History Main / Outgambitted

* ''Series/ParksAndRecreation'' has Ron's stash of gold, mentioned in S2E8 "Ron and Tammy". When she claims she dug it up...

* ''[[https://www.fanfiction.net/s/11574569/1/Dodging-Prison-and-Stealing-Witches-Revenge-is-Best-Served-Raw Dodging Prison and Stealing Witches]]'': Dumbledore frames Harry for attempted murder of his twin John and convinces the boys' parents to let him defend Harry at trial, intending to lock Harry up in Azkaban until he has to face Voldemort. Unfortunately, not only does Harry refuse to sign a confession, but the prosecution informs him they plan to push for execution. Come the trial, Dumbledore learns that not only is the prosecution pushing for exoneration, but a good deal of evidence he thought was inadmissible is presented. Due to the prosecution insisting the defendant is innocent and the defense declaring him guilty, Amelia forces the two to switch sides.

* 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 [[Literature/HarryPotterAndTheHalfBloodPrince book six]], [[spoiler:to trusting Snape and having him as the mole, to having Snape kill him]]. Though in ''Literature/HarryPotterAndTheOrderOfThePhoenix'' Dumbledore admits he was outgamitted by Voldemort in the short run when he acknowledges that his [[PoorCommunicationKills hiding of information]] made it considerably easier for Voldemort to trick Harry.

* ''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, Hondo poisons ''all the air in the room''.]]

* 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/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 surprise, 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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* 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 gambit 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 his 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. Wasteland Tornado would allow Yusei to destroy a spell or trap card on the field; targeting it for destruction would be pointless because Yusei could activate it in response to the effect anyway. If Limiter Break is sent to the Graveyard, Yusei can Special Summon Speed Warrior to protect against SKYFIRE's attack. But since Greiger doesn't destroy either card, Yusei reveals that was covered, too: he activates Wasteland Tornado ''himself'' 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, along with 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 shut out the other senses to focus on sensing spirit energy and used it to fight Yusuke in the dark. The mask however is also the reason Kibano was unable to see or smell the cigarette Yusuke put on him to find him in 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 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. Earlier, Jotaro successfully Out-Gambitted D'Arby in their [[AbsurdlyHighStakesGame poker game,]] where the stakes were the souls of him, Joseph, Polnareff, Avdol, Kakiyoin, and Jotaro's mother Holly, alongside the secret to Dio's Stand - 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 added too much to the stakes, with the possibility that losing would equal D'Arby's death from blabbing Dio's secret, 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 Out-Gambitted, such as Joseph's battle with Esdisi in part 2.
** One of the earliest examples lies in part 1, when Dio planned to have Jonathan cut him in order to take hold of and freeze him. Jonathan Out-Gambitted him by cutting him at an area with the tip of his sword at the torch that allowed him to defrost himself.
** Joseph Joestar's epic chariot battle against Wham/Wamuu. Every tactic one fighter used was immediately countered by the other, with Joseph barely prevailing in the end.
** In Part 4, [[SerialKiller Angelo]] pulled a Batman Gambit, predicting Josuke would choose to break through a specific wall in his house to escape Angelo's [[MakingASplash Aqua Necklace.]] so he set a humidifier into overdrive behind that specific wall. Aqua Necklace successfully entered Josuke's body...and then [[CrazyPrepared Josuke]] revealed he had shredded and swallowed a rubber glove. One use of Crazy Diamond, and Aqua Necklace was trapped.

* In ''Manga/DeathNote'', [[spoiler:Near & Mello beat Light by anticipating his "fake Death Note" plan and exploiting it for their own purpose.]]
* In ''Anime/SailorMoon'', this happens twice:
** 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 her boyfriend and ally Mamoru. Kunzite, however, sees right through her and almost gets her killed.
** During the GrandFinale, Neptune and Uranus are convinced that Galaxia cannot be defeated without some [[MartyrWithoutACause horrible angsty sacrifice that only they have the moral strength to make]], and thus [[spoiler: pull off a FakeDefector act that includes [[KillTheCutie killing Pluto and Saturn]] (depriving Moon of two valuable allies ''right after the death of Princess Kakyuu and the {{Heroic Sacrifice}}s of the Inners''), attacking Moon herself and her remaining allies the Starlights (so she wouldn't suspect them, but also [[CurbStompBattle weakening her physically]] [[BreakTheCutie and devastating her emotionally]]) and ultimately take Galaxia on by themselves]]. Unfortunately, [[MagnificentBitch Galaxia]] was on to their plan from the start. The end result is that [[spoiler: Neptune and Uranus are killed in front of Moon, Chibi-Chibi Moon and the Starlights [[SenselessSacrifice without accomplishing]] [[AllForNothing anything]]]].
* This is how the main characters in ''VisualNovel/HigurashiWhenTheyCry'' finally [[spoiler:[[EarnYourHappyEnding win.]] Rika, using her GroundhogDayLoop induced prescience and ThePowerOfFriendship, successfully out-gambits the people trying to kill her]].
* Happened in ''Manga/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]] [[ExplainingYourPowerToTheEnemy 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 Hogyoku]] 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 Out-Gambitted by Urahara from the start; while Urahara outsmarted and nearly killed Aizen several times in their fight, Aizen walked away victorious but failed to notice it had all been an elaborate distraction for a seal to lock Aizen[[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.]]
* Every major battle in ''{{Manga/Kingdom}}'' comes down to this, with each side trying their best to come up with innovative moves to blindside their opponents while trying to predict what their opponent was trying to do.
** Perhaps the superlative example in-series occurs in the Gyou Campaign. Qin wants to invade Zhao, and the planned route would be through the mountains. Riboku [[spoiler: sees through this and heavily fortifies the region, potentially turning the campaign into a costly war of attrition.]] So, Qin decides to [[spoiler: surprise Riboku by attacking through a different route, aiming to capture the cities of Retsubi and Gyou.]] However, Riboku has [[spoiler: seen through this, and purposefully leaves Retsubi weak while fortifying Gyou, hoping that the Qin get overconfident and bogged down, where he can capture back the weak Retsubi, bottling the Qin in and leisurely destroying them.]] Ousen, the Qin commander [[spoiler: sees through this, and makes a new plan to conquer Gyou - creating a refugee flood that will overwhelm Gyou's resources sooner than expected by Riboku.]] The lord of Gyou then tries to [[spoiler: control these refugees by only allowing in those on their ledgers]], but Ousen ''has seen through this as well'' and [[spoiler: has his spies sneak in by replacing injured members of the refugees and disposing of the originals.]] At the end of this, [[spoiler: Qin wins.]] And this is just ''one part'' of ''one campaign'' in the story.

