[[quoteright:273:[[ComicStrip/SpyVsSpy http://static.tvtropes.org/pmwiki/pub/images/Spy_Vs_Spy_Out_Gambitted_5539.jpg]]]]
[[caption-width-right:273:He's got him right where he wants him.]]
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->'''Vizzini:''' I switched glasses when your back was turned. Ha ha! YouFool! You fell victim to one of the classic blunders[...]never go in against a Sicilian when ''death'' is on the line!\\
''(Vizzini [[EvilLaugh laughs maniacally]] for a few seconds, then stops abruptly and falls over dead.)''\\
''[...]''\\
'''[[DamselInDistress Buttercup]]:''' And to think, all that time it was your cup that was poisoned.\\
'''The Man in Black''': [[TakeAThirdOption They were both poisoned.]] [[CrazyPrepared I spent the last few years]] building up [[AcquiredPoisonImmunity an immunity to iocane powder]].
-->--''Film/ThePrincessBride''

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 [[CrazyPrepared before]] the first plan or [[XanatosSpeedChess 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 A.
# Bob makes Plan B in response
# Plan A goes down in flames.

Or alternatively:

# Bob makes Plan B [[CrazyPrepared in anticipation of]] Alice making plan A.
# Alice makes Plan A
# Plan A goes down in flames.

Sometimes this situation is TheChessmaster vs. a superior Chessmaster, and sometimes it's [[SmugSnake somebody who only]] [[BigBadWannabe thinks he's the Chessmaster]] vs. [[MagnificentBastard someone who actually is]].

Compare SpannerInTheWorks (Alice is outdone by accident), KansasCityShuffle (Alice thought Bob was using a ''different'' Plan B), BigBadWannabe, GambitPileup, IKnowYouKnowIKnow, {{Touche}} (graciously admitting you were beaten), XanatosSpeedChess.

----
!!Examples:

[[foldercontrol]]

