A character has come up with a perfect plan to ensnare an opponent(s). Whether kind of plan it is this character's foe is surely doomed... But it backfires. That opponent has set up a plan of his/her own (whether before the first plan or in response). A superior plan, that makes the first character's plan look pathetic by comparison. In short, the first plan has been Out-Gambitted.
This trope specifically has three parts:
Alice makes Plan 1.
Bob either makes Plan 2 in response, or it turns out he already made Plan 2.
In Fullmetal Alchemist, Hohenheim manages to completely undo Father's transformation of everyone in Amestris into a philosopher's stone using a transmutation circle made from the shadow of the solar eclipse. And this was possible because Father's own Evil Plan required that solar eclipse. Furthermore, Hohenheim's allies undo the seal Father put on everyone else's alchemy by using Father's own transmutation circle.
Yu-Gi-Oh! is this trope. Every duel seems to boil down to "Who will Out-Gambit who?". All players use their cards and strategies, putting a gambits against enemies and sometimes two duelists can be Out-Gambitted multiple times in the same duel. Yami Yugi's duels are almost always about how his gambit destroys enemy's gambit.
Here's an example from 5D's done by Yusei. Yusei has on his field nothing except two face-down cards, against Greiger/Bommer's Flying Fortress SKYFIRE/Giant Bomber AIRRAID. If SKYFIRE's attack goes through, then Yusei will lose - and SKYFIRE allows Greiger to destroy a card on the field once per turn by discarding a card. Greiger decides not to destroy either one, speculating that it's actually a ploy to make him deplete his hand uselessly. It turns out he's right: the two cards are Wasteland Tornado and Limiter Break. If Wasteland Tornado was destroyed while set, Yusei would be able to destroy a face-up card - in this case, SKYFIRE. If Limiter Break is sent to the Graveyard, Yusei can Special Summon Speed Warrior to protect against SKYFIRE's attack. And since Greiger doesn't destroy either card, Yusei instead activates Wasteland Tornado to destroy his own Limiter Break and get Speed Warrior to intercept the attack.
Happens incredibly often in YuYu Hakusho. Technically Yusuke's death falls in this category; Jaki's attempt at turning Kuwabara to the Dark Side, possibly for a stronger host; Yusuke outwitting Goki (with little difficulty) and then later Hiei, back when they first met; Yusuke accidentally foiling Rando's plans by getting his ears clogged with algae; Kurama's fight with Roto; Kurama outwitting Kaito (although that was technically supposed to happen); Sensui and Toguro both getting their way despite the team's actions. Phew! Quite the list.
There's also the fight between Yusuke and Kibano. Who used a mask that shuts out the other senses to focus on sensing spirit energy and uses it to fight Yusuke in the dark. The mask however is also the reason Kibano was unable to see or smell the cigarette Yusuke puts on him to find him through the darkness.
Although Dio would've gotten Jotaro, who couldn't move as the result of stopping his own heart for too long. Jotaro was only saved because Polnareff took that opportunity to try and kill Dio, which gave Jotaro just enough time to recover.
Jotaro successfully Out-Gambitted D'Arby in their poker game, where the stakes were the souls of him, Joseph and Polnareff - the boy that Jotaro choose to give the cards was working for D'Arby, and gave Jotaro weak cards, but Jotaro refused to look at them, making D'Arby think that he had switched them, and adds too much to the stakes, with the possibility of losing would equal D'Arby's death, playing a Batman Gambit that made D'Arby break down.
Pretty much every fight in Jojo, considering that it's a series where intelligence goes far beyond strength, results in one of the fighters being Out-Gambitted.
This pretty much describes every match in Akagi; Akagi manipulates everyone around him (even people who are watching the entire Mahjong games from the outside) as they think they have him cornered.
Hunter × Hunter, during the hunter exams. Gon had a choice between two candles that he had to keep burning in a windy room longer than the villain's candle, he picks the long one (both are rigged to burn quickly) but because it burns so strong he is able to leave it unattended to run over and blow out the villain's candle.
How about a few minutes later with the room where they must leave two people behind or take the long road? (Explained: the team loses 50 hours in a gambling match just after the above example, so they have about 2 hours left, one route which only 3 of the five can travel down takes 5 minutes, the other route takes about 12 hours. The solution Gon sees is to chose the long route, then break down the wall to the short route, then sled down the hill on a door—they make it to the finish with less than a second to spare.)
Shikamaru Nara from Naruto pulls this off quite a lot. All of his battles involve him making his opponent so sure of their victory that they inevitably screw up and fall to his masterfully laid Batman Gambit.
In Death Note, this is how Near & Mello beat Light, although Light also seemed to have become stupider in the second season.
It's more that he stopped getting convenient strokes of luck, like getting an easily manipulated minion with the shinigami eyes right after L just so happened to reveal his identity to Light or just happening to be in the right place when Naomi drops by the police station with evidence that could get him arrested. Plus Light already had a tendency to make rash mistakes.
In Sailor Moon Stars, Sailors Uranus and Neptune, in the face of death, come up with a brilliant plan to escape: fake a Face Heel Turn (and even kill Sailors Pluto and Saturn to fool Galaxia), and right when Galaxia least expects it, do her in. However, it turns out that Galaxia had seen it coming, since she had already been Crazy-Prepared with immortality, and so she instantly destroys both Uranus and Neptune in front of Eternal Sailor Moon and the Sailor Starlights.
This is a mix of both this and Spanner in the Works, really. Galaxia had cast her starseed out long ago, but for an entirely different reason: To protect it from Chaos who was slowly possessing her after sealing it within herself. Once she cast it out to keep it safe from him, he fully takes her and turns her evil. While she was planning ahead, she wasn't expecting someone to try and take the starseed she no longer had. She was also taken off guard by the attempt because every other Senshi that wore her golden bracelets were under her control, unlike Uranus and Neptune; Galaxia herself admits so openly before killing the two. Had she not casted her Seed away, Uranus and Neptune would've won.
Also, like Uranus and Neptune before her, Moon pretends to pull off aFace Heel Turn in the first season, greatly risking her own life to try getting into the Dark Kingdom to rescue Mamoru. Kunzite, however, sees right through her and almost gets her killed.
Happened in Liar Game, where Akiyama was out-gambitted by Yokoya, who walked away with a huge amount of the winnings and left him in debt. However, Nao pointed out to Yokoya that even though he had won, he still lost the game, because he went back on his philosophy of complete dominance and instead turned to common cheating and stealing and three of his teammates had betrayed him.
In Bleach, Shinji explains his reversing ability to Aizen, but leaves out the fact that he can reverse each of the three dimensions individually. Just when Aizen has him "figured out" Shinji reverses only front and back, allowing Hitsugaya to stab Aizen from behind, which he never suspects because he's not reversed in the other two directions. Cut to Aizen revealing that he's been using Kyoka Suigetsu this whole time, and just made Hitsugaya stab Hinamori.
Aizen's on the receiving end of this trope several times during his end-game. The first and most obvious one is when Gin pulls a Starscream and tries to kill Aizen. Aizen has, of course, been expecting this all along, but Gin reveals he was the only shinigami that completely lied about how his powers worked while biding his time to figure out the weakness in Aizen's abilities. He proceeds to instantly kill Aizen with his Bankai's true power, making Aizen experience true fear for the first time in his life. Unfortunately, the Reality Warper grafted to Aizen's chest is able to save him and use that fear to help him evolve, but this means that Aizen's new form completely fails to adapt to Ichigo's Look What I Can Do Now power-up later. After Aizen's defeat, it turns out that Aizen was also Out-Gambitted by Urahara from the start; while Urahara outsmarted and nearly killed Aizen several times in their fight, Aizen walked away victorious but failed to notice it had all been an elaborate distraction for a seal to lock Aizen away when he inevitably grew too reliant on the Hogyouku and was rejected by it.
