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* Obadiah Stane did a masterful job of bringing every part of [[ComicBook/IronMan Tony Stark's]] life crashing down. Chess was the theme of his campaign against Stark; he went so far as to outfit his henchmen as Knights, Bishops, and Rooks, with appropriate gimmicks.

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* Obadiah Stane did a masterful job of bringing every part of [[ComicBook/IronMan Tony Stark's]] life crashing down. Chess was the theme of his campaign against Stark; he went so far as to outfit his henchmen as Knights, Bishops, and Rooks, with appropriate gimmicks. It's revealed in his origin story that he began playing chess at a young age, and at age eight won a school chess tournament by slitting the throat of his opponent's dog and stuffing the body into the kid's locker. The victory only cemented his obsession with the game.

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* Judge Death is portrayed this way in the ''ComicBook/JudgeDredd'' prequel arc ''Fall of Deadworld''. He's mostly an OrcusOnHisThrone and only makes sporadic appearances, but seems to be anticipating various events somehow. At one point, he's actually shown hunched over a chessboard with ghoulish pieces reflecting different characters, knocking one off the table after someone was just caught as a traitor.

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* ''FanFic/ChildOfTheStorm'' has a truly epic GambitPileUp, meaning that ''loads'' of characters are this trope.
** Loki is ReformedButNotTamed. Instead of resenting being in his brother's shadow, he ''is'' Thor's shadow. He put together an information network comprising the homeless, cleaners, janitors, taxi drivers, and the like, simultaneously creating an invisible network across the world while actually helping the lower classes. However, he acknowledges Odin as being even better, the latter able to make Loki do exactly what he wants with just three words.
** Lucius Malfoy is a master manipulator whom even Nick Fury takes his hat off to. In a number of months, he goes from sitting on his laurels to becoming Master of HYDRA and temporarily [[spoiler: basically in charge of the ''entire world.'']] However, he makes a fatal mistake or two, which leads to...
** Lucius' somewhat-ally Alexander Pierce is the head of HYDRA within SHIELD, and [[AsskickingEqualsAuthority just as good of a manipulator as that implies]], even putting on an AffablyEvil act good enough to fool other chessmasters like Albus Dumbledore and Nick Fury. He's even implied to [[spoiler: have known about the Shadow Initiative after the Avengers fell, and said nothing so that he could take advantage of the chaos]]. However, [[spoiler: Lucius' desperate phone call to him]] gets intercepted by Fury, who locks him up. Even then, Pierce stays alive by leaking just a few secrets here and there to his interrogators, making himself more useful alive than dead. However...
** He gets cracked in minutes by Alison Carter, [[spoiler: daughter of Peggy and Steve]], though admittedly she does have a trump card. Later, it's revealed that she was able to pull a BatmanGambit on ''Nick Fury and Phil Coulson,'' without them even realizing.
** Fury himself is, as per usual, no slouch. As Tony puts it, "his secrets have secrets." He even manages to catch Malfoy red-handed, though he takes his hat off to Malfoy and Dumbledore, the latter of whom is somewhat OvershadowedByAwesome, though still a highly competent strategist. He and Loki even discuss chess metaphors early on, describing their allies and enemies as chess pieces.
** And manipulating the heck out of absolutely ''everyone'' is Doctor Stephen Strange, who gets everyone from {{Badass Normal}}s to the freaking Endless to do what he wants, often even when they ''know'' they're being manipulated and can't do anything about it, because he's arranged his plans so that [[BatmanGambit whatever people choose to do]], [[XanatosGambit it will work out in his favour]]. The one time he hits a blind spot, he's still capable of highly effective XanatosSpeedChess, and jumps right back on the ball afterwards. When confronting [[spoiler: Chthon]], who's just pulled a VillainOverride and looks like he's going to win, the latter smugly asks if he has any last words. He does, actually. "Check."
*** Cue BigDamnHeroes and Strange unfolding the last few steps of his plan, with a triumphant "Check. Check and mate."