* In the ''Manga/{{Bokurano}}'' anime, [[spoiler:Koeyemshi]] is trying to get [[spoiler:Kana Ushiro]] to be the next Zearth 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]] secretly asks [[spoiler:his and Kana's friend Youko Machi]] to help, and she stops [[spoiler:Koeyemshi]] by [[spoiler:shooting him to death and then taking over the pilot system, de-contracting Kana and taking her place to use Zearth in the next battle. She dies as a result, and later Jun pilots Zearth and dies too, [[SparedByTheAdaptation but Kana is ultimately safe]]]].
* 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 faithful 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 ''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 [[StarfishAliens 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.

* Subverted in the ''Manga/CaseClosed'' anime. [[spoiler: The AntiVillain Akemi Miyano met up with 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. Law, however, ''was'' counting on that and mocked Doflamingo for not seeing it coming despite knowing of the Straw Hats reputation]].
* 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's 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 SacrificialLamb for the sake of giving Goten and Trunks just two more 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 outplay them or outsmart them. Another 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'' ([[AchievementsInIgnorance though it should be noted that this had no planning whatsoever]] and he was just ''really'' angry at being denied sweets) 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's so much stronger than Super Buu.
* ''Franchise/LupinIII'':
** The main character is the world's greatest thief, so he enjoys doing this to his enemies. And Fujiko. Sometimes it happens among his antagonists even without his involvement.
** In ''Anime/LupinIIIMysteryOfTheHemingwayPapers'', arms dealer Marces tried to pull a fast one over on rebel leader Consano, but it turned out Consano anticipated that and hired away Marces's PsychoForHire to put a bullet through his former boss's heart.
* In ''Manga/AttackOnTitan'', the [[spoiler: Central Military Police, who had tortured Pastor Nick to death and had been working for a shadowy conspiracy in order to kidnap Eren seemingly get the upper hand on Levi and co when they flush them out of their hideout and then enact a plan to kidnap Eren and Christa that goes off without a hitch]]. But then it turns out that [[spoiler: Levi and the 104th were not only warned about their location being compromised, but also of the kidnapping plot: Eren and Christa were in a different area, completely safe. They'd kidnapped Armin and Jean disguised as Christa and Eren. Levi and co never even lost them]].

* The "Kanna's Dad" arc of ''Manga/MissKobayashisDragonMaid'' involves this. [[spoiler: Azad, a wizard that plots to [[FantasticRacism exterminate dragons]] by [[PlayingBothSides manipulating rival factions to killing each other]], attempts to get his hands on the Dragon Stone, an item which would allow him to force dragons to do his will (thus allowing him to [[BrainwashedAndCrazy make dragons kill each other just through brainwashing]]) by becoming a human colleague to Chaos-faction dragon Kimun Kamui, who possess a Dragon Stone and then take advantage of how [[ParentalNeglect Kimun's daughter, Kanna, is seeking his attention]] first by tricking her into destroying the stone absorbing its power and then by creating a conflict where she is needed to make a new Dragon Stone. However, Kanna would not only become suspicious of him after the destruction of the Dragon Stone, but also [[TheExile her exile due to the incident]] resulted in her heading to Earth to find Tohru, which led to her becoming used to modern technology and finding a ParentalSubstitute in Kobayashi (whose [[WorkplaceAcquiredAbilities computer programming skills would make her a powerful magic user in the Dragon World]] ). Thus, as she agrees to make a new Dragon Stone for her father, Kanna sets up a plan to have Kobayashi and Tohru enter the Dragon World and, via Kobayashi being able to use magic in this world and a cell phone and tape recorder that Kanna brought with her, aide in exposing Azad's true nature and eventually defeating him.]]
* ''Manga/HaremRoyaleWhenTheGameEnds'' has an exchange of plots between [[spoiler:Serika]] and [[spoiler:Ren]] that eventually results in the former's victory. First, [[spoiler:Serika]] impersonates Asunaro and sends a request for a meeting to the fifth heroine to lure her out. [[spoiler:Ren]] suspects a trap and sends someone else to the site of the meeting. However, [[spoiler:Serika]] predicts this and is able to deduce [[spoiler:Ren]]'s identity and location. Not only that, but she later arranges a loss for [[spoiler:Ren]] and convinces her to work with the others.