[[folder:Anime and Manga]]
* In ''Manga/FullmetalAlchemist'', [[spoiler: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 EvilPlan 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''.]]
* ''Anime/YuGiOh'' 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 ''[[Anime/YuGiOh5Ds 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 ''Manga/YuYuHakusho''. Technically Yusuke's [[spoiler:death]] falls in this category; Jaki's attempt at turning [[spoiler:Kuwabara]] to the DarkSide, possibly for a stronger host; Yusuke outwitting Goki (with little difficulty) and then later Hiei, back when they first met; 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. 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.
* Dio to Jotaro in ''Manga/JojosBizarreAdventure'':
** In part 3, Dio launched a barrage of knives against Jotaro, which made him fall quite a long distance. Knowing Jotaro was probably NotQuiteDead because NoOneCouldSurviveThat, he decided to [[DangerouslyGenreSavvy chop his head off with a Stop sign]]. Too bad that's just what Jotaro wanted, because he got a free hit while Dio was closing in. Later, Jotaro successfully OutGambitted D'Arby in their [[AbsurdlyHighStakesGame 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 BatmanGambit that made D'Arby break down.
** Every fight in ''Jojo'', considering that it's a series where intelligence goes far beyond strength, results in one of the fighters being OutGambitted.
** One of the earliest examples lies in part 1 when Dio planned to have Johnathan cut him in order to take hold and freeze him. Johnathan OutGambitted him by cutting him at an area with the tip of his sword at the torch that allows him to defrost himself.
** Joseph Joestar's epic chariot battle against Wham. Every tactic one fighter used was immediately countered by the other, with Joseph barely prevailing in the end.
* This describes every match in ''Manga/{{Akagi}}''; Akagi manipulates everyone around him (even people who are watching the entire TabletopGame/{{Mahjong}} games from the outside) as they think they have him cornered.
* ''Manga/HunterXHunter'':
** 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.
** Another test involves the room where they must leave two people behind or take the long road. 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 [[TakeAThirdOption solution]] Gon sees is to chose the long route, then [[CuttingTheKnot 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).
* ''Manga/{{Naruto}}'':
** Shikamaru Nara 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 BatmanGambit.
** Sasuke (take a deep breath) thought that Itachi killed his clan out of hatred but [[spoiler:he really did care about him because he was ordered to by the Konoha elder Danzo, who was than revealed to have been manipulated by Tobi who had also manipulated Pain into becoming evil. Sasuke was then manipulated by Orochimaru to steal his body, but Sasuke saw through this and was met up by Tobi who revealed that he was responsible for the Uchiha clan massacre by unleashing the Nine-taled Fox on Konoha, causing Sasuke to kill Danzo and then target Konoha, but then Kabuto blackmailed Tobi by resurrecting the real Madara whom Tobi had impersonated. Itachi was resurrected by Kabuto as well, but then he defeated him and sealed his own soul away, but then Madara revealed he had caused the death of Rin which caused Tobi to become evil as he was originally Obito and then tricked Tobi into restoring his natural body. Orochimaru, Sasuke, and Tobi (still struggling with the Black side of Zetsu) then try to help everyone else by defeating Madara. Black Zetsu is revealed to have the manifestation of Princess Kaguya who was the first human to use chakra whom Madara was descended from who in turn incapicates him]]. Whew.
* In ''Manga/DeathNote'', this is how [[spoiler:Near & Mello beat Light, although Light also seemed to have become [[ThirdActStupidity stupider in the second season]]]].
* In ''Anime/SailorMoon'', the title character [[FakeDefector pretends to pull off a]] FaceHeelTurn 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.
* This is how the main characters in ''VisualNovel/HigurashiNoNakuKoroNi'' finally [[spoiler: [[EarnYourHappyEnding win.]] Rika, using her GroundhogDayLoop induced prescience and the PowerOfFriendship, successfully outgambits the people trying to kill her.]]
* Happened in ''LiarGame'', where Akiyama was out-gambitted by [[MagnificentBastard Yokoya]], who walked away with a huge amount of the winnings and left him in debt. However, [[spoiler: Nao [[HannibalLecture 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 ''Manga/{{Bleach}}'', [[spoiler: [[CrouchingMoronHiddenBadass Shinji]] explains his reversing ability to [[MagnificentBastard 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 [[KnightTemplarBigBrother Hitsugaya]] to [[ItsPersonal 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 [[MasterOfIllusion Kyoka Suigetsu]] this whole time, and just made Hitsugaya [[IronicHell stab Hinamori]].]]
** [[spoiler: 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 RealityWarper 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 LookWhatICanDoNow power-up later. After Aizen's defeat, it turns out that Aizen was also OutGambitted 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[[note]]The kido that Urahara had hidden inside of another kido back in that fight? Turns out the hidden kido was itself a distraction, and had ''another kido hidden inside of it''.[[/note]] away when he inevitably grew too reliant on the Hogyouku and was rejected by it.]]
* In ''Manga/MahouSenseiNegima'', Negi out gambits [[spoiler: Kurt Godel]] by simply not revealing that [[DidntSeeThatComing he has an informant from the future]], which allows him to guess his rival's goals.
* In the ''Manga/{{Bokurano}}'' anime, [[spoiler: Koeyemshi]] is trying to get [[spoiler: Kana]] to be the next pilot by putting mental pressure on her and threatening to force [[spoiler: her brother Jun]] to do it instead if she refuses. However, [[spoiler: Jun]] asks [[spoiler: his friend Youko]] to help, and she stops [[spoiler: Koeyemshi]] by [[spoiler: shooting him to death.]]
* The Washimine yakuza clan ended up with this in ''Manga/BlackLagoon''.