* Joan Ferguson of ''Series/Wentworth'' spends whole seasons crafting elaborate plots and most of them being largely successful. In season 5, she is often seen playing chess and eventually comes to carry around one of the pieces with her around the prison.

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* Joan Ferguson of ''Series/Wentworth'' ''Series/{{Wentworth}}'' spends whole seasons crafting elaborate plots and most of them being largely successful. In season 5, she is often seen playing chess and eventually comes to carry around one of the pieces with her around the prison.prison.
* The Russian spymaster Igor Panin in the Cold War spy drama ''Chessgame'', based on the spy thrillers of Creator/AnthonyPrice.


** However, it's [[spoiler: Alex who turns out to be the real chessmaster with a brilliantly planned and executed strategy that incorporates elements of Xanatos Speed Chess.]]

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** However, it's [[spoiler: Alex who turns out to be the real chessmaster with a brilliantly planned and executed strategy that incorporates elements of Xanatos Speed Chess.]]XanatosSpeedChess]].



*** [[spoiler: Alex plays the tough Deadpan Snarker while undergoing physical torture, but later - after Washington brings up her tragic CIA history and suggests FemalesAreMoreInnocent and can't compartmentalise - she pretends to break.]]
*** [[spoiler: Alex lets Mr. Washington see a brush pass exchange with an accomplice, pretending to be sloppy because of her injury. In reality this is an intentional DivideAndConquer strategy that forces Washington to split his team up and send a henchman after the other woman, thus leaving himself more vulnerable.]]
*** [[spoiler: Alex pretends to be reluctant to open the airport storage locker, making Washington think it's a trap. When he threatens to inform a security guard, Alex appears to give in. She continues the bluff by hesitating several times while opening the locker and metal case inside. Only when Washington is convinced it's safe does he instruct his henchwoman to retrieve the data drive. Of course it was never there, and the case does contain a bomb after all.]]

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*** [[spoiler: Alex plays the tough Deadpan Snarker DeadpanSnarker while undergoing physical torture, but later - after Washington brings up her tragic CIA history and suggests FemalesAreMoreInnocent and can't compartmentalise - she pretends to break.break, fooling him into thinking he has the upper hand.]]
*** [[spoiler: Alex lets Mr. Washington see a brush pass exchange with an accomplice, pretending to be sloppy because of her an injury. In reality this is an intentional DivideAndConquer strategy that forces Washington to split his team up and send a henchman after the other woman, accomplice, thus leaving himself more vulnerable.]]
*** [[spoiler: Alex pretends to be reluctant to open the airport a storage locker, making Washington think it's a trap. When he threatens to inform a security guard, Alex appears to give in. She continues the bluff by hesitating several times while opening the locker and metal case inside. Only when Washington is convinced it's safe does he instruct his henchwoman to retrieve the data drive. Of course it was never there, and the case really does contain a bomb after all.bomb.]]



--> [[spoiler: '''Alex:''' I had to let you catch me, otherwise this wouldn't have worked.]]
--> [[spoiler: '''Mr. Washington:''' You... [[MagnificentBastard MAGNIFICENT BITCH!]] ]]

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--> ---> [[spoiler: '''Alex:''' I had to let you catch me, otherwise this wouldn't have worked.]]
--> ---> [[spoiler: '''Mr. Washington:''' You... [[MagnificentBastard MAGNIFICENT BITCH!]] ]]
]]



--> [[spoiler: '''Alex:''' Queen to bishop five. Checkmate.]]

*** [[spoiler: As the Coup de Grâce Alex sets up Mr. Washington one last time, making him think she's hidden ''something else'' behind his tie. When he instinctively reaches to check, all Alex has to do is provoke the nervy police into firing.]]
--> [[spoiler: '''Alex:''' Gun!]]

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--> ---> [[spoiler: '''Alex:''' Queen to bishop five. Checkmate.]]

]]
*** [[spoiler: As the Coup de Grâce Alex sets up Mr. Washington one last time, making him think she's hidden ''something else'' behind his tie. When he instinctively reaches to check, all Alex has to do is provoke the nervy police into firing.]]
--> ---> [[spoiler: '''Alex:''' Gun!]]

