History Main / OutGambitted

[[caption-width-right:273:[-[[PreAssKickingOneLiner You've got me right where I want you.]]-] ]]

* Why [[UsefulNotes/TheRomanEmpire Roman emperor]] Tiberius remained in power 'till his natural death in spite of being widely hated by the Senate and surrounded by [[TheStarscream untrustworthy allies]]: he could easily play them against each other [[MagnificentBastard without even leaving his villa on the island of Capri]]. Best shown by the fall of Sejanus, the chief of the PraetorianGuard who was using his role as Tiberius' representative in Rome to prepare for a coup: upon learning of his treachery, Tiberius started sending out letters and orders made specifically to confuse the situation and undermine his authority in general and over the Praetorians in particular while at the same time showing the outmost respect for Sejanus, then, once the groundwork was laid, he sent to Rome a man named Macro and had him summon the Senate and Sejanus for the public appointment of Sejanus to tribune (thus effectively making him as powerful as Tiberius himself)... Except the letter, before announcing the appointment, suddenly ordered the arrest of Sejanus and two senators loyal to him, and while the letter was being read the Praetorians guarding the place had been replaced by ''vigiles'' (Rome's police force and firefighters) and Macro had announced the Praetorians that Tiberius had just appointed ''him'' to their command.

* Happens all the time in TabletopGame/{{chess}}, but it should be noted that the word 'gambit' has a specific meaning in that context (a minor offer of material, usually a pawn, in the opening in exchange for another type of advantage), and a 'countergambit' specifically refers to a gambit offered in response to another gambit - instead of taking your opponent's offered pawn, for example, you reply by offering your own. This, of course, is no guarantee of success for either side.

** Sasuke (take a deep breath) thought that Itachi killed his clan out of hatred, but [[spoiler:he really did care about him because he was ordered to by the Konoha elder Danzo, who was than revealed to have been manipulated by Tobi, who had also manipulated Pain into becoming evil. Sasuke was then manipulated by Orochimaru to steal his body, but Sasuke saw through this and was met up by Tobi, who revealed that he was responsible for the Uchiha clan massacre by unleashing Kurama on Konoha, causing Sasuke to kill Danzo and then target Konoha, but then Kabuto blackmailed Tobi by resurrecting the real Madara, whom Tobi had impersonated. Itachi was resurrected by Kabuto as well, but then he defeated him and sealed his own soul away, but then Madara revealed he had caused the death of Rin, which caused Tobi to become evil as he was originally Obito and Madara placed a seal on Tobi's heart which prevented him from becoming the Ten Tails Jinchuuriki in case he tried to side step Madara on the plan. Later, Madara tried to force Tobi into restoring his natural body, but actually Tobi foresaw this and previously get rid of seal Madara in order to become the Ten Tails Jinchuuriki. But later, when Tobi is defeated by Naruto and the Alliance, Madara pulls out his resurrection with the help of Black Zetsu. Orochimaru, Sasuke, and Tobi (still struggling with the Black Zetsu) then try to help everyone else by defeating Madara. Black Zetsu is revealed to have the manifestation of Princess Kaguya who was the first human to use chakra whom Madara was descended from who in turn incapacitates him.]] Whew.

* This is how the BigBad of ''{{WesternAnimation/Zootopia}}'' gets taken down; [[spoiler: Bellwether traps Judy and Nick in a pit then darts the latter with a Night Howler pellet, intending him to turn savage and kill Judy. Bellwether calls the ZPD reporting a savage fox and an officer down. While waiting for them to arrive, she intends to watch the gruesome death all the while carrying on her EvilGloating. This backfires on her ''massively'' as it turns out Judy and Nick anticipated this and replaced the pellet with blueberries. While Nick faked going savage, Judy used her carrot pen recorder to [[CaughtOnTape capture Bellwether's gloating]] leading to an EngineeredPublicConfession. By the time Bellwether realizes she's been tricked, [[TheCavalry the ZPD are behind her and blocking off all means of escape]], catching her red-handed leading to her arrest and the end of TheConspiracy.]]

* 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.]]

* 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 ''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 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.]]

** 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, Raphiel and Crowley force Castiel to flee, leaving behind all the ingredients for the spell. - Unfortunately for Crowley and Raphael, Castiel wasn't taken by surprise at all. What he left behind include a fake version of one ingredient; something rare, hard to get, and crucial to the spell. He'd already hidden the real item away somewhere else. While Raphael and Crowley waste their time trying to cast a spell that can never work, Castiel is able to complete his work without threat or interruption. By the time he finishes, he's pretty much the most powerful being in the Supernatural universe. Only God, and probably Death, are stronger. Raphael doesn't fare very well after that.

