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Some characters have an amazing gift not only for making The Plan but for revising it whenever new circumstances arise. Even a Gambit Pileup does not prevent this character from working around it to success.
The Chessmaster may be skilled at pulling off a Xanatos Gambit. When The Chessmaster is aware of the threat of being Out-Gambitted or of a Gambit Pileup and he also happens to be an Opportunistic Bastard, more often than not he will be playing Xanatos Speed Chess. While the plots can be as complex as anything The Chessmaster lays out, they tend to function differently. The plotting character tends to be more The Trickster. We usually follow, if not the plotter himself, then characters near him, so we can see his continual and brilliant improvisations. This is likely to be pulled off by heroes rather than villains because the plot is always teetering at the edge of failure, making its success more dramatic. If it is used by both, then the drama is squared.
Xanatos Speed Chess players build in the need for such flexibility in advance because of the old adage that 'no plan survives contact with the enemy'. Closely related to the Indy Ploy, which has simpler goals like "escape" or sometimes "hope for the best," but in this case, the plan is still in operation, just modified to fit new situations. The distinction here is that Xanatos Speed Chess involves changing an existing plan quickly, while an Indy Ploy involves there being no plan whatsoever.
Contrast the Gambit Roulette, where the planner incorporates events that he would have no way of foreseeing into his plans - they rely on chance as much as on brilliance. Contrast the Clock King, a consummate planner who is rarely good at this. If prophecy, time travel, or being able to see the future are involved, may escalate to Scry vs. Scry.
Not all people who attempt Xanatos Speed Chess can pull it off. This is why Xanatos Speed Chess is one of the defining marks of the Magnificent Bastard.
Light Yagami, when things first started to get out of hand, but it didn't last. Misa forced more Speed Chess on him than anyone else; sometimes by being smarter than he expected but usually by being impulsive. Before long Light could flawlessly predict even her actions.
L was also good at Speed Chess, but not as good as Light. A major unexpected twist once left L at a loss for weeks, although this was simply due to not knowing all the details of Kira's power.
Near and Mello are also masters of this trope because they were raised in the same way and for the same purpose as L. The entire series can be summed up as Xanatos Speed Chess on crack.
The supplementary "How to Read" volume includes a list describing every trick used by anyone and rating them by level.
Lelouch Lamperouge from Code Geass does this out of necessity, because the writers love screwing all of his plans by unexpected events that no sane person would ever consider. He turned the tables when pitted against the Britannian military and their Chinese allies right after losing his best fighter and a large part of his army. Lampshaded with the fact that he can play real chessvery well.
According to Gundam 00's World Report Book, Veda seems to operate in this manner, allowing for deviations to the original plan that are caused by unknown factors, if it manages to be in line with the same end result.
Well, since Veda is some sort of quantum supercomputer, Speed Chess is pretty much its normal speed.
Bleach: Aizen and Urahara have been opposing each other for a century. As they're both chessmasters, their entire battle has consisted of elaborately designed plans and constant revision of those plans as first one then the other gains the upper hand. From Aizen framing Urahara for catching him red-handed, to Urahara using his exile to set up an elaborate protection of the Hougyoku. From Aizen losing the element of surprise so preparing for war in one month instead of four, to Urahara anticipating exactly that and setting up a series of secret kidou traps to ensure Aizen is depowered by Ichigo in the end... most of the characters freely admit they can't keep up and eventually even Aizen is forced to admit he can't keep up with Urahara's intelligence.
Detective Conan has a fair amount of it, especially whenever Conan's directly up against the Black Ops and needs to not get killed.
It's not just Conan who pulls this off. The other high-school detectives do this regularly. And, of course, the absolute winner of this trope is Kaitou Kid - who is constantly changing his heist plans (which are, more often than not, successful).
In A Certain Magical Index, Aleister Crowley constantly uses this so that whenever something unexpected happens, he weaves it in to complete his plans even faster.
But even Crowley cannot keep up with everything: Shiage Hamazura defeating Mugino caused a domino reaction that completely threw his plans all out of whack, and he's now desperately attempting to get everything back under his control.
Marshall D. Teach of One Piece, also known as "Blackbeard", appears to have a fully-formed plan in mind with which to reach the top of the pirate world. Despite a reckless streak, he has shown himself to be highly adept at taking advantage of unexpected opportunities to progress this plan and acting quickly when something appears to threaten it.
Donquixote Doflamingo as well. While well established early on that he is a man who tries to remain several steps ahead of his foes, Doflamingo's ability to tweak plans and make new ones on the fly is best evidenced when he managed to sneak out of Trafalgar Law's ultimatum. When Luffy and Law arrive in Doflamingo's homeland of Dressrosa simultaneously, Doflamingo continues to compensate for unexpected setbacks, such as the presence of a Marine admiral on the island, Sabo taking Luffy's place in the Colosseum, a full-scale invasion by the Tontattas, and the liberation of the Toys, using psychological judo to sway people to his side or render certain crucial tasks impossible. This includes taking the hatred the entire populace soon has of Doflamingo and redirecting it towards all of Doflamingo's enemies.
It is difficult to know how much of Akagi's playing is this and how much he actually plans out. In any case, he's a Magnificent Bastard.
Keima Katsuragi from The World God Only Knows has a knack for this, frequently adapting his plans in response to events, no matter how unexpected.
Tobi of Naruto ends up sliding into this category by default. His attempts at gambits and roulette have a tendency to fall apart, allowing him to only make small amounts of progress with each ploy.
His mentor, Madara, plays the same game. When reunited after two decades, they subtly maneuvered against one another until it was time to seal the Juubi, at which point both began openly moving against the other to come out on top.
In a filler episode, Shikamaru plays this straight against the Villain of the Week. Even though he already had most of his plans laid out beforehand, the reason why it goes here is because there was a particular hitch in the plan but he manages to pull it off by making a small gamble.
Desert Punk the main charachter modus operandi is trickery and traps, as seen in the hostage rescue episode he forms a complex number of backup plans, flips between them on the fly and always ends up with his opponent caught in one of his traps even if not in the way originally planned. Beaten at his own game when after turning to the dark and on the cusp of victory his apprentice maneouvers him into her own pre-planned trap.
Why Hanbe from Sengoku Basara is considered a genius: he has a plan for every possible outcome. Demonstrated when he brings out a series of maps of the country, and they all depict different potential strategies by other characters, including ones based on the assumption that their allies might betray them (which they do).
In Zeta Gundam, Enigmatic Minion and eventual Big Bad Paptimus Scirocco is the undisputed master of this. He's got his own designs on power pretty much from day one, but for most of the series he's content to sit back and let his enemies destroy themselves, telling characters he's "only a witness to history". That facade goes out the window the moment he knocks off Jamitov, and by the end of the series he's gone from a minor official from Jupiter to the unquestioned leader of the Titans.
Super Buu of Dragon Ball Z is very good at doing this, despite being a mere thug in personality. He noticed Gohan's growing power, so he fought against Super Saiyan 3 Gotenks and tested the limits of his strength and his weaknesses (e.g. fusion limit). After briefly fighting Gohan and finding himself overwhelmed, he goes through an intentional Super Power Meltdown, knowing he will regenerate and buys time (and getting Goten and Trunks to recuperate, to fuse again). When he returns he goads Goten and Trunks into fusing again at full power and absorbs Gotenks and Piccolo into his being, deciding 30 minutes is more than enough to handle Gohan (he was right). Goku arrives and the fusion breaks down. Goku says Gohan alone is strong enough to defeat Buu, but then Buu reveals that he planned for this eventuality as well, and had a piece of himself ready to absorb Gohan the whole time, who he goaded into standing still until it was too late. Interestingly, the only character this didn't work on is Vegito, who was too strong, toowily, and had plans of his own, as he later found out...
In the final battle of Jojo's Bizarre Adventure Part II: Battle Tendency Joseph Jostar defeats Kars by defending himself from an attack with the Stone of Aja, which he wasn't even aware he had, and having the resulting explosion jam debris into Kars's arm and launch him into space. Joseph even admits that he didn't plan for that to happen.
While claiming to be the luckiest man alive, Kira Yoshikage's continued survival and anonymity owe more to using every little advantage that presents itself to its absolute maximum, generally through using his powers to construct a series of ingenious traps, tailored to his opponents and situations.
This is Miho Nishizumi's main strength in Girls und Panzer. While all of the tank commanders are decently good strategists, Miho has a knack for split-second opportunistic decisions and coming up with unexpected plans on the fly that take her enemies by surprise.
ReformedThe Flash villain Trickster, being blackmailed by another villain to steal a relic from a museum, set up an elaborate plot to convince that villain to leave him alone. When Impulse confronted him with the fact that a museum employee was being unjustly blamed for the theft, Trickster adapted the plan to ensure that the employee appeared a hero, saving his job by getting him to catch the crooks, even though the relic was lost. (Trickster took the opportunity to return it to the church he had stolen it from. Told you he had reformed.)
Sleeper (along with its prequel Point Blank) by Ed Brubaker and Sean Phillips is pretty much built out of this trope, with Tao and Lynch using ever more convoluted plans to entrap each other and manipulate Double Agent Holden (who has plans of his own).
Marvel's Loki and his spiritual twin Dr. Doom are both masters of this trope and employ it regularly. Loki uses it more due to his preference for indirect manipulation and lies.
In the Jackie Chan Adventures fic Queen Of All Oni, when Jade's Batman Gambit to get a mask on Jackie and get him to use it goes wrong when the Sumo-khan mask ends up on Captain Black like in canon, she quickly modifies the plot and manages to lure him away, and get him to use the mask by throwing him off a building, and the plan goes ahead.
Precia is a master of this in Game Theory. Although her carefully laid plans are severely disrupted by Nanoha's presence and the dimensional quake that attracted the attention of the TSAB, she manages to adjust smoothly, and acquires everything she needs to reach Alhazred. And it turns out that she had actually come up with an entirely different plan by incorporating the new elements, to revive Alicia and fake her own death, which she implemented successfully without telling anyone.