In the Bokurano anime, Koeyemshi is trying to get Kana to be the next pilot by putting mental pressure on her and threatening to force her brother Jun to do it instead if she refuses. However, Jun asks his friend Youko to help, and she stops Koeyemshi by shooting him to death.
The Washimine yakuza clan ended up with this in Black Lagoon.
To start, they attempted to make an alliance with Hotel Moscow, with hopes that they'll take care of their enemies. Hotel Moscow sends Balalaika and her Badass Army to help them. Her brutal tactics against Washimine's other Yakuza rivals quickly spiral out of control and the Washimine head attempts to assassinate Balalaika... Big mistake. The head got his neck snapped and with this Casus Belli in hand, Hotel Moscow allies with the rest of the Yakuza Council against Washimine and begins destroying them piecemeal.
Yukio, a high school girl and the lead's last relative, takes control over the clan and manages to restore some semblance of fighting strength and strikes back, taking out the local head of Hotel Moscow... Who was one of Balalaika's hated rivals. Since Balalaika's troops are made of former Soviet Airborne Troops who fought at Afghanistan and can start and win World War III, Balalaika quickly fights with much more cunning and brutality, which almost completely destroy Washimine...
Once this is done, Balalaika uses the guise of her new alliance to murder the heads of the entire rest of the council, throwing the entire Tokyo underworld into all-out chaos and giving Hotel Moscow carte blanche to move in and seize control. Which had been Balalaika's objective all along, and she outplayed at least three other factions in the process. Once she realized that Balalaika had won the war, and Yukio's bodyguard and most faitful supporter Ginji died in a duel with Revy, Yukio chose to commit suicide rather than giving Balalaika the ultimate laugh. It wasn't better that Washimine clan itself suffered a civil war between those who supported Yukio and those who supported Chaka, which finished when Chaka was brutally slain by Ginji for kidnapping Yukio, beating her bloody, and intending to sell her into sex slavery.
In the case of Neon Genesis Evangelion, we have numerous plots going along side-by-side. We have Seele who's trying to manipulate everyone into activating Instrumentality, we have Gendo trying to reunite with his wife Yui, the angels who plan on reuniting with Adam, and later Ritsuko who plots to kill Gendo and stop his plans due to how he used her. The one who emerges on top? Rei Ayanami, who undermines Gendo after he sees an end to both the Angel's plot (sort of) and Ritsuko's plot. However, it's debatable that Yui Ikari planned everything out from the very beginning in a huge plan, but that's up for debate. It's Eva, after all...
Zero's altercation with Mao (both times actually.)
Zero leading the Black Knights against Xing-ke. Once again Zero is Alice.
In Monster a hooker connects the dots and realizes that Johan Liebert has been committing a slew of murders for the past few years, so she attempts to blackmail him with this information. Johan had planned on this possibility and planted his hitman, Roberto, to act as her "boyfriend" days, maybe even weeks, ahead of time. It doesn't go well for her when she pulls a gun on Johan.
A masterful one happens in Puella Magi Madoka Magica. Madoka is in a tight spot since three Magical Girls (Mami, Sayaka and Kyouko) have died at different spots and only Homura is left to fight off Walpurgis Night, which will destroy the world if not stopped. Madoka can defeat Walpurgis if she makes a contract with Kyuubey and becomes a Magical Girl, but will end up turning into an even more powerful witch herself. In either event, the world will end and Kyuubey will harvest the witch's energy output. Faced with this situation, Madoka becomes a Magical Girl... but uses her wish to erase every witch from existence before they're born, including all witches born in the past and future, taking advantage of how Homura's time loops have actually let her get access to more and more raw magical power, thus Kyuubey is unable to deny her. This ends up altering reality and effectively rewriting the whole Magical Girl system so that magical girls will no longer turn into witches, leaving Kyuubey to gather energy from sources other than the broken dreams of young girls like Madoka and her "teammates".
Another one happens at the end of the sort-of prequel Puella Magi Oriko Magica. So Kyouko, Mami and Homura have managed to kill Witch!Kirika and corner Oriko, and Homura finishes her off via destroying her Soul Gem after Kyoko impales her with her spear? No, Oriko won't be stopped by that. She will use her last moments to take a shard of Kirika's witch body and shoot it out of the witch's barrier... and fulfill her original "mission": killing Madoka Kaname via getting her Impaled with Extreme Prejudice with that shard. Oy vey.
Kanba Takakura from Mawaru-Penguindrum. Several times. First his sister Masako kidnaps his brother Shouma and sets a Hostage Situation... to get a kiss from him, which she does. Later, when Himari dies for real, he fails to stop it... but Sanetoshi is able to do so, also roping Kanba in a Deal with the Devil. Which may be the same Deal with the Devil that Masako is implied to have taken for the sake of her brother Mario. This means, Kanba is out-gambitted by Masako, who then is "defeated" by Sanetoshi, and then Sanetoshi plays both of them like violins, or their precious siblings (Himari and Mario) will die again. Ultimately, Kanba is so involved in Sanetoshi's plot and so desperate to save Himari for real, that he ends up having a Face Heel Turn despite Shouma and Masako's pleas, and he can only get "free" of it via having himself Ret Goned (alongisde Shouma, who does it to save Ringo from dying to Screw Destiny) Phew!
Another time, Brian killed the last member of a species milking it for the XP bonus and argued his way into getting a relic since the god of this species wouldn't have left him unarmed. The relic gave him wishes which allowed him to wish for immortality using an elaborate ironclad runon sentence wish that he'd had reviewed by a paralegal in real life. BA had no way of squirming out of the contract (even with the help of multiple other game masters) but they eventually realized that, since Brian was no longer mortal, he could be assaulted directly by the aforementioned god of the relic. This activated a clause in Brian's wish that gave him absurd amounts of GP.
Doctor Strange and Doctor Doom: Triumph and Tormentis this trope. At the end of a rollercoaster of magical action, double-crossings, and double-double-crossings, the reader is left just as much in the dark as the viewpoint character of the book, Doctor Strange, whether everything went just as Doctor Doom planned or not..
This happened once in the Sleepwalker comics when the Kingpin was confronted with a rival crime boss named Crimewave, who was planning to usurp his position. The Kingpin's response was to manipulate Sleepwalker and Spider-Man into capturing Crimewave for him after luring Crimewave's disgruntled second-in-command into his service. Crimewave has never appeared again in large part because no writer has ever been interested in using him.