* 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.

** On the January 26 (taped January 20), 1998 ''Raw'', he was supposed to defend the [[http://www.wrestling-titles.com/wwe/wwf-eu-h.html WWE European Heavyweight Title]] against Wrestling/OwenHart. HHH sent Wrestling/{{Goldust}}, who was dressed as HHH, as his replacement. Owen won the match. Wrestling/{{DGenerationX}} (Wrestling/ShawnMichaels, HHH and Wrestling/{{Chyna}}) appeared on the [[Franks2000InchTV [=TitanTron=]]] to brag about getting out of the match. Then Commissioner [[Wrestling/SgtSlaughter Slaughter]] came out and ruled that Goldust was an acceptable substitute and that Owen was the new Champion. In other words, HHH lost the title ''without even being in the match''.
** ''Wrestling/SurvivorSeries 99'', November 14, 1999. HHH was supposed to defend the [[http://www.wrestling-titles.com/wwe/wwe-h.html WWE World Heavyweight Title]] against Wrestling/StoneColdSteveAustin and [[Wrestling/DwayneJohnson The Rock]]. Austin got hit by a van in the parking lot. So, fresh off of having {{Squash|Match}}ed [[Wrestling/BigBossman The Big Bossman]]'s team in [[https://www.youtube.com/watch?v=lb1Qvuj5sXs record time]][[note]]It was supposed to have been Big Show, Wrestling/TheBlueMeanie and Kaientai (Wrestling/TakaMichinoku and Shoichi Funaki) vs. Bossman, [[Characters/WWENewGeneration Mideon, Viscera]] and [[Wrestling/MattBloom Prince Albert]], but Big Show beat up his partners backstage and went to the ring alone. He Chokeslammed and pinned Mideon at the 19-second mark, then the same to Albert at the 30-second mark, punched, bodyslammed, chokeslammed and pinned the 500 lbs. Viscera at the 55-second mark, and Bossman took the hint and got counted out at the 1:24 mark.[[/note]] earlier that night, '''[[Wrestling/BigShow THE BIG SHOW]]''' took Austin's place and won the match and the title.

* 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]].

* 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 BreakingSpeech to leave the Fright Zone virtually undefended when Glimmer and Scorpia infiltrate.]]

* In ''WesternAnimation/YoungJustice'', this happens to the Light on a few occasions. Near the end of the first season, they try to use blackmail to get Artemis, Superboy and Ms. Martian to join them, but they defuse the blackmail by telling the other team members their secrets. Then they manage to create a cure and vaccine to the mind-controlling Starro-Tech, and catch the Light by surpise, allowing them to free the JL from the Light's control. Then, in season 2, [[spoiler: not only does Aqualad get the Light and Reach to admit their actions, he also revealed how they had double-crossed each other at multiple points, utterly SHATTERING their alliance]]. Then in the third, for Vandal Savage, a 50,000 year-old immortal himself says NO-ONE has EVER upset his plans like that in his entire life. ''Then'' the Team shows up, and not only did the Light fall for Aqualad and Artemis's fake deaths, the Team managed to infiltrate the assassins and capture nearly half the Light.

* Happens all the time in chess, but it should be noted that the word 'gambit' has a specific meaning in that context (a minor offer of material, usually a pawn, in the opening in exchange for another type of advantage), and a 'countergambit' specifically refers to a gambit offered in response to another gambit - instead of taking your opponent's offered pawn, for example, you reply by offering your own. This, of course, is no guarantee of success for either side.

** 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 Retusbi 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.

** 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 Retusbi 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.

* This is how the BigBad of ''{{Disney/Zootopia}}'' gets taken down; [[spoiler: Bellwether traps Judy and Nick in a pit then darts the latter with a Night Howler pellet, intending him to turn savage and kill Judy. Bellwether calls the ZPD reporting a savage fox and an officer down. While waiting for them to arrive, she intends to watch the gruesome death all the while carrying on her EvilGloating. This backfires on her ''massively'' as it turns out Judy and Nick anticipated this and replaced the pellet with blueberries. While Nick faked going savage, Judy used her carrot pen recorder to [[CaughtOnTape capture Bellwether's gloating]] leading to an EngineeredPublicConfession. By the time Bellwether realizes she's been tricked, [[TheCavalry the ZPD are behind her and blocking off all means of escape]], catching her red-handed leading to her arrest and the end of TheConspiracy.]]