** To start, they attempted to make an alliance with [[TheMafiya Hotel Moscow]], with hopes that they'll take care of their enemies. Hotel Moscow sends [[MagnificentBitch Balalaika]] and her BadassArmy 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 by Balalaika herself 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 [[ChronicBackstabbingDisorder 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 [[spoiler: Yukio's bodyguard and most faitful supporter Ginji died in a duel with Revy]], Yukio chose to [[spoiler: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 [[spoiler: Chaka was brutally slain by Ginji for kidnapping Yukio, beating her bloody, sexually humiliating her via [[ShamefulStrip stripping her almost naked]], intending to sell her into sex slavery ''and'' trying to use her as a human shield]].
* In the case of ''Anime/NeonGenesisEvangelion'', 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.
* ''Anime/CodeGeass'', a series that contains ''several'' {{Magnificent Bastard}}s and [[TheChessMaster Chess Masters]], frequently uses this throughout the series. Just a few at note include
** Zero's first battle with [[TheBaroness Princess Cornelia]]. With Zero playing the "Alice Role."
** Zero's altercation with Mao (both times actually.)
** Zero leading the Black Knights against Xing-ke. Once again Zero is Alice.
* In ''Manga/{{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 ''Anime/PuellaMagiMadokaMagica''. [[spoiler: Madoka is in a tight spot since three {{Magical Girl}}s (Mami, Sayaka and Kyouko) have died at different spots and only Homura is left to fight off [[TheEndOfTheWorldAsWeKnowIt Walpurgis Night]], which will destroy the world if not stopped. Madoka can defeat Walpurgis if she makes a contract with Kyuubey and becomes a MagicalGirl, but will end up turning into an even more powerful witch herself. In either event, the world will end and [[StarfishAlien Kyuubey]] will harvest the witch's energy output. Faced with this situation, Madoka becomes a MagicalGirl... but uses her wish ''to erase every witch from existence before they're born'', including all witches born in the past and future, and even including the witch that she would have become, 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 and she's able to make the system ''and'' Kyuubey her bitches. This ends up altering reality and effectively rewriting the whole MagicalGirl 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 ''Manga/PuellaMagiOrikoMagica''. [[spoiler: 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, [[PluckyGirl 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 ImpaledWithExtremePrejudice with that shard.]] Oy vey.
* [[spoiler: Kanba Takakura]] from ''Anime/MawaruPenguindrum''. [[spoiler: ''Several times'']]. First [[spoiler: his sister Masako kidnaps his brother Shouma and sets a HostageSituation... to get a kiss from him, which she does.]] Later, [[spoiler: when Himari dies for real, he fails to stop it... but Sanetoshi is able to do so, also roping Kanba in a DealWithTheDevil.]] Which actually is [[spoiler: the same DealWithTheDevil that ''Masako'' took for the sake of her brother Mario.]] This means, [[spoiler: 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, [[spoiler: Kanba is so involved in Sanetoshi's plot ''and'' so desperate to save Himari for real, that he ends up having a FaceHeelTurn despite Shouma and Masako's pleas, and he can only get "free" of it via having himself {{Ret Gone}}d (alongisde Shouma, who does it to save Ringo from dying to ScrewDestiny)]].
* Subverted in the DetectiveConan anime. [[spoiler: The AntiVillain Akemi Miyano met up with [[ThoseTwoBadGuys Gin and Vodka]], fellow members of the Black Organization, and told them they wouldn't kill her or they'd never know where she put the HUGE sum of money that she stole for them... but they shot her to death and took the key to the locker where she hid it. However, Akemi had the last laugh: said locker key was false, and she gave the real one to Conan (who had tried to disuade her from the robbery) before dying.]]
* ''Manga/OnePiece'': The Dressrosa arc amounts to a gigantic gambit pile-up between [[spoiler:Law and Doflamingo]]. Ultimately, the winner is [[spoiler:a third party -- the Straw Hats, who save Law (completely disregarding the fact that he ended their alliance in order to save them and kill Doflamingo, knowing full well he'd probably die in the process) and screw up Doflamingo's plan anyway. Considering their notorious reputation as a collective SpannerInTheWorks, ''nobody'' should've been surprised.]]
* The Buu Arc of ''Manga/DragonBall'' is full of gambits and plans that end up being nullified by even ''superior'' gambits and plans. Probably the ''worst'' example was when Super Buu demanded seeing the "Strong Fighter"/[[spoiler: Gotenks (Goten and Trunks fused together)]] he was promised by Goku, and in an effort to buy more time [[WhatTheHellHero Piccolo suggests that Buu amuse himself by terrorizing the people of Earth]], [[DeathIsCheap knowing they can be revived with the]] [[ResetButton Dragon Balls]]. Despite Majin Buu previous rampage there were still ''billions'' of humans left on earth so Piccolo thought that with that many humans left it would take Super Buu at least a few hours to fly across the world and terrorize every single one of them. [[spoiler: Super Buu instead [[KillEmAll kills every single human]], with the exception of Mr Satan, Tien, Chiaotzu and all those present on Kami's Lookout in only '''two minutes''' and ''never left Kami's Lookout while doing it.'' All of humanity had essentially become a sacrificial lamb for the sake of giving Goten and Trunks just two more of minutes of time to train]]. It's safe to say that Piccolo's plan of trying to outsmart Super Buu to gain more time backfired on him ''tremendously''. ''Every time'' the heroes would come up with a plan of defeating Super Buu, Super Buu would just out play them or out smart them. Another ingenious example would be when Piccolo destroyed the only exit of the Hyperbolic Time Chamber forever trapping himself, Gotenks and Super Buu in the Hyperbolic Time Chamber. What does Super Buu do? ''He rips a hole through dimensions by screaming'' and escapes the Hyperbolic Time Chamber leaving Gotenks and Piccolo trapped inside while he turns the rest of the Z-Fighters into candy and then eats them. Probably the only person who was ever able to out-gambit Super Buu was [[ShowyInvincibleHero Vegito]]. Who ''intentionally'' wanted to be absorbed by Super Buu and beat the shit out of him effortlessly to piss him off enough to make Super Buu desperate enough to absorb him. Super Buu instead ''[[BalefulPolymorph turns Vegito into a jawbreaker]]''. Vegito then uses his new form to '''kick Super Buu's ass'''. Vegito then points out that being turned into candy actually works as an advantage to him because he is extremely fast and far too small for Super Buu to hit and also retains all of his power because he so much stronger than Super Buu.
[[/folder]]