A young Imperial Naval gunnery officer named Garil Dox became an instant Rebel sympathizer when the Death Star destroyed his homeworld, Alderaan. Feeling that he could do more good from the bridge of the Imperial Star Destroyer Reprisal than if he jumped ship to seek out the Alliance, he waited until Darth Vader himself came aboard to oversee the capture of several Rebel groups by Commander Demmings. Knowing Vader's temper when it came to failure, each time the Reprisal closed in its target, Dox discreetly fired a killing shot despite orders to capture. Vader's anger rising, he ordered one last mission. They arrived at a remote planet with one small settlement on it that Vader claimed was a Rebel outpost. Once again, he ordered Demmings to neutralize the enemy without killing them, and Demmings ordered the best gunner, Dox, to make the shot. Dox annihilated the outpost and waited to see Demmings' summary execution, only to be arrested on the spot. Vader revealed his knowledge of Dox's plan to discredit Commander Demmings, a valued soldier of the Empire, along with preventing capture of Rebel operatives who could reveal damaging information about the Alliance. He then twisted the knife by telling Dox that the outpost that he had just destroyed was not a Rebel base at all, but a settlement of Alderaanian refugees. Dox then expects Vader to kill him, but the Dark Lord knows it's what he wants and orders him sent to an Imperial labor camp instead, where he can serve the Empire in a useful way via Fate Worse Than Death.
Spy vs. Spy, as demonstrated in the page image, was a comic consisting of the two spies Out Gambitting each other in ridiculous and amusing ways. It would almost universally end with one of them getting shot, blown up, or hit with something due to the other spy using their plan against them.
Jadina from Les Légendaires is able to outgambit the God of Evil Anathos during the Anathos Cycle in a quite impressive way: She first let her Dark Action Girl Tenebris get captured so she can lead the Castlewar, Anathos' mobile fortress, into an Ambush inside a Canyon. Anathos sees through the trap and replies by forcing Jadina's Legendaries to split up when they attempt to infiltrate the Castlewar and having them forced to fight against his Hellions while he gets Jadina for interrogation, as he deduced this infiltration attempt was a diversion for a bigger plan. Turns out he's right, but finds that out too late: the Legendaries are able to defeat their Hellion counterparts, and both them and Jadina are able to distract him long enough for the plan to works. The Elves then open several portails between the place and their world's sea, filling the Canyon with water and thus making the Castlewar's weaponry unfunctional while they attacks it with their ships. When Anathos tries riposting by sending his Vulturs attack the ships, the Pirahni and humans arrive with flying machines and rides, quickly destroying them. Even the other Legendaries are impressed to see Jadina planned this all along.
Rock And Roll High School marks possibly the only time where one gambit (Riff Randall waiting for three days to be first in line to get tickets to the Ramones concert and getting a hundred tickets for her friends and her music teacher) is Out Gambitted by another gambit (Mrs. Togar donating her ticket and her best friend's ticket to charity), which is then Out Gambitted by the Gambit Roulette that was Riff Randall's knowledge of the Ramones getting her and her best friend a free ticket each to the same concert. (Granted, neither party knew about the giveaway until Riff and her friend got the tickets from it.) Riff's words to Mrs. Togar? "Screw you, Mrs. Togar, we made it to the concert anyway!" And those words were broadcast over the radio, no less!
Batman Returns: The Penguin orchestrates a crime wave to make the people of Gotham lose faith in the current administration. He has one of his mooks abduct the Mayor's infant child in broad daylight, only to show up himself and "rescue" it. He wins over the people's sympathies with his pitiful life story. He frames Batman for murder, and uses a remote controlled Batmobile to cut a path of destruction, making it seem as if Batman had finally snapped. All to instigate a recall election and get himself elected Mayor. But he didn't count on the Goddamned Batman having a disk drive in his Cool Car to record the Penguin's rants and broadcast them at his next speech:
The Penguin: You gotta admit, I've played this stinking city like a harp from Hell!
Batman: The Movie features multiples layers of this. The Penguin dons a Paper-Thin Disguise and tries to convince Batman and Robin that he's Commodore Shmidlab. Batman and Robin take him to the Batcave so they can prove that he's the Penguin and arrest him—once inside the Batcave, Penguin re-hydrates the mooks he's carrying (don't ask) and orders them to attack, which was his plan all along. However, the tragic demise (again, don't ask) of these same mooks apparently convinces Batman that Penguin really is Commodore Schmidlab - but as Batman and Robin are escorting him out of the Batcave, Penguin gasses both of them and steals the Batmobile. As soon as Penguin is out of sight, Batman and Robin wake up (they were faking unconsciousness, having taken an anti-knockout gas pill beforehand) and follow the Batmobile's homing beacon right back to the Penguin's lair.
In Diggstown, Bruce Dern gets out-gambitted by James Woods in an overtly crooked boxing wager. Realizing that he'd been bested by a superior conman, Dern shrugs and says, "You beat me fair and square!"
Sands of Once upon a Time in Mexico wanted druglord Barillo and General Marquez killed after allowing them to kill the President of Mexico in exchange for a pile of money. He gets Out-Gambitted on both sides, first when the Mariachi and his crew decide to fight for the President instead of letting him die, and when Ajedrez, a key player in his scheme, turns out not only to be a mole for Barillo, but also his daughter.
The finale of Krystof Kieslowski's White is a beautiful example of this.
The finale of Hunting Humans is just one borderline ludicrous example of this after another. Let's see:
Serial Killer A goes to the home of the detective that Serial Killer B hired to keep tabs on him, and kills him. Serial Killer B (revealed to be the detective that Serial Killer A hired to keep an eye on Serial Killer B's detective) shows up to ambush him.
Serial Killer A reveals the detective isn't really dead, and that he hired him to his side.
Serial Killer B reveals that he knew Serial Killer A would try to bribe the detective to his side, so he offered him $5,000 on top of whatever Serial Killer A offered him to remain loyal.
Serial Killer A then reveals that he hacked into the detective's accounts and took all his money, and that the only way he can get it back is if Serial Killer A remains alive. After Serial Killer B kills the detective, Serial Killer A states he didn't take the money, he just made it look like he did.
Serial Killer A reveals he has an ally outside ready to snipe Serial Killer B at his command.
Serial Killer B manages to get outside, and into a wooded area, and when Serial Killer A follows him, Serial Killer B reveals that years of training have made him a fighting machine capable of countering everything that Serial Killer A throws at him.
Serial Killer A kills him using one of eighteen guns he had hidden in the forest, knowing the Serial Killer B would come to the detective's house, and that their battle might take them outside.
In Diamonds Are Forever, Shady Tree gets James Bond out of the retort with the intent to question him about where he hid the real diamonds. Neither he nor Morton Slumber counted on Bond having leverage against them to the tune of 50 grand (courtesy of Tiffany Case):
James Bond: You wouldn't burn up 50,000 real dollars, would you? [...] You bring me the real money, and I'll bring you the real diamonds.
The plotters in The Spanish Prisoner had a brilliantly detailed and multi-layered plan to get ahold of the process and leave Joe to take the fall. In the end the Feds were watching them the entire time and were just letting them proceed to gather evidence.
In Animorphs, Visser One's plan worked well. Tom's worked even better. Jake's worked best of all.
If you pay attention to the Man in Black's challenge, he says "Where is the poison? The contest ends when you choose and we drink." In other words, under the literal rules of the game, even if Vizzini had figured out they were both poisoned, he still would have drank and died. Unless he decided to Take a Third Option and NOT DRINK.
At one point when Vizzini is saying "you may be relying on your strength to save you", Westley looks concerned that he will indeed figure it out. Instead he goes off into various tangents, much to Westley's relief.
For example, Voldemort wants to kill Harry. Dumbledore guesses (and therefore knows) that if Harry dies at Voldemort's hand, then Harry'll just come right back to life, and Voldemort will be weaker. That was pretty much the plan for two books.
