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* ''Literature/BookOfTheDead2021'': Even though Tyron specifically mentioned that he had noticed rising tensions and suspected something would happen, [[spoiler:Filetta still tries to lead an ambush to assassinate him, to tie off the loose end that he represents to their business. Tyron promptly reveals that he brought dozens of minions ''and'' an artefact that floods the area with opaque smoke, giving him time and space to start casting area debuffs. None of Filetta's people survive.]]
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* ''Literature/MagicExLibris'': At the end of the third book, some of the Porters take advantage of [[spoiler: Johannes Gutenberg's death]] and Isaac's [[NiceJobBreakingItHero breaking the locking spells on prohibited books]] to mass-duplicate an automaton and power the copies with the Ghost Army. When they're interrupted and drawn away, Isaac, fearing both a Porter civil war and the Porters' enemies behaving like [[CorneredRattlesnake Cornered Rattlesnakes]], plants a bomb inside the automaton's head that will exorcize any ghost in the blast radius, and gives the detonator to a colleague because he knows the rogue Porters will focus on him.
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* 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.
** That cost, at least at first? Being called a kinslayer for killing his half-brother and his sons. How? During honorable melee battle at Redgrass Field, Bloodraven won at sword fighting by using his longbow and leading a hundred archers into raining arrows at rebel leadership. But even before the battle, he assasinated one of rebels' most capable commanders by disguising himself as a commoner and shooting the commander (Quentyn "Fireball" Ball) in the throat.

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* 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 Aegor "Bittersteel" Rivers made to gain the Iron Throne. If at a cost.
** That cost, at least at first? first at a start of his career? Being called a kinslayer for killing his half-brother and his sons. How? During honorable melee battle at Redgrass Field, Bloodraven won at sword fighting by using his longbow and leading a hundred archers into raining arrows at rebel leadership. But even before the battle, he assasinated one of rebels' most capable commanders by disguising himself as a commoner and shooting the commander (Quentyn "Fireball" Ball) in the throat.
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** That cost, at least at first? Being called a kinslayer for killing his half-brother and his sons. How? During honorable melee battle at Redgrass Field, Bloodraven won at sword fighting by using his longbow and leading a hundred archers into raining arrows at rebel leadership. But even before the battle, he assasinated one of rebels' most capable commanders by disguising himself as a commoner and shooting the commander (Quentyn "Fireball" Ball) in the throat.
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* ''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]].

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* ''The Literature/SinisterSixTrilogy'' has ''Literature/SpiderManSinisterSixTrilogy'': The Gentleman thinking thinks he got away with his plan, only for [[spoiler: the [[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]].
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* The events of ''Literature/EmperorMolluskVersusTheSinisterBrain'' were all orchestrated by the Council of Egos, who intend on enslaving Mollusk under instruction of a Future-Mollusk sending them instructions with the anti-time radio. Except it was all devised as a trick by Future-Mollusk, tricking them into building a LotusEaterMachine that traps them all in a dream-state while Present-Mollusk goes off scot-free, creating a StableTimeLoop.
--> '''Zala:''' This plan of yours seems needlessly complicated. There must have been a simpler way than to put yourself through all that.\\
'''Mollusk:''' If it were too simple, the Council would never have believed it. It had to be reidiculous, even unnecessary, in order to fool the Council.
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* ''Literature/WitchKing'': This is TheReveal at the end. The protagonist Kai and deuteragonist Ziede were kidnapped and kept comatose for a year, which turns out to have been orchestrated by their dear friend Prince-Heir Bashat to prevent them from interfering with his plans to reform TheFederation into TheEmpire. However, Kai had anticipated his aspirations ''five years'' earlier and already did the diplomatic work to ensure that the other leaders would vote down the plan. Bashat's ally is crushed to realize their betrayal was all for nothing.
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* 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.

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* 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 [[ParentalIncest 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.
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* In ''LightNovel/TheUnexploredSummonBloodSign'', this is the only way that Kyousuke can fight against the White Queen, an omnipotent EldritchAbomination. However, the Queen is far smarter than she normally lets on, and [[spoiler:due to her twisted love for him]], doesn't mind losing.

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* In ''LightNovel/TheUnexploredSummonBloodSign'', ''Literature/TheUnexploredSummonBloodSign'', this is the only way that Kyousuke can fight against the White Queen, an omnipotent EldritchAbomination. However, the Queen is far smarter than she normally lets on, and [[spoiler:due to her twisted love for him]], doesn't mind losing.
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* ''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''.

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* ''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 In the end Sauron is actually ''right'' in the end, except that he couldn't have foreseen no one can summon enough willpower to actually destroy the Ring. However, Illúvatar out-gambited Sauron by setting things up so that Gollum destroying would destroy the ring Ring ''by accident''.



* Done in ''Literature/TheQueensThief''. 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.]]