[[folder:Comic Books]]
* ''ComicStrip/KnightsOfTheDinnerTable'':
** RulesLawyer Brian exploits a [[TabletopGames hole in the rules]] that led them [[{{Gamebreaker}} to getting a cheese loop of money]]. GameMaster B.A. sets up (unbeneknownst to the players) an ingenious MassiveMultiplayerCrossover BatmanGambit which ended up with the players' {{Time Travel}}ing characters from a ScienceFiction MirrorUniverse destroying the loot they gained in their HeroicFantasy universe. So what do the players do? [[DidntSeeThatComing They have their time-travelling characters join up with their fantasy characters]] and use their superior technology to TakeOverTheWorld.
** 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 [[CrazyPrepared 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.
* ''Comicbook/DoctorStrange and SelfDemonstrating/DoctorDoom: Triumph and Torment'' '''is''' 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 [[TheChessmaster 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 Franchise/{{Spider-Man}} into capturing Crimewave for him after luring Crimewave's disgruntled [[TheDragon 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 [[Franchise/StarWars Imperial Naval]] gunnery officer named Garil Dox became an instant [[HeelFaceTurn 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 [[YouHaveFailedMe 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. [[TheChessmaster 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 [[MyGodWhatHaveIDone 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 FateWorseThanDeath.
* ''ComicStrip/SpyVsSpy'', as demonstrated in the page image, was a comic consisting of the two spies {{Out Gambitt|ed}}ing 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 [[ComicBook/{{LesLegendaires}} Les Légendaires]] is able to outgambit the GodOfEvil Anathos during the Anathos Cycle in a quite impressive way: [[spoiler:She first let her DarkActionGirl 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 [[ThePsychoRangers 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 [[AirborneMook 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.]]
* JusticeLeagueOfAmerica: Luthor's new [[LegionOfDoom Inustice League]] are using corporate tactics to weaken the JLA's power base before the full-scale attack. He thinks the League won't be prepared for this, but since Franchise/{{Batman}} also runs a multinational corporation, he recognizes the plans and turns them on Luthor by [[spoiler: having Green Arrow [[FakeDefector pretend to join them]] and giving [[OnlyInItForTheMoney Mirror Master]] a better offer.]] Later, both groups are both OutGambitted by TheJoker, who briefly gets his hands on the [[RealityWarper Philosopher's]] [[ArtifactOfDoom Stone]] and turns the world into a giant smiley face.
** Meanwhile in the same story, Metron leads Flash, Aquaman, and GreenLantern on a wild goose chase to find the philosopher's stone landing them in a Bad Future this version of Metron comes from where Darkseid has conquered Earth. They team up with the surviving leaguers, Batman beats Metron by challenging him to experience humanity and then knocking him out.
-->'''Metron''': This is absurd. Ceaseless particle motion? What am I meant to experience.
-->'''Batman''':This (knock out punch).
* ''Comicbook/OneHundredBullets'' is essentially nothing but a massive GambitPileup from beginning to end, but as it nears its conclusion it becomes clear that the plot revolves around a three-way war between the older [[AncientConspiracy Trust]] members led by [[BigBad Augustus Medici]], the younger Trust members, and [[CarnivalOfKillers the Minutemen]]. [[spoiler: In the final issues, one of the Younger Trust members hires an assassin to take out a key ally of the Minutemen and one of the most influential older Trust members, crippling Augustus's power base and forcing him to admit he's been OutGambitted by the new generation and resign from the Trust... only for the Minutemen's leader, Graves, to out-gambit ''them'' by resigning himself over their objections... only for the very last issue to reveal Augustus had OutGambitted ''everyone'', engineering everything up to and including ''his own out-gambitting'' so that everyone else involved in the war annihilates each other in the power vacuum resulting from his departure. He's entirely successful, too, though he doesn't live long enough to appreciate it, because the one thing he ''didn't'' count on was Graves [[EvenEvilHasStandards having more standards than he expected]].]]
[[/folder]]

[[folder:Film]]
* The ending of ''Film/DirtyRottenScoundrels'' [[spoiler:has both male leads be out gambitted by who they thought was their mark]].
* In ''Film/{{Spider-Man|Trilogy}} 3'', Spider-Man is framed for a bank robbery thanks to Eddie Brock Jr. As it turns out, there never was a bank robbery the day earlier, and Brock's plan to get the office job at the Daily Bugle would've succeeded if Peter Parker hadn't recognized the photo from a previous photo of Spider-Man returning stolen loot to the bank (not to mention that Peter Parker had [[BecauseImJonesy very good reason to be 100% certain that Spider-Man had never robbed any bank]]) and made sure Brock's scam was revealed to J. Jonah Jameson. In a later scene, [[ExposeTheVillainGetHisJob Parker takes Brock's place in the office]].
* ''Film/RockAndRollHighSchool'' 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 GambitRoulette that was Riff Randall's [[TakeAThirdOption knowledge of the Ramones]] getting her ''and'' her best friend a free ticket each to the same concert. Riff's words to Mrs. Togar? "Screw you, Mrs. Togar, we made it to the concert anyway!"
* ''Film/BatmanReturns'': 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 [[MemeticMutation Goddamned Batman]] having a disk drive in his CoolCar to record the Penguin's rants and [[EngineeredPublicConfession broadcast them at his next speech]]:
--> '''The Penguin:''' You gotta admit, I've played this stinking city like a harp from Hell!
** ''Film/BatmanTheMovie'' features multiples layers of this. The Penguin dons a PaperThinDisguise 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 ([[ItMakesSenseInContext don't ask]]) and orders them to attack, which was his plan all along. However, the tragic demise ([[ItMakesSenseInContext 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 ''Film/{{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 ''OnceUponATimeInMexico'' 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 OutGambitted on both sides, first when the Mariachi and his crew decide to fight for the President instead of letting him die, and when [[spoiler:Ajedrez, a key player in his scheme, turns out not only to be a mole for Barillo, but also his ''daughter'']].
* ''Film/WildThings'' essentially consists of this trope and FanService.
* 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 ''Film/DiamondsAreForever'', 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 ''Film/TheSpanishPrisoner'' had a multi-layered plan to get ahold of the process and leave Joe to take the fall. In the end [[spoiler:the Feds were watching them the entire time and were just letting them proceed to gather evidence]].
* ''Film/StarTrekIITheWrathOfKhan'': How Admiral Kirk was able to outwit Khan and escape from being marooned inside the Regula planetoid. Khan had left [[spoiler: Captain Terrell and Commander Chekov]] behind to spring a trap on Kirk, while Kirk was able to determine [[spoiler: exactly how long it would take to restore main power and rescue the landing party]], leading Khan to believe [[spoiler: it would take days instead of hours]]. Once the trap failed to kill Kirk, he [[LargeHam made damn sure to convince Khan of his helplessness]], counting on Khan to continue his pursuit of the ''Enterprise'' knowing that he could come back to finish Kirk at his leisure.
* ''Film/StarTrekIntoDarkness'': How Spock [[spoiler:defeats Khan, by allowing the latter to retrieve the armed torpedoes he thought contained his crewmates]].
* ''{{Film/Equilibrium}}''. DuPont uses John Preston as an UnwittingPawn in his scheme to expose the Resistance, but underestimates the latter's ability to strategically kill all of his mooks. Despite being the same person who decided to piss off a First Class Grammaton Cleric, who is a skilled master of plenty of deadly weapons and Gun Kata. Meaning he's made another fatal error where he specifically mentioned previously that someone who is a master of the latter ''is an adversary not to be taken lightly''.
[[/folder]]