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* ''Film/{{Momentum|2015}}'': Near the end of the movie assassin Mr. Washington attempts to recover a data drive from Alex Faraday, an ex-CIA operative turned thief.
** Mr. Washington plays chess and fancies himself a master. He prides himself on being GenreSavvy and outsmarting clever opponents, and knows what tactics to employ to gain their co-operation. While interrogating a captured Alex he challenges her to a match. She refuses.
--> '''Mr. Washington:''' You might want to rethink this whole chess thing. It's good for people in our line of work. This situation - that's what we call check.
** However, it's [[spoiler: Alex who turns out to be the real chessmaster with a brilliantly planned and executed strategy that incorporates elements of Xanatos Speed Chess.]]
*** [[spoiler: Prior to her capture (which is part of her plan), Alex plants the data drive on ''Mr. Washington himself'' during a struggle, using his tie as a hiding place. This ensures the drive will remain hidden, but always be close by.]]
*** [[spoiler: Alex plays the tough Deadpan Snarker while undergoing physical torture, but later - after Washington brings up her tragic CIA history and suggests FemalesAreMoreInnocent and can't compartmentalise - she pretends to break.]]
*** [[spoiler: Alex lets Mr. Washington see a brush pass exchange with an accomplice, pretending to be sloppy because of her injury. In reality this is an intentional DivideAndConquer strategy that forces Washington to split his team up and send a henchman after the other woman, thus leaving himself more vulnerable.]]
*** [[spoiler: Alex pretends to be reluctant to open the airport storage locker, making Washington think it's a trap. When he threatens to inform a security guard, Alex appears to give in. She continues the bluff by hesitating several times while opening the locker and metal case inside. Only when Washington is convinced it's safe does he instruct his henchwoman to retrieve the data drive. Of course it was never there, and the case does contain a bomb after all.]]
*** Lampshaded in a post-reveal exchange.
--> [[spoiler: '''Alex:''' I had to let you catch me, otherwise this wouldn't have worked.]]
--> [[spoiler: '''Mr. Washington:''' You... [[MagnificentBastard MAGNIFICENT BITCH!]] ]]

*** And even more explicit lampshading later.
--> [[spoiler: '''Alex:''' Queen to bishop five. Checkmate.]]

*** [[spoiler: As the Coup de Grâce Alex sets up Mr. Washington one last time, making him think she's hidden ''something else'' behind his tie. When he instinctively reaches to check, all Alex has to do is provoke the nervy police into firing.]]
--> [[spoiler: '''Alex:''' Gun!]]


* ''ComicStrip/CalvinAndHobbes'' parodies this trope:
--->'''Calvin:''' "Ah, you've fallen right into my trap! Perhaps you'd like to take that move over?"

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* ''ComicStrip/CalvinAndHobbes'' parodies this trope:
trope, with checkers. Hobbes obliterates Calvin's pieces in one series of jumps, and Calvin spends a few panels staring blankly at the board.
--->'''Calvin:''' "Ah, "[[BlatantLies Ah, you've fallen right into my trap! trap!]] Perhaps you'd like to take that move over?"


* Subverted in ''Market Forces'' by Richard Morgan, a 2004 sci-fi novel in which CorruptCorporateExecutive types battle for promotion by fighting MadMax-style road duels. The protagonist Chris Faulkner has been manipulated into a fatal road duel with his friend Mike Bryant (a more skilled driver) in order to eliminate them both as potential rivals. In a JustBetweenYouAndMe moment the antagonist derides Faulkner and Bryant's chess hobby, pointing out that its restricted field and strict rules make the game useless training for real life.

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* Subverted in ''Market Forces'' by Richard Morgan, a 2004 sci-fi novel in which CorruptCorporateExecutive types battle for promotion by fighting MadMax-style ''Film/MadMax''-style road duels. The protagonist Chris Faulkner has been manipulated into a fatal road duel with his friend Mike Bryant (a more skilled driver) in order to eliminate them both as potential rivals. In a JustBetweenYouAndMe moment the antagonist derides Faulkner and Bryant's chess hobby, pointing out that its restricted field and strict rules make the game useless training for real life.