* ''VisualNovel/DanganronpaV3'': Miu convinces everyone to go into her virtual reality simulation, assuring them she has gotten rid of weapons. In reality, she also edited and added several settings, designating her avatar an object, and thus unable to be broken, creating a wall only objects could pass through, and making it so Kokichi's avatar could be paralyzed by her, in order to kill him. Kokichi quickly catches on but agrees to enter and forms his own scheme. [[spoiler:Knowing Miu would make it impossible for him to kill her, Kokichi shows Gonta a flashback light, convincing him to murder Miu to mercy kill everyone at the ensuring trial. When the inventor calls Kokichi to the roof, Gonta appears and strangles her with a roll of toilet paper]]. This act shatters any respect the remaining students had for Kokichi.

* ''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 they 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/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, Joker was able to exit police custody without being spotted.]] After all this, a television interview makes Black Mask realize they they've been tricked, [[{{Touche}} and admits to being impressed at the Phantom Thieves pulling it off]].

* ''VideoGame/Persona5'': You and your team pull off a masterful one near the end. [[spoiler:After figuring out the traitor's identity, your team sets him to help bust the Conspiracy he's working for, and successfully plan two steps ahead of him for every move he makes, up to and including him trying to kill you.]]

* ''Film/{{Circle}}'': 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.

* ''Film/{{Flightplan}}'': 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]].

* 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. Juno had the Apple force Desmond to kill Lucy to keep the Apple out of Templar hands]].

** 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.

** Sasuke (take a deep breath) thought that Itachi killed his clan out of hatred but [[spoiler:he really did care about him because he was ordered to by the Konoha elder Danzo, who was than revealed to have been manipulated by Tobi who had also manipulated Pain into becoming evil. Sasuke was then manipulated by Orochimaru to steal his body, but Sasuke saw through this and was met up by Tobi who revealed that he was responsible for the Uchiha clan massacre by unleashing Kurama on Konoha, causing Sasuke to kill Danzo and then target Konoha, but then Kabuto blackmailed Tobi by resurrecting the real Madara whom Tobi had impersonated. Itachi was resurrected by Kabuto as well, but then he defeated him and sealed his own soul away, but then Madara revealed he had caused the death of Rin which caused Tobi to become evil as he was originally Obito and Madara placed a seal on Tobi's heart which prevented him from becoming the Ten Tails Jinchuuriki in case he tried to side step Madara on the plan. Later Madara trying to force Tobi into restoring his natural body but actually Tobi foresaw this and previously get rid of seal Madara in order to become the Ten Tails Jinchuuriki. But later when Tobi is defeated by Naruto and the Alliance, Madara pulls out his resurrection with the help of Black Zetsu. Orochimaru, Sasuke, and Tobi (still struggling with the Black Zetsu) then try to help everyone else by defeating Madara. Black Zetsu is revealed to have the manifestation of Princess Kaguya who was the first human to use chakra whom Madara was descended from who in turn incapacitates him.]] Whew.

** [[spoiler:Aizen's on the receiving end of this trope several times during his end-game. The first and most obvious one is when Gin pulls a Starscream and tries to kill Aizen. Aizen has, of course, been expecting this all along, but Gin reveals he was the only shinigami that completely lied about how his powers worked while biding his time to figure out the weakness in Aizen's abilities. He proceeds to instantly kill Aizen with his Bankai's true power, making Aizen experience true fear for the first time in his life. Unfortunately, the RealityWarper grafted to Aizen's chest is able to save him and use that fear to help him evolve, but this means that Aizen's new form completely fails to adapt to Ichigo's LookWhatICanDoNow power-up later. After Aizen's defeat, it turns out that Aizen was also 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.]]

* ''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 the Straw Hats SpannerInTheWorks and mocked Doflamingo for not seeing it coming despite knowing of the Straw Hats reputation]].

* ''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 them 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 BreakingSpeech to leave the Fright Zone virtually undefended when Glimmer and Scorpia infiltrate.]]

* ''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 does some complicated con but [[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.

** Joseph Joestar's epic chariot battle against Wham. Every tactic one fighter used was immediately countered by the other, with Joseph barely prevailing in the end.

* In ''Literature/{{Animorphs}}'', Visser One's plan worked well. Tom's worked even better. Jake's worked best of all.

* ''Literature/TheLordOfTheRings'': [[TheChessmaster Sauron]], the guy who when taken prisoner by the Númenóreans was in control of them within a year, out-gambits almost everyone during the War of the Ring. He anticipates [[TheStarscream Saruman]]'s betrayal and gives [[RegentForLife Denethor]] the right information to draw the wrong conclusions, but just as Gandalf planned, [[EvilCannotComprehendGood Sauron simply couldn't imagine]] that anyone would try and ''destroy'' the One Ring instead of claiming it for themselves. He's actually ''right'', except that he couldn't have foreseen Gollum destroying the ring ''by accident''.