[[folder:Literature]]
* In ''Literature/{{Animorphs}}'', Visser One's plan worked well. Tom's worked even better. Jake's worked best of all.
* Vizzini from ''Literature/ThePrincessBride'' is a very notable one.
** 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 TakeAThirdOption 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.
* The entire, seven book series of ''Literature/HarryPotter''. Voldemort makes Plan 1. Dumbledore, [[spoiler:along with Snape]], makes Plan 2. Voldemort goes down. For example, Voldemort wants to kill Harry. Dumbledore guesses (and therefore knows) that if Harry dies at Voldemort's hand, then [[spoiler: Harry will just come right back to life, and Voldemort will be weaker. That was 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, [[spoiler:to trusting Snape and having him as the mole, to having Snape kill him.]]
* WellIntentionedExtremist King Pryderi of the ''Literature/ChroniclesOfPrydain'' makes an [[DealWithTheDevil alliance]] with resident EvilOverlord 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 [[UnwittingPawn outmaneuvered him.]] Unsurprisingly, he doesn't live long after.
* In ''[[Literature/OutboundFlight Survivor's Quest]]'', the [[spoiler: Vagaari]] turn out to have a rather large gambit involving [[ObfuscatingStupidity Obfuscating Fawning Idiocy]]. But, it's revealed, the Chiss planned for this all along, letting word leak out so that the [[spoiler: Vagaari]] formed their plan in the first place, setting up safe spaces for their crew, inviting along Jedi and [[BadassCrew 501st stormtroopers]] and not letting the [[spoiler: Vagaari]] see what they could do. All to make that nomadic people of slavers strike, satisfying the Chiss [[MartialPacifist Martial Pacifism]] so that they could seek out and attack the [[spoiler: Vagaari]]. After it's all over Mara Jade looks at that plan in disbelief, and says that [[TheThrawnTrilogy Thrawn's]] fingerprints are all over it. But Thrawn is dead, and [[HandOfThrawn his clone was destroyed]].
** In ''[[Comicbook/XWingSeries 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 GoldenMeanFallacy. This leaves both sides nice and distracted so Isard can launch her real plan, [[spoiler: 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.]]
** At the climax of ''TheThrawnTrilogy'', the New Republic plans on striking at the Imperial shipyards at Bilbringi, [[KansasCityShuffle but try to play Thrawn by not-quite-as-secretly making plans for an attack at Tangrene]]. Thrawn sees through the Rebels' ruse and prepares accordingly, but gets surprised by the [[NeutralNoLonger Smugglers' Alliance]], who assumed that the New Republic ''was'' attacking Tangrene and planned their own strike at Bilbringi that just happened to coincide with the New Republic offensive. In other words, a cunning plan was defeated by a cunning-er plan [[SpannerInTheWorks but rescued by a]] ''[[GambitPileup botched]]'' [[GambitPileup plan]] - and even then it could've gone the Imperials' way were it not for a critical BodyguardBetrayal.
* ''Literature/TheLordOfTheRings'': [[TheChessmaster 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 [[TheStarscream Saruman]]'s betrayal and gives [[RegentForLife Denethor]] the right information to draw the wrong conclusions, but just as Gandalf planned, [[EvilCannotComprehendGood Sauron simply couldn't imagine]] that anyone would try and ''destroy'' the One Ring instead of claiming it for themselves. He's actually ''right'', except that he couldn't have foreseen Gollum destroying the ring ''by accident''.
* This describes every single one of Zhou Yu's schemes against Zhuge Liang in ''Literature/RomanceOfTheThreeKingdoms''. 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,[[spoiler: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 in the ninth book of the ''Literature/{{Everworld}}'' series. Senna Wales, the witch who has been previously [[TheChessmaster pulling all the strings]] and [[ManipulativeBastard guiding the other characters along]] has the tables turned on her when [[spoiler: her mother, Anica Wales]] makes a deal with Merlin to capture her. Their plan is to [[spoiler: 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 [[spoiler: 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 [[spoiler: 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, [[spoiler: Merlin brings a dragon to the party for back-up.]] And then [[spoiler:Senna, MagnificentBastard 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 CrazyPrepared and vastly more experienced than herself, with no prior warning or prep time, and thwarted them. ''She's that good at XanatosSpeedChess''.]] After the confrontation is over, [[spoiler: Senna]] is heavily exhausted by clearly enjoying the victory, and comments to [[spoiler: Anica]], "You underestimated me."
* If you are a character in the ''Literature/CodexAlera'', 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 [[spoiler:Lord Kalarus]], whose plan to make himself a LoadBearingBoss and blow up half the countryside was foiled by [[spoiler:Gaius walking into the heart of his territory and detonating the volcano himself]], or [[spoiler: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.]] Also, chronic traitor [[MeaningfulName Invidia]] eventually learns that, if you [[ChronicBackstabbingDisorder betray everyone you've ever worked with]], people ''will'' eventually notice. And when you try to do it again, [[spoiler:they'll leave you stranded in the woods. Naked.]]
* One of the ''Literature/{{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."
* The BigBad of ''Raised by Wolves'' had a very simple plan: [[spoiler: 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, [[spoiler: Callum, the pack's alpha, turned out to have precognitive abilities, a mastery of XanatosSpeedChess, and a grudge against the BigBad for what he did to Bryn.]] DidntSeeThatComing.
* It's common for someone be out-gambitted in DanBrown novels.
* Done in ''[[Literature/TheQueensThief The Thief]]''. The Magus of [[TheKingdom Sounis]] frees Gen, a low-born thief who stupidly brags about his successes, from prison and forces him to steal [[MacGuffin Hamiathes' Gift]] so the king can use it to claim rightful rulership to the throne of neighboring kingdom Eddis. [[spoiler:Except that he's been played since BEFORE the start of the book by Gen, or rather [[MagnificentBastard Eugenides]], the Thief of Eddis and the Queen of Eddis' COUSIN, who [[IKnowYouKnowIKnow knew that the Magus knew]] where Hamiathes' Gift was, [[ObfuscatingStupidity 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 ''[[KittyNorville Kitty and the Silver Bullet]]'': Kitty, trying her hand at being a Chessmaster, tries to [[spoiler: use Detective Hardin and the Denver PD as an UnwittingPawn 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: [[spoiler: Rick's attempt to unseat Arturo is thwarted by Mercedes, with the help of a spy in his ranks. But then Arturo becomes the SpannerInTheWorks by opting for RedemptionEqualsDeath, thus leaving Rick in control of Denver anyway.]]
* ''Literature/{{Dune}}'', being a millenial tale of galactic intrigue that accumulates [[GambitPileup 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 a MessianicArchetype 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 [[GrandTheftMe possessed]] by the GeneticMemory of Baron Harkonnen, plots to have Paul's children assassinated to [[RegentForLife 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 ''Literature/{{Mistborn|TheOriginalTrilogy}}'' trilogy is basically a GambitPileup by the end, so naturally a lot of people end up OutGambitted, In roughly chronological order [[spoiler: 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 HeroicSacrifice to kill Ruin.]]. And really there are other examples, these are just the major ones.
* In ''[[Literature/{{Daemon}} Freedom]]'' this turns out to be the case: [[spoiler: 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 ''Literature/WarOfTheDreaming'', 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 [[spoiler: Prometheus]], who outmaneuvers him simply by having a son [[HeroicLineage whose descendents]] will interbreed with humanity and spread the ability to ScrewDestiny at much less cost.
* Black Arthur in ''Literature/TheDemonsLexicon'' thinks he's been very clever indeed: he first managed to [[spoiler: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 [[spoiler: 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 [[spoiler:Nick's demon nature and their original bargain]] to win out. Unfortunately, what Arthur didn't count on is that [[spoiler:Nick's adopted brother Alan]] is a lot better at this than he is: most of the events of the book are [[spoiler: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 ''Literature/{{Helm}}'', [[spoiler:Arthur de Noram]] is no match for the man he tried to conspire with, [[spoiler:Siegfried Montrose]].
* Unsurprisingly, given its high concentration of [[TheChessmaster Chessmasters]] and {{Magnificent Bastard}}s, as well as [[BigBadWannabe those who aspire to be such]], this happens a lot in ''Literature/ASongOfIceAndFire''. In particular, pretty much everything that happens to [[SmugSnake Cersei Lannister]] in ''A Feast For Crows'' is this trope.
* In the historical novel ''Literature/WingsOfDawn'': [[spoiler: Waleran]], spokesperson for not using the same gambit all the time, even when it ''does'' seem to be working. %% This entry was added automatically by FELH2. In case the wording doesn't make sense, rewrite it as you like, remove this comment and tell this troper.
* ''[[Literature/TheMillenniumTrilogy The Girl Who Kicked The Hornets' Nest]]'' has an ''immensely'' satisfying occurrence of this against all the (many) people who have screwed over Lisbeth for all of her life.
* In ''Literature/CourtshipRite'': 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 [[spoiler:destroying the local grain store, which they had originally planned to make look like an accident.]]
* SergeyLukyanenko's ''Literature/NightWatch'' novels are made up of {{Gambit Pileup}}s by two [[TheArchmage Great Others]], the Light Geser and the Dark Zabulon. They've been doing this for decades. It helps that they're able to foresee the probabilities of future events very clearly.
* Lord Vetinari every Discworld book, to the point where he has prepared his own deepest dungeon for when he will be thrown in when he is overthrown.
[[/folder]]