** Tyrion Lannister is a great ''cyvasse''-player, and has his moments of setting things up, including losing a few weeks' worth of ''cyvasse'' games on purpose so he could gamble and important piece of information after his opponent grows cocky.

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** Tyrion Lannister is a great ''cyvasse''-player, and has his moments of setting things up, including losing a few weeks' worth of actual ''cyvasse'' games on purpose so he could gamble and successfully for an important piece of information after his opponent grows cocky.rather too cocky. However, in the grander scheme of things, Tyrion's political game often gets stomped on within the massive GambitPileup that the Seven Kingdoms becomes. Mostly its not due to his own fault, but sometimes it can be because 1) he couldn't keep his mouth shut and 2) having to trust the wrong people thanks to having few right ones to turn to (despite knowing they're not reliable).


* In ''Webcomic/{{Freefall}}'', Dr. Bowman says that another character keeps losing to him because he can't see five moves ahead.

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* In ''Webcomic/{{Freefall}}'', Dr. Bowman says that another character keeps losing to him because he can't see five moves ahead. The "several moves ahead" matter applies to the rest of Bowman's plans, since every last hang-up, problem and unforeseen consequence his project might have ran into had already been covered before anyone even considered the possibility it might come up, and even end up covering the problems he couldn't have thought of (like Kornada's scheme, foiled by one of his creations).


[[folder: Web Animation]]
* ''WebAnimation/{{RWBY}}'' has Cinder Fall, the BigBad of seasons 2 and 3. She manipulated all events surrounding the Vytal Tournament using a virus that spread through Beacon's network, therefore spreading to the Atlesian Army's Network, from there, she was able to choose every fight that would happen while manipulating the characters around her. The virus she used had the image of the queen piece of a chess game.
[[/folder]]


** Inspired in part by ''Film/{{Yojimbo}}'' and ''The Glass Key'', or ''Red Harvest''.
*** Retold in Creator/TheCoenBrothers' ''MillersCrossing''.

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** Inspired in part by ''Film/{{Yojimbo}}'' and ''The Glass Key'', ''Literature/TheGlassKey'', or ''Red Harvest''.
*** Retold in Creator/TheCoenBrothers' ''MillersCrossing''.''Film/MillersCrossing''.


* One of the bounties in ''Anime/CowboyBebop'', appropriately named Chessmaster Hex. He set up a revenge plot for a company he worked for by supplying plans for defrauding their customers to several dozen random people on the internet (and provided each of them with a chess piece so the company would know he was behind it). The twist is that he set it up fifty years ago to just happen now and he has since become a senile old man that just plays chess online all day.

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* One of the bounties in ''Anime/CowboyBebop'', appropriately named Chessmaster Hex. He set up a revenge plot for a company he worked for by supplying plans for defrauding their customers to several dozen random people on the internet (and provided each of them with a chess piece so the company would know he was behind it). The twist is that he set it up fifty years ago to just happen now and he has since become a senile old man that just plays chess online all day. Despite his senility, he still plays a mean game of chess, and his match with Ed lasts ''a week'' before Hex puts her in checkmate.

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* Joan Ferguson of ''Series/Wentworth'' spends whole seasons crafting elaborate plots and most of them being largely successful. In season 5, she is often seen playing chess and eventually comes to carry around one of the pieces with her around the prison.