Professor Moriarty is The Chessmaster in the season 1 finale for Children of Time and changes his plans according to every shift in circumstances to meet his goals, but Beth Lestrade is the player with the most moves throughout the three episodes. She gambits with Holmes, the entire Time/Space Continuum, and Moriarty and Moran, moving from half-formed plans to well-plotted schemes to going in blind. When something goes wrong, she might blank out for a few minutes but she will adjust accordingly. Better still, her gambits win more than anyone else's...
The Dark Lords Of Nerima: Tanizaki Kazuo is established as being an accomplished chessmaster, but he's not above playing an unexpected card, and is able to think fast to turn sudden events to his advantage.
In "The Universe Doesn't Cheat" Lieutenant Commander Kanril Eleya responds to the Kobayashi Maru computer trying to blunt one tactic by switching to another one. Computer tries to jam her transmissions so she can't negotiate with the Klingons? She switches to plain old radio. Klingons brush off her attempt to negotiate? She uses a preprogrammed macro to fire the phasers disrupt the Maru's shields and beam the crew off, while simultaneously going to warp straight through an enemy battlecruiser. Klingons come about impossibly fast? She pulls a Crazy Ivan. It gets to the point where the computer apparently says "screw it" and quite blatantly spawns a battleship directly in her path to take her down.
Films — Animated
Initially, the plan of the Dazzlings in My Little Pony Equestria Girls: Rainbow Rocks is simply to show up at Canterlot High School to find the source of the magic they saw. They continuously adapt to their surroundings by brainwashing the principal and vice-principal, spreading a Hate Plague through the school, and even bumping the Rainbooms forward in the Battle of the Bands, just so they could manipulate Trixie into trapping the Rainbooms beneath the stage.
Details from the beginning of the The Lion King strongly imply that Scar's initial plan was to have Simba killed only, so he'd remove competition for the throne. It wasn't until the hyenas failure to kill Simba due to Mufasa's interference, as well as Banzai's sardonic question of whether Scar should kill Mufasa to get the throne that Scar even considered the idea of killing Mufasa in the first place.
Even more impressively, when Simba makes his big return, after getting over his initial shock at Simba being alive, Scar is able to improvise and nearly win again by killing Simba.
Over the course of Tangled Gothel's plan to keep Rapunzel's hair for herself quickly evolves from manipulating Rapunzel into staying in the tower, to framing Flynn for abandoning Rapunzel while staging a fake rescue, to outright chaining Rapunzel up and murdering Flynn.
Mulan: Shan Yu can still improvise and nearly win after the wipeout of most of his army.
In Frozen, pulled off expertly by the villain, whose identity and plans remain obscured until just before the climax. His original plan to marry the young queen Elsa couldn't hold up against a sudden magical catastrophe so he quickly adapted it to usurping the throne and regicide instead. Even before the catastrophe, he swaps his marriage targets when Anna appears to be a perfect candidate for his trickery.
In The Bourne Ultimatum (he gets better at this with each film), he has several Xanatos Speed Chess triumphs, one of the more Oh Shnap of which culminates in:
If you were in your office, we would be having this conversation face-to-face.
In the ironically-named A Perfect Murder, Michael Douglas' relatively simple plot to arrange for his cheating wife to be killed by her lover is quickly derailed when the wife kills her attacker, only to have it be revealed to not be the lover after all. The rest of the film consists of his ever-more-complex game of Xanatos Speed Chess against the wife, her lover, and the cops, as he attempts to bump her off, tie up a proliferating number of loose ends, and keep the police in the dark about it all.
This was a remake of Dial M for Murder, in which the husband was so good that his hastily-improvised new plot was arguably a better way of getting rid of his wife than the murder.
Daniel Ocean's crew in the Oceans Eleven series are surprisingly adept at this.
Naturally, they continue this in Ocean's Thirteen, particularly with The Cartwheel by Basher. They attempt this in Ocean's Twelve as well, but they fail. But it's okay because they had already won before they started.
The franchise is extremely fond of speed chess, as the characters learn quickly that no one in the cast can be trusted. A trickster's plans are often derailed by some Spanner in the Works, forcing them into countless on-the-fly renegotiations.
Cutler Beckett, though, is arrogant enough that he thinks he doesn't need to do this, relying solely on his schemes as he originally conceived them. He's wrong, and the aggregate chess games of Jack Sparrow, Barbossa, Calypso, Will, and even to an extent Davy Jones all come around and bite him hard.
Jack, in particular, is an absolute master of the game. The reason everyone thinks he's mad? He's playing multiple games at double speed. He looks crazy because no one else can keep up.
The Brethren Court meeting is a game of Gambit Speed Chess between Barbossa and Jack using whatever resources they have, culminating in the climax of the film.
If anyone might be considered a Xanatos Speed Chess grand master, it would be James Bond. None of his plans go off without a ton of snags, but he's always able to come out on top in the end, using every means at his disposal and in general having a feel for what his adversaries and allies might end up doing at any given moment.
In Licence to Kill, Bond's assassination attempt against Franz Sanchez fails, however he gets Sanchez to think that one of his associates arranged the attempt, and Sanchez has him brutally executed, getting Bond a place inside his circle.
Goldfinger actually outplays Bond through most of the film. At least once he does it unknowingly since Bond secretly placed a note with a tracking device on someone Goldfinger killed for other reasons. In fact, Bond only succeeded due to to a Heel-Face Turn by Pussy Galore and he didn't even know she'd turned.
Walter Burns in His Girl Friday. He's ALWAYS got a plan. Really, the only thing keeping him from being a (relatively nice) Magnificent Bastard is that he's so easy to see through.
Emperor Palpatine from Star Wars ... so much that people now assume every single aspect of the series is his doing, and all went as planned (except dying). They forget that most of The Phantom Menace has him quickly changing his game plan, either because he overestimated the heroes or because X-factors kept popping up. He ends up getting what he wanted, but Word of God says there were enough setbacks that he had to wait a decade to get the ball rolling on the next big step in his plan, including the loss of an apprentice. That he was able to take one of those X-factors and befriend him early so he could turn him into a replacement apprentice is testament to his speed-chess abilities.
It's eventually revealed that he did anticipate and plan for Maul's death (he's a Sith Lord, duh). However, the Jedi being sent to deal with the Trade Federation, as well as Amidala's arrival on Naboo, were not part of his plans according to supplementary materials (Valorum consulted the Jedi without informing the Senate first, and he did expect Maul to succeed in retrieving Amidala). In fact, his original plan was that he and his agents would create turmoil, draw the occupation out for months or even years, and cause enough pressure to cow the Senate into electing him. Almost everything after Amidala turned up on Coruscant was improvisation and moving up the timetable considerably.
Plus, he and Banking Clan big shot Hego Damask (alias Darth Plagueis) meant for Amidala to be a martyr. And there was a nine-year-old hydrospanner in the works as a side effect of Plagueis' experiments.
Fargo: Jerry Lundegaard finds himself in a game of this, and is not very good at it, but never gives up.
Inception: One can assume that the core extraction team of Cobb, Arthur, and Eames are exceptionally good at this. Going into a mark's subconscious has to be a tricky prospect no matter how much is planned out ahead of time.
Hoffman in Saw VI and 3D proves to be a master at this. Every time one of his plans disintegrates, he improvises a new, better, plan within roughly 10 seconds. It's fun to watch.
Kimble vs. Gerard in The Fugitive, particularly towards the end, as Kimble goes from trying to evade Gerard to realizing that he needs him on his side. So when Kimble finally finds the man who killed his wife, he deliberately lets Gerard trace him there (escaping before he arrives, of course), knowing that Gerard (who has already begun to suspect that Kimble is innocent) will start putting things together. To top it off, both men soon realize the extent of the conspiracy surrounding Kimble and how it was masterminded by his so-called friend Dr. Nichols, leading Gerard to race to find Kimble not to arrest him, but to protect him from the police and prevent him from committing murder for real in order to avenge his wife.
The main character in The Next Three Days managed to pull the strings of enough Batman Gambits in order to break his wife out of prison and escape the American authorities. However, there were many factors which throws off his plans off, either unforeseen circumstances or miscalculations on his part. This includes: him being cheated out of his money, his first attempt to break into the prison using a "bump key" failing spectacularly, his wife is being moved to another prison in 3 days, the police managed to figure out part of his plan beforehand, the party he left his son on was at the zoo, and his wife refusing to leave without their son. Despite all that, he still managed to pull off his plan by lots and lots of improvisation.
Porter from Payback continually sees complications come up in his simple plan to track down his backstabbing ex-partner and get back the share of his money from the last job they pulled together. He adapts to circumstances and finds new ways to persevere, probably best exemplified when his plan to use the son of the head of The Syndicate (Porter had kidnapped the son) goes to hell when the Syndicate goons grab him after a shootout and start trying to torture the information out of him. In the midst of the torture session, Porter comes up with a new plan, and leads the Syndicate bosses into a booby trapped room.
CRS in The Game (1997). Although at times it seems that the success of the company's gambit depends upon Nicholas Van Orton doing exactly the thing he does, upon further reflection, it seems very likely that no matter what move Nicholas makes, they've planned for it and can adjust their "game."
Feingold: Thank God you jumped, because if you didn't, I was supposed to throw you off.
Various Illuminati in Duumvirate are so good at this it's impossible to know whether or not they planned everything out in advance.
In Kushiels Legacy, by Jacqueline Carey, most of the principle cast has some basic training in XanatosGambits. Melisande is just so good at it, other characters have to play Speed Chess to keep up.
Grand Admiral Thrawn. Of course. He was tripped up by some unforeseen elements coming together at once, and his initial backup plan in case of death was also thwarted, but damn if he didn't adapt when he could see it.
Thrawn also gets credit for recognizing the unforeseen elements possibly being a problem...he just didn't have a plan for them YET.
Also, his three would-be successors in the two-book series Hand of Thrawn, who are sometimes frantic in their behind-the-scenes efforts to maintain the illusion that Thrawn has returned. Thrawn's student Pellaeon demonstrates it too.
