[[TheChessmaster Back to the main page.]]
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[[foldercontrol]]

[[folder: Anime & Manga]]
* Chessmaster vs. Chessmaster example: Light vs. L in ''Manga/DeathNote'', creating a GambitPileup to no end. Unlike most chessmaster stories, this one usually lets the audience in on each move of the game. When we're suddenly denied this privilege, you can bet something hardcore is about to go down. At one point, a Chessmaster is drawn moving figurines of the ''dramatis personae'' around a chess board. L is even seen to toy with chesspieces when contemplating.
** Near and Mello.
** L, Near and Mello are clearer examples of Chessmasters, as all three of them carefully and deliberately set the board in the first few episodes from their introduction. Light had to scramble for pieces to put immediately into play; what saved him was that he was a quick study of his opponent and had powerful and unpredictable gambits.
** Similarly, in one of the Film adaptations, L and Light actually play a game of chess with each other while having a discussion, with Light winning.
* ''Manga/BlackButler's'' Ciel Phantomhive exudes this, despite the fact that he's only 13 years old - he's a keen observer, a strategist, and knows precisely when to strike his enemies - or, more often, when to send in his [[DealWithTheDevil demonic]] BattleButler to strike. And he's ''very good'' at making people think that he's [[BewareTheNiceOnes just a cute, innocent little kid]] to lure them into a false sense of security, despite the fact that, behind closed doors he's a DeadpanSnarker crossed with a MagnificentBastard with a pinch of CrazyPrepared. We see him playing chess quite often during the manga - he's even undefeated.
** Along with the ChessMotifs scattered throughout the manga and anime (especially the opening), there's quite a few chess metaphors and direct references thrown around.
-->'''Sebastian:''' [[WhamLine If it's your wish I will follow you everywhere. Even if your throne crumbles, and your shiny crown turns to rust. Even if the bodies pile up endlessly. Above the bottomless pile of corpses beside you as you lie softly down, I will follow you... until I hear the words "checkmate."]]
* Kaname Kuran of ''VampireKnight''. In the opening credits for the first series, there's even a massive chessboard, and Kaname is often described as "moving all the pieces into place", that Zero is a pawn, and he says "checkmate" at least once in that series... He's also been seen playing actual chess.
* Lelouch, the Hero of ''Anime/CodeGeass'', is almost a textbook example of the good-guy Chessmaster: highly intelligent WellIntentionedExtremist who excels at chess. When Mao gets the advantage on him, the point is emphasized by his clobbering of Lelouch at chess (by reading Lelouch's mind and revealing every single strategy Lelouch was thinking of at a single moment...including ones to misdirect Mao's telepathy).
** The "almost" comes from the fact that, rather than sitting on the sidelines, he fights in the field with his men, and that WordOfGod, LampshadeHanging, and direct statements from Lelouch himself ("I can't win if I abandon my people",) demonstrate that he actually cares about the well-being of those he commands.
** Though just to add to the "chess" metaphor, Lelouch is compared to a king more than once. Like the king piece, he's the most valuable piece on the board but extremely poor at combat, being one of the most physically weak characters in the show. This is even partly why he's on the field, actually: his own personal chess strategy seems to have the king move around a lot more than his opponents consider 'normal'. "If the King doesn't lead, his men won't follow." His MindControl power is even referred to as, "The Power of the King"
*** And to drive the point home even further, the King piece used in the series' chess set was explicitly modeled on Lelouch's alter-ego Zero (the Queen was modeled on his partner C.C., incidentally).
** Lelouch carries this to the hilt by using standard chess notation to designate his soldiers in battle - his most trusted ally Kallen is "Q-1" (Queen), second-in-command Ohgi is N-1 (Knight), and TheFool Tamaki is "P-1" (Pawn).
** He even uses novelty trigger switches shaped like chess pieces to set off traps and explosives.
** His brother Schneizel is also a competent Chessmaster in his own right, and is the only one who can take Lelouch on on an even footing.
* Yugi in ''[[TenchiMuyo Tenchi in Tokyo]]'' has a floating crystal formation in her evil lair that represents the relationships between Tenchi and all the other major characters.
* 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.
* Several characters in ''LiarGame''. One of the antagonists, while not playing chess, uses chess pieces to demonstrate headcount in a Minority Rule game. The three pieces (rook, knight, bishop) all representing the same person are then dramatically replaced with a king, complete with grand sweeping gesture.
* AffablyEvil Prime Minister Wong Wunfat from ''GGundam''. ''Humongous'' chess board included.
* ''OnePiece'''s anime-only G8 Arc has the Straw Hats trapped in an island fortress that happens to be a Marine Base. The base's commander, Jonathan, makes several allusions to chess as he strategizes on how to capture the now-infamous Straw Hat Pirates, having the board in front of him many times. In fact, this guy is so good of a chessmaster that if it hadn't been for a visiting vain Marine official's interference, he might have actually succeeded in capturing the Straw Hats.
* ''VisualNovel/UminekoNoNakuKoroNi'' has Chess motifs all over the place, but the one who ''seems'' to be doing all the manipulation isn't the one using the chess metaphors.
* Vampire king Akabara Strauss as well as others from ''TheRecordOfAFallenVampire''.