* ''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 (unbeknownst 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.

* This happened once in the ''ComicBook/{{Sleepwalker}}'' comics when ComicBook/TheKingpin 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/SpiderMan 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'' was a comic consisting of the two spies Out-Gambitting each other in ridiculous and amusing ways. It would almost universally end with one of them getting shot, blown up, or hit with something due to the other spy using their plan against them.
* Jadina from [[ComicBook/{{LesLegendaires}} Les Légendaires]] is able to out-gambit 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]].

* ''ComicBook/NewAvengers2015'' has both SHIELD and the Maker trying to outwit ComicBook/{{Sunspot}} and failing spectacularly. SHIELD send a {{Kaiju}} to the Avengers island base, drawing out the heavy-hitters and leaving the island vulnerable to being taken over. Except that Sunspot planned for that eventuality and had an entire second base to evacuate his personnel to. Then the Maker bugs the new place and attacks it while their defences are low. Except not quite: Sunspot ''knew'' about the bugs and deliberately fed them false information to lure the Maker to the base right when Sunspot wanted him to be there. For good measure he bugged the Maker's base in return, which gave one of his agents the opportunity to trick SHIELD into blowing it up.

* ''Fanfic/AChanceMeetingOfTwoMoons'': When Blueblood/Bluebelle tries to submit a proposal for a summer house he/she wants to build outside of Ponyville, Luna/Artemis sees it for what it really is - an attempt to set things up to establish a power base down there and make life miserable for the Element Bearers, and she/he immediately rejects it as a result. Later, when Blueblood/Bluebelle tries to convince Celestia/Solaris to their side, they are again made to look a fool by Luna/Artemis.

* ''Film/{{Maverick}}''. Bret and Zane out-gambit everyone who is trying to out-gambit ''them'', and are topped themselves by [[spoiler:Annabelle, who doesn't go ahead with some complicated con but instead [[LastPlanStanding just waits until all hell calms down]], [[BoringButPractical walks in on them while they are taking a bath with a gun in hand, takes the money and leaves]]]]. They don't mind - they think it's all a game and the fun will be in getting the money back from her. [[spoiler:Plus Bret anticipated something of the kind and stashed half the money in his boots.]]
* The ending of ''Film/DirtyRottenScoundrels'' [[spoiler:has both male leads be out-conned by the woman they thought was their mark]].
* In ''Film/SpiderMan3'', 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 [[ConfrontingYourImposter 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/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.

* Sands of ''Film/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 Out-Gambitted on both sides, first when the Mariachi and his crew decide to fight for the President instead of letting him die, and when [[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 Krzysztof Kieslowski's ''[[Film/ThreeColorsTrilogy White]]'' is a beautiful example of this.

* 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''.

* How Jackie finishes her scheme in ''Film/JackieBrown''. The cops want her to turn informant so she can help bring down her boss Ordell, a notorious ArmsDealer but Ordell has a nasty habit of [[YouHaveFailedMe killing people who turn informant]] (and has already attempted to do so before she pulled a gun on him). Ordell wants her to continue her money smuggling as an air stewardess, but if she does so the cops will just throw her ass in jail. So, instead, [[spoiler: she understates how much money Ordell wants her to traffic for her to the cops, [[StealingFromTheTill takes the majority for herself]] and, when Ordell realizes what she's done, gets the cops to wait for him at her apartment then get him killed with a single sentence - "He's got a gun!"]].
* Happens quite often in ''Film/DrunkenMaster''. In one instance, Jackie Chan's character has to scoop water from a bucket with teacups to fill another bucket while hanging upside down. When he notices his mentor is taking s nap, he quietly gets down, quickly fills the bucket with a much larger pan and then splashes waster on himself to make it as he's sweaty and tired. However, the napping teacher is one step ahead and when Jackie's character announces he's finished, the teacher hands him two extremely tiny teacups and tells him to do everything in reverse.
* In ''Film/BatmanAndRobin'' Poison Ivy spends most of the film seducing the title duo, turning them against each other and trying to kill them with her kiss. She eventually gets Robin alone and reveals what Freeze's plan is, in exchange for a kiss from 'her lover for luck'. Robin keeps the deal and kisses her [[spoiler:but doesn't die thanks to wearing a rubber lip, stopping her poison. Unfortunately, he didn't expect her to shove him from her throne into her pond and try to have her plants drown him instead. Even more unfortunately for Ivy, Barbara shows up as Batgirl, and not only saves him, but also provides Batman with the key to destroying Ivy's lie to Freeze about his wife]].
* In ''Film/AdventureInKiganCastle'', Osami is arrested after he's mistaken for a spy trying to kill the king of Kigan Castle, and is thrown in the dungeon to be executed. Granny the Old Witch tries to take advantage of this. She disguises herself as the queen, and visits Osami in his cell to try and make him join forces with her. However, Hermit the Old Wizard, Granny's sworn enemy, has already put Osami under a sleeping spell so that Granny can't talk to him.
* ''Film/Flightplan2005'': The villains' plans relied on them [[spoiler:framing Kyle Pratt as the one who was taking the plan hostage and creating a mass disturbance by 'faking' a mental breakdown about her deceased daughter having been taken onto the plan, but once Kyle works out what's going on, she takes advantage of the fact that everyone else thinks ''she's'' the criminal to act as a genuine hijacker so that she can follow up a new lead until she can find her daughter]].
* ''Film/{{Circle}}'':
** When the room decides to force a universal tie in an attempt to cheat the game, one person secretly switches his vote to kill Pregnant Lady. Another astute person notices this, and switches his vote to that guy so he'll be trapped in a tie with Pregnant Lady. Of course, [[HoistByHisOwnPetard the room chooses to save her over him]].
** When the cast is whittled down to less than ten people, Eric manages to outmaneuver Bearded Man twice in a row. First, by observing that the Quiet Man never votes, he agrees to a deal to trade the Fake Wife for the Little Girl, voting in an order he knows would default to a majority for Fake Wife. Then, he makes up a story about the Quiet Man being untouchable and suggests voting for him, so that Bearded Man will waste his vote on Quiet Man and get eliminated himself.