There is a set of four short stories, collectively a novella, where Timothy Zahn and Michael Stackpole collaborated. In very, very short it involved Thrawn going in disguise, reporting a Rebel meeting near the home of a criminal who supported someone that Vader hated but wasn't allowed to interfere with, and calling down the nearest Imperial forces. He ended up working a pair of planetary policemen into that plan, getting them in through a convoluted scheme and letting them arrest the man. We never, ever get to see his thoughts, but at the end he confesses to a trusted subordinate that he hadn't known about the policemen, but when he saw them and determined they were after that criminal, it was too good an opportunity to miss.
In Outbound Flight, Thrawn's plan is to destroy the Vagaari threat, and he uses all the new species and technology and ships he encounters for the first time over the course of the book to do so. All of them. Humans, a stolen gravity-well generator, Neimodians, droids, the Trade Federation, Darth Sidious, Outbound Flight, Jedi... all of them. Magnificent.
His plan nearly fails, though, when Jorus C'baoth goes over to the dark side and tries to Force Choke him. This was because he had never even heard of a "Jedi" until recently, and had no idea of the kind of power they possessed.
A certain amount of speed chess helps prop up Wraith Squadron's plans when things start going off script. Face Loran is perhaps the greatest practitioner of the art, exacerbated by his tendency to never tell anyone anything, except when strictly necessary (for reasons of operational security), meaning that even when he has planned for something, his allies are usually unaware. His more-or-less-designated successor, Voort or "Piggy", is more of a pre-planner, but embraces the need for this trope at the climax of Mercy Kill, dragging his wayward plan back into line with a combination of mechanical know-how, reliable subordinates, money, and Gamorrean striptease.
Littlefinger himself believes (or at least would have others believe) that it is this trope; he claims that one of his favourite tactics is to simply create chaos and then trust his own ability to sense opportunities on the fly whilst everyone else is reeling from having their careful plans disrupted by Spanners in the Works.
Less problematic for the fanbase is defining the other side of the Mega-Duo Of Utter Moral Ambiguity as a speed-chess player. Good, old, fog-bank Varys. He definitely plans, counter-plans and contingencies up to his eyeballs and beyond with the various plate-spinning political games he can choose to change at the drop of a hat. And, if all else fails, he falls back on plan Indy Ploy to see what he make of the results, later. He might have put Tyrion in the position that enabled him to kill Tywin, as helping him escape to Essos was part of the deal, sure... but... It's very unlikely that he actually fully planned on that specific thing to happen right then — not that that'll stop him using it. Other things he's done have been similar to that.
Tywin Lannister isn't half bad when it comes to this trope, either (which goes a long way to explaining why he's held up as a general example of what it is to be a Hand of the King). Particularly when it comes to the realms of battlefield planning and cutting the knees of political opposition off outside it. He's not so hot when it comes to tempering his chessmastery, plotting and c-changes with human, social insights aka "the carrot approach", however.
A historical one can be found in Brynden "Bloodraven" Rivers. The sheer amount of direction and hard work he put into defeating the Blackfyres included an awful lot of making do with whatever tools came to hand, whenever they came to hand. Including a certain errant hedge knight and erring Targaryen princeling. He's utterly hated for it.
In Lois McMaster Bujold's The Vor Game, the Big Bad makes up about four or five new plans in a single day as Miles tries to counter them and new chances arise. She even uses her old plans as pawns in her new plans. It backfires. In the end, Miles pointed out that if she had stuck to any of them, she would have been better off.
Miles learns a valuable lesson here, and in subsequent books he is shown to be a great player.
In Shogun Toranaga and Ishido do it through the whole book. Ishido seems to be better at it, as during much of the second half Toranaga mainly just goes through desperate attempts to buy more time and needs the help of several others to figure out how to counter Ishido's latest move. But in the end it's enough...
Victor Cachat specializes in these kinds of plays, usually with only a general plan to guide his decisions.
The Mesan Alignment (and Albrecht Detweiler in particular) is playing its own game of Xanatos Chess, albeit on a much slower time scale. Just how successful they are remains to be seen.
In Ben Counter's Warhammer 40,000Horus Heresy novel Galaxy In Flames, when Angron attacks the survivors of their treacherous attack, Horus (after being angry with himself for not predicting it) considers including him in the strike and so being rid of a dangerous ally. But he reminds his advisors of how he never lost, because he always managed to turn everything that happened in victory. He could bomb and take Angron out, or he could adapt his plan to use it and make a still more glorious victory. He explains afterward that by fightingtheir battle brothers, he had ensured their commitment.
Trying to get someone else framed for a crime, especially for attempted murder, is probably harder than committing the crime itself. The Missing Clue, the last of the Usborne Whodunnits series for younger readers, for ultimately failing. But boy could he think on his feet. Being the screenwriter for a popular soap opera, he managed to frame his target not just once but, failing that, made a second fresh attempt within a single day while only touching the weapons once. With the series of arrests this triggers, he's then forced to not just make his third attempt - framing a third person by getting them to murder his target on live TV - but to write up an entirely new script in the same period of time. That's diligence.
The Denarians in The Dresden Files are rather distressingly good at this. However, Harry's getting progressively better and better at it as well, meaning he can still crash their plans despite now being factored into them.
Debatable. It's been noted that, with the exception of Nicodemus, the Denarians immortality and massive experience lend themselves greatly to their ability to plan but makes them horrible at improvisation.
Arsène Lupin in the second and third canonical Crossovers with Sherlock Holmes read like this. In the second crossover, The Blonde Phantom, Holmes manages to find and capture Lupin's main accomplice the eponymous Blonde Phantom herself, and has a cab waiting outside to take them both to the station while he plans his next move. Three guesses on who is driving the cab. Later Lupin sends Holmes all tied up back to England, hoping to never see him again, then gets ready to clear his hideout of many years, since Holmes knowing about it compromises its safety. Guess which English Detective is waiting for Lupin to show up.
Artemis Fowl: the Time Paradox is essentially a game of Xanatos Speed Chess between Opal Koboi and Artemis, with Time Travel added in to make it a bit more interesting.
David from Animorphs plays a mean game too, which is only appropriate as Senna is his Expy. He loses mainly because he gets sidetracked trying to humiliate Rachel, as Cassie predicted he would.
The final battle eventually breaks down into this, as the kids run around the ship wreaking havoc and looking for any edge to save Rachel, with Visser One (unsuccessfully) attempting to contain the situation.
Neuromancer - the AI Wintermute describes himself this way: "I try to plan, in your sense of the word, but that isn't my basic mode, really. I improvise. It's my greatest talent. I prefer situations to plans, you see..." The plot of the book never makes a big point of this, though: when Molly decides to take a detour and when Case gets tricked by Neuromancer into thinking he's Wintermute, he doesn't manage to stop them.
Moiraine Damodred never has trouble manipulating everyone around her even when they are ta'verenand aware she is manipulating them. When she ADMITS she is manipulating them, they only seem more compliant. The best example has to be when she goes through the ter'angreal to fulfill the prophecy about her needing to die to save the hero but she is rescued from the dimension she'd been trapped in with another well laid plan.
Another candidate might be Cadsuane Melaidhrin. On the military side, Rodel Ituralde most definitely counts.
Crowley from Good Omens pulls this when two Dukes of Hell are sent to drag him back down to... well, hell. After Crowley's Plan A works on only one of his foes, he turns to Plan B, which fails in record time. Time for Plan C! ...Unfortunately, there is no Plan C. He comes up with Plan C on the fly, which boils down to tricking the Duke, Hastur, into chasing him intophone lines, winding back and forth over miles and miles of cable, and then timing his own escape perfectly... back into Crowley's own apartment, where his own phone was ringing, at the exact moment before his answering machine picked up. The result? Hastur is now trapped in Crowley's answering machine. Doubles as a Crowning Moment of Awesome for Crowley.
Phaethon from John C. Wright's The Golden Age starts off with a straightforward plan, which unfortunately Didn't See That Coming. Fortunately, he's also an engineer and believes in triple redundancy. The rest of the book is basically him working down the Xanatos index one by one.
The Martians from The War of the Worlds were good at this; when the British army and their artillery took down a tripod, the Martians understood that they had underestimated the humans' determination and strength in numbers and from then on used poison gas to clear new territory before they walked in with the tripods. Later, as there are no seas on Mars, the Martians had no idea how to battle the HMS Thunder Child of the British Navy and attempted to sink it with both gas and heat rays. They destroyed the ship, but not before it took two tripods with it and defended the escaping refugee vessels. After the battle, it's hinted that the Martians began to develop a sort of air force to combat the human navies. However, the Martians lacked any backup plan against the earthly diseases that eventually killed them.
In the New Jedi Order, General Wedge Antilles proves to have some skill at this on Borleias. He's trying to strategically lose to fool the Vong forces, while keeping his own as intact as possible, when the Lusankya and the Millenium Falcon come into system in exactly the wrong time and place. He couldn't let those be destroyed, so he has to rearrange forces that were in retreat to rescue them, while still preserving as much of his fleet as possible. And he does, and it is awesome.
The tactic he needed clicked into Wedge's mind. In the span of a second, he evaluated it, tested it for major weaknesses, dismissed the weaknesses as irrelevant because of the Yuuzhan Vong's current state of confusion, and decided that he could probably use the tactic again - once - at a later time.
The downside of course is that he ends up winning despite trying to lose, which turns into a Springtime for Hitler situation when the enemy then sends a much smarter commander to oppose him. (For those wondering, he fooled and out-strategized that one too.)
In any Culture novel you'll find varied experts at every version of gambit, especially with some of the Minds, standout examples of of The Chessmaster. However, in Xanatos Speed Chess specifically, awards go to The Player of Games (where the protagonist decides to bring down an entire civilisation using this trope (his original plan having been cast aside for the continuous analysis of modifiers he discovers half-way through), Use of Weapons (where the protagonist lives on this trope (usually literally his own survival)), and Excession (where the Interesting Times Gang are long-time veterans of Xanatos Speed Chess and have elevated it to an artform).
Wilkie Collins seems to have been fond of this trope; Lydia Gwilt in Armadale and Captain Wragge in No Name are both excellent Xanatos Speed Chess players.
Common in the Dream Park novels, especially The California Voodoo Game.