* Father in ''Manga/FullmetalAlchemist'' has a chessboard, and [[spoiler:actually uses it as the activation point for his plan]].
** Also [[ColonelBadass Roy Mustang]]: he often plays chess, and when [[spoiler:his loyal team is taken from him, he laments their loss by putting away the corresponding pieces in his chessboard]]. Although he is ''definitely'' not gonna sacrifice anyone for his plans.
* ''Manga/FairyTail'' villain Jellal uses a circular chessboard with custom-shaped pieces to note when certain players are taken out of the game and new ones put in.
* ''SDGundamForce'' has Kibaomaru, who has a ''shogi'' theme. At one point in the Ark arc he plays several games against Shute, effortlessly winning each one. He translates his strategic ability into real life by easily figuring out the Gundam Force's strategy and come up with a counter-plan instantly.
* ''GundamSeedDestiny'' has [[DarkMessiah Chairman Gilbert Durandal]], who manipulates both events and [[ManipulativeBastard people]] with incredible ease; unlike many on this list, he's also a GracefulLoser. His predecessor as BigBad, [[GundamSeed Rau Le Creuset]] was also one of these, successfully getting the entire world caught up in a war of [[OmnicidalManiac mutual extinction]]. Durandal regularly messes around with a chessboard, and at one point they're seen playing against one another. [[spoiler: [[WoobieDestroyerOfWorlds Le Creuset]] wins]].
* Seto Kaiba during the Death-T arc in the ''Manga/YuGiOh'' manga. He gets extra points for having an ''actual chess board'' right in front of him during most of the arc.
* Izaya Orihara from ''{{Durarara}}'', although ordinary chess bores him. He instead uses a bizarre board game, [[{{Calvinball}} the rules of which only he knows and which incorporates pieces from at least three different board games]], to illustrate his manipulation of Ikebukoro and its residents.
** To a lesser extent, Aoba as well. Oh, and [[spoiler: Mikado]]. No, seriously.
* Taikobo from ''HoushinEngi'' is the most heroic Chessmaster you'll ever find. He acts like a complete idiot and failure, but uses that to manipulate every single person he knows. Dakki also matches up as one, just in the more pure evil style, causing the two to constantly butt heads as their pawns clash.
* The entire third season of ''HellGirl'' can be viewed as a desperate chess game ... perhaps even a deadly game of speed chess. It slowly grows over the season and when it culminates in the very last episode the unspoken central question is who won? The Lord of Hell, finally trapping Ai Emna into the Hell Girl role for eternity .... or was it Ai Emna's final victory ... saving a soul from an eternity in Hell?
* Kabuto, from ''{{Naruto}}'' does this with a board more resembling of the game "Go", to keep track of all his Edo Tensei pawns.
** Far more so than Kabuto is Shikimaru whose only passions are playing Go with his teacher (there are several scenes of his games with Azuma) and lazing about. He's also the second most cunning strategist in the Leaf village (beaten only by his father) and his battle with Temari in the Jounin exam makes a lot of references to his anticipating her moves and using misdirection to lead her into a trap. He was the only one to get promoted in the entire exam group despite forfeiting his match.
* Sora and Shiro in ''LightNovel/NoGameNoLife'' were teleported into a world where chess metaphors become literal objects of power and status. Their first major battle is a chess game that [[spoiler: due to the use of magic by their opponent]] goes OffTheRails by [[spoiler: the players directly addressing the pieces, appealing to their humanity, logic or fear]], foregoing the game's typical rules. All of this becomes the first game against 15 other enemies who hold symbolic chess pieces in a meta-tournament to qualify squaring off [[spoiler:against Tet, the world's God.]]
[[/folder]]

[[folder: Comic Books]]
* In TheMightyThor, Odin has sometimes been seeing poring over a chessboard with the characters as the pieces (ususally to show he's going through a morally ambiguous phase).
** Now [[ComicBook/{{Loki}} Kid!Loki]] has been doing it too. He's got figurines of several people that he's dealing with, and uses a map as his chessboard. However, it was drawn at too far an angle to see what he was arranging.
* ''{{JLA-Avengers}}'' has Metron and The Grandmaster as such.
* Obadiah Stane did a masterful job of bringing every part of [[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.
* ''CalvinAndHobbes'' parodies this trope:
--->'''Calvin:''' "Ah, you've fallen right into my trap! Perhaps you'd like to take that move over?"
--->'''Hobbes:''' "Your remaining piece must have one heck of a plan..."
* ''SupermanRedSon'' has LexLuthor (naturally) and Brainiac. Superman, on the other hand, is more of a chess novice... He's ''good'', but he's not ''Luthor'' good.
** Luthor's introduction as the Chessmaster in ''Red Son'' isn't entirely subtle, but effective: he's just won fourteen simultaneous games of chess on his coffee break, while also reading Machiavelli and teaching himself Urdu by tape (in a tape player he designed himself, no less) "to keep my mind occupied". How good is "Luthor good"? [[spoiler:The end sees Brainiac destroyed, (and apparently Superman too), the world united and ready to accept "Luthorism" to lead it. He regards the chessboard and remarks "It's like it was planned to the tenth decimal point forty years ago."]]