See also almost anything Dumbledore does, from leaving Harry at the Dursley's, to giving Hermione the time-turner, to going to the cave in book six, to trusting Snape and having him as the mole, to having Snape kill him.
Well-Intentioned Extremist King Pryderi of the Chronicles Of Prydain makes an alliance with resident Evil Overlord Arawn in an attempt to conquer Prydain and put an end to the infighting and bickering between lords that has long plagued his land. After he has conquered Prydain he planned to make Arawn into his servant by virtue of his superior army. Too bad for him, Arawn is well-known and feared for his evil trickery and, too late, the King realizes that the Death Lord has outmaneuvered him. Unsurprisingly, he doesn't live long after.
In Survivor's Quest, the Vagaari turn out to have a rather large gambit involving Obfuscating Fawning Idiocy. But, it's revealed, the Chiss planned for this all along, letting word leak out so that the Vagaari formed their plan in the first place, setting up safe spaces for their crew, inviting along Jedi and 501st stormtroopers and not letting the Vagaari see what they could do. All to make that nomadic people of slavers strike, satisfying the Chiss Martial Pacifism so that they could seek out and attack the Vagaari. After it's all over Mara Jade looks at that plan in disbelief, and says that Thrawn's fingerprints are all over it. But Thrawn is dead, and his clone was destroyed. Wasn't it?
In Isard's Revenge, Ysanne Isard neatly outgambits both the New Republic and her clone, who is aligned with a former Imperial warlord the New Republic is campaigning against. She builds a secret lab near one of the warlord's bases she knows the New Republic will attack, researching yet another Imperial superweapon. The New Republic instantly seizes on it as justification for their invasion, while the warlord protests that he had never heard of the lab until the New Republic "found" it, making both sides look worse due to the Golden Mean Fallacy. This leaves both sides nice and distracted so Isard can launch her real plan, stealing the newly-repaired Super Star Destroyer Lusankya from under the collective nose of the New Republic fleet. Unfortunately for her, two astromech droids managed to escape her clutches, allowing some pro-Republic smugglers and a New Republic Intelligence agent to set a trap for Isard to stroll right into.
The Lord of the Rings: Sauron, the guy who when taken prisoner by the Númenóreans was in control of them within a year, out-gambits almost everyone during the War of the Ring. He anticipates Saruman's betrayal and gives Denethor the right information to draw the wrong conclusions, but just as Gandalf planned, Sauron simply couldn't imagine that anyone would try and destroy the One Ring instead of claiming it for themselves.
This describes every single one of Zhou Yu's schemes against Zhuge Liang in Romance of the Three Kingdoms. Time and time again, Zhou Yu create schemes after schemes to kill Zhuge Liang. Zhuge easily saw through each one of them, making a fool out of Zhou Yu. In the end,he dies of illness and the reopening of an old wound, caused by the rage at Zhuge beating him time and again; knowing that he could never match Sleeping Dragon.
Done brilliantly in the ninth book of the Everworld series. Senna Wales, the witch who has been previously pulling all the strings and guiding the other characters along has the tables turned on her when her mother, Anica Wales makes a deal with Merlin to capture her. Their plan is to lure Senna out in the streets of Egypt at night, separating her from the others of the group who could potentially help her, forcing her to confront them alone, leaving her to face Merlin, a mage even stronger than she is and with a thousand years of experience, with Senna's mother there to lend her witch powers in case Merlin somehow fails while the entire city they're in is under the control of the Amazons, who are allied with Senna's mother. And just to make totally and completely sure that Senna has no escape and is caught like a rat in a trap, Merlin brings a dragon to the party for back-up. And then what happens? Senna, Magnificent Bastard that she is, instantly readjusts her plans, fools them both, uses Christopher as a decoy, tricks Merlin into wasting his magic, uses all of her powers as a witch and a gateway to their full extent, and she wins. The battle ends with Merlin exhausted and running in defeat, his dragon dead, the Amazons driven from Egypt with their queen no longer among the living, and Anica begging her daughter for forgiveness. Basically, Senna faced two mages who are Crazy-Prepared and vastly more experienced than herself, with no prior warning or prep time, and thwarted them. She's that good at Xanatos Speed Chess. After the confrontation is over, Senna is heavily exhausted by clearly enjoying the victory, and comments to Anica, "You underestimated me." If that isn't a Crowning Moment of Awesome for the whole book, or the entire series, it's pretty hard to imagine what is.
If you are a character in the Codex Alera, you should try to avoid going up against Gaius Sextus. Even if you seem to win against him, he's probably still using you somehow or other. Witness Lord Kalarus, whose plan to make himself a Load-Bearing Boss and blow up half the countryside was foiled by Gaius walking into the heart of his territory and detonating the volcano himself, or Lord Aquitaine, who almost got his wish to be First Lord when Sextus legally adopted him as secondborn to Tavi, leaving the country in the most capable hands possible between his death and his grandson's return.
One of the Gor books had a character warn the fellow kidnapping her that she planned to scream. He admitted that was an excellent plan. When she opened her mouth to scream, though, he stuffed in a wadded-up scarf, gagging her. "I, too, had a plan—a counter-plan. My plan, which I have now put into effect, was clearly superior to yours."
Almost a parody of the trope, and the simplest Xanatos Gambit on record: if she screams, he gags her and if she doesn't scream, he doesn't need to gag her.
The Big Bad of Raised by Wolves had a very simple plan: infect Chase with lycanthropy, then leave him in Stone River Pack's territory. Chase would be taken in by Stone River, where he'd make contact with Bryn- a former target who got away- and bring her back to him. Unfortunately for him, Callum, the pack's alpha, turned out to have precognitive abilities, a mastery of Xanatos Speed Chess, and a grudge against the Big Bad for what he did to Bryn.Didn't See That Coming.
It's common for someone be out-gambitted in Dan Brown novels.
Done brilliantly in The Thief. The Magus of Sounis frees Gen, a low-born thief who stupidly brags about his successes, from prison and forces him to steal Hamiathes' Gift so the king can use it to claim rightful rulership to the throne of neighboring kingdom Eddis. Except that he's been played since BEFORE the start of the book by Gen, or rather Eugenides, the Thief of Eddis and the Queen of Eddis' COUSIN, who knew that the Magus knew where Hamiathes' Gift was, pretended to be commoner of Sounis and purposely bragged about his skill to draw the Magus' attention so that he'd be hired to steal it, and once he did stole it a second time in such a way to make the Magus think he lost it, and finally returned it to his queen.
Minor example from Kitty and the Silver Bullet: Kitty, trying her hand at being a Chessmaster, tries to use Detective Hardin and the Denver PD as an Unwitting Pawn to take down Carl for her. Hardin turns it around by being fashionably late to the fight, thus making Kitty bait to trap Carl into an assault charge. They're on the same side, though, so it's all good. Bigger example from the same book: Rick's attempt to unseat Arturo is thwarted by Mercedes, with the help of a spy in his ranks. But then Arturo becomes the Spanner in the Works by opting for Redemption Equals Death, thus leaving Rick in control of Denver anyway.
Dune, being a millenial tale of galactic intrigue that accumulates Gambit Pileups like some books accumulate minor characters, has numerous examples of this trope.
In the first novel, the Emperor travels to Arrakis to "put down the Fremen rebellion" once and for all and to severely discipline the Harkonnens he was using as his tools. The Guild travels there to safeguard their precious Spice, having foreseen a crisis with their oracular powers. Paul Muad'dib, however, has become The Messiah possessed of far greater powers and takes advantage of having all his enemies together to pull a surprise attack that winds up with him dethroning the Emperor and taking his place.
