiers and not only ensured the coup's success, but shifted himself from a minor plotter to the lead figure.
In 1815, Napoleon escaped from his first exile on the island of Elba with the help of a few soldiers. When he met the first French troops sent to arrest him, he simply walked forward and dared them to shoot him. Not one did, and they (along with the rest of the French army) went over to Napoleon's side.
Conspiracy Theorists tend to use this trope in regards to their target to explain and justify their theories.