* ''{{Hellblazer}}'' - If you're ever associated with John Constantine, chances are you're already dead.
** Celebrated more in {{Justice League Dark}}, where Constantine's has a full arsenal of pieces, albeit he calls it a "band" rather than chess pieces.
** A perfect example was during the ''Reasons to be Cheerful'' arc. John's demonic children attempted to kill everyone that John has ever met and knew. That includes his family, close friends, and those he hasn't seen for a long time. They almost succeeded.
* DCComics' {{Darkseid}} is also fond of moving figure of his minions and enemies around on a chessboard when hatching his latest evil scheme.
** Since everything ''CountdownToFinalCrisis'' touches turns to fail, when he does it in that series he just winds up looking like [[Film/{{Spaceballs}} Dark Helmet.]]
* ''YTheLastMan'' has the Daughters of Amazon led by Victoria, a master of chess; they argue, among other things, that the queen is the most powerful chess piece, like women are the superior sex.
* The very first time we see DoctorDoom, he's toying with chess-piece replicas of the Comicbook/FantasticFour, so that tells you all you need to know. He's usually ranked as Reed Richards' evil ''doppelganger'' regarding intellect, and his plans range from the complicated to the ''really'' complicated to the one that played both [[{{Satan}} Mephisto]] and Comicbook/DoctorStrange like Stradivarius violins. Simultaneously. With one move.
** ...which is parodied in [[http://www.nuklearpower.com/2003/10/16/episode-342-hypothetically-speaking/ these]] [[http://www.nuklearpower.com/2003/10/18/episode-343-check-mate/ two]] ''Webcomic/EightBitTheater'' strips.
** An issue of ''Comicbook/{{Excalibur}}'' parodied the characters-as-chess-pieces visual metaphor, with the characters standing on a chessboard, and Captain Britain saying "Call me paranoid, but I think we're being manipulated."
*** Probably also a reference to a classic earlier ''Captain Britain'' storyline, where the same manipulator, Merlin, played a quite literal game of chess with the characters' fates. He continues to do so during a pivotal story arc of ''Excalibur'', including a time in which he fakes his own death and has his daughter Roma (who's not in on the deception) play the game in his place for a while. When he returns (in the very issue with the above-mentioned cover), he's carrying a chess piece representing Roma, and places it on the board.
* Mother Freya, the goddess of love in Mark Crilley's ''MikiFalls'', is eventually revealed to be one of these.
* In the Franchise/{{Batman}} story ''Hush'', Hush is thought to be it, but it actually turns out to be [[spoiler:The Riddler]] who ironically, Batman had dismissed as a threat earlier on in the story.
* ComicBook/{{Cyclops}} from ComicBook/{{X-Men}}, the "General of the Mutants", is the [[DeconstructedTrope Deconstruction]] of the trope. While his grand plans allows him to get the job done, it also served as the catalyst for the more recent split of the X-Men, with Wolverine leaving with half of the team out of disgust due to Cyclops using members as pawns.
** DependingOnTheWriter, how self-aware Scott is of this trope varies. He can go from being TheChainsOfCommanding, to a WellIntentionedExtremist, to even a [[TyrantTakesTheHelm borderline tyrant.]]
* In ''ComicBook/AllFallDown'', [[spoiler: AIQ Squared]] becomes this, hatching an elaborate plot to try and kill Siphon, using [[spoiler: Phylum and Pronto]] as his less-than-willing pawns.
* In ''ComicBook/DeathOfTheFamily'', SelfDemonstrating/TheJoker has spent his year-long absence becoming this. The ''Catwoman'' story even shows the chess motif!
* In ''ComicBook/TheInvisibles'', there is an extremely mysterious and shadowy character known as the Blind Chessman who, well, plays chess, both literally and metaphorically. It also doubles as a BlindSeer.
[[/folder]]

[[folder:Fanfiction]]
* [[ManipulativeBastard Checker]] [[TheSociopath Monarch]], the BigBad of ''FanFic/GettingBackOnYourHooves'', who uses a chess board (chess itself being described at one point as her favorite game) as a representation of her plans to ruin [[spoiler: her sister]] Trixie's life. Her full first name is actually Checkmate as well.
* In ''Fanfic/KyonBigDamnHero'', Kyon is most definitely a Chessmaster, often using chess metaphors as he makes strategies.
* [[EldritchAbomination Herald]], BigBad of ''FanFic/TheStarsWillAidTheirEscape''. He drops a few chess metaphors over the course of the story, as he manipulates ''everyone'' to follow his plan.
* ''FanFic/JewelOfDarkness'': The mysterious leader of [[TheConspiracy the White Glove]] qualifies as one of these, and is even seen playing a game with VandalSavage at one point. Notably, Savage warns him that it's harder to treat people like pieces, as life isn't as simple as a chess game.
** Midnight also counts, having learned the art of manipulation from Slade.
[[/folder]]

[[folder:Film]]
* ''Dangerous Moves'' subverts the trope: the two grandmaster chess player protagonists are realistically high strung and emotional, with little aptitude for or interest in the manipulation of people and events. It's the hangers-on and government handlers surrounding them who engage in all the intrigues, scheming, and chess metaphors.