Even earlier, the Atreides were themselves victim of this when they knowingly walked into the Harkonnen trap on Arrakis, counting on their superior training and potential alliance with the Fremen to see them through. What Leto failed to realize was that the Emperor was backing the Harkonnens and the sheer amount of money both were willing to spend to defeat him.
In Dune Messiah, the Bene Tleilax construct a complicated gambbit involving forcing Paul to discredit himself out of love for his consort, Chani. Paul, of course, has anticipated this, but it's the loyalty of the ghola Duncan Idaho, whom they were counting on to either kill Paul (forcing Alia to make the same choice) or recover his memories, showing Paul what could be achieved with Chani, that allows Paul to evade the trap.
In Children of Dune, Alia, now possessed by the Genetic Memory of Baron Harkonnen, plots to have Paul's children assassinated to cement her rule. Meanwhile, the Bene Gesserit are trying to manipulate the children into returning to their control. Leto II, however, by willingly embracing his father's messianic role, successfully discredits Alia and becomes the God Emperor.
The Mistborn trilogy is basically a Gambit Pileup by the end, so naturally a lot of people end up Out-Gambitted, In roughly chronological order Preservation outgambits Ruin, trapping him, then Ruin outgambits a lot of people by changing prophecies in order to try to get somebody to free him, then Kwaan and Rashek outgambit Ruin by figuring out his deception and killing Alendi so that Rashek can take the power of the Well of Ascension for himself, becoming the Lord Ruler, and stopping Ruin from getting out. Then Kelsier outgambits the Lord Ruler in order to kill him. Ruin outgambits everyone again to get Vin to go to the Well of Ascension and free him. After that it turns out that the Lord Ruler had prepared for the possibility of his death and Ruin's release and prepared storage places for people to hide to protect them, and hid the atium stockpile, which contained most of Ruin's power where Ruin couldn't get at it. Then it turns out that Preservation had planned for everything, in spite of having had most of his mind destroyed when he trapped Ruin thousands of years before, and he managed to get Elend and his army to destroy the atium stockpile, keeping the power away from Ruin, meanwhile he'd also arranged for Vin to take his power, and perform a Heroic Sacrifice to kill Ruin.. And really there are other examples, these are just the major ones.
In Freedom this turns out to be the case: The villains thought that they had finally managed to pull one up on Sobol and beat the Daemon. Turns out that he had expected someone would try to do so and had planned against it.
In War of the Dreaming, this happens to Azrael's plan to free mankind from tyranny by destroying the magical realm's power over them, carried out by a complex line of murder, betrayal, backstabbery, and replacing Congress with shapeshifting doppelgangers. The counter-gambit to this is set up by Prometheus, who outmaneuvers him simply by having a son whose descendents will interbreed with humanity and spread the ability to Screw Destiny at much less cost.
Black Arthur in The Demons Lexicon thinks he's been very clever indeed: he first managed to make a deal with a demon in return for unprecedented power by providing the demon with a human body that will not deteriorate - that of his infant son - and when that plan went awry thanks to the baby's mother running away with him, allowing him to grow up among humans as Nick Ryves with no memory of his true nature, he managed to lure Nick into a magic circle and trap him there, counting on Nick's demon nature and their original bargain to win out. Unfortunately, what Arthur didn't count on is that Nick's adopted brother Alan is a lot better at this than he is: most of the events of the book are part of Alan's plan to get Nick trapped in just such a magic circle, so that he could then set him free in a way that would ensure he could never be bound by another magician.
In Helm, Arthur de Noram is no match for the man he tried to conspire with, Siegfried Montrose.
In Courtship Rite: Joesai manan-Kaiel, by Storm Master Tonpa of the Mnankrei clan. Joesai has planned to make people think the Mnankrei are responsible for the Death Rite on Oelita the Gentle Heretic; when Tonpa realizes he's being framed, he not only comes up with a way to put the blame back on the Kaiel, but to make them take the blame for destroying the local grain store, which they had originally planned to make look like an accident.
Captain Dylan Hunt of the Andromeda has a knack for pulling this off, especially when dealing with the Nietscheans. The episode "Double Helix" in season 1 features multiple layers of outsmarting each other.
In Cheers Sam is often out-gambitted by rival bar owner Gary in the "Bar Wars" episodes. Other times it's the snooty owner of the restaurant upstairs, "Melville's".
The perps in Columbo usually think that their plans are pretty damn foolproof, actually, and that this shabby little detective has no chance of uncovering them. Unfortunately for them, Columbo has a tendency to prove them very wrong with his own cunning plans.
Any time on Doctor Who that someone tries to play the Daleks or Cybermen for personal gain.
In those cases they usually forget that the races in question have very straight-forward goals (exterminate everything and assimilate everything, respectively), and so are not as vulnerable to convoluted maneuvering from anyone who isn't The Doctor.
Inverted in "The Five Doctors", where the Master, knowing that the Cybermen will kill him once he has outlived his usefulness, leads them all into a death trap once they have outlived theirs.
People often forget that the main reason the Master always loses is that we mostly see him go up against the Doctor. His batting average against not-the-Doctor opponents is very good.
Also the Doctor Who spoof for Red Nose day (starring Rowan Atkinson as the Doctor) is practically the embodiment of this trope.
And in "The End of Time", The Master prepared for the possibility of his death, but his plan gets derailed when his widow reveals she's been making plans of her own. Not enough to stop him entirely, but it kind of ruins the man's day.
Also in "The End of Time", the Master summons Rassilon, leader of the Time Lord High Council, in a gambit to resurrect the Time Lords and turn them all into copies of himself. One hand motion by Rassilon and the smile is wiped off of the Master's face...
Not that Rassilon was ready for the Doctor *and* the Master's combined opposition.
Game of Thrones: Constantly. Almost every time someone engages in intrigue, or even a conversation. That's when things don't turn into a Gambit Pileup.
Really, everyone else in the cast to House. What's extra hilarious is that after their long diatribes informing him that he's miserable, his response is inevitably some version of "yes, I know".
Wilson is the only one who ever really matches House, in fact he pulls off one of these himself in "Safe" where House plays a series of practical jokes on him in the hopes of getting him to respond. Wilson stoically takes it all without complaint and House seems to give up, then at the very end of the episode House's cane snaps in two and he falls flat on his ass. Wilson deadpans that "someone" must have sawn halfway through his cane during the night.
You magnificent bitch. You just invoked the name of your dead girlfriend to play me? You're my hero. (From "Saviors", when House finally realizes Wilson's been screwing with him the entire episode.)
Epically done on an episode, in which both House and the audience are led to believe that the pranks are being played first by Foreman and his ex-con brother, in a bonding ritual, and then by Lucas, in an effort to force House and Wilson out of Cuddy's dream home. At the very end of the episode, after House declines to get revenge on whom he thinks is the prankster, Wilson simply says "I win."
A season six episode depicts Foreman observing Thirteen wearing a magnificent watch and Chase driving an awesome car that they felt like "treating themselves to." This leads Foreman to conclude that everyone else on the team is making more than him, despite his position as a senior fellow. When he goes to Cuddy and tries to bluff his way into raising his salary by threatening to leave for another hospital, the team starts to worry that Foreman might actually quit. When Foreman leaves for a job that doesn't exist, the team appeals to Cuddy to hire him back, saying it was all a ploy on their part to stop Foreman from acting like such an affected twit (The watch and the car were both borrowed from friends). After agreeing to bring Foreman back, reduce the team's salary, and add it to Foreman's, she tells them that she has no idea what they're talking about, and hasn't seen or spoken with Foreman in four days. Cue Foreman's appearance right outside Cuddy's office, smug smile and all.