* Though he is seldom thought of that way, Gandalf of ''Literature/TheLordOfTheRings'' has a little bit of the Chessmaster in him. He uses the whole war of the ring as a gambit to get Frodo close to Mt. Doom, and describes it in chess terms, referring to Pippin as a pawn who was as likely to see as much of the action as the other pieces on the board. If we look at it that way, the whole War of the Ring is a conflict between two spectacularly skillful chessmasters, Gandalf and Sauron. Sauron may be slightly better on the whole, but Gandalf is good enough to take skillful advantage of his [[EvilCannotComprehendGood one weakness]].
** Gandalf's ulterior motive for organizing the Thirteen Dwarves and Bilbo's expedition in ''Literature/TheHobbit''. He needed to do several things: investigate reports of Sauron's rise to power over Mirkwood, defeat a dragon that Sauron could bend to his will and use in the war, re-establish the strong Human and Dwarfish kingdoms of the area, and get everybody allied with each other, so that they could repel an invasion from the east that would allow Sauron to flank and crush Gondor. In the end, [[spoiler:Smaug was killed, Sauron was driven to Mordor, and gave the world warning of his impending arrival, The Battle of Five Armies greatly weakened the Orc's presence in the north, and the Kingdoms of Dale and Erebor were re-established]]. This gambit would work beautifully during the War of the Ring, as the force of Easterlings and Orcs that actually made it through the north alive was ''much'' reduced.
** This bit of Gandalf's {{chessmaster}}y is not at all clear in ''Literature/TheHobbit'', is described a little in Appendix A to ''Literature/TheLordOfTheRings'', and then is laid out plainly in ''Literature/UnfinishedTales'':
--->'''Thorin:''' You are playing some crooked game of your own, Master Gandalf. I am sure that you have other purposes than helping me.
--->'''Gandalf:''' You are quite right. If I had no other purposes, I should not be helping you at all. Great as your affairs may seem to you, they are only a small strand in the great web. I am concerned with many strands. But that should make my advice more weighty, not less.

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* Though he is seldom thought of that way, In [[Literature/TolkiensLegendarium Tolkien's Legendarium]], Gandalf is a bit of a chessmaster. Sent to Middle-earth [[AngelUnaware in the form of an old man]] and forbidden from showing his power openly, he mostly brings about Sauron's downfall by exerting strategic influence on various key players opposed to Mordor. At one point in ''Literature/TheLordOfTheRings'' has a little bit of the Chessmaster in him. He uses the whole war of the ring as a gambit to get Frodo close to Mt. Doom, and he describes it in the approaching war as a chess terms, referring to Pippin as a pawn who was as game ("And pawns are likely to see as much of the action it as the other pieces on the board. If we look at it that way, the whole War any, Peregrin son of the Ring is a conflict between two spectacularly skillful chessmasters, Gandalf and Sauron. Sauron may be slightly better on the whole, but Gandalf is good enough to take skillful advantage Paladin, soldier of his [[EvilCannotComprehendGood one weakness]].
**
Gondor. Sharpen your blade!") Gandalf's ulterior motive chessmaster qualities are also highlighted in "The Quest of Erebor", a narrative account (intended for organizing the Thirteen Dwarves and Bilbo's expedition in ''Literature/TheHobbit''. He needed to do several things: investigate reports of Sauron's rise to power over Mirkwood, defeat a dragon that Sauron could bend to his will and use inclusion in the war, re-establish [=LotR=] appendices but cut for space) of how Gandalf and Thorin came to arrange the strong Human and Dwarfish kingdoms of journey to the area, and get everybody allied with each other, so that they could repel an invasion from the east that would allow Sauron to flank and crush Gondor. In the end, [[spoiler:Smaug was killed, Sauron was driven to Mordor, and gave the world warning of his impending arrival, The Battle of Five Armies greatly weakened the Orc's presence Lonely Mountain in the north, and the Kingdoms of Dale and Erebor were re-established]]. This gambit would work beautifully during the War of the Ring, as the force of Easterlings and Orcs that actually made it through the north alive was ''much'' reduced.
** This bit of Gandalf's {{chessmaster}}y is not at all clear in ''Literature/TheHobbit'', is described a little in Appendix A to ''Literature/TheLordOfTheRings'', and then is laid out plainly in ''Literature/UnfinishedTales'':
--->'''Thorin:'''
''Literature/TheHobbit''.
--> '''Thorin:'''
You are playing some crooked game of your own, Master Gandalf. I am sure that you have other purposes than helping me.
--->'''Gandalf:''' --> '''Gandalf:''' You are quite right. If I had no other purposes, I should not be helping you at all. Great as your affairs may seem to you, they are only a small strand in the great web. I am concerned with many strands. But that should make my advice more weighty, not less.

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