* ''Film/JamesBond''
** Kronsteen in ''Film/FromRussiaWithLove'' who is an actual chess grandmaster as well as being SPECTRE's chief strategist. His plan in the film tops even that of the book for complexity, involving pitting members of the British and Russian secret service against each other in order to acquire a valuable coding machine.
** M certainly counts. In ''Film/TomorrowNeverDies'' she even uses [[ChessMotifs chess-based code names]] when corresponding with Bond.
* Historical gangster "Bumpy" Johnston (played by Laurence Fishburne) is depicted in this manner in the film ''Film/{{Hoodlum}}''. The director even goes so far as to show Johnson playing chess (playing the black pieces, and knocking over the white king) in the film's SpinningPaper sequence.
* In the film ''Film/JasonAndTheArgonauts'', the gods are shown playing a boardgame, with the heroes and villains as pieces.
* In ''Film/LuckyNumberSlevin'' there is a scene where Slevin and the Boss discuss how Slevin will kill the Rabbi's son, interposed with a scene where Goodkat tells the Boss how he can manipulate Slevin into performing the murder, while all are playing a chess game. The scene takes on new relevance when [[spoiler:it turns out that "Slevin" and Goodkat were working together from the beginning to manipulate the Boss AND the Rabbi, in order to get revenge for them murdering Slevin's parents]].
* Creator/ClintEastwood's [[NoNameGiven Man With No Name]] in ''Film/AFistfulOfDollars'' rolls into town, sizes up the situation, and immediately starts playing the two local powerhouses against each other.
** Inspired in part by ''Film/{{Yojimbo}}'' and ''The Glass Key'', or ''Red Harvest''.
*** Retold in Creator/TheCoenBrothers' ''MillersCrossing''.
*** And remade starring Bruce Willis in Prohibition days as ''Film/LastManStanding.''
* Michael Corleone of ''Film/TheGodfather'' trilogy - especially Godfather II. He started out as a NiceGuy who becomes a true [[TheMafia Mafia]] Chessmaster, only to lose it all in the end. At the height of his power, he proved quite adept as a Mafia Don, with amazing intuition, excellent observational skills, good combat instincts (he did earn a Navy Cross in the Marines, after all), a keen understanding of masculine psychology (arranging the suicide of one of his enemies, for example), the ability to pick the right people for the right job, and sharp financial acumen. If Michael had more charisma, extroversion, and a better grasp of feminine psychology, he would be a true MagnificentBastard.
* Lord Cutler Beckett of ''PiratesOfTheCaribbean''. He even had a strategy board, one with a little Beckett piece-. (R.I.P.)
* Allenby and Feisal in ''LawrenceOfArabia''. They spend as much time plotting against each other as fighting the Turks.
* The titular character of the movie ''{{Fresh}}'' develops a plan to [[spoiler: get himself and his sister out of the ghetto, and getting revenge on everyone who screwed either him (metaphorically) or her (literally).]] The plan shares more than a few aspects of the chess lessons his father gives him, and results in [[spoiler: Fresh sacrificing his savings and friendships (and one friend), half a dozen gangsters killing each other, with the survivors being arrested thanks to Fresh calling the cops and planting evidence. He and his sister get put into witness protection far away from his old home.]] [[BewareTheNiceOnes Oh, and Fresh is 12.]] The WhatHaveIDone bit at the end is quite understandable.
* Miles Cullen, a nebbish bank teller whose two hobbies are tropical fish and chess, suddenly turns into a master of XanatosSpeedChess when he decides to horn in on a planned robbery of his bank in ''The Silent Partner''. His chess set is given more screen time than some of the actors, even though he's never actually seen playing it.
* Paul Newman's character in ''Absence Of Malice'' is a good guy (and thoroughly unexpected) Chessmaster. He manages to play the DA, the police, and a newspaper against each other without anyone realizing what he's up to.
* In ''Film/StarWars'', Emperor Palpatine is SUCH a chessmaster - playing the Old Republic and the Jedi like a cheap fiddle in the culmination of a 2000 year legacy of Chessmasters.
** You have to give Luke Skywalker props for this as well. At the start of ReturnOfTheJedi, his positioning of Artoo, Threepio, Leia, Han, Chewie and Lando in the rescue of Han is actually quite brilliant, as each of his friends ended up with a very particular role to play.
*** Artoo smuggled in his lightsaber; Threepio's obliviousness to the plan ensured Jabba didn't get wise to the other players, either.
*** Leia brought in Chewie, freed Han from carbonite, and later killed Jabba.
*** Han's subsequent failure to escape ensured Jabba thought he'd won, as well as his part in the sailbarge fight later.
*** Chewbacca...well, when ISN'T a 7-ft tall Wookiee useful in a fight? There's also his role in Leia's cover.
*** And Lando, who infiltrated Jabba's palace before anyone, helped clear the prisoner skiff for their escape by sneak attacking the guards while they distracted by Luke's Force-powered acrobatics.