Foreman: The phrase... Who's ya daddy?" comes to mind.
This occurs in the season 8 episode "Chase," surprisingly on House against Taub. Throughout most of the episode, House is constantly attempting to successfully ambush Taub, who's been taking self defense classes, and Taub is shown to be surprisingly adept at reacting to whatever House throws at him. He also reveals, however, that constantly being on guard against House's attacks forces him to try to think three steps ahead of House; in one scene, House assigns Taub to "obviously fraudulent lab work" so that he'd know exactly where Taub would be at the time so he could leap out and blast him with a squirt gun (and as a bonus, he'd get to watch Taub's paranoia at work beforehand, watching him look in all the wrong places for the oncoming attack.) After he leaps out and fires, however, it turns out Taub already rigged the squirt gun to misfire, and instead it squirts at House's own face.
Pretty much how the team beats the Villain of the Week in every episode of Leverage.
A season finale involves the team squaring off against their most dangerous opponent yet - the guy from the pilot who put the team together in the first place. He knows every single con they pull to the point of knowing exactly which algorithm Hardison will use to hack a hydroelectric plant's computer. Fortunately, the team realize this and get the help of several acquaintances (including Parker's aging Gentleman Thief mentor and Nate's ex-wife) and former opponents (The CrackerChaos and the bruiser who beat up Eliot in the first season). In the end, Nate has the two Big Bads cornered on a precipice with a gun pointing at them, choosing which one to kill. Then he sees his team and changes his mind. He leaves the gun at the edge of the precipice and walks away, knowing full well that the Big Bads would lunge for it and fall.
In Mad Men, Duck Phillips tries to leverage Don Draper out of his position at Sterling Cooper through a corporate buyout that would leave him as President and Draper's creative division nearly devastated. He does all this, since any contract Draper was working under would definitely have a clause restricting him from taking clients with him should he leave the firm. The hitch in Duck's plan? Don doesn't have a contract at all.
Happens to Jane in The Mentalist virtually every time Red John comes around, with Jane thinking he's playing Red John, while Red John is always playing him.
Probably the most notable example is in The Crimson Hat when Jane thinks he's tricked Red John and is going to meet him while in reality, Red John not only knows it's a trick and adjusts accordingly, but takes it a step further by setting up Wainwright as his stand-in to be ultimately shot and killed by the FBI.
In Noah's Arc, Guy has an elaborate plan to manipulate both Alex and Trey, involving staging random accidents that Guy can "fix", breaking down Alex's credibility in the eyes of Trey and Alex's friends, and a Wounded Gazelle Gambit. As complex as Guy's plan is, he's Out-Gambitted by Alex and his friends concocting a simple fake note, tricking Guy into revealing his feelings for Trey (who was never interested to begin with).
In the season 2 finale of The Sandbaggers, Burnside spends the entire episode maneuvering to convince Wellingham to appoint Peele as the head of SIS, as Gibbs, the other candidate for the job, is someone he has a long-standing rivalry with; he spies on Wellingham to find out what he wants and feeds the information to Peele, goes looking for skeletons in Gibbs' closet and tells Wellingham they're common office gossip, and so on. Then Peele writes a memo that clearly displays him to be unfit for the job, and Burnside has to go back to Wellingham and walk back everything he's said, and Wellingham reveals that he knew all along what Burnside was up to, had already made the decision to appoint Gibbs, and had maneuvered Peele into writing the memo in order to convince Burnside that he wasn't a suitable candidate.
Victoria Hardwick, one of Lex's early love interests in Smallville, persuaded him to help her father take over LuthorCorp. Lex suggested they take over both their fathers' companies together. She then stole information from him that Cadmus was a prosperous lab and that LuthorCorp had sunk all their money into a bid for the company, and arranged for Hardwick to outbid them. When she revealed this to him, he explained that the data was fake and Hardwick had bought a worthless company, leaving them financially vulnerable and allowing LuthorCorp to buy them in turn.
In the sixth season finale of Supernatural, Castiel and Crowley have a simple plan: open the door to Purgatory and harvest the power of all the souls within. Castiel (being the more powerful of the two) decides to cut Crowley out of the deal at the last minute, and take all the power for himself. Very quickly, this starts to look like a bad decision on Castiel's part, because Crowley immediately seeks out and 'defects' to Castiel's most powerful enemy: the Angel Raphael. Crowley offers Raphael the original deal and together, Raphiel and Crowley force Castiel to flee, leaving behind all the ingredients for the spell. - Unfortunately for Crowley and Raphael, Castiel wasn't taken by surprise at all. What he left behind include a *fake* version of one ingredient; something rare, hard to get, and crucial to the spell. He'd already hidden the real item away somewhere else. While Raphael and Crowley waste their time trying to cast a spell that can never work, Castiel is able to complete his work without threat or interruption. By the time he finishes, he's pretty much the most powerful being in the Supernatural universe. Only God, and probably Death, are stronger. Raphael doesn't fare very well after that.
Happens in Third Watch in the final season. A serial killer is playing games with two cops and won't tell them where his latest victim is hidden before she dies - he knows pretty much the exact hour this happens. However, he's willing to divulge her location after that hour. What the cops do? Since the perp has no way of knowing the time outside of the interrogation room, they switch the clocks.
The History Of The Devil: Lucifer is out-gambitted twice; once in a flashback by Jesus Christ, and again at the ending by the prosecution. His goal had been to reenter heaven by proving himself innocent of humanity's suffering. The prosecution acquits him on the caveat that he can never leave heaven again, knowing that heaven is utterly empty, having been abandoned by God and the other angels.
The final case of Apollo Justice Ace AttorneyKristoph Gavin set up a long Gambit involving poisoning a painter via postage stamp and his daughter via nail polish after using the two of them to take revenge on Phoenix. But, Phoenix Wright set up an even greater Gambit that overhauled the entire legal system of the country just to catch Kristoph.
Seeing as Ocelot's plan was to play the part of the villain and pretend to work for the Patriots in order to get Old Snake to fulfill his goal of taking them down... No. But Ocelot DID Out-Gambit the Patriots as part of that plan, so the game still falls under this trope.
Embarrassing photo used to instigate a blackmail scheme? Check. Allergy information to put a young boy in a dangerous situation? Check. Non-integral minions bribed into disloyalty? Check. Said young boy made angry enough to want to kill the blackmailer? Check-a-roony. Maderas' scheme to inherit the throne by killing Laharl was made one of these by Etna herself, and he never saw it coming up until it actually happened. Can we say "owned", boys and girls?
Seraph Lamington trumps that by a wide mile, by acting like a gullible fool around his right hand man, Archangel Vulcanus. Vulcanus believed Lamington was completely blind to his plan to conquer the Netherworld, Celestia, and the Human World, while it turned out Lamington was very aware of his schemes from the start, and in fact he was using Vulcanus' plan in order to lure Laharl and Flonne to Celestia so he could begin the last step in his own Gambit. Damn.