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* Done in ''Literature/TheQueensThief''. 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 a 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 did, stole it a second time in such a way to make the Magus think he had lost it, and finally returned it to his queen.queen, securing her rule.]]
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* ''Literature/{{Animorphs}}'':
** In the finale, Visser One's plan worked well. Tom's worked even better. Jake's worked best of all.
** [[SixthRangerTraitor David]] was never really more than a BigBadWannabe, but he was still able to run circles around the Animorphs for the first half of Book #22, and they (and he) even thought he'd killed Tobias at one point. They let him think they're beat and will give him what he wants, but they've already devised a plan in private thought-speak.
* WellIntentionedExtremist [[spoiler:King Pryderi]] of ''Literature/TheChroniclesOfPrydain'' makes an [[DealWithTheDevil alliance]] with resident EvilOverlord Arawn in an attempt to conquer Prydain and put an end to the infighting and bickering between lords that has long plagued his land. After he has conquered Prydain he planned to make Arawn into his servant by virtue of his superior army. Too bad for him, Arawn is well-known and feared for his evil trickery and, too late, the King realizes that the Death Lord has [[UnwittingPawn outmaneuvered him.]] [[spoiler:Unsurprisingly, he doesn't live long after.]]
* If you are a character in the ''Literature/CodexAlera'', you should try to avoid going up against Gaius Sextus. Even if you seem to win against him, he's probably still using you somehow or other. Witness [[spoiler:Lord Kalarus]], whose plan to make himself a LoadBearingBoss and blow up half the countryside was foiled by [[spoiler:Gaius walking into the heart of his territory and detonating the volcano himself]], or [[spoiler:Lord Aquitaine, who ''almost'' got his wish to be First Lord when Sextus legally adopted him as ''secondborn'' to Tavi, leaving the country in the most capable hands possible between his death and his grandson's return]]. Also, chronic traitor [[MeaningfulName Invidia]] eventually learns that, if you [[ChronicBackstabbingDisorder betray everyone you've ever worked with]], people ''will'' eventually notice. And when you try to do it again, [[spoiler:they'll leave you stranded in the woods. Naked]].
* 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]].
* In the ''Literature/{{Daemon}}'' novel ''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.]]
* 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]].
* 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.
* ''Franchise/{{Dune}}'', being a millenial tale of galactic intrigue that accumulates {{Gambit Pileup}}s like some books accumulate minor characters, has numerous examples of this trope.
** In the [[Literature/{{Dune}} first novel]], the Emperor travels to Arrakis to "put down the Fremen rebellion" once and for all and to severely discipline the Harkonnens he was using as his tools. The Guild travels there to safeguard their precious Spice, having foreseen a crisis with their oracular powers. Paul Muad'dib, however, has become a MessianicArchetype possessed of far greater powers and takes advantage of having all his enemies together to pull a surprise attack that winds up with him dethroning the Emperor and taking his place.
*** Even earlier, the Atreides were themselves victim of this when they knowingly walked into the Harkonnen trap on Arrakis, counting on their superior training and potential alliance with the Fremen to see them through. What Leto failed to realize was that the Emperor was backing the Harkonnens and the sheer amount of money both were willing to spend to defeat him.
** In ''Literature/DuneMessiah'', the Bene Tleilax construct a complicated gambit involving forcing Paul to discredit himself out of love for his consort, Chani. Paul, of course, has anticipated this, but it's the loyalty of the ghola Duncan Idaho, whom they were counting on to either kill Paul (forcing Alia to make the same choice) or recover his memories, showing Paul what could be achieved with Chani, that allows Paul to evade the trap.
** In ''Literature/ChildrenOfDune'', Alia, now [[GrandTheftMe possessed]] by the GeneticMemory of Baron Harkonnen, plots to have Paul's children assassinated to [[RegentForLife cement her rule]]. Meanwhile, the Bene Gesserit are trying to manipulate the children into returning to their control. Leto II, however, by willingly embracing his father's messianic role, successfully discredits Alia and becomes the God Emperor.
* 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."
* ''Literature/HarryPotter'':
** The entire, seven book series plays this trope mostly straight: 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 the "Babbitty Rabbitty and her Cackling Stump" section of ''Literature/TheTalesOfBeedleTheBard'', the charlatan finds himself outwitted when he tries to make Babbitty Rabbitty do his bidding.[[note]] To elaborate: Upon meeting Babbitty Rabbitty and discovering that she's a ''real'' witch, the charlatan coerces her to use her power to help him perform acts of magic, dismissing her question of concern that her magical power has its limit. When the moment does come in which Babbitty can't fulfill the king's demand on the charlatan, the charlatan decides to use her as TheScapegoat to escape the king's wrath. Unfortunately for the charlatan, Babbitty makes a false claim while hiding within a tree stump about the power of immunity against the king's weaponry that the wizards and witches possess that everyone else in the story is too ignorant to be able to refute, resulting in the king's executioners readying themselves to test the "theory" on the charlatan. Forced into the SadisticChoice of either coming clean about his falsified claim of being a wizard or dying by the executioners' weapons, the charlatan confesses to the king and his executioners about his deceitful schemes and is then taken away into the dungeon.[[/note]]
* In ''Literature/{{Helm}}'', [[spoiler:Arthur de Noram]] is no match for the man he tried to conspire with, [[spoiler:Siegfried Montrose]].
* "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.]]