* 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.
** Really, the whole scene is Vizzini trying several different gambits. First, he tries probing for information, trying to get Westley to unknowingly give away some hint of which cup is poisoned. (The book version of Westley does start becoming agitated and concerned that Vizzini may figure out the whole setup, while the movie version stays cool and lets Vizzini ramble away and go on tangents.) When that fails, he [[LookBehindYou gets Westley to look away]] and [[PoisonedChaliceSwitcheroo then switches the cups]]. Before drinking, he carefully watches Westley's reaction to see if there's any hesitation on Westley's part. When Westley doesn't hesitate to drink, Vizzini figures that Westley ''thought'' that he was reaching for the "safe" cup, but due to Vizzini switching the cups, now Vizzini has the safe cup. Had Westley hesitated, Vizzini would have inferred that he was now holding the poisoned cup and tossed it aside. Of course instead Westley had [[SelfPoisoningGambit poisoned both cups]] and was exploiting his AcquiredPoisonImmunity.
* 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 [[Literature/HarryPotterAndTheHalfBloodPrince book six]], [[spoiler:to trusting Snape and having him as the mole, to having Snape kill him]]. Though in ''Literature/HarryPotterAndTheOrderOfThePhoenix'' Dumbledore admits he was outgamitted by Voldemort in the short run when he acknowledges that his [[PoorCommunicationKills hiding of information]] made it considerably easier for Voldemort to trick Harry.

* 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 [[Literature/TheThrawnTrilogy Thrawn's]] fingerprints are all over it. But Thrawn is dead, and [[Literature/HandOfThrawn his clone was destroyed]].
** In ''[[Literature/XWingSeries Isard's Revenge]]'', Ysanne Isard neatly out-gambits 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 ''Literature/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.
** The overarching plot of ''Mercy Kill'': the head of Galactic Alliance intelligence is a traitor and has turned one of his crack teams, the Wraiths, loose on a co-conspirator, hoping for one of two outcomes. Either they expose the conspirator and the head of Intelligence can figure out how and patch the leak, or they don't and both men are safe. Face Loran, head of the Wraiths, comes up with a suitably brilliant counter-scheme: [[ProperlyParanoid suspecting his boss from the outset]], he creates ''two'' teams for the job [[FeedTheMole and reports on the activities of a third]] that is completely fictitious. Sure enough, the head of Intelligence warns his ally about the fake Wraiths, implicating himself and warning Face to bring hidden backup to [[HaveYouToldAnyoneElse their confrontation]].
* ''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'' in the end, 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."

* 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 Creator/DanBrown novels.
* Done in ''[[Literature/TheQueensThief The Thief]]''. The Magus of Sounis frees Gen, a low-born thief who stupidly brags about his successes, from prison and forces him to steal [[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 ''[[Literature/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]].

* The ''Literature/{{Mistborn|TheOriginalTrilogy}}'' trilogy is basically a GambitPileup by the end, so naturally a lot of people end up Out-Gambitted, In roughly chronological order [[spoiler: Preservation out-gambits Ruin, trapping him, then Ruin out-gambits a lot of people by changing prophecies in order to try to get somebody to free him, then Kwaan and Rashek out-gambit 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 out-gambits the Lord Ruler in order to kill him. Ruin out-gambits 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 by breaking into the Daemon and exploiting flaws in the code. It turns out he'd planned for this, knowing no system is secure, and purposely placed those flaws there. When the villains attempted to use them the Daemon detected it and, now knowing precisely who was attempting to hijack the system, proceeded to wipe out their finances.]]
* 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]].