Although primarily designed to be humorous, Peasant's Quest falls into this trope when the expected victory scene is replaced with a short speech by Trogdor informing the player that despite having met all of the said conditions for vanquishing the dragon, he is invincible and cannot be killed. Fortunately, you get a statue built of you because you've come closer than anyone else!
In Command & ConquerTiberian Dawn, Kane spends most of the GDI campaign outmaneuvering you, using his control of the media to paint your organization as a bunch of murderers, until your funding gets slashed and your leaders are bogged down by inquiries and investigations. Then a few missions later your commanding officer returns to reveal that the entire thing was a ploy to lure Nod into making a hasty offensive, so not only are you able to counterattack, but a surge in GDI funding has led to new toys like Orca VTOL craft and Ion Cannons.
The Gambit Pileup of Chrono Cross occurs when two factions compete on manipulating entire civilizations (and one of fiction's greatest Unwitting Pawns) to further their schemes across time and space, little realizing that they themselves are being played by a Chessmaster who nobody had accounted for, despite making little effort to hide himself and even having exposition-heavy chats with the protagonist on several occasions.
The player's interaction with Drakuru in World of Warcraft becomes this. While he initially uses you as a pawn in his schemes to breach Drak'tharon Keep and enable the Scourge invasion of the Gun'drak zone, things change once you get there. He tries to turn you into a ghoul and make you into his right hand, but the Knights of the Ebon Blade fake the transformation and have you secretly sabotage all of his plans while pretending to serve him. Eventually you manage to turn his secret weapon against him and he asks the Lich King for help, who kills him. This turns out to be because Arthas is working on a gambit of his own, and you're more important to it than Drakuru.
The Game ModBlue Planet: War in Heaven for FreeSpace 2 has a magnificent example of this. Admiral Calder of the United Earth Federation thinks he's driven a Galactic Terran-Vasudan Alliance fleet into a trap by tricking Admiral Lopez of the GTVA into making rash actions to protect her ships. However, Lopez's entire fleet was nothing more than bait set out by Admiral Steele, the commander of all GTVA forces in the Sol system. He knew exactly what sort of gambit Calder would pull on Lopez, and when Calder's battered, exhausted force finally began to close the noose on Lopez's flagship GTD Carthage, Steele brings the GTD Imperieuse out of its Silent Running Mode in the Asteroid Belt—Calder thought he had left Sol system to resupply—and jumps out of subspace into the fray at the exact right location to start tearing Calder's ships to pieces with his main beam cannons from beyond the Earth ships' effective range. The "Tevs" lose a few small ships and a number of fighters, while the most elite task force in the entire United Earth Federation is almost completely destroyed save one ship in a matter of minutes. Also doubles as a Player Punch as the player is stationed on that one ship that makes it out alive only to emerge from subspace too close to the sun and doom the crew to an agonizing death...or so it seems.
In every Resident Evil game except 5, Wesker always wins. Everything is set up to rebound to his benefit, even if he takes a hit or two along the way. Until 5, the only character to hand Wesker a defeat of any kind is Ada Wong, who pulls off a successful doublecross at the end of Resident Evil 4.
In Sonic Adventure 2, Eggman pulls this on Sonic and Tails. Eggman kidnaps Amy, in order to get Sonic to give him the last Chaos Emerald. However, earlier, Tails made a fake, which would ultimately blow up the Eclipse Cannon. Sonic plans to exchange it for Amy, to kill "two birds with one stone". However, Eggman tricks Sonic into getting trapped in an escape pod rigged to explode. What follows can only be expressed in dialogue.
Eggman: You thought you could trick me with that fake Emerald?
Tails: So... How did you know it wasn't the real one?
Jade Empire: The plot is a series of these, each getting sprung on by the next gambit. The ending even comes down to which one ultimately pays off: Yours, now as the Villain Protagonist (the bad ending for everyone else), The Big Good's (good ending for everyone except the Big Bad), and The Big Bad's (bad ending for everyone except for the Big Bad).
In Batman Arkham City, Batman and Bane join forces to destroy all of the Titan drug in Arkham City. Bane actually wants it all for himself, and only worked with Batman because it would be easier to find everything this way. However, at the resolution of the quest, Batman reveals that he knew full well Bane's intentions and that he let Bane collect his half anyway so he could dispose of them in one go.
The Assassins Creed Revelations "Lost Archives" DLC reveals that Warren Vidic and Lucy were working together all along to use Desmond to obtain the Apple for the Templars. This plan would have gone without a hitch if it didn't run counter to the plans of Those Who Came Before. One of Those Who Came Before, Juno, was aware that Lucy had betrayed the Assassins. Juno had the Apple force Desmond to kill Lucy to keep the Apple out of Templar hands.
BlazBlue: Continuum Shift plays with this trope in Arcade mode - while in Story mode Yuuki Terumi's scheme comes to fruition with few flaws, he needed to view the entire Continuum Shift to do it, and two characters in Arcade mode came dangerously close to obliterating his plans. Both act on the exact same flaw - Terumi's dependence on the Sword of the Godslayer, Kusanagi, aka Noel Vermillion.
Rachel Alucard knew fully well that Terumi was on the hunt for Noel Vermillion, the "Eye of the Azure", and in her penultimate fight, she encounters the girl and fights her to help her understand just what she is and what she's capable of. Even though Rachel explained things quite clearly, Noel did not want to accept reality, and that left a window for Terumi to come in, grab her, and toss her into the cauldron for her scheduled smelting.
Makoto Nanaya, empowered by her knowledge of events in Slight Hope, cut right on through and disabled Tsubaki so she wouldn't try to kill Noel, and right after took Noel down to break her mindrape induced trance. Logic dictates that Terumi had no choice but to pull Noel out of Makoto's grasp at this time - Makoto knew full well what Noel was, had every intention of explaining herself to Noel, and Noel was more inclined to believe her close friend than the vampire in the poofy dress. The resulting battle between Makoto and Terumi saw the latter chomping at the bit to kill the "little bitch" once and for all.
The Illusive Man himself gets outwitted by the Reapers. Although he came really close to fulfilling his plans to control them and use them to take over the galaxy, he ultimately ends up indoctrinated from prolonged contact with Reaper technology.
Done masterfully by theAvatar in Fire Emblem: Awakening. Near the end of the game, the Big Bad, in his bid to release Grima, puts you into a situation where it appears you have killed the game's main character, as was foreshadowed in a dream sequence at the very beginning of the game. This leaves the villain with one hero dead, the other his puppet, and the legendary treasure in his possession... except that one of the parts of said treasure is actually a forgery, making it incomplete and thus insufficient for his plans, plus the Avatar purposely weakened their magic and faked their own possession BEFORE attacking Chrom to make it look like it had all played out like the dream. Cue Villainous Breakdown.
Starcraft and the expansion Brood War feature a massive Gambit Pileup, where Kerrigan ultimately Out Gambits everyone, kills most of the characters, and only spares those not worth it because mercy is worse. And then it's revealed that she was out gambitted by someone else.
In the Strong Bad e-mailstupid stuff, Strong Bad makes a bet with e-mailer Kevin Grumbles (Pronounced Kevin *grumbling noises*) that he can get Homestar to say something smart in order to win some "grumblecakes." Turns out that Homestar had made a bet with Kevin *grumbling noises* that he could make Strong Bad say something stupid (which he does in an attempt to make Homestar sound smarter) and claims the grumblecakes for himself!
Strong Bad: I'LL GET YOU, KEVIN *GRUMBLING NOISES*!!!!!