** That's quite a few pieces that needed to be in JUST the right places to make the whole thing work.
* [[AntiHero Andy]] from ''TheShawshankRedemption'', is an example of a {{Chessmaster}} who is the "good" guy. ([[BlackAndGreyMorality Well, relatively speaking.]]) It's clear from his conversation about halfway through the movie that he's very clever, talking about [[spoiler:using invented fake names to help his boss launder money]] and all, but it later turns out that even that isn't the start of it. The further aspects of it shouldn't even be spoiled even from behind spoiler tags, but let's just say he figures out a way to kill ever so many birds with one stone. Well, figuratively speaking. As for the ChessMotifs, it's repeatedly mentioned in the movie that Andy likes chess, and he remarks that he finds it to be a "civilized" game.
-->'''Red:''' I like to think the last thing going through [[spoiler:[Norton's] ]] head, [[spoiler:other than that bullet]], was to wonder how the hell Andy Dufresne ever got the best of him.
* Chili Palmer in ''GetShorty'' moreso than in the novel (as mentioned in Literature below); in the movie he seems accustomed to running games on anyone he perceives as a threat.
* [[spoiler:Inspector Clouseau]] is revealed to have been this all along at the end of the 2006 remake of ''ThePinkPanther'', having [[spoiler:screwed around with his English teacher after taking in the proper pronunciation of "hamburger" (a pronunciation he demonstrates to Dreyfus at the start of the sequel to shut off an alarm) and deliberately caused a scene at an airport checkpoint involving the improper pronunciation of the word "hamburger" after letting a hamburger fall out of his pocket so he'd get photographed at the exact right moment so he could inspect the photograph for an important clue to the murder mystery he's in the middle of investigating (seriously, DontTryThisAtHome; he's a trained professional at pretending to be clumsy for the sake of his investigations)]].
* Cardinal Richelieu's EvilPlan makes up most of the plot of ''Film/TheThreeMusketeers2011'' and he uses ChessMotifs quite frequently. Most notably when he plays a game of chess against himself as he cannot find a WorthyOpponent.
* [[GeniusBruiser Professor]] [[BigBad Moriarty]] from ''Film/SherlockHolmes Game Of Shadows'' is this to Sherlock Holmes's GuileHero. The film even climaxes with them playing speed chess and finishing their game verbally.
* In ''Tinker, Tailor, Solider, Spy'' Control affixes photos of his five suspects, including Smiley, to chess pieces, with a six representing Karla. When Smiley takes over the investigation he removes his own piece and adds a with a photo of a Polyakov. Neither Control nor Smiley uses the pieces on a chess board, and the symbolism of each piece is debatable, in contrast to the more straight-forward symbolism of the codenames (Tinker = Alleline, Tailor = Hayden, &c) which is played down in contrast to the book and miniseries. It is notable that Smiley and Karla are both represented by the most powerful piece, the Queen.
[[/folder]]

[[folder:Literature]]
* Literature/ChungKuo has a ''Go master'', Howard deVore, who compares manipulating people to placing pieces on the Go board
* Romeo Dallaire's ''ShakeHandsWithTheDevil'' features Paul Kagame, Chessmaster extraordinaire.
* K.A. Applegate's ''{{Everworld}}'' series of books. Initially narrated by Senna, who explicitly thinks about how manipulating other people (and gods!) has some things in common with the strategy of chess, but the skills required are different.
* In Kristen Britain's ''GreenRider'' during the final showdown, the protagonist is abruptly yanked away from the action and sees the battle as an elaborate game of that 'verse's equivalent to chess, which is played with 2-4 players. The chessmaster villain invites her to sit and play, as it is the only way for her to break the stalemate and save her friends. Instead, she [[spoiler:smashes the chess board with her sword, causing enough magical backlash to win the day.]]
* Creator/JohnBrunner's novel ''The Squares of the City'' not only has an obvious chess metaphor in its title, and many literal chess players and games in the story, it's modelled after a historic chess game between two real world chess masters. [[spoiler:The president of a fictional Latin American country, and his Minister of the Interior, have a severe disagreement about treatment of the poor, serious enough to lead to civil war. But instead, they play a game of chess against each other, on an actual board and then manipulating real people to enact the moves.]]
* In the ''Literature/HarryPotter'' series, Ron Weasley is a literal "chessmaster" and his abilities on the wizard's board that lead Harry onto Voldemort's trail in ''Harry Potter and The Philosopher's Stone''.
** Not least, they both demonstrate an exceptional chess move: [[spoiler: They realize the best way to win the game is to sacrifice ''themselves'' like a pawn, so that the hero can win.]]
* Although the storyline is purposefully haphazard and dream-like in Creator/LewisCarroll's ''Literature/ThroughTheLookingGlass'', all the events take place on a chessboard and every character Alice meets- whether visibly or not- is a chesspiece upon it, including Alice herself. Consequently, although no single person is particularly a villain, the Red Queen, at the beginning of the story, could also be seen as the Chessmaster by telling Alice what route to take on the White piece's side of the board with a view to her own side winning.
* Casper Gutman and [[spoiler:Brigid O'Shaughnessey]] from Creator/DashiellHammett's ''Literature/TheMalteseFalcon'' are both opposing chessmasters who manipulate Sam Spade and a cast of minor characters in order to obtain the Maltese Falcon for themselves. [[spoiler:Though in the end, they both fail.]]