* Crops up regularly in a ''Literature/ASongOfIceAndFire'' to practically everybody involved. Unsurprisingly, given its high concentration of [[TheChessmaster Chessmasters]] and {{Magnificent Bastard}}s, as well as [[BigBadWannabe those who aspire to be such]] meeting such things as [[UnwittingPawn pawns]] and [[SpannerInTheWorks random spanners]].
** More specifically, however; the prize for getting herself Out-Gambitted most regularly has to go to [[SmugSnake Cersei]] [[GodSaveUsFromTheQueen Lannister]], particularly through the well-named ''Literature/AFeastForCrows''.
* In ''Literature/TalesOfDunkAndEgg'', the Blackfyres historically got pulverized due to their own egos getting repeatedly used against them by the then-Hand, [[TheExtremistWasRight Brynden Rivers]] aka "Bloodraven". He outright won a [[BattleOfWits war of wits]], not just a battle, by undercutting each and every attempt they and Ageor "Bittersteel" Rivers made to gain the Iron Throne. If at a cost.
* 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]].
* Creator/SergeyLukyanenko's ''Literature/NightWatchSeries'' 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 Literature/{{Discworld}} book, to the point where he has prepared his own deepest dungeon for when he will be thrown in when he is overthrown.
* ''The Literature/SinisterSixTrilogy'' has The Gentleman thinking he got away with his plan, only for [[spoiler: the Chameleon to betray him, only for HIM to be caught by Doc Ock who had the exact same plan, then they're all foiled by Spider-Man when he gets Pity on his side]].

* In ''Literature/TheWitchlands'', when Vaness is captured, she manipulates her captors to lead her towards Baedyed territory, as her recent (not yet publicly known) treaty with them should compel them to rescue her. Unfortunately, the Baedyeds aren't satisfied with the treaty and have already planned to murder Vaness, so the entire idea backfires on her.

** The seventh volume is a back-and-forth example of this, ultimately ending in [[spoiler:the Queen's victory. She pretends that her plan was to sabotage Kyousuke's attempt to kill her (which he 'discovers' and makes a counter-plan for), but she actually wanted him to succeed. She was able to survive through currently-unknown means, while Kyousuke's means of defeating her [[NiceJobBreakingItHero would become a threat to the world in its own right]]. As a result, he is now forced to work with her - her goal all along]].

** Diamondback's plan for her Combat Final [[BatmanGambit relied on Hekate backstabbing her]] - it would have worked out for both of them if she didn't, but would work much better for Sandra if Hekate decided to cheat. Kallysta obliging grabs the VillainBall with both hands and pays the price for it.

* John French's ''[[Literature/ThousandSons Ahriman]]'' trilogy features several of these:
** In ''Ahriman: Exile'', Ahriman, having learned that his unseen enemy is his old ally Amon, travels to a desolate space station and summons a powerful daemon in order to question it about Amon’s plans. Amon predicted that Ahriman would summon that specific daemon, however, and pre-emptively bound it into his service. When Ahriman summons the daemon, it easily breaks free of his control and unleashes a horde of lesser daemons upon the station, forcing Ahriman and his allies to flee for their lives.
** In ''Ahriman: Sorcerer'', [[TheStarscream Ahriman’s lieutenant Sanakht]] conspires with Ignis to kill Ahriman and take control of his Chaos Space Marine warband. While Ignis recruits people to their cause, Sanakht sets up a ManchurianAgent that will cripple Ahriman’s flagship when the time is right, and accompanies Ahriman on his mission to retrieve the Athenaeum of Kallimakus. Sanakht knows the Athenaeum is guarded by [[AntiMagic blanks]], which will prevent Ahriman from defending himself with his sorcery and give Sanakht (who is the better swordsman) a chance to kill him. Unfortunately for Sanakht, [[spoiler:Ignis is loyal to Ahriman and has not only kept his master informed of the plot, but also fed the conspirators misinformation so that they will fire on each other instead of Ahriman’s loyalists during the coup. Ahriman’s own plans also ''require'' the destruction of his flagship, as this will tear open a Warp rift and let the warband escape from the Inquisitorial fleet that is pursuing them. Finally, Ahriman needs someone to act as a [[DemonicPossession vessel]] for the Athenaeum, and by letting it possess Sanakht, he’s killing two birds with one stone]].
* In ''Literature/NightmareAlley'', the evil [[TheVamp Lilith]] does this to [[ConMan Stan]] spectacularly, firstly by seducing and controlling him and then, once Stan has began conning the wealthy Ezra Grindle at her suggestion, by keeping the cash results of their con in her safe where she secretly replaces the five hundred dollar bills with singles. When Stan takes the money back, discovers what she's done and attempts to confront her, she tells him he is deluded and is projecting [[OedipusComplex his sexual feelings for his mother]] onto her and then tries to have him committed to an institution. He narrowly manages to escape and has to go on the run as a result of her duplicity, sinking into alcoholism and depression.
* "His Last Bow" by Creator/SirArthurConanDoyle is about a spy, Von Bork, who's been outwitting the British in and out and is about to return to Germany at the outset of the First World War after having already given his government a wealth of information about just about everything. He just needs that final piece on British naval codes from his Irish-American informant... [[spoiler: Who promptly captures him and reveals himself to be Literature/SherlockHolmes in disguise, having come back from retirement at the government's request for long enough to assume this role and play against Von Bork. Oh, and feed him and his government false information all along.]]

* ''Series/AgentsOfSHIELD'': In the second season, Raina threatens to expose Jemma Simmons (who is currently undercover at HYDRA) in order to blackmail Coulson into helping her. Coulson just smiles and lets her go through with it, to Raina's consternation, as she knows that Coulson is AFatherToHisMen. She didn't know that [[spoiler:Coulson had ''another'' mole in HYDRA--Bobbi Morse, who had gotten a job as chief of security for that base, and was thus in a perfect position to extract Simmons when things went south]].
* 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 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"]].

** 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.]]

** 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.

** 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 the season 2 finale of ''Series/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.
* 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]].