[[folder:Live Action TV]]
* Captain Dylan Hunt of the ''Series/{{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 ''Series/{{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 ''Series/{{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.
* ''Series/CriminalMinds'': In the fourth season episode "Masterpiece", Creator/JasonAlexander plays a serial killer who confesses to [[TheChessmaster Agent Rossi]] that he's committed seven murders and is about to kill five more people, unless the BAU can find where he's hidden his victims. He does this as a massive TakeThat to Rossi himself, who [[MyNameIsInigoMontoya caught his serial-killer brother and watched as he was executed]]. It does not end well for him - Rossi lets him believe he's won, confess his entire scheme, and then reveals he's [[LyingToThePerp recorded the entire thing]]. And his team is fine, thank you very much, he knew the place was booby-trapped. This is why one [[PapaWolf does not threaten Rossi's "family"]].
** In the episode "Lessons Learned," Gideon tricks a terror suspect by altering his sense of time. Done more cleverly than most as he doesn't use a clock. Over a 48 hour period he slightly alters the man's prayer times. At the end they convince him the attack has already happened and get him to reveal the real target in time.
* Any time on ''Series/DoctorWho'' 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 [[YouHaveOutlivedYourUsefulness outlived his usefulness]], leads them all into a death trap once they have outlived theirs.
** 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", [[spoiler: 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).
* ''Series/GameOfThrones'': Constantly. Almost every time someone engages in intrigue, or even a conversation. That's when things don't turn into a GambitPileup.
* Many examples from ''Series/{{House}}''.
** Happens to Cuddy again and again every time she tries to play House.
-->(in response to her switching his painkillers with laxatives) ''I know when my Vicodin isn't Vicodin. [[OhCrap Do you know when your birth control pills aren't birth control pills]]?''
** 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 [[spoiler: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.)
** In another episode, both House and the audience are led to believe that the pranks are being played first by [[spoiler:Foreman and his ex-con brother, in a bonding ritual,]] and then by [[spoiler: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 [[DrJerk 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. [[MagnificentBastard 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 ''Series/{{Leverage}}''.
** A season finale involves the team squaring off against their most dangerous opponent yet - [[spoiler: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 GentlemanThief mentor and Nate's ex-wife) and former opponents (TheCracker [[Creator/WilWheaton Chaos]] and the bruiser who beat up Eliot in the first season). In the end, Nate has the two {{Big Bad}}s cornered on a precipice with a gun pointing at them, choosing which one to kill. Then he sees his team and changes his mind. [[spoiler:He leaves the gun at the edge of the precipice and walks away, knowing full well that the {{Big Bad}}s would lunge for it and fall]].
* In ''Series/MadMen'', Duck Phillips tries to leverage [[MagnificentBastard 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 ''Series/TheMentalist'' 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 [[spoiler: setting up Wainwright as his stand-in to be ultimately shot and killed by the FBI]].
* In ''NoahsArc'', [[spoiler: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 WoundedGazelleGambit. As complex as Guy's plan is, he's OutGambitted 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 ''TheSandbaggers'', 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 ''Series/{{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.
** [[BadassNormal Tess]] manages to outgambit (the AlternateUniverse version of) her own father, Lionel Luthor, who is the [[TropeCodifier epitome of]] MagnificentBastard, after he usurps control of [=LuthorCorp=] from her. He really should have known better than to underestimate [[InTheBlood his own daughter]], even if the version of her from his universe is a BastardBastard who doesn't meet any of his expectations. He honestly seems a mix between shocked, furious, and [[YourApprovalFillsMeWithShame impressed]].
* In the sixth season finale of ''Series/{{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 {{Archangel 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.
** Anytime anyone is up against Crowley it's one bit game of who can out gambit who.
** All the Winchesters have managed to successfully pull this on occasion. Henry, John and Sam are all pretty good, but the really master has to be Dean. More often than not, Dean manages to defeat what ever being of much greater strength, power or intelligence (or all three) he is up against, but making them think they are winning. 9/10 if Dean is surrendering, losing his cool and acting irrationally or seemingly being defeated badly, your five seconds away from him defeating them in one big master stroke.
* Happens in ''ThirdWatch'' 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.
* In the third season finale of ''Series/{{Sherlock}}'', Sherlock Holmes himself is the recipient of this trope, at the hands of "[[CorruptCorporateExecutive the Emperor of Blackmail]]," [[BigBad Charles Augustus Magnussen]]. Holmes has made a DealWithTheDevil to take Magnussen down - in exchange for Magnussen's blackmail materials, especially those related to [[spoiler: Mary Watson's bloody past as a CIA agent]], Magnussen will receive Mycroft's laptop, which contains valuable UsefulNotes/MI6 secrets. Magnussen agrees to the deal and flies Holmes and Watson to his island mansion, where he reveals that [[spoiler: there ''never were'' any blackmail materials - Magnussen's memory is just so good that he can remember every incriminating detail he's ever learned about everyone he's ever met. And he's already called [=MI6=] to arrest Holmes and Watson for selling state secrets]]. Holmes is so [[HeroicBSOD utterly dumbfounded]] at being gotten the better of that to prevent the villain from getting away with his crimes and save Watson from Death Row, he decides to [[spoiler: [[VigilanteExecution kill Magnussen himself]] and surrender to government custody]].
[[/folder]]