** Spade himself is this to some degree, as well.
* In the ''Literature/JamesBond'' novel ''Literature/FromRussiaWithLove'', SMERSH agent Kronsteen (a literal chessmaster in his own right) creates a tremendously intricate plan to the express purpose of assassinating Bond in such a way as to hurt [=MI6=]'s image. In fact, the setup for the plan is so complicated that the entire first third of the novel is devoted to it, with Bond himself not appearing in the book until more than a hundred pages into it. Kronsteen also explicitly thinks of all the people he sees as chess pieces.
** The film adaptation took the plan in question, put it in the hands of SPECTRE, and made it even ''more'' complicated. The audience is left in the dark as to just what the bad guys are up to until Bond himself figures it out.
* Moridin in Robert Jordan's ''Literature/TheWheelOfTime'', albeit with a CaptainErsatz of Chess called ''sha'ra'' (though he is stated to be a master of all strategy games, which presumably would include chess).
** Several other characters are Chessmasters, or aspiring Chessmasters. Among the aspiring Chessmasters, Egwene stands out. When she successfully manipulates the heads of two fractions into giving her the power she needs...
-->'''Egwene''': They couldn't have done it better if I had told them what to do.
* 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.
* In AndreNorton's ''Victory on Janus'', Ayyar at one point has a vision of playing a boardgame against THAT WHICH ABIDES, with his own people and the Great Crowns on one side, and the Larsh and enemy robots on the other.
* Lord Havelock Vetinari, Patrician of Ankh-Morpork and all-around MagnificentBastard of the ''Literature/{{Discworld}}'' is an amazing chessmaster ("It's like being a puppet, only he gets you to pull your own strings"). In ''Discworld/GoingPostal'' he gets his very own not-quite-chess metaphors, getting into a little discussion with CorruptCorporateExecutive Reacher Gilt on the merits of playing the two sides in Thud.
** According to ''The Discworld Companion'', Vetinari, in addition to being a Thudmeister, is also a Grandmaster at Stealth Chess, where some pieces ''are not necessarily where they appear to be''.
* Two crazy-awesome examples exist in Sergei Lukyanenko's ''Literature/NightWatch Trilogy'' in the form of the two heads of the Watches; Boris, head of the titular Night Watch and [[spoiler: Zabulon]], head of the Day Watch. At one point they are even described as two people playing chess with their agencies as the pieces.
** They often steer towards GambitRoulette (Yes, both of them quite happily) and seem to willingly fling themselves headlong into a GambitPileup.
* In Ellen Raskin's ''TheWestingGame'', Samuel Westing arranged a will so that whoever discovered his murderer's identity would inherit his fortune. Turns out, that wasn't all he'd arranged. [[spoiler:The will puzzle was actually an elaborate scheme to get revenge on his wife by framing her for his murder. A murder that never occurred - he faked his death and continued running his company under a different identity. One of three false identities he created post-death - he also posed as an heir and a landlord who brought the heirs together. His heir identity secretly plays long-term chess with another character over the course of the book. Characters refer to Westing as the king, his wife as a queen they're fooled into taking and the rest of them as pawns.]]
* Creator/IainBanks' ''Literature/ThePlayerOfGames'': A very complex strategy game is both a metaphor for the conflict of two civilizations, and crucial to a real-life struggle; the protagonist is being manipulated, though the identity of those pulling the strings remains shadowy.
* Constantin Demeris and his mistress Noelle Page in ''The Other Side of Midnight'' by SidneySheldon both got rich and powerful via skilled Chessmaster tactics. By the end of the book, [[spoiler:when she's on trial for the murder of her lover's wife]], she sees her relationship with him in terms of a chess game [[spoiler:with her and her lover's lives as the pawns and the stakes. Constantin wins.]]
* Another Sidney Sheldon novel, aptly titled ''Master of the Game'', is a GenerationalSaga bringing us three generations' worth of Chessmasters who create/belong to the internationally famous and powerful Kruger-Brent, Ltd.: Jamie [=MacGregor=], his daughter Kate, and her granddaughter Eve. The first founds the company, the second inherits it and makes it even more powerful, and the third (who has an innocent twin) plots to become Kate's successor.
* The [[EvilSorceror Demon Queen]] from ''DavidDrake's'' series ''Lord of the Isles'' had a magical chessboard that represented her actual opponents. After her defeat one of the pieces melted, and they mentioned after examining it that she'd never realized she was herself was on the board.
* Though ''Literature/CodexAlera'' has these in spades, the ones who actually use [[strike:chess]] ''ludus'' metaphors are mostly the Canim. Tavi considers beating enemy commander and WorthyOpponent Nasaug at a game to be [[ArsonMurderAndJaywalking worthy of inclusion]] in a list of {{badass}} feats he accomplished as Captain of the [[BadassArmy First Aleran Legion]]. At another point, professional {{Chessmaster}} Gaius Sextus makes a [[BlackComedy joke]] about how the situation ''doesn't'' resemble the game, since at that moment, the [[PersonOfMassDestruction First Lord]] and a Knight are at the mercy of a lowly steadholder.