* In the ''Series/StarTrekVoyager'' episode "Counterpoint", ''Voyager'' is smuggling telepathic refugees to a hard-to-find, mobile wormhole, so they can escape a repressive telepathic regime, despite repeated inspections by soldiers led by Inspector Kashyk, who lets his men search the ship (ineffectively, since the telepaths are kept in the transporter buffer during the inspections). Then he arrives on his own, claiming to be a defector and to have always known about the transporter trick and never told his men. Together, he and Janeway make great headway in finding the wormhole, but before the work is completed he has to return to his crew to keep them being ineffectual and prevent them becoming suspicious. He then returns in an official capacity and, with his second-in-command out of the room, asks Janeway if she's located the wormhole. As soon as she tells him where it is, [[spoiler: he [[FakeDefector calls in his second]], orders his men to materialise the telepaths and flies ''Voyager'' to the wormhole, intending to destroy it to prevent further escapees]]. Except [[spoiler: the wormhole isn't there, the transporter buffer is full of vegetables, and the telepaths are already on their way to the actual wormhole location in cloaked shuttles - using cloaking methods Kashyk shared with Janeway as part of his defector ruse]].

** In the sixth season finale, 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, Raphael 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.
** 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, you're five seconds away from him defeating them in one big master stroke.
* Happens in ''Series/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 ''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 ''VideoGame/FreeSpace2'' 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]]]].

* ''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.

* ''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 the Precursors. One of them, Juno, was aware that Lucy had betrayed the Assassins and, taking control of Desmond via an Apple of Eden, forces 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 Out-Gambitted by [[MagnificentBastard the Illusive Man]] and [[NGOSuperpower Cerberus]] in between the events of ''VideoGame/MassEffect2'' and ''VideoGame/MassEffect3''.
** The Illusive Man has his plan to subvert Shepard in ''VideoGame/MassEffect2'' by giving a false impression of Cerebus as the misunderstood good guys by ensuring the ''Normandy'' SR-2 was crewed by generally morally upright and sympathetic Cerebus members blow up in his face. By putting good people on the ship, they respond to being led by Shepard, especially the Paragon version, by promptly showing they're far more loyal to Shepard when Shepard tells their boss to get stuffed. Note this mass defection also includes ''[[SpaceshipGirl the ship]]''.
** [[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. It's heavily implied (but never directly stated) that he was actually indoctrinated before you met him and they were behind his plan to control them from the beginning as a way to cause infighting among galactic resistance; Javik tells Shepard they pulled a similar gambit successfully in his cycle.]]
* ''VideoGame/FireEmblemAwakening'':
** Near the end of the game, [[spoiler:the BigBad, in his bid to release {{Gr|eaterScopeVillain}}ima, 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 [[GreaterScopeVillain 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.]]
** A villainous and [[TearJerker tragic]] example occurs in chapter 9. [[spoiler:Thanks to the knowledge the Hierophant gives him, Validar is able predict every single tactic the Avatar uses in their attempt to save Emmeryn and effortlessly counters them each time, ultimately resulting in the death of Phila and Emmeryn's HeroicSacrifice.]]

* Given that ''VideoGame/TheWitcher2AssassinsOfKings'' has a massive GambitPileup, this trope is in full effect as [[TheChessmaster Chessmasters]] 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]].
* Thuris from ''VideoGame/SoulNomadAndTheWorldEaters'' is said to be the smartest of the three world eaters. While he DOES do some pretty creative things with the fact that 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]].

* ''VideoGame/Persona5'': The Phantom Thieves pull off a caper against TheConspiracy using their knowledge of the Metaverse. After figuring out that Black Mask had tricked them into going to the Casino Palace, the rest of the Phantom Thieves knew that Black Mask was going to try to kill Joker, though they weren't quite sure why yet. Black Mask believes that they've managed to bait the Phantom Thieves into giving up Joker, get him into police custody, and make it look like Joker committed suicide during questioning rather than pay for his crimes in jail. However, knowing Black Mask was going to try something, the Phantom Thieves came up with a plan. [[spoiler:The Thieves used the fact that a Palace's distortions only affect one area to make Black Mask think he was in the real world while secretly transferring him to the Metaverse, making Black Mask kill a cognitive version of Joker rather than the real one. Then, they used spyware on Black Mask's phone to spy on him reporting his "success" to the BigBad, all while the real Joker sat safe and sound in the real police custody, with Black Mask none the wiser. And, thanks to Sae Niijima being convinced by Joker to help the Phantom Thieves, Joker was able to exit police custody without being spotted.]] After all this, a television interview makes Black Mask realize that they've been tricked, [[{{Touche}} and admits to being impressed at the Phantom Thieves pulling it off]]. What makes it even more impressive is that Joker had been drugged by corrupt police earlier, and didn't remember there even was a gambit until the last minute.
* ''VideoGame/MortalKombat11'': at the climax of the ''Aftermath'' expansion's story, once [[MagnificentBastard Shang Tsung]] is done killing and betraying everyone around him and has seized both Kronika's crown and the hourglass, [[spoiler:Fire God Liu Kang emerges from a time hole to confront him, looking not at all surprised, and calmly reveals he [[ILied straight-up lied]] about being unable to intervene. Shang Tsung realizes that the Hourglass must have shown him this outcome, and by striking at the last moment, the sorcerer had deprived himself of all his resources, preventing any XanatosSpeedChess. Even Shang Tsung's attempt to call the sacrifice of all his allies cold-blooded falls on deaf ears, as Liu Kang points out this timeline and everyone in it was already doomed, so he lost nothing by waiting until the last possible second.]]
* In ''VideoGame/{{Portal 2}}'', [[spoiler:''Wheatley'' of all characters manages to pull this on Chell and [=GlaDOS=]. He spends so much time building up a trap a few chambers ahead, all while trying and failing to act like it's not a trap, that nobody suspects the ''real'' trap was the Aerial Faith Plate that hurls them sideways into a DeathTrap rather than ahead to the "real" trap a ways further. Even ''[=GlaDOS=]'' is taken aback by how well it was done, as it actually ''counted'' on her trying to take advantage of his idiocy to out-gambit him.]]
--> [[spoiler:'''Wheatley:''' ''Surprise!'' We're doing it now!\\
'''[=GlaDOS=]:''' Okay, credit where it's due: for a little idiot built specifically to come up with stupid, unworkable plans, that was a pretty well laid trap.]]