* About halfway through ''Literature/HollowPlaces,'' Austin blackmails Warden Tim White into stopping his guards from abusing the prisoners by threatening to release a recording of him bribing a judge. This plan backfires months later when the Warden obtains a security video of Austin breaking into the judge’s apartment to obtain said recording.
* ''Literature/HowARealistHeroRebuiltTheKingdom'':
** During the Elfrieden occupation of Amidonia's capital Van in volume 3, Amidonian General Margarita Wonder, who had surrendered with Van's garrison, asks to sing on King Souma Kazuya's first variety show on the Jewel Voice Broadcast from Van. She sings Amidonia's national anthem, which calls for [[OccupiersOutOfOurCountry the recapture of the land taken from Amidonia in the two countries' last war]], hoping to inspire PatrioticFervor and resistance to the occupiers, expecting to be executed afterwards. Instead, Souma says there's no law in Elfrieden against singing another country's national anthem and applauds her performance, proving he's the furthest thing from the tyrant the House of Amidonia made him out to be.
** The occupation of Amidonia is ended with a peace treaty negotiated by the Gran Chaos Empire, where Amidonia is required to pay reparations. Souma withdraws, arranging things such that either the returning Prince Julius Amidonia will have to abandon Amidonia's irredentism or ruin his country further. What neither they nor the Empress expect is Julius's sister Princess Roroa to exploit Julius's political weakness to foment a revolt ''in favor of'' annexation by Elfrieden. Julius is forced to flee the country, and Roroa pledges herself to marry Souma, uniting the countries. {{Lampshaded}} by Souma, who laments to Empress Maria after all's said and done that "We were all outwitted by a little girl."
* ''Literature/TheHungerGames'': For all President Coriolanus Snow's talk about destroying Katniss's image so the unhappy districts would have nobody to rally behind, [[spoiler:Plutarch completely played him for a fool]].
* 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]].
* ''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''.
* Anyone in ''Literature/TheMentalState'' who thinks that Zack State is just a gullible youth tends to end up in this situation. Most of the antagonists are simple-minded brutes, but there are a few who actually have an objective and a plan for achieving it. The best examples are [[TheCorruptor Harry Jacks]], [[CorruptPolitician Commissioner Viceman]] and [[SmugSnake Saif]]. They all underestimate Zack's deviousness and ruthlessness.
* ''[[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.
* 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/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.
* 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.
* In the ''Literature/OutboundFlight'' novel ''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]].
* 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.
* Done in ''Literature/TheQueensThief''. 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.]]
* 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.
* In one ''Literature/{{RCN}}'' book, Daniel Leary's corvette ''Princess Cecile'' is being pursued by a {{privateer}}, ''Estremadura'', that is continually dropping out of FTL right on top of him, too close for effective use of kinetic-kill missiles. Daniel fires missiles off in another direction entirely then tricks the privateer into dropping out of FTL directly in their path; they hit at terminal velocity and ''Estremadura'' is obliterated, a trick that only worked ''because'' the other pilot was so good.
* 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]].
* ''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]].
* 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.
* John French's ''Literature/ThousandSons'' novel ''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 ''LightNovel/TheUnexploredSummonBloodSign'', this is the only way that Kyousuke can fight against the White Queen, an omnipotent EldritchAbomination. However, the Queen is far smarter than she normally lets on, and [[spoiler:due to her twisted love for him]], doesn't mind losing.
** A good example of this is the fourth volume, when the Queen pretends to let Kyousuke use her sword as a handicap, but is in fact damaging the building in a way that would kill the people Kyousuke is trying to save. However, Kyousuke had already figured out that the building's design deviated from the original plans, so he knew that this wouldn't work.
** 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]].
* 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.
* Literature/WhateleyUniverse:
** the Intelligence Cadet Corps puts a tracker on one of the Masterminds and figures out where their secret hideout is; but Stopwatch is way ahead of them, using a fake hideout and planting false clues in it, so when the Cadets search the hideout, they leap to the wrong conclusion about the intended heist.
** 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.
** She-Beast uses her duel against Nemesis to set up the Spy Kidz, by leaving a gap in her defenses that Nemesis could only know about if the Intelligence Cadets were spying on her (against the direct order of their faculty advisor) and passed it on to her opponent. Not only does she humiliate Nemesis, the Secret Squirrels get caught red-handed as a result.
** The Bell Witch's plans for the Telechines' Astrolabe involved her getting the power and her daughter Nacht getting all the negative repercussions. Katie saw it coming a mile away and turned the tables on her.
** Scapegrace manages to out-gambit three opposing supervillains ''and'' [[TheFamilyThatSlaysTogether her own family]], all with an eye toward achieving her desired GenderBender transformation.
* 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.
* 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.
* In ''Literature/{{Worm}}'', [[spoiler:Tattletale and Skitter]] outmaneuver [[spoiler:Coil, having anticipated that he would betray them]], and put him in a position that he cannot escape from, whereupon [[spoiler:Skitter]] shoots him in the head.

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