* In ''Literature/{{Daemon}}'' by Daniel Suarez, Matthew Sobol certainly qualifies. What makes this case particularly special is that Sobol is ''dead'' for the entirety of the novel. He left behind an AI entity with detailed and brilliant plans for world domination, playing the protagonists against each other expertly.
* GeorgeRRMartin's ''ASongOfIceAndFire'' is loaded with {{Chessmaster}}s and those aspiring to or dreaming they are one. Off the top of my head:
** Varys - Essentially controlled 90% of information to reach or not reach the King and his council, having utterly complete knowledge of everyone's actions, playing at least 3 Kings and 2 dynasties for decades and surviving the transition between them, playing off at least 4 Great Houses against each other for own goals, and in the midst of orchestrating another coup to restore previous dynasty. It is unknown exactly how much of a role Varys played in the events of the novels, but the mere fact he knows about the details of events only a handful of characters even witnessed across the world...says he probably played a big one.
** Euron Crow's Eye - Returns home at least 2-3 in succession and generally disliked just in time (the day before...with no way to find out) for a 'Kingsmoot', where he manipulates his rivals and their men into making him King, by having spent his time in exile seemingly preparing solely for this day he offered loot and riches far beyond his opponents, countering their promise of conquering some easy but poor lands with the promise of conquering ALL of Westeros. With dragons.
** [[spoiler:Doran Martell, the Prince of Dorne]] plans his revenge for the atrocities performed against his sister and her children for fifteen years, and is so subtle and low-note about it that his own family insults him to his face about his apparent forgiveness. The setting has a chess analogue called ''cyvasse'', but [[spoiler:Doran, despite being denied all physical sports and leisures,]] does not play it. Why? He never plays any game he could potentially lose.
** 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.
** Cersei Lannister - [[spoiler: Failed. Spectacularly.]]
** Lord Petyr "Littlefinger" Baelish - [[spoiler:The mastermind responsible for, directly or indirectly, the War of the Five Kings, the Lannister-Stark divide, the betrayal of Ned Stark and the assassination of King Joffrey. He now has plans for the North, using Sansa Stark.]]
*** YMMV on whether Littlefinger is a Chessmaster or simply a XanatosSpeedChess master. He doesn't really have an endgame, his only plan is to create chaos which he can then exploit for personal gain. He's very good at this - [[spoiler: he began the war as the King's Master of Coin and an insignificant Lord. As of A Dance With Dragons, he's Lord Paramount of the Riverlands, Lord Protector of the Vale and Lord of Harrenhal.]]
* A short story by George R.R. Martin called ''Unsound Variations'' featured a man seeking revenge on the former members of his chess team. He ruined their lives without them realizing he was involved, by using MentalTimeTravel to go back and destroy their careers. He stopped one from publishing his bestselling novel by hiring a man to write the same book just a few months before he did, and released everything another would have invented while he was still working on it, becoming incredibly rich in the process. Then in an attempt to fully break them he told them what he'd done, and offered them a fortune if they could win a chess match from the position they'd berated him for losing in decades (in his case many many decades) earlier. A definite SmugSnake, his plan falls apart when they realize that this means there's a very definite ''reason'' their careers failed and rather than despairing, gain new hope. He responds to them refusing to play his game by using his machine again, which in their reality leaves him dead.
* {{Petaybee}}: In ''Powers That Be'', Sean is a very clear example, but he loses that aspect of his character later on in the series.
* 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.
* In LenDeighton's ''SS-GB'', an AlternateHistory novel set in a Nazi-occupied Britain, the character Mayhew is a formidable Chessmaster who uses the German Nazi occupiers and the British anti-Nazi underground for his pawns, and is described as fond of "playing God and writing the future history books". In his master stroke, unfolding in the later part of the book, Mayhew gets the underground to[[spoiler: smuggle King George VI out of the Tower of London where the Germans kept him imprisoned]]; then Mayhew betrays the underground and gets the Germans to[[spoiler: set an ambush, shoot and kill the escaping King]]; then he gets the underground to [[spoiler:rouse the British people against the "Nazi Regicides"]] and create the myth of [[spoiler:a matryred, heroic King]] (when in fact [[spoiler:the poor George VI had been a broken man)]]; then he gets [[spoiler:the young Princess Elizabeth crowned Queen-in-Exile at Australia]]; then he gets the various rivaling Nazi factions in charge of occupied Britian [[spoiler: to engage in bitter infighting, blaming each other for the fiasco, and ending with one group of Nazis summarily executing]] the leader of the other group; and meanwhile, Mayhew's part in all this remains unknown, and he remains on excellent terms with both the Nazis and the underground and free to start working on his next gambit.
* The ''Literature/SixteenThirtyTwo'' series is bursting at the seams with these. Mention must be made of Cardinal Richelieu, who is just as good in the new history as he was in the old, and Mike Stearns, who is on the record as trying to set up a more long-term-successful series of gambits than ''OttoVonBismarck'', the RealLife guy who created the modern state of Germany almost entirely with use of gambits and chessmastery.
* Dorothy Dunnett's "Lymond" novels derive their titles from chess and feature two very chessmasterly characters whose opposition culminates in a terrible game of chess.