* In ''VisualNovel/SilverCrisis'', [[spoiler: the titular Silver]] does this to Ganondorf, [[spoiler: having fully intended to betray him from the beginning, and doing the research to figure out how to defeat him.]] He bluffs Ganondorf into allowing him to go through with his plan, knowing that Ganon [[spoiler: needs his help in order to achieve the power of a God and become unstoppable.]] During the final battle, he takes [[spoiler: Din’s Aura from Ness himself, who she was residing in]], angering Ganondorf, and causing him to attack Silver. But Silver then [[spoiler: lands a fatal blow on him with a Silver Arrow he had hidden, absorbing his Aura for himself and becoming the “Ultimate Life Form”, in his own words.]]

* 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/tales-of-the-questor-0524/ blowing up in his face]].... with good evidence that Lady Absinthe [[http://www.rhjunior.com/tales-of-the-questor-0518/ 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.

* In ''Webcomic/ElGoonishShive'', Sirleck planned to [[spoiler:possess Magus]] as soon as [[spoiler:he got his new body]] but [[spoiler:Magus]] saw it coming [[spoiler:and kills Sirleck as a result]].

* In the season 3 finale of ''WesternAnimation/CarmenSandiego'', Roundabout sets up a gambit to bait Carmen into attempting to steal St. Edward's crown so that she'll get arrested and he'll be able to steal the crown easily afterwards. Unfortunately for him, [[spoiler:Carmen and Shadow-san knew him well enough to know that he'd pull something like this and so set up their ''own'' gambit to work around his. The result: Roundabout's cover as a member of Her Majesty's secret service is blown out of the water, leading to his arrest.]]

*** In "Injustice for All" 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, ComicBook/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. ComicBook/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 Out-Gambitted the Injustice League, though, was the Ultra-Humanite, who had already agreed to help Batman out...in return for a [[ViewersLikeYou generous donation in his name]] to his favourite public broadcast station.]]

*** And again in "[[Recap/MyLittlePonyFriendshipIsMagicS6E20VivaLasPegasus Viva Las Pegasus]]", involving an EnemyMine alliance between [[spoiler:Applejack and the Flim Flam Brothers]], who [[spoiler:make Gladmane think he's thwarted their EngineeredPublicConfession gambit and gloats--Oh ''sulat'', my gloating's just been broadcast on the PA!]]
* In one ''WesternAnimation/RickAndMorty'' episode, Rick is kidnapped and put in a simulation of his life by alien scammers who are, once again, trying to steal his formula for concentrated dark matter (a powerful spaceship fuel). Rick knows he's in a simulation, [[spoiler:but this time the aliens are prepared for this, and allow Rick to think that he's escaped the simulation and is returning home, and then enter the code to his safe filled with scientific secrets... before revealing that he was still in the simulation, they always had his formula, but now they have the code to his safe too. Rick tries countering this by escaping and attempting to fly home to change the safe code, but while being chased in the flight back to earth he needs to mix up some more of his special high-power fuel to escape. But as soon as he instructs Morty on which ingredients to mix, it's revealed that - once again - he's still in the simulation, and now the aliens have his formula. The aliens, flush with pride and having finally gotten what they wanted, let Rick leave. As Rick flies back to Earth, the aliens throw a party for their success and prepare the first batch of concentrated dark matter, only for the formula to result in a volatile compound that [[ExplosionsInSpace instantly destroys their entire ship]]]].
* ''WesternAnimation/SheRaAndThePrincessesOfPower'': Twice in season 4, a scheme involving [[spoiler:Double Trouble]] leads to this happening to someone. [[spoiler:In "Mer-Mysteries", Double Trouble gets caught because Adora and Glimmer set a trap in the dining room, baited it with a lie about a backup communications unit that DT would have to destroy, and staged an argument to provide a "distraction" that DT would be able to exploit; even though that specific job of DT's was a success because it distracted the princesses from the conquest of Salineas, being captured takes them out of play until they switch sides out of self-interest. After switching sides, they blow open Catra's manipulation of Hordak by tipping him off about the ''real'' reason Entrapta disappeared; Hordak's resultant rampage sets a decent chunk of the Fright Zone on fire and is only stopped when Catra destroys his ArmCannon and crushes him under a pile of metal, which combines with the Hordes' forces being stretched thin and Catra being rendered virtually catatonic by DT's [[BreakThemByTalking Breaking Speech]] to leave the Fright Zone virtually undefended when Glimmer and Scorpia infiltrate.]]