[[folder:Theatre]]
* ''Film/DirtyRottenScoundrels'' (TheMusical)
-->'''Freddy:''' That [[HypocriticalHumor lousy, stinking, lying, cheating, totally dishonest, dirty, rotten-]]
-->'''Lawrence:''' Yes Freddy, isn't [[spoiler: [[SamusIsAGirl she]] ]] wonderful!
* ''Theatre/TheHistoryOfTheDevil'': Lucifer is out-gambitted twice; once in a flashback by [[spoiler: Jesus Christ]], and [[spoiler: again at the ending by the prosecution]]. His goal had been to reenter heaven by proving himself innocent of humanity's suffering. [[spoiler: 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.]]
* Richard of ''Theatre/ThrillMe'' plans the perfect crime, and Nathan acts as his accomplice because Nathan is better at details. However, Nathan wants them to get caught. And he's...better at details. Nathan leaves evidence kind of everywhere.
[[/folder]]

[[folder:Video Games]]
* The final case of ''VisualNovel/ApolloJusticeAceAttorney'' [[spoiler:Kristoph Gavin set up a long Gambit involving poisoning a painter via postage stamp and his daughter via nail polish [[YouHaveOutlivedYourUsefulness after using the two of them]] to [[DisproportionateRetribution 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.]]
** This also happens in case 4 of ''VisualNovel/PhoenixWrightAceAttorneyDualDestinies'' to [[spoiler:Yuri Cosmos, who was given a bomb threat by the Phantom to stop the HAT-2 launch. When the government wouldn't cancel the launch, Yuri took matters into his own hands by switching Launch Pad 1 with the Space Museum (formerly Launch Pad 2) and having Clay Terran drug Sol Starbuck with his own anxiety pills to keep him none the wiser. However, the Phantom wiretapped his phone and used this information to kill Clay and escape.]]
* ''Franchise/{{Disgaea}}'':
** From an embarrassing photo used to instigate a blackmail scheme, to allergy information to put a young boy in a dangerous situation, to non-integral minions bribed into disloyalty, to said young boy made angry enough to want to kill the blackmailer, 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.
** [[TheChessmaster Seraph Lamington]] does the same by [[ObfuscatingStupidity acting like a gullible fool]] around his right hand man, [[BigBad 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.
* Although primarily designed to be humorous, ''VideoGame/PeasantsQuest'' falls into this trope when the expected victory scene is replaced with [[spoiler: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 ''VideoGame/CommandAndConquer [[VideoGame/CommandAndConquerTiberianDawn Tiberian Dawn]]'', Kane spends most of the GDI campaign outmaneuvering you, using his [[VillainWithGoodPublicity 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 [[KillSat Ion Cannons]].
** In the ''[[VideoGame/CommandAndConquerTiberiumWars Tiberium Wars]]'' expansion ''Kane's Wrath'', Kane [[MagnificentBastard (of all people)]] manages to be outfoxed by [[spoiler: Alexa Kovacs]]'s FalseFlagOperation. It's the only time in the series we've seen him ''speechless''.
* The GambitPileup of ''VideoGame/ChronoCross'' occurs when two factions compete on manipulating entire civilizations (and one of fiction's greatest {{Unwitting Pawn}}s) 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 ''VideoGame/WorldOfWarcraft'' 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 [[TheDragon right hand]], but the [[DarkIsNotEvil 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. [[spoiler: 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 GameMod ''Blue Planet: War in Heaven'' for ''[[FreeSpace 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 [[MagnificentBastard 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 [[HopeSpot finally began to close the noose]] on Lopez's flagship GTD ''Carthage'', Steele brings the GTD ''Imperieuse'' out of its SilentRunningMode in the Asteroid Belt--Calder thought he had left Sol system to resupply--and jumps out of [[SubspaceOrHyperspace subspace]] into the fray at the exact right location to start tearing Calder's ships to pieces with his main [[WaveMotionGun 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 PlayerPunch as the player is stationed on that one ship that makes it out alive [[spoiler:only to emerge from subspace too close to the sun and doom the crew to an agonizing death...[[CliffHanger or so it seems]].]]
* In every ''Franchise/ResidentEvil'' game except ''[[VideoGame/ResidentEvil5 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 ''VideoGame/ResidentEvil4''.
* ''VideoGame/GoldenSun''. [[spoiler:Alex [[TheChessmaster Chessmasters]] his way to attaining the ultimate power of the Golden Sun, only to find that [[DungeonMaster The Wise One]] had [[GambitRoulette foreseen the possibility of this happening]] and arranged events at the beginning of the first game such that Alex would be screwed over at the last possible second of the second game.]] Ouch.
* In ''VideoGame/SonicAdventure2'', 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 [[KillSat 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?
--> '''Eggman''': [[Awesome/SonicAdventure2 Because You Just Told Me, Fox Boy!]]
* ''VideoGame/JadeEmpire'': 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:[[spoiler: Yours, now as the VillainProtagonist (the bad ending for everyone else), The BigGood's (good ending for everyone except the BigBad), and The Big Bad's (bad ending for everyone except for the BigBad).]]
* In ''VideoGame/BatmanArkhamCity'', Batman and Bane join forces to destroy all of the [[PsychoSerum Titan drug]] in Arkham City. [[spoiler: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 ''VideoGame/AssassinsCreedRevelations'' "Lost Archives" DLC reveals that [[spoiler: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 [[spoiler: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.]]
* ''VideoGame/BlazBlueContinuumShift'' 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[[spoiler:, aka Noel Vermillion]].
** [[spoiler: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.]]
** [[spoiler: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. [[FridgeBrilliance 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 [[ChewingTheScenery saw the latter chomping at the bit]] to kill the "little bitch" once and for all.]]
* ''Franchise/MassEffect'': Despite their efforts to prevent it, Aria, Liara, the Shadow Broker, and the various merc groups on Omega ''all'' get OutGambitted by [[MagnificentBastard the Illusive Man]] and [[NGOSuperpower Cerberus]] in between the events of ''VideoGame/MassEffect2'' and ''VideoGame/MassEffect3''.
** [[spoiler: The Illusive Man himself gets [[EvilIsNotAToy outwitted]] by the [[EldritchAbomination 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 [[BrainwashedAndCrazy indoctrinated]] from prolonged contact with Reaper technology.]]
* Done masterfully by [[TheStrategist the]] [[PlayerCharacter Avatar]] in ''VideoGame/FireEmblemAwakening''. Near the end of the game, [[spoiler:the BigBad, in his bid to release [[BiggerBad 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 [[TheHero Chrom]] to make it ''look'' like it had all played out like the dream. Cue VillainousBreakdown.]]
** [[spoiler: Then the [[BiggerBad Hierophant,]] who is [[TheReveal the Grima from the Bad Future,]] jumps into the Awakening ritual, using his own power to resurrect the present Grima, effectively completing the plan and out gambitting the Avatar at the same time.]]
* ''VideoGame/{{Starcraft}}'' and the expansion ''Brood War'' feature a massive GambitPileup, where Kerrigan ultimately Out Gambits everyone, kills most of the characters, and only spares those [[NotWorthKilling not worth it]] because [[CruelMercy mercy is worse]]. [[spoiler:And then it's revealed that she was out gambitted by someone else.]]
* Given that ''VideoGame/TheWitcher2AssassinsOfKings'' has a massive GambitPileup, this trope is in full effect as {{Chessmaster}}s are pitted against each other - however, [[spoiler: the winner being ''[[ObfuscatingStupidity Letho]]'' came out of left field for most players, albeit at the behest of the Emperor of Nilfgaard]].
* [[SoulNomadAndTheWorldEaters Thuris]] is said to be the smartest of the three world eaters. While he DOES do some pretty creative things with the fact that [[AGodAmI most people can't see him]], he's simply playing against several other, much better, chess masters. [[InformedAbility Including one of the other world eaters]].
* It occurs often in ''VideoGame/TearsToTiara2'' as two very capable commanders duke it out. Worth mentioning is that quite a few of [[TheHero Hamil's]] plans seems to be very accurately predicted by Izebel, who counters it handily and makes life very hard. She actually knew exactly what he's going to do because [[spoiler: he told her before his memories were wiped and stashed away. When he finally defeats her, it was with a plan that she had insisted he not tell her.]][[/folder]]

[[folder:Web Animation]]
* In the [[WebAnimation/HomestarRunner Strong Bad e-mail]] [[http://www.homestarrunner.com/sbemail98.html stupid stuff]], Strong Bad makes a bet with e-mailer Kevin Grumbles ([[InsistentTerminology 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*!!!!!'''
[[/folder]]

[[folder:Web Comics]]
* In ''Webcomic/ComingUpViolet'', [[AlphaBitch Racquel]] gives [[TheChessmaster Abby]] two cups of punch, one for Abby and one for Violet. Violet's cup is spiked so that Racquel can humiliate her. Abby swaps the cups so Racquel is [[HoistByHisOwnPetard drinking her own punch,]] since Abby wants to be rid of Racquel.
* In ''Webcomic/TalesOfTheQuestor'', the fae princeling Dolan had set up a gambit both to shaft the human Duke, after DECADES of extortion, into releasing the Wild Hunt, and another to raise the princeling's own status in the Unseleighe Court and to debase a family enemy from the Seleighe court by forcing his enemy's daughter, Lady Absinthe, to ride the wild hunt for him. This led to the whole thing rather famously [[http://www.rhjunior.com/totq/00524.html blowing up in his face]].... with good evidence that Lady Absinthe [[http://www.rhjunior.com/totq/00517.html had known the score all along and had helped set Dolan up for his fall.]]
** Quentyn himself managed to do this with a group of people who tried to repossess half his home village, including his parents' farm: upon realizing that the covenant clause the group used to pin the debt on him, specifically, fails to specify the number of successors beholden to the debt (which by racconan law, it must or be limited to a single generation), he takes the quest specified in the contract, saving the village and ending the matter with him--and no one can do a thing about it.
* ''Webcomic/{{Chainsawsuit}}'' [[http://chainsawsuit.com/2009/01/12/strip-144/ presents]]: double sting. ''Series/{{Dateline}}'' tries To Catch A Predator. Meanwhile, a fan tries to see live Stone Phillips.
* The basis of [[http://www.penny-arcade.com/comic/2009/08/31/iteration this]] ''Webcomic/PennyArcade'' strip.
* [[http://exterminatusnow.co.uk/2012-05-20/comic/the-bookend-of-unimaginable-power/karma-chameleon/ This]] exchange between TheDragon and the BigBad leader of a cult dedicated to the god of ChronicBackstabbingDisorder in ''Webcomic/ExterminatusNow''.
* Caliborn and Calliope in ''WebComic/{{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 [[ChessMotifs 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 ''[[RulesLawyer technically]]'' made any illegal moves. Calliope, quite understandably, {{Rage Quit}}s.
** More importantly, he short-circuits most of her plans instantly by just [[spoiler:[[MurderIsTheBestSolution having her dreamself assassinated]] before their session even starts]].
[[/folder]]