While Belisarius demonstrates an awe-inspiring level of long-term strategic planning (several of the characters realize that he'd set up the endgame of the war several years,and five books, before, ahead of it actually starting), on a tactical level he's constantly improvising on the fly and leaving everyone in the dust.
Shift the ape, the villain of the final The Chronicles of Narnia book The Last Battle, is very good at adjusting his plans in seconds. When a Bolt of Divine Retribution strikes nearby after he and Bumbling Sidekick Puzzle think up a plan to pass himself off as a false Aslan, Shift claims it is a sign of divine approval for their deceptive plan. When a lamb protests allying with the Calormens because they worship the evil Tash, Shift just rebukes him and tells him Aslan and Tash are the same being. When Puzzle is captured and Tirian the king plans to reveal him as the false Aslan, Shift does their job for them by spreading the word about it but blaming Tirian for being the one to deceive everyone.
Frederick Forsyth often has his characters doing this, and sometimes at the end (especially in The Devil's Alternative) they find out that they were being used in the Speed Chess of someone at a higher level than them.
Tavi from Codex Alera by Jim Butcher is an exemplar of this trope. In book five, across the ocean from his home continent, surrounded by anthropomorphic wolves who easily outclass him, he plays a game of Xanatos Speed Chess with limited resources against a villain who has hundreds of thousands of extremely powerful fodder. AND WINS.
The entire Korval clan in Miller & Lee's "Liaden Universe" books - particularly Delm Val Con Yos Phelium and his lifemate Miri.
In Enders Game, Ender is able to lead Dragon Army to an unprecedented 7:0 win/loss ratio in his first week as a commander because of this trope. Most of his opponents used pre-planned formations and had little room for improvisation; Dragon Army was structured to operate as much smaller units and even had a specific team whose job was to come up with "stupid ideas" to keep the enemy off-balance. In short, Ender made use of the fact that his troops weren't just soldiers, but genius-level soldiers.
From the Ender's Game spinoff Shadow series there's Achilles de Flandres. Despite being of ordinary birth and growing up a crippled street urchin, he's able to complete with genetically-engineered supergeniuses and effectively turn the world into his personal game of Risk. At one point mentor figure Colonel Graff pointedly tells Peter Wiggin that Achilles is not unbeatable, and that the reason why he keeps outwitting geniuses is because he's mastered the art of creating chaotic situations and then seizing opportunities.
The Doctor from Doctor Who is a renowned master of the Indy Ploy. However, on those rare occasions where he actually has a semblance of a plan, if things go awry, he'll tend to only pause momentarily in shock before dashing off to salvage victory regardless. The Seventh Doctor, who always had a plan, did this more often than not (including at least one long, drawn-out game with an Ancient Evil from the Dawn of Time).
The Master has his own knack for turning bad situations to his advantage - witness his magnificent comeback from accidentally destroying about a quarter of the universe to holding the rest to ransom in 'Logopolis'.
And in the first part of "The End of Time", after his scheme to come Back from the Dead went awry, killing his support network and causing him to Come Back Wrong, and he gets kidnapped by someone who wants his help with fixing some Applied Phlebotinum, he quickly hatches and executes a scheme to take control of said Phlebotinum and use it to take over the world. He succeeds. Unfortunately for him, he gets out-gambitted by Rassilon, Lord President of the Time Lords, who fixes the population of Earth with a wave of his hand. He then proceeds to tell the Master he's outlived his usefulness and, well, the Master decides to take his revenge.
The fifth season of the revived series ended with not one but two quite brilliant examples by the Doctor himself. The first to save the universe and the second to save himself, both fully exploiting the possibilities of time travel in a way he doesn't usually try.
In "The Invasion of Time", the Doctor succeeds in spite of learning the people he was foiling were only the facade.
Not so much in spite of - it's implied that the Doctor knew they weren't the Big Bad the entire time - and only dealt with them in the first place solely so that they would reveal who or what the real threat actually was. The first half of Invasion of Time actually goes exactly according to the Doctor's original plan.
River Song's first encounter with the Doctor consists of her repeatedly pulling weapons out to kill him, which he has unloaded (or in one case switched with a banana) moments before. As he puts it: "I know you know." In the end, she poisons him with a kiss and points out she was planning to do it like that anyway. "I know you know I know".
Michael Scofield of Prison Break is excellent with this. When he isn't planning large gambits, he's doing this anyway (especially in the fourth season). However, due to various interventions even his large gambits such as the Fox River prison break are always threatened to be ruined unless Michael plays some speed chess.
Whereas there have been complaints that Tony's plan in Season 7 involved the use of elements he couldn't predict, in fact he was employing this trope rather than a Gambit Roulette He had been working patiently to gain the trust of the real Big Bad and it just so happened that Jack screwed up his original plan and simultaneously gave Tony a new opportunity to carry out his revenge against the Big Bad.
The characters from Star Trek are really good at these. Picard may have the slight edge in execution, in that he generally tried to stick to the plan and obey orders. Kirk on the other hand just made shit up, thus he's more a master of the Indy Ploy.
Gul Dukat only ever had goals (mostly involving power or revenge) rather than long term plans. He was always willing to switch sides (which he did a lot), grab any opportunity that presents itself, or try to work situations to his favor.
The form of strategy generally practiced by wannabe Chessmasters in Survivor, to effectively counter the numerous Shocking Swerves the show tends to throw that has been the bane of their predecessors. Some like to pretend that they're really playing Roulette, just to seem more impressive than they really are.
Benjamin Linus of LOST is the poster child of this trope, adapting and changing to events around him with such ease over the course of the series that one can't help but find the constant Gambit Roulettes fairly plausible.
Then season 5 & 6 happened, where so many events come at him out of left field, even his actor admits he's being forced to act less more like Indy.
"I think Ben has a lot of layers of plans, but I think we're way off the main stem of anything that works for him. I mean, Ben's doing like moment-to-moment scrambling now."
The Man in Black has been shown to play a round or two in the final season, one example culminating in him blowing up a submarine and killing 3 of the main cast.
This is most of what Vic Mackey does in The Shield, especially in the later seasons.
Michael Westen of Burn Notice is a master at this trope, sometimes pulling off two per episode (one for helping his clients, and another for gaining more information on the people who burned him, although the latter ones don't always succeed).
In one episode Michael faces off against a guy so Genre Savvy that the entire episode consists entirely of Michael coming up with modifications of modifications of his original plans.
The beauty being that Michael sets things up such that, even though the guy KNOWS Michael's playing him, he has no choice but to play along.
There's another great example in "Question and Answer", in the "reverse-interrogation" scene. Michael's undercover as a junkie snitch, Sam as a corrupt cop, and they have to let the bad guy interrogate Michael about information neither of them have. The entire scene is Sam playing head games with the bad guy, while Michael pretends to know information he doesn't, and pull it off.
Jeeves and Wooster: Jeeves is a master at this, even when Bertie isn't and comes up with plan Bs like "Feign amnesia!"
Nate Ford of Leverage prides himself on being a Crazy-PreparedChessmaster. However, his plans usually always go awry and he has to create a new one on the fly, which actually works out spectacularly well. Every single episode.
Except when things are going as they planned but they're operating on the Unspoken Plan Guarantee, so it appears to viewers that something has gone wrong.
Lamp Shaded in Stargate SG-1 in the Season 7 episode "Evolution part 1". When SG-1 and SG-3 set a trap for one of Anubis' Kull warriors, O'Neill orders Reynolds of SG-3 to set up a secondary perimeter. The man jokes with O'Neill about not having "much faith in Plan A" causing O'Neill to respond "Since when has Plan A ever worked?"
Several instances also occurred in Stargate Atlantis. Example: when two hives force the Daedalus to retreat, Sheppard quickly latches onto one of them before they jump to hyperspace; once they come out, Sheppard blows away the hyperdrive of one, delaying them until the Daedalus comes back with the Orion. Another instance is when he was instructed to man an Ancient ship, he tried to hijack it but Larrin foiled his plan; he responded by alerting his teammates with an SOS signal disguised as hyperspace background radiation. I swear, that guy is a chessmaster.
Having a Mensa-level I.Q. certainly helps. And he does beat Rodney in chess at least once.
It helps that Sheppard's intelligence is highly focused on tactical scenarios (being military), whereas Rodney's genius applies to much different subjects, while he also suffers from overconfidence and a tendency to make poorly-considered mistakes (especially in cases where significant foresight is required - Rodney very much lives in the moment). It's entirely possible (if not likely) that even Ronon could beat Rodney in a game like chess, especially since Rodney would probably be thinking of ten different things during the game.
The Thick of It and Absolute Power contain many examples. Both feature characters working in crisis management PR, which is essentially the profession of Xanatos Speed Chess.
The Evil Plan over the course of Supernatural is definitely speed chess: the first seal was supposed to be broken by John, not Dean, and the entire Ruby ploy is pretty obviously a response to Sam failing to fall in line the way Jake did or Ava would have.
Debatable. It was pretty much stated that the way it played out was the way it was planned. With the exception of the Power of Love saving the day, even that has been written, elsewhere.
Very debatable. With the possible exception of Azazel's death, every single thing in the series goes exactly as he planned. And as of season four, it's revealed he knew that Dean was going to kill him a good twenty years in advance. Lucifer openly calls Sam's life "Azazel's game". The only things that actually go wrong, The Horsemen's deaths, losing track of the Anti-Christ, not actually being able to spread the Croatoan Virus, and possibly the death of The Whore are all incredibly minor, in the grand scheme of thing.
Let's be honest, this is less a case of the characters playing Xanatos Speed Chess and more of an Indy Ploy from the writers, who have pretty much been making it all up as they go since the Writer's Strike.
And then its all for naught. Lucifer is defeated and sent back to his cage, and the angels don't get to actually start the apocalypse. For all their planning they failed at the very end.
Crowley. Oh, Lord, Crowley. He has to be the master of Xanatos Speed Chess in Supernatural, and he's Genre Savvy. He's the only demon who has EVER been able to convince the Winchesters to actually DO WHAT HE WANTS! And as of the end of S6, he has yet to die, even though his "death" has been shown onscreen many times, it was always fake and/or a setup. Crowley is a Xanatos master.