* ''WesternAnimation/StarWarsRebels'': In GrandFinale [[Recap/StarWarsRebelsS4E13FamilyReunionAndFarewell "Family Reunion]] [[Recap/StarWarsRebelsS4E14FamilyReunionAndFarewellPartII — and Farewell"]], an outgambit gets defeated by another outgambit. [[spoiler:The Rebels take the main dome of the Imperial complex and make preparations to launch it into space with all hands on board, essentially wiping out the entire occupying force of Lothal in one swoop. Thrawn arrives and puts his own Star Destroyer right above the dome to prevent the launch, while secretly sending his own team to disable the city shields, and then fires upon the city until Ezra agrees to surrender himself. However, Ezra realized that Thrawn might arrive and made a contingency plan: summon a gigantic pod of [[SpaceWhale purrgil]] that he'd previously befriended and use the Force to direct them to disable the Star Destroyers' hyperdrives, then use the purrgil's own natural abilities to hyperspace the entire fleet to somewhere they can't return from.]]

* 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 surprise, 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.

* ''Fanfic/PokemonHarmonyAndChaos'': This happens to Team Shadow when they first try to invade the Crystal Empire. [[spoiler:[[BigBad Sombra]] is able to enter the Crystal Empire without issue [[TheMole due to being on good terms with everyone]], and secretly installs a virus in Androrg that messes with its security in its systems, allowing Chrysalis and the grunts to invade while also turning Androrg and all the Guardroids against everyone in the Crystal Empire. Team Shadow attempts to obtain the Heart Fragment of the Crystal Heart and the Shadow Spear, contained in two cases, with Sombra subtly assisting them by taking the cases and planning to hand them off to one of the grunts and make it look like he was robbed, and Chrysalis at one point pretending to threaten his life to force everyone to hand over the cases. In the end though, although Chrysalis manages to snatch both cases and escape, she finds out too late that Shining Armor and Cadance already thought ahead and hid both of the atifacts somewhere else. The cases were just empty decoys, and the whole battle was just buying Cadance time to remove the virus and get Androrg and the Guardroids back on their side so Team Shadow could not immediately attack again after realizing they were tricked, or try the same trick in the future. The only silver lining for Team Shadow is that Sombra managed to keep his cover, with nobody realizing he is the leader of Team Shadow.]]

** 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 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. Earlier, Jotaro successfully Out-Gambitted 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 added too much to the stakes, with the possibility that losing would equal D'Arby's death, playing a BatmanGambit that made D'Arby break down.

* On ''Series/StarTrekDeepSpaceNine'', the Obisdian Order and Tal Shiar team up to launch a sneak attack on the changeling homeworld using a fleet of cloaked ships. However, after their opening barrage, they find out the planet is deserted and there are 150 Jem'Hadar warships screaming out of the nearby nebula. Turns out the changelings had known about the plan and deliberately allowed them to walk into a trap, Battle of Midway style. A changeling had even replaced the Romulan commander to ensure their own success. While the Tal Shiar eventually recover, the Order is annihilated and the Cardassian Central Command is overthrown shortly thereafter.

* 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]].

* Subverted in the ''Manga/DetectiveConan'' anime. [[spoiler: The AntiVillain Akemi Miyano met up with 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.]]

** In "Harvest Dinner", Cricket and Gramma end up buying a papaya instead of the intended paprika for the family stew, so they distract Tilly and switch the groceries; however, when they get home, Bill reveals the jar is empty. Turns out, Tilly knew they would switch the groceries, so she hit the paprika in her pocket to throw them off.

* In the ''Series/StarTrekVoyager'' episode "Counterpoint", ''Voyager'' is smuggling telepathic refugees to a hard-to-find, mobile wormhole, so they can escape a repressive telepathic regime, despite repeated inspections by soldiers led by Inspector Kashyk, who lets his men search the ship (ineffectively, since the telepaths are kept in the transporter buffer during the inspections) while he engages in FoeYay with Captain Janeway. Then he arrives on his own, claiming to be a defector and to have always known about the transporter trick and never told his men. Together, he and Janeway make great headway in finding the wormhole, but before the work is completed he has to return to his crew to keep them being ineffectual and prevent them becoming suspicious. He then returns in an official capacity and, with his second-in-command out of the room, asks Janeway if she's located the wormhole. As soon as she tells him where it is, [[spoiler: he [[FakeDefector calls in his second]], orders his men to materialise the telepaths and flies ''Voyager'' to the wormhole, intending to destroy it to prevent further escapees]]. Except [[spoiler: the wormhole isn't there, the transporter buffer is full of vegetables, and the telepaths are already on their way to the actual wormhole location in cloaked shuttles - using cloaking methods Kashyk shared with Janeway as part of his defector ruse]].

* "His Last Bow" by Creator/SirArthurConanDoyle is about a spy, Von Bork, who's been outwitting the British in and out and is about to return to Germany at the outset of the First World War after having already given his government a wealth of information about just about everything. He just needs that final piece on British naval codes from his Irish-American informant... [[spoiler: Who promptly captures him and reveals himself to be SherlockHolmes in disguise, having come back from retirement at the government's request for long enough to assume this role and play against Von Bork. Oh, and feed him and his government false information all along.]]