[[folder:Web Original]]
* Literature/WhateleyUniverse: 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 ''WebVideo/ThereWillBeBrawl'', [[spoiler: Ganondorf]] attempts to overthrow the Mushroom Kingdom by using [[spoiler: the Butchers]] to create fear among the residents. Unfortunately, he also underestimates the amount of influence that [[spoiler: Kirby still holds over them...]]
* In ''Literature/{{Worm}}'', [[spoiler:Tattletale and Skitter]] outmaneuver [[spoiler:Coil, having anticipated that he would betray them]], and put him in a position that he cannot escape from, whereupon [[spoiler:Skitter]] shoots him in the head.
[[/folder]]

[[folder:Western Animation]]
* In one episode of ''WesternAnimation/BatmanTheAnimatedSeries'' (adapted from an issue of ''ComicBook/TheBatmanAdventures''), Harley Quinn actually gets Batman to fall for one of her traps, but then Batman (rather expectedly) uses a BatmanGambit to exploit both her feelings for the Joker and how the Joker would react.
-->'''Batman''': She almost had me, you know. Arms and legs shackled, dizzy from the blood rushing to my brain... I had no way out other than convincing her to call you. I knew [[TheOnlyOneAllowedToDefeatYou your massive ego would never allow anyone else the honor of killing me]], though I have to admit she came a lot closer than you ever did, ''puddin'.''
** 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 [[BatmanGambit the best]].
** In an episode of ''WesternAnimation/JusticeLeague'', 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, SelfDemonstrating/TheJoker- the member who actually ''caught'' Batman for the team- is the only guy [[spoiler:(except for the Ultra-Humanite)]] who fully expects Batman to escape, and pleads for the right to kill him immediately. SelfDemonstrating/LexLuthor doesn't listen, and the team listens to Lex, which means, of course, that ''The Joker'' was the OnlySaneMan in that situation. [[spoiler: The ''real'' man who OutGambitted 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.]]
** ''[[WesternAnimation/JusticeLeague 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, GreenArrow versus TheQuestion in the GailSimone 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.
* [[WesternAnimation/LooneyTunes Elmer Fudd and Yosemite Sam]] are "masters" of this trope.
** As is "super genius" Wile E. Coyote, at least in those shorts where he's pitted against arch KarmicTrickster Characters/BugsBunny. (In the [[RoadRunnerVsCoyote Road Runner]] shorts, he's not really outwitted so much as victimized by fate, gravity, poorly designed ACME products, and his own ineptitude.)
** Daffy Duck is a victim of this due to HoistByHisOwnPetard. ([[DuckSeasonRabbitSeason "Wabbit season!" "Duck season."]] "Wabbit season!" "Duck season." "Wabbit season!" "''Wabbit'' season." "Duck season! Fire!"
** 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.
* ''WesternAnimation/StarWarsTheCloneWars'' had Obi-Wan and Anakin negotiate for a captured Count Dooku. The negotiations concluded, they celebrate by having a party. Our heroes are wise to the fact their drinks are spiked, and use TheForce to switch theirs with some nearby partiers. [[spoiler:Not to be outdone, the DangerouslyGenreSavvy VillainOfTheWeek poisons ''all the air in the room''.]]
* In ''WesternAnimation/AvatarTheLastAirbender'', Long Feng and Azula are savvy enough to know they are BOTH attempting this, but [[spoiler: Azula's HannibalLecture is just too good and he concedes.]]
* ''WesternAnimation/SouthPark'': Scott Tenorman. He thought he was getting around Cartman's BatmanGambit, only to run straight into one that [[DisproportionateRetribution was far,]] [[MoralEventHorizon far worse]] and cry the [[EvilTastesGood delicious]] tears of [[HarsherInHindsight unfathomable sadness]].
* ''WesternAnimation/{{Gargoyles}}'': 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. [[spoiler: 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.
* In one ''WesternAnimation/AmericanDad'' 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 ''Film/ThePrincessBride'', [[spoiler:and naturally Steve put Barry's meds in both cups. Unlike Westley, however, Steve has no immunity to the meds.]].
* In ''WesternAnimation/BeastMachines'', [[spoiler: Tankor/Rhinox]] is OutGambitted by [[BigBad Megatron]] when he reveals that [[spoiler: Tankor/Rhinox can't actually hurt Megatron thanks to the RestrainingBolt Megatron hardwired into him when he first implanted Rhinox's Spark into the Tankor body.]]
* In ''WesternAnimation/TeenTitans'', Robin creates the identity of Red X so he can finally meet with [[BigBad 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 ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' Discord has seemingly won, having [[BreakTheCutie broken Twilight]] and {{brainwashed}} her friends so they can't use the Elements of Harmony against him. What Princess Celestia does next is send back all of Twilight's friendship reports, and the memories sparked by reading those old letters convinces Twilight to fight for her friends and the bonds they share. That way, Celestia outwitted a RealityWarper spirit of chaos by ''mailing a bunch of letters''.
** In "[[Recap/MyLittlePonyFriendshipIsMagicS3E11KeepCalmAndFlutterOn Keep Calm and Flutter On]]", [[spoiler: 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, which made Discord realize that her friendship ''did'' matter to him.]]
* In ''WesternAnimation/GeneratorRex'', all of the villains who spent the entire series scheming to obtain the Meta-Nanites, the keys to godhood, [[spoiler: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 ''WesternAnimation/YoungJustice'', 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, [[spoiler: 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]]. Then in 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.
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[[folder:Real Life]]
* A well-known example 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.
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