The Trickster/Gabriel was pretty good at this too, faking his death in virtually every episode and throwing in the occasional Batman Gambit in his manipulations of the Winchesters. He gets outplayed in the end though, and Killed Off for Real.
Chuck, if you think about his true identity. He can play Xanatos Speed Chess with the best of them, though he is very secretive about it and never reveals his true intentions ( Of course, being as he's GOD, this is quite easy for him and his intentions are always for the Greater Good).
Lionel Luthor, obviously, from Smallville is breathtakingly good at this. To exemplify: When Chloe is blessed/cursed with the gift of having anyone answer her questions truthfully, she does of course start asking Lionel questions. He realizes what's going on after the first question and immediately counter-attacks her on her weak spots, thereby distracting a highly intelligent, pretty fearless and incredibly nosy young woman from using her golden chance to get into the secrets of a powerful, rich baddie. She could have asked questions every moment, she was just too stunned to do so.
Chloe herself pulled one in Roulette, regarding a complicated Batman Gambit, manipulating Oliver and Clark in an attempt to help Oliver find his inner heroism.
Mission: Impossible is made of this trope. Rarely, if ever, does the IMF's complex plot go completely according to plan. The IMF team simply improvises around whatever does go awry, and eventually achieves its goal anyway.
Of course, there were several instances where the audience thought this was happening, but it was really just the plan working perfectly (for instance, when the bad guy becoming wise to the con was actually part of the con).
This trope only kicks in for them when their Batman Gambit is about to go awry, which is roughly once an episode. Their use of Xanatos Speed Chess is to draw the villain back to the gambit and/or away from discovering The Masquerade.
In one first-season episode, it was all Xanatos Speed Chess. Rollin was specifically sent in without a plan because the mission was to recover a wire recording that an agent had hidden in the few minutes between losing his tail and his death. With no one knowing where he had hidden it, they had to rely on Rollin figuring out how to find it, how to recover it, how to return it, and do it all under the eyes of enemy agents.
Similarly, Hustle frequently includes spontaneous modifications to existing plans in order to stop the entire elaborate con collapsing. More common during Danny Blue's brief stint as head of the crew, since improvisation is his forte. It does occur under Mickey Bricks as well, but less often; Mickey is more likely to have Plan B, C and D than an improvised change.
Heroes: Unlike earlier Big Bads who seemed to have Fate in their corner always dropping events in their favor, Volume 5 Big Bad Samuel Sullivan has a general master plan but is also frequently forced to adjust when unexpected events unfavorable to his scheme pop up.
Wizards of Waverly Place Justin wants an Alex-proofing monster for his room but because of Max he has to use a computer for a brain instead of something else. Frankengirl captures Alex and is then outsmarted by her, so Justin resets Frankengirl into a clingy BFF. It only takes a few minutes for Alex to turn Frankengirl into her Sidekick Ex Machina. Justin eventually wins though, by turning Frankengirl into a 'cheerleading fool' and then convincing her to drag Alex to the try outs. Apparently Alex is more afraid of being a cheerleader than a monster's captive. Justin hits three snags, but his original goal of keeping Alex out of his room is ultimately acomplished.
Xena: Warrior Princess. Both Xena and Gabrielle are particularly adept at this, it was even Lamp Shaded in the episode "A Day in The Life", where Xena is reluctant to re-use a trap from a previous episode.
In addition to "A Day in The Life", Gabrielle shows a remarkable penchant for this in the series finale, when she Uses a ladder as a means of acrobatically reaching a water tower, and putting out a massive fire that was destroying the town of Higuchi.
The show is basically made of these. Xena: Warrior Princess, is also Xena: Queen of Xanatos Speed Chess.
The Xena comic "Contest of Pantheons" also has a pretty note worthy moment on the part of Callisto, where she Sees the army of Egyptian dead, infers that Anubis has stolen the power of the Greek god Hades, and kills Xena, to send her to the Underworld where she could defeat Anubis, and restore Hades to power.
Buffy the Vampire Slayer. Similarily to Xena, Buffy has a talent for this, notably in the episode "Helpless" she replaced the water in a Vampire's water bottle with holy water. When the Vampire took his painkillers with the holy water, it burned through, and killed him.
Angel. Both the Angel gang and Wolfram& Hart are very adept at this. For the first three seasons, Angel repeatedly stops Wolfram & Hart from committing some act of heinous evil or another, just to watch the evil machine keep on chugging along. They even congratulate him every now and then. Eventually, he does manage to derail into their Ancient Conspiracy, if only temporarily.
In Kamen Rider Double, there's a game of Xanatos Speed Chess going on between Ryubee Sonozaki and Shroud going on throughout the series, both trying to work around the plans of the other. Shroud ultimately wins by sending Shotaro to ruin his plan.
The Kill Point is basically eight straight hours of this (well, OK, seven hours of this and one hour of Villainous BSOD). John Leguizamo leads a team of bank robbers who end up taking hostages when their plan goes bad. He spends the rest of the series cooking up no less than three separate escape plans, while stringing the hostage negotiator along.
The Cranes from Frasier are masters at this whenever they get into a tight situation (i.e., most episodes), as are Roz and Daphne. Granted, they frequently fail on a level or two by the end of the episode, but the skill and slickness with which they lie, manipulate events, think up new plans, and navigate a tangled thicket of cross-purposes and plot threads to keep everything running smoothly for 20 minutes of airtime is impressive to watch.
Emily Thorne from Revenge spends her days manipulating people into manipulating each other, but when this doesn't always go to plan, Emily will adjust her plans accordingly. In the second season episode Penance, no less than three people go rogue on her (two of which do so in order to commit homicide). She adjusts her scheme mid-episode without breaking stride, and still comes out getting exactly what she wanted all along.
The third season finale and basically the entirety of Season 4 of Breaking Bad is one long game of this between Gus and Walt.
Alfred Bester, in the fourth season of Babylon 5, implemented a plan involving Michael Garibaldi that was basically a big one of these mixed with Gambit Roulette (several factors not under Bester's control worked in his favor, as he later admitted). The goal? Finding the root of an anti-telepath conspiracy, so that the Psi Corps could deal with it.
The entirety of Season 3 of Scandal is either this crossed with a Batman Gambit or a Gambit Roulette on behalf of Command/Rowan/Eli Pope, depending on how much he could have anticipated given his access to all of B613's intelligence. There's also some ambiguity over how much he instigated versus how much he took advantage of. Regardless, he certainly got what he wanted by the season's end: his daughter got on that plane, the President owes him and is unlikely to interfere with B613 ever again, his most troublesome agent is out of the picture, and he got to torment his terrorist wife and kill her lover.
Forgotten Realms God Cyric. His Crowning Moment of Awesome and claim to master of Xanatos Speed Chess comes during a Trial where the other gods claim he is unfit for his duty as Greater God of Strife, Lies, Murder, and other nasty things due his (fake) holding of the Idiot Ball for years. The thing is, Cyric SET UP the trial as a way to get the gods to bow down and worship him through use of the Cyrinishad, his book of evil that convinced anyone, god or mortal, that Cyric was the greatest god ever and only true god. When his lackey failed to get the Cyrinishad on time and had the wrong book, Cyric immediately had two other ways of assuring he would win the Trial. And he did. One was the aforementioned lackey being made into a demi-god of lies, even though he couldn't tell a single lie due to a curse from the goddess of magic. Cyric said this made him perfect, because the best lie is the most unbelievable truth, once again showing Cyric is a Xanatos master. Oh, and he also gained the loyalty of an Eldritch Abomination during the course of all this and tends to threaten his enemies with the thing occasionally.
More like losing and calling it winning. Bane's the real master. He, Bhaal, and Myrkul all had backup plans in the event of the failure of their gambits during the Time of Troubles. Bane didn't bother with mortal progeny (Bhaal) or depositing his essence in an artifact (Myrkul)—he created a demigod child to inherit his mantle. Even said child didn't know he was a glorified chrysalis—when he grew sufficiently powerful, Bane erupted from within him like a horrible, horrible butterfly. The Lord of Darkness was back in business, baby!
The galaxy of Warhammer 40,000 is the chessboard for a four-way free-for-all game of Xanatos Speed Chess between Tzeentch, the Deceiver, the Eldar farseers, and the Emperor, with a few others dabbling on the side. All players involved are very, very good at it.
It's probably worthwhile to note that, at the same time as all those groups work against each other, Tzeentch is playing an additional 1000 games of Speed Chess against himself, and at least 100 more against each of the other Chaos Gods. When you have literally thousands of Gambit Roulettes in action all at the same time (and almost all of them are solely because you love doing it), you tend to have to do a bit of multitasking. Then again, Tzeentch IS the Magnificent Bastard.
And insane. Or, possibly worse, very very sane.
Then there's the alternate character interpretation: it's all a Gambit Roulette by Tzeentch, and everyone else only THINKS it's a game of speed chess...
Actually, Tzeentch is the only player in this four way game who cannot win. Because then he would have no one else to play against...
Anybody who has ever played the group strategy game Mafia/Werewolf as a bad guy has had to attempt this. A detailed original plan NEVER goes off without problems.
Pretty much all Cheapass Games work this way, with other players (and pure randomness) changing conditions so fast that any strategy has to adapt just as fast. Looney Labs games (Fluxx, Chrononauts) are similar.
Chess, of course. Under a time control of 1 minute for the entire game, the only way to make your moves quickly enough is to choose a move because it is the most active move that stops the opponents threats.
Any and every CCG or competitive boardgame ever. There's always that one person who whips out with "WTF" strategies that can and will throw the group off guard.
The strategy game Hellgame runs on this trope. Not only do each player control three characters, positioned in different places in the turn order (so a player can be both the first and the last to act in a single turn), this turn order can be manipulated by the playing of cards. Random events abound; every turn begins with a random event (which can in turn cause other random events to occur, or put down triggers which cause them to happen later, often several times), and a typical spell causes random events to happen to other players (or yourself). Combat is resolved by die rolls, often modified by spell cards and said random events. A player can seem to be unstoppable, only for a completely harmless-looking opponent to suddenly jump to the end of the turn order to cut of the expected victory and grab it for himself, only for _another_ player to do the same, and then some. A game can last a single turn, or ten; which is in no way an indication of the elapsed time of the game. Successfully wading through this sea of random happenstances and quirky rules, battling the other players (five of them) for supremacy over the turn order is the path to victory.