Quentyn himself has managed to do thise with a group of people who try to repossess half his home village (including his parents' farm): upon realizing that a covanent clause cannot be indefinite (if it doesn't specify the number of generations, it will only affect the immediate successor), he takes the quest specified in the contract—and the Archivist Guild can't do a thing about it.
Caliborn and Calliope in Homestuck. Calliope typically comes across as by far the smarter of the two, but unfortunately for her, Caliborn is really good at thinking outside the box. At one point, their relationship is reflected by a game of chess they're playing, and Calliope comments that Caliborn is playing really badly and wonders why he bothered pestering her into letting him switch the positions of his king and queen. A few turns later, he calls checkmate, and she thinks he's crazy... only for Caliborn to reveal that he hadn't switched their positions, he'd just made little hats that made his queen look like his king and vice-versa, and he hadn't technically made any illegal moves. Calliope, quite understandably, Rage Quits.
Whateley Universe: the Intelligence Cadet Corps puts a tracker on one of the Masterminds and figures out where their secret hideout is; but Stopwatch is way ahead of them, using a fake hideout and planting false clues in it, so when the Cadets search the hideout, they leap to the wrong conclusion about the intended heist.
In There Will Be Brawl, Ganondorf attempts to overthrow the Mushroom Kingdom by using the Butchers to create fear among the residents. Unfortunately, he also underestimates the amount of influence that Kirby still holds over them...
In "You Scratch My Back", Catwoman should have known better that to try and play Nightwing, Batman's protege. He has after all been taught by the best.
In an episode of Justice League, the Injustice League has captured Batman, and begins working on different ideas to tear the league apart to defeat them. What they don't realize before it's too late is that a) Batman's manipulating THEM into screwing up, and b) He can escape whenever he wanted.
Naturally, The Joker- the member who actually caught Batman for the team- is the only guy Except for the Ultra-Humanite who fully expects Batman to escape, and pleads for the right to kill him immediately. Lex Luthor doesn't listen, and the team listens to Lex, which means, of course, that The Joker was the Only Sane Man in that situation. The real man who Out-Gambitted the Injustice League, though, was the Ultra-Humanite, who had already agreed to help Batman out...in return for a generous donation in his name to his favourite public broadcast station.
Justice League Unlimited's third season revolves a great deal around the conflict between super villains Lex Luthor and Grodd. In their final confrontation, Luthor manipulates Grodd into using his own powers to destroy himself, resulting in this exchange:
Luthor: Goodbye, Grodd. It could have gone the other way. Grodd:: It really could have, couldn't it? Luthor: No. But why speak ill of the dead?
Also, Green Arrow versus The Question in the Gail Simone written Unlimited episode "Double Date". Arrow spots Question pocketing evidence, and confiscates a locker key. Once he's gone, Question then reveals that the key was a fake-out, and the real evidence he palmed was a shipping manifest. And then we find out that Arrow knew he was being conned, and hid outside so that he could follow Question when he chased up the real lead.
As is "super genius" Wile E. Coyote, at least in those shorts where he's pitted against arch Karmic TricksterBugs Bunny. (In the Road Runner shorts, he's not really outwitted so much as victimized by fate, gravity, poorly designed ACME products, and his own ineptitude.)
The theatrical compilation film 1001 Rabbit Tales starts with Bugs and Daffy as door-to-door booksellers. After they get out of the opening meeting with their boss at the publishing company, they take the elevator down. Daffy switches territories with the utterly apathetic Bugs about six times.
David Xanatos in episode 12, "Her Brother's Keeper". No, seriously. His plan is to woo Elisa's brother to his side, first taking advantage of the fact that she can't tell him about the gargoyles (and hence why she thinks Xanatos is an evil mastermind) and then tell him his own version to make sure not even their testimony will help anymore. He even orders Fox to tell Elisa this outright, because with her brother no longer believing her, it will do her no good. Except that it does, because she brought a tape recorder. Duh. This plan is hardly Xanatos's best anyway, since it involves setting hypercompetent killers on himself with serious lethal intent and real weapons.
Arguably, in that episode paid off; by the time Elisa got around to giving the recording to Derek, Derek had already decided not to listen to it. A better example of Xanatos being Out-Gambitted would be in "Double Jeopardy", in which Thailog plays Xanatos, Sevarius, and Goliath against each other.
Also notable in that he shows honest surprise and dismay as to the beast he's created, meanwhile in other so-called 'Xanatos loses' episodes he gains something and has a way out of jail or capture anyway.
In one American Dad episode, Steve's mildly retarded friend Barry turns out to be a criminal mastermind kept in check only by powerful anti-psychotic "vitamins". After he goes off them and causes havoc, Steve challenges him to a game involving two cups, one of which contains his medication. The scene that follows is a parody of the one from The Princess Bride, and naturally Steve put Barry's meds in both cups. Unlike Westley, however, Steve has no immunity to the meds..
In Teen Titans, Robin creates the identity of Red X so he can finally meet with Slade. Slade figures this out and not only does Robin only meet with a Sladebot, but this causes tension between him and his friends.
In My Little Pony: Friendship Is Magic Princess Celestia defeats Discord's efforts to keep the Elements of Harmony powerless by returning all of Twilight's friendship aesop letters, which convinces Twilight to fight for her bonds with her friends. Yes, Celestia outwitted a Reality Warper spirit of chaos by mailing a bunch of letters.
In Keep Calm and Flutter On, Discord tries to ensure his safety by driving a wedge between the Mane 6 and getting Fluttershy to promise never to use the Element of Kindness against him. However, Fluttershy knew this was happening and managed to reform him by threatening to withdraw the friendship she had been building with Discord throughout the episode.
In Generator Rex, all of the villains who spent the entire series scheming to obtain the Meta-Nanites, the keys to godhood, were outmaneuvered before the series even began. The Salazars — Cesar and his parents — had programmed the Meta-Nanites in such a way that only Rex could tap into their full power.
In Young Justice, this happens to the Light on a few occasions. Near the end of the first season, they try to use blackmail to get Artemis, Superboy and Ms. Martian to join them, but they defuse the blackmail by telling the other team members their secrets. Then they manage to create a cure and vaccine to the mind-controlling Starro-Tech, and catch the Light by surpise, allowing them to free the JL from the Light's control. Then, in season 2, not only does Aqualad get the Light and Reach to admit their actions, he also revealed how they had double-crossed each other at multiple points, utterly SHATTERING their alliance. These count as CMOAs especially the third, for Vandal Savage, a 50,000 year-old immortal himself says NO-ONE has EVER upset his plans like that in his entire life! THEN the Team shows up, and not only did the Light fall for Aqualad and Artemis's fake deaths, the Team managed to infiltrate the assassins and capture nearly half the Light!
One of the best examples was the Battle of Midway. The reason for the Japanese attack was to force the American carriers to come out to fight. By breaking the Japanese code, the Americans knew this and so were able to get their carriers in a position where they could catch the Japanese carriers by surprise.
The endgame of US-Iraq war. The United States wanted a government loyal to American interests that could be shown off as a secular-democratic state in a region marked by theocratic regimes and/or authoritarian states. Iran then set up a decade-long conflict to undermine the US effort in Iraq, forcing America to create a Shia-majority, non-secular government to achieve any sort of popular support or legitimacy, which is exactly the last thing that its Sunni allies wanted for a neighbor. Sure enough, the new Shia-majority government quickly fell under Iranian influence.