Paranoia sets the PCs up with mutually conflicting goals, then throws rapid-fire obstacles at them along the way. One suggested game mechanic is to ask each PC "What are you doing?", then only give them about five seconds to answer:
Friend Gamemaster: Okay, you've just been dropped off in Outdoors Sector. Suddenly, some people appear at the top of a hill, charging down toward you with long pointy sticks. *to PC #1* What are you doing? PC #1: Uh, what do these people look like? Friend Gamemaster: Dirty smelly Infrareds with ragged uniforms. One of them sticks his long pointy stick into your chest. *to PC #2* What are you doing? PC #2: *realizing that PC #1 just dropped the team's camera* I shove PC #3 toward them. PC #3: Hey!
Online freeform roleplaying combat at a high level is this; prima makes their attack, secunda makes a response that is nigh-unavoidable, prima has to respond and try and take back momentum, and so on back-and-forth until someone runs out of moves to make. It's fun!
The Munchkin card game has some of this, too, especially in epic games with high levels and four or more players. Given that the official time limit for interfering in seemingly successful Combat rounds is "a reasonable amount of time (defined as 2.6 seconds)," things can get a bit... hectic, when players are trying to aid/hinder another player's efforts, especially the final level(s).
Magic: The Gathering is powered by this trope, especially in tournament play. Control mirrors are dozens of turns of this, with each player pretending they had it planned all along.
Actually averted the better one gets at the game- there's a limit to how much strategies can be modified without bending one's deck and game out of shape. Good play is more like using this trope to back up a straight Batman Gambit.
This is the only way to play the card game Fluxx, because the rules of play and victory conditions are constantly changing.
Classes with the Leader role from Dungeons & Dragons 4th Edition lend themselves to this style of play, especially Warlords. Generally, they employ subtle long-term buffs that shape their team's playstyle combined with dramatic short-term buffs that let them compensate for surprises that upset their planning. Given the right player and a good DM, battles can be fascinating affairs.
Cyrano de Bergerac: Cyrano is good at this in Acts II and III, but he cannot fool Christian nor Roxane in Act IV. However, he manages to fool Roxane again in Act V:
Cyrano: Nothing; 'tis... (He shows his hand, smiling) This scratch!
BIONICLE: Makuta didn't take the rescue of the Matoran of Metru Nui into account, though managed to get past that. When part of his plan called for leaving his body, he didn't expect it to be destroyed by the end, but he still managed to keep his plan going smoothly, taking overMata Nui's body and the Matoran World within it at the end of 2008's arc.
Most multiplayer games that have an element of strategy end in this when played competitively. As it's bound to happen when you pit several experienced strategists against each other, the match often turns into a battle of dismantling the enemy plan while you repair and protect yours, while they do the same to you, only ending when someone gets hit with a big enough spanner and can't recover in time.
In Deus Ex, each faction has someone playing this as the rogue piece — the player — changes the board every step of the way. One could say that the villains are most adept at this, but of course they lose in the end and really their situation is more along the lines of planning out a dozen or so counters to any foreseeable action. The nominal good guys, on the other hand, actually have to make it up as they go.
The only faction that refuses to play the game are the Omar in the second game. Their strategy is based around waiting for the day they'll replace humanity as the dominant species through natural selection — though by the end this only becomes possible if you kill all the other conspiracies that would supplant or exterminate them.
It could be argued that they're playing the game as well, especially from the point of view of their ending. Their fair and helpful dealing with the player through the entire game? Laying the groundwork to put him (or her) in the right place at the right time. The recruitment of (and eventual modification of) Leo? Setting up a pawn close enough to the player to influence their decision at the proper time. Leo refusing the final upgrade? With as much modification has already been completed, how can he (or you) truly know for sure whether or not he still retains any free-will at all? By seemingly rejecting their offer and asking for your help, Leo becomes the ONLY character in the entire game who is seemingly both free of outside influence as well as complicated plots or goals of his own - putting him in a perfect position to offer advice without the player looking for an ulterior motive (thus making him the perfect way for the Omar to influence the player without their knowledge). Note that's it's LEO'S advice at the crucial moment that convinces you to kill every faction (thus killing off every hope of stablizing society and eliminating the only real threats to eventual Omar hegemony). By following the advice of the man who is quite possibly an Omar puppet, you guarantee Omar victory. It might sound like too far-fetched and overly complex a gambit to even remotely be true - until you remember you're basically playing a game which is almost entirely built around the idea that most conspiracy theories are real, the fate of the entire world is regularly decided by insanely complex plots, and that the more insane a plot seems, the more likely it is to have been true the entire time. Both Billie and Klara were deliberately recruited by other factions, and both were used in attempts to influence Alex's actions. Did you honestly believe that Leo's cultivation by the Omar was a coincidence?
In Command & Conquer 3, Kane's complex Gambit Roulette is threatened multiple times by the actions of GDI, the Scrin, or HIS OWN FORCES! However, he's still Kane, so he has the player character iron out all the wrinkles in his plan. And by "iron out", I generally mean obliterate.
And even when things don't work out, he has proven time and again that he is practically immortal, being able to resurface after things like a Ion Cannon strike on the head.
And in Command & Conquer 4: Tiberium Twilight, he finally got what he wanted, and so is the tactical victor of the Tiberium wars, even if it took him like 70-80 years and the blood of bilions to reach the victory.
In the first game, SHODAN's plan amounts to this (backup plans listed after initial plans):
Destroy life on Earth using the space station's mining laser, so she can remake life in her image. The player responds by destroying the laser.
Conquer earth by unleashing the (biological) virus she created to transform everyone into her servants. The player responds by jettisoning the part of the station which was incubating the virus.
Transmit herself to Earth (she is an AI). The player responds by blowing up the station's antennae.
Crash the station into Earth, to unleash the virus that way. The player responds by setting the station to self-destruct.
Eject the station's bridge, which houses her mainframe. The player responds by gaining access to the bridge and manually purging her from the computers.
The second game originates from the player's actions in the first game. The incubator that the player jettisons in the first game is discovered and found to be overrun by SHODAN's spawn... and SHODAN herself had a backup on the computers. This probably happened by chance, however, and not through SHODAN's plan. SHODAN acts more as a Manipulative Bastard in the sequel, however, manipulating the player with less of a multi-tiered plan. At the start of the game, the player is one of her few resources, but by the end she's clawed her way back up and is on the brink of literal near-omnipotence.
Xemnas in the Kingdom Hearts series is very good at this. There are many points where things do NOT go exactly as planned for him...and yet he always seems to quickly make whatever happens work in his favor. Sora won't comply to aid you? Use his Nobody Roxas instead. Roxas gains a will of his own? Use a Sora clone that can absorb power from Roxas, and if that's successful then mass produce them. The clone develops a will of its own? Make Roxas and it fight each other to the death, and use the one that's left. Roxas disappears? Then go back to Sora and manipulate him into helping you without knowing it. Sora finds out about this? Kidnap his girlfriend and force him to keep fighting Heartless for you. All of this fails and you're destroyed? Have a way prepared to come Back from the Dead in a fashionable black and white coat and do them in when they're weakened. Truly, Xemnas is a master Xanatos speed chess player.
He probably gets it from Master Xehanort. Wanna know about the Keyblade Wars? Recreate them. Need someone to turn into the X-Blade for you? Grab some orphan no one will miss. Orphan not quite what you need, but it's too late to drop him? Cut his heart in half and see if that works. Getting on in years and the plan's not quite done? Find some Unwitting Pawn to commit Grand Theft Me on. Pawn, orphan, and their spanner-friend wise up to all this? Lure them to your home turf and take them out that way. It's actually way more complicated than even that, but this guy is on top of ALL OF IT.
Perhaps it should be renamed "Xehanort Speed Chess"?
And then there's DiZ AKA Ansem the Wise, who might be, perhaps, just as good - he was, after all, taking on the Organization, headed by Xemnas, and he was winning. In fact, at least at the end of Chain of Memories (and, one could argue, even the end of Days), everything was going pretty much according to plan. In the end, the only thing that toppled him was his own arrogance causing him to bite off more than he could chew (something which he admits to the King, just before his Heroic Sacrifice, as well as in the Secret Reports) and the fact that, consequently, his game became a Gambit Roulette. Like Xehanort and Xemnas, he lost track of all the players - Sora isn't anywhere close to being a Speed Chesser, but he's rather effective as a Spanner in the Works, and Riku's just as bad, since DiZ isn't as able to predict his actions as he'd like to think he is. Couple this with the fact that his cynicism and bitterness were pretty much incapable of predicting Sora's idealistic, selfless heroism, and by the end of it all, even he had to admit he'd lost the game.
Though it's hard to tell what he's thinking, Jon Irenicus in Baldur's Gate II seems to do this. His original plan is simply to experiment on Imoen and the player character in his own personal lair. However, this runs into trouble when Shadow Thieves attack him, his prisoners escape and, on top of all of this which he could have handled simply by virtue of his great power, the local wizard authorities get wind of the unsanctioned use of magic and teleport in to arrest him. Killing hundreds of them is not the path of least resistance even for him, so he suddenly decides to go peacefully, but making sure they also arrest Imoen. They are both taken to a wizard asylum, which Irenicus soon takes over, continuing his experiments with Imoen and waiting for the player character to come after him. The player character already has two potential motives for doing this - wanting revenge on Irenicus and to rescue their "little sister" - but a third one is added when Irenicus somehow appears in their dreams and speaks of unlocking their potential as a descendant of a god, speaking as if the player character could gain great power though he really has no interest in giving it to them but rather just stealing it away. Unless that's just the Bhaal in you talking and not Irenicus at all. (This is also, in a way, the game masking its But Thou Must plot element. You have to go after Irenicus and Imoen, but at least you get to pick your motivation out of a fair selection.) The player may make various choices along the way and choose to ally or not with two characters who are actually Irenicus's pawns, but the end result is the same - in a non-contrived way - and they end up just where Irenicus wants them.
Sarah Kerrigan of StarCraft plays Xanatos Speed Chess in the expansion pack. She allies with the Protoss by brainwashing the Matriarch Raszagal and helps them kill some rogue Zerg opposing her, and when she kills off the member of their group that was getting wise to her schemes she takes off laughing as they realize they've been played. She then recruits Raynor and Fenix to rescue the Dominion emperor Mengsk from the UED, uses the three of them to destroy the UED's main bases of operations, then backstabs them and kills Fenix and Mengsk's general leaving the two demoralized and de-powered. She then kidnaps the Protoss Raszagal and uses her to blackmail her co-commander Zeratul into giving her access to special assassins that will kill the Zerg hivemind and leave her in complete control of them. By the end, Kerrigan plays all of her enemies against each other, weakening them in turn while she accumulates power for herself to the point that the developers said in materials for Starcraft II she basically could have wiped all of them out at the end of the game, but chose not to.
It's somewhat implied that while devious himself, Lekain was mostly just Sephiran's pawn. Sephiran, on the other hand, has been playing chess since before Ashera went to sleep.
When the Dark Elf steals one of the four Crystals of Light in Final Fantasy IV, Golbez kidnaps Rosa, forcing Cecil and his party to go get the crystal in exchange for her life.
Kuja from Final Fantasy IX had no less than two of these. First, it's revealed that his entire plan was revolved around stealing Alexander, the most powerful of all Eidolons (summon monsters). This fails when his boss shows up and blows it to hell. Panicked, his next plan involves using the protagonists to fetch a powerful stone for him and extracting other, lesser summon spirits from a little girl. This fails when her Moogle guardian goes Trance and proceeds to kick ass. Kuja then changes his plans AGAIN in order to gain his own Trance power. Kuja finally achieves this and proceeds to kill his former boss. It's too bad that he learns that he's going to die soon anyway, prompting the mother of all Villainous Breakdowns.
BlazBlue has Rachel Alucard and Hazama/Terumi Yuuki who are playing Speed Chess against each other with the fate of the world on the line. Calamity Trigger involved gathering the pieces, with the game proper beginning in Continuum Shift, with extra rounds shown in Extend. While Terumi's record is impeccable, Extend reveals a scorch mark that keeps it from being unwavering - this mark was left not by Rachel, but by Makoto, who fell on the board due to Terumi's own machinations against her. Undoubtedly, Rachel is factoring this into her future plans...
And in the sequel, Chronophantasma, The Imperator quickly cancels out Kagura's entire game's worth of planning a rebellion by resigning from the position and naming a successor, throwing most of the NOL into confusion and dissention.
In Modern Warfare 2, General Shepherd proves to be a mean player of this. Sure, he didn't expect Price to fire a nuke at Washington D.C., but he capitalized on it very quickly in the subsequent cutscene; before the nuke even hits, he's already convinced the Secretary of Defense that the nuke was fired by Makarov, and gets government approval to track Makarov down with what is essentially a blank check.
Happens in Marathon whenever two AI's go up against each other, perhaps the most epic instance being Durandal vs Tycho in Marathon 2. Durandal pretty much always eventually wins.
The Reapers of Mass Effectaren't bad at this. Their original plan (which has worked for millions of years), is to let civilizations grow using the Citadel and mass relays. They then use these to harvest every space farig civilization. Here are the adjustments they've had to make:
Ancient race, the Protheans, disabled a system in the Citidel integral to their plans so they indoctrinated the rachni and started a war, hoping to capture the Citadel and manually activate it.
Krogan wiped out said species? Try again with the Geth.
Shepard defeated Sovereign and put the kibosh on that plan? Kill him/her, try and recover the corpse, then build a human Reaper to take Sovereign's place.
Shepard came Back from the Dead, killed your servants, and destroyed the, human reaper, Sovereigns future replacement? Fine, get everyone to the Alpha Relay. Oh, and use indoctrinated servants to capture Shepard, so you can turn him/her to your side.
Shepard escaped capture and took out the Relay? No matter, that only delays the invasion a few months anyway.
Once in the galaxy, brutally attack Earth and Khar'Shan immediately and hopefully take out Shepard. Even if Shepard survives, humanity gets crippled right at the start. All your other preparations can proceed as planned either way.
Presumably, their adjustments to the plan are so ideal that by their arrival proper - assuming Shepard doesn't stop them - people expect the Reaper invasion to finish quicker than the last time it happened, where things did go according to plan. All the past wars they created had left the galaxy divided and much easier to defeat than in the previous cycle.
This is part of what makes Malefor from The Legend of Spyro such an effective Chess Master. Spyro turns out to be alive and frees The Dragon from his control? Trick Cynder into luring Spyro to the Well of Souls and freeing him. In fact, taking Cynder in the first place may have been an adjustment in response to Spyro's egg not being present at the Dragon Temple.
Surprisingly for an educational game, Malicia from The Clue Finders Reading Adventures. She kidnaps Leslie and Santiago at the start of the game, and later on it's revealed She was posing as the princess to get the ClueFinders to find and assemble the Amulet of Life for her. When that failed and she grabbed the wrong one, she still got Joni and Owen to come to her with the amulet anyways since she still held their friends hostage. It's even lampshaded in a cutscene...
"Why would they give you what you want?"
"Because I have what they want...you."
Emperor Mateus from Final Fantasy II. His plans begin with simply wanting to take over the world and whenever the heroes cause him trouble, he drives them back with rapidly escalating methods of destruction or clever scemes. The heros barely get a moment to savour a current victory before he turns it around on them. He even dodges death by splitting his soul in half, because now he wants heaven and hell too.
Toshimi Tagami, from Ghost in the Shell on the PS2: Her plans begin with high political intrigue to gain a region it's independence all for her brother's cause, and when section 9 shows up to throw in some spanners, she quickly switches gears and manipulates the lot of them to get her way in the end. Even her death didn't stop it.
Kotomine of Fate/stay night has a pretty good one of these in Heavens Feel. Plan A: start with sending Lancer to figure out who everyone is, where they are and how strong. Crap, after roflstomping True Assassin he got his heart pulled out and eaten. Ok, uh, well we still have Gilgamesh, and he's pissed about the serial killings going on. Damnit, he got eaten too. Fine, we'll set up Sakura, the monster eating everyone to turn into the gate and destroy the world. Uh oh, the Core of the Grail just got hijacked, time to team up with Shirou to recover it. Oops, True Assassin came after him and humans can't kill Servants with the tools he has. Guess we'll destroy Zouken's body, using my fake heart as a decoy and then drive off Assassin. Woops, the Grail doesn't like me and just destroyed my heart. And, breaking the narration, he still makes it to the end of the path and still nearly unleashes a plan that is in fact much worse than the scale of what he was trying in the first two. Plus, Shirou's ideology has been neatly discarded, and Kotomine really hated it.
Archer's plan in "Unlimited Blade Works". His repeated gambits to kill Shirou and set up either himself and Rin or a Rin/Saber team as the winners of the Grail War by playing Caster, Kotomine and the protagonists against each other are truly inspired.
Maou from G-Senjou no Maou has a gift for revising convoluted plans on the fly, being an expy of Lelouch, which is how he keeps beating the protagonists, even until the very end.
Ace Attorney wouldn't be interesting if it were not for the ability of every opponent to counter your arguments. Add the fact that frequent surprise evidence tends to shock all parties forces everyone to reconsider their plan on a regular basis and you've got a wild ride.
The leader of a team of magical thieves in The Dragon Doctors starts off with a straightforward plan to rob a hospital of valuable materials, but are continually stymied by one lone surgeon defending the hospital. Elizabeth (the leader) continually adapts her plan towards a profitable solution even as all her teammates are taken out one at at time, and if it hadn't been for a slip-up she'd have still gotten away with it.
Parson gives the other characters a lecture on playing Xanatos Speed Chess in this page of Erfworld.
In Girl Genius, Gil needs to get into the castle and have it be known that he did — so his father knows, and doesn't attack it. His plot to convince the crowd that he's Gilgamesh Wulfenbach convinces them that he's putting on a show. So — he tells them they're right, and by this means lures them to the castle and breaks the truth them only there. (With some unexpected backup from his friends.)
Additionally, in chapter 6, both Tarvek and Anevka Sturmvoraus seem to be playing Xanatos Speed Chess with each other for control of Sturmhalten and The Other, executing back up plan after back up plan. Tarvek even says in this strip that "None of this was in my original plan, but it's all working out so beautifully!"
Helen Narbon, of Narbonic, is another case where the fanbase—and even the characters in the strip—are never fully certain if Helen is playing Xanatos Speed Chess, Gambit Roulette, or if she's just luckier than anyone has any right to be. At several points, it seems Helen, herself, is not certain.
Artie: My last thought before blackout is this: That every aspect of my nature—my mind, my sense of ethics, the body in which I currently reside—seems, now, engineered for this moment, for shielding this woman from impact. I have never been able to fathom the disjointed workings of Helen's mind. Did she surmise that someday she would be in danger? Did she create me specifically to save her life? And, if she really can plan this far ahead, why couldn't she just find a way to avoid the whole stupid situation? I always knew I'd die with a headache.
It doesn't help that some Sunday strips have suggested mad scientists may be able to see the future to a limited degree.
The scene taken from Sluggy Freelance to demonstrate speed chess is actually a poor example, being at best an aversion. Bun Bun is not actually manipulating events, he is simply moving dolls on a chessboard to reflect events outside his influence, a fact that enrages him when it's pointed out.
The Sixth Doctor is a pro at this in The 10 Doctors, where he repeatedly manipulates a group of Renegade Daleks to do his bidding — even when circumstances around him are rapidly changing.
In Associated Space, Fatebane's plan is constantly adjusting, due to the situation changing in almost every system he goes to.
Chessmaster goes insane (well, further insane) when he loses a literal game of this.
Subverted in Ayla 5, Ayla and the Networks, in the Whateley Universe. The bad guys TRY for this, but since they can't play NEARLY as well as each other, it comes down to 'Crap! When she did that, Plans A-J can't work, and now K-Y are useless...'
Meanwhile, Ayla and Thurban are working a Vizzini Gambit/Xanatos Gambit. They'd won the game before a piece was played. Ayla's Laptops is useless, and the blackmail information is false!
The Chessmaster does this in his massive Halloween attack. He even had a recovery plan that would have been perfect if the best precognitive on the planet hadn't chosen that very second to take over his communications system so he couldn't launch his recovery plan.
The villian in "The Big Idea" tries to play this, but needless to say, ends up failing miserably.
On Fairly Odd Parents, Norm the Genie's plans usually work like this: In "Fairy Idol", when he comes second to Cosmo and Wanda, he hits them with a wrecking ball and he gets in first.
Shockingly, Fry, from Futurama, pulls a simple version off in the fourth season episode "The Why of Fry." After his Scooty Puff, Jr. falls apart, he's trapped in The Infosphere with some gigantic brains that want to destroy the universe. Regardless, he activates a Quantum Interface Bomb, trapping himself and the brains in an alternate dimension. The brains inform him that the Nibblonians, who he was acting on behalf of, were actually responsible for getting him frozen until the year 3000 in the first place, and enable him to return to the past in order to prevent it from ever happening. Thus returning, Fry briefly interrogates Nibbler in Applied Cryogenics, and, after Nibbler explains the situation, Fry agrees to allow his past self to freeze. He begins to disappear, and realizes he's on the verge of creating a time loop. Showing uncharacteristically quick thinking, he then tells Nibbler "Just remember that the Scooty Puff, Jr. suuuucks!" It's simple, but for Fry's simple standards it was genius.
David Xanatos himself does this in the Gargoyles episode "Eye of the Beholder," as each of his plans to get the Eye of Odin back from Fox go awry. Goliath's responses to the gradual deterioration of his Machiavellian plots are utterly hilarious: "I hope you have a 'Plan D'" and "Not a good night for you"... though Xanatos actually does come up with a Plan D, and it's one of the last things you'd ever expect: telling the truth and asking Goliath and Elisa for help.
In "Upgrade" he and his wife Fox pit The Pack and the Manhattan clan against one another in a game of literal Xanatos Speed Chess, complete with an actual chessboard and pieces modeled after their respective teams.
Alluded to in Max Steel (which had the same developer as Gargoyles): Dragonelle was tasked with a mission, but the good guys manage to interfere and prevent their plan from being completely successful:
Dragonelle: Sir, I take personal responsibility for the failure of Chaos Strike.
Dread: Mmm, you're too hard on yourself, my dear. The great pyramid has been desecrated, and the explosion's left no evidence to trace the crime to us. Tensions in the region will rise, as planned. Besides, the test of the Dread probes was a qualified success, certainly more R&D is required. But I believe our ultimate victory is right at hand.
Nerissa from W.I.T.C.H. adjusts her season-long plan a few times, most notably in the season finale where she seizes an opportunity to free herself from The Starscream's imprisonment and get the heroes under her control, while congratulating herself on coming up with such a great plan on the fly. Too bad it's actually a Lotus-Eater Machine
The two-part My Little Pony: Friendship Is Magic episode "A Canterlot Wedding" features Queen Chrysalis, the ruler of a race of shapeshifters called Changelings that feed off of The Power of Love. Her evil plan is to disguise herself as Princess Cadance, marry the royal guard captain and Twilight's brother Shining Armor, and brainwash him into loving her, thereby not only providing a constant food source for her subjects, but also lowering Canterlot's defenses and paving the way for a full-scale invasion of Equestria. Twilight notices something amiss with the (fake) princess and calls her out on it? Chrysalis gets her kicked out of the wedding reception with a Wounded Gazelle Gambit and throws her in a dungeon while no one's looking. Twilight breaks out with the real Cadance and exposes the impostor to all, forcing her into a Beam-O-War with Princess Celestia? Chrysalis would be screwed, except she's absorbed enough love from Shining Armor to curb-stomp Celestia (keep in mind, even CHRYSALIS was surprised by the sheer POWER she had gained). Twilight and her friends seek out the Elements of Harmony to stop her? Chrysalis sends out a whole army of Changelings and captures them. Unfortunately for Chrysalis, this all leads up to a Near Villain Victory since she lets Cadance get close enough to Shining Armor to free him from his brainwashing and combine their powers to blast Chrysalis and all her subjects over the horizon.
The Flim Flam brothers pull off a simpler one in "Leap of Faith". When Applejack finds out that the miracle tonic that Granny Smith bought from them was a fake, they don't even panic, cunning convincing her not to reveal their secret as it would ruin the newfound confidence and happiness that Granny Smith has gained. They even capitalize on it when Applejack comments that the tonic 'seems to work for Granny' saying she approves it, causing everypony who trusts Applejack to continue buying it, while at the same time, striking a blow at Applejack's conscience.
The German strategist Helmuth von Moltke the Elder once said "No plan survives first contact with the enemy." This quote is usually used to mean that the victorious general is the one who is better at playing Xanatos Speed Chess. Molkte himself preferred being Crazy-Prepared. Plan A will not survive first contact, so develop a Plan B for every single point of failure, then a fallback Plan C, and then develop some excess capacity in case none of your fifty plans is working.
Arthur Wellesley, First Duke of Wellington:
"They planned their campaigns just as you might make a splendid piece of harness. It looks very well; and answers very well; until it gets broken; and then you are done for. Now I made my campaigns of ropes. If anything went wrong, I tied a knot; and went on."
Sun Tzu's The Art of War emphasizes the importance of adapting one's battle plans on the fly to adjust to sudden changes in battle.
"Those who win thanks to tactics adapted to different situations can be called Masters of War."
Dwight D. Eisenhower
"In preparing for battle I have always found that plans are useless, but planning is indispensable."
Mike Tyson Joe Louis, "Everyone has a plan until they get punched in the face."
Erwin Rommel, General in the Wehrmacht and the original Magnificent Bastard, built his entire career and reputation on this. If he was ordered to take an objective he wouldn't just launch an attack and take it. He'd launch an attack and take it, then plan another attack to exploit any weaknesses he'd created, then plan another attack to exploit any more weaknesses he'd created, and keep on inventing new attack plans on the fly until the other side surrendered or his side quite literally ran out of gas.
Rommel was not alone in this, as it was an integral part of Blitzkrieg as devised by Guderian and the German doctrine emphasized including subordinates into the plan so they could improvise on the spot or take over should you fall. This was a large part of German success on the tactical level. Of course there were Speed Chess players amongst other armies as well, but to the Germans it was an integrated part of their doctrine.
Most professional modern militaries use it these days: the standard format for issuing orders includes the larger context, why the orders are being issued and what the goal is. This allows junior officers (and troops) to be aware of the ultimate objective so that they can respond on the fly to changing conditions.
The Cuban Missile Crisis and the Cold War. Not just between the United States and the Union of Soviet Socialist Republics, but internally between the hardliners and moderates of each government. Adaptation is of the highest priority if "chess" here is more defined as "a Lensman Arms Race that involves getting nuked into oblivion for the littlest mistake."
It's unclear whether President Anwar Sadat of Egypt planned the October War of 1973 (known as the Yom Kippur War in Israel and many other places) as one of these, or if his actions afterward were just a very successful Indy Ploy, but either way, it turned out like this. The main Egyptian goal in '73 was recapturing the Sinai Peninsula (and, if possible, to destroy Israel), so Egypt launched an invasion across the Suez Canal on Yom Kippur, the one day when the Israelis with Infrared Missiles would be praying, fasting, and at services (Yom Kippur is the most significant Jewish 'holiday' as a day of repentance, remembrance, and introspection). This allowed Egyptian forces to retake a substantial proportion of the Sinai (until bad generalship screwed things up and allowed the IDF to push them back out), but the first few days were just enough of a victory that Sadat could claim just enough political capital to allow him to start peace negotiations with Israel...and get back the Sinai (if Israel and Egypt are at peace, Israel doesn't need the Sinai as a buffer). Whether he knew this all along or just took advantage of opportunities as they came up is unclear, but either way, it really was a win-win (until Sadat got an assassin's bullet to the head for his trouble...oh, well).
You might argue that he could have just asked for peace. That would be wrong. It's questionable whether the Israelis would have accepted a peace deal had he offered it—despite official policy statements, some members of the Cabinet (e.g. Defense Minister Moshe Dayan, who famously said "Israel has no foreign policy—only defense policy") might not have been so willing to take the deal. Even assuming that the Israelis' rhetoric matched their intentions, there's the matter of whether the Egyptians would have accepted a deal; the 1967 War was a humiliating defeat, and it would be difficult to sell a peace agreement to his people and even to the other generals who ran the government—it would be regarded as giving in to Israel's holding Sinai hostage. Starting a war with Israel in which Egypt won substantial military victories early on was necessary to show that Egypt and Israel were on an equal footing militarily, allowing any deal with Israel to be an agreement of equals rather than blackmail. Once the war started and the early victories assured, however, the path to securing Sinai was assured—either by military conquest (with the final peace treaty saleable because Egypt would be the victor) or by negotiation (as part of a negotiated settlement after an armistice seen as honorable because both sides had bloodied each other enough to show rough parity).
American Civil War general, George B. McClellan—subverted. He believed that victory went to the commander who outsmarted his enemy. McClellan was always trying to decide what old Lee would have done and then come up with a really elaborate counterstrike that would wreck his plans. But his methods led to a loss as to what the objective was, leading him to pass up opportunities where all that was needed was a direct attack following a plan no more complicated than "keep shooting until the other side is all dead".
William T. Sherman's march through Atlanta was an example of Xanatos Speed Chess. His adversary, Joseph Johnston, was the finest defensive general that the Confederacy could field. Rather than attacking him outright, Sherman adopted maneuver tactics. Johnston would set up a defense, and Sherman would go around him. The one major assault Sherman launched, the Union was driven back. In the end, he won the game—the Confederate government got fed up, replaced Johnston with John Bell Hood, a "fighting" general... and Sherman whipped him quite soundly.