* Mr. Guppy of ''Literature/BleakHouse'' WANTS to be a chessmaster, but his plains fail due to lack of opposition.
-->"Mr. Guppy suspects everybody who enters on the occupation of a stool in Kenge and Carboy's office, of entertaining, as a matter of course, sinister designs upon him. [. . .] he in the most ingenious manner takes infinite pains to counterplot, when there is no plot; and plays the deepest games of chess without any adversary."
* DarrenShan's ''Literature/TheDemonata'' series has a heavy chess theme running throughout, and several characters probably qualify for this trope, but none moreso than Lord Loss, the BigBad of the first four books and later TheDragon to the BigBad of the overall series. In terms of literal chess, he's obsessed with the game, and only ever beaten rarely. Figuratively... [[spoiler: he shines most in the very last book, where he manages to trick ''Death itself'' by conspiring with Bec, one of the heroes. The result? ''Every other demon master except him is wiped from existence, whereas he is allowed to remain 'till the end of time, unmolested by the Kah-Gash, doing what he loved doing all along.'' Which also makes him a KarmaHoudini ''par excellence''.]]
* KurtVonnegut's "All the King's Horses" is about an Army colonel, his wife and sons, and 12 men who are captured by a communist Chinese officer, who will let them go free if the colonel can beat him at a game of chess. The only catch is, they are also human chesspieces, and any piece captured is immediately executed.
* ''GetShorty'''s Chili Palmer is a low-end ChessMaster, though the point of the story seems to be that it's not so much because he knows chess as because he's mastered the one particular strategy that none of the other players are prepared for.
* While there isn't a chess motif for him, referring to [[spoiler:The Sphinx]]'s plans as a game of chess is mentioned several times in the ''Literature/{{Fablehaven}}'' series.
* Elsworth Toohey, the journalist, critic and social activist who is the main villain of Creator/AynRand's ''Literature/TheFountainhead''. He has been manipulating people since childhood - first his parents and schoolmates, then people on a worldwide level. He observes people and plans meticulously what to say and do which would push person A to an act which will influence person B to make person C - who never heard of Tohhey - to do exactly what Toohey wants.
* In the historical novel ''Literature/WingsOfDawn'': Thomas of Magnus. Lord Mewburn. [[spoiler: Lord Hawkwood. Waleran.]] %% 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.
* The Duchess in Literature/ThePrincessSeries is this.
* In JohnCWright's ''[[Literature/CountToTheEschaton The Hermetic Millennia]]'', Larz's story where he [[UnreliableNarrator claims]] to have seen Menelaus confront D'Arago has D'Arago argue that he's got the same enhancement as Menelaus, and Menelaus countering that he's still sloppy, while Menelaus plans out checkmate twenty moves ahead.
* In ''Literature/TheFifthWave'' by Rick Yancey, Commander Vosch is so good he [[spoiler: gets human teens to kill the rest of humanity for him. Without them knowing.]] Ringer also seems to be quite TheChessmaster in training.
* In [[TheChroniclesOfAmber The Chronicles of Merlin]], Merlin in his travels encounters Dworkin and Suhuy playing chess, and during their game making commentary on current events in the timeline using chess metaphores.
[[/folder]]

[[folder: Live Action TV]]
* Sylvester [=McCoy=]'s Seventh Doctor in ''Series/DoctorWho''. The chess metaphor is part of a StoryArc; it first appears in "Silver Nemesis", when he moves the pieces on Lady Peinforte's board; in "Curse of Fenric" this is revealed to be how he knew fellow Chessmaster Fenric was the force behind it all. Played with in "Battlefield" when Morgan La Fey taunts "I could always beat you at chess, Merlin" and he retorts "Who said anything about chess? I'm playing poker. And I have an Ace up my sleeve!"
** The Celestial Toymaker from the eponymous First Doctor serial, who embroils the Doctor and his companions in a series of challenges for their freedom. One of these is a board game with counters similar to chess which he plays against the Doctor.
** In "Nightmare in Silver" the Cyber Planner is attempting to take control of the Eleventh Doctor, the mental battle is externalized in the form of a chess game while they're also trying to guide the Cybermen and an Imperial Guard unit currently fighting over the planet. [[spoiler: Eventually the Doctor claims mate in three moves and the Cyber Planner unintentionally devotes the processing power of all the Cybermen to figuring out how which disables them long enough for the Doctor to break free and then evacuate all the humans before the planet is blown up.]]
* "Series/TheSarahJaneAdventures" [[spoiler: Mr Smith]]
* One of Monk's suspects in ''Series/{{Monk}}'', who is an actual chessmaster (a Grand Master, in fact). He uses chess metaphors to taunt Monk about the exact method he used to murder his wife and get away with it. Most notably, he mentions the "Poisoned Pawn" (a name for a particular chess opening) move in which he fooled his second wife into poisoning herself, and Monk's attempt to find the answer buys him enough time to cremate the body in the event that Monk does find out the chess opening. In fact, his actions, and Monk's irritation towards not being to figure out how to nail him, actually caused Monk to nearly cross the line by planting evidence to get him arrested. Monk then [[EurekaMoment gains inspiration]] from [[spoiler:the tactic of swapping the positions of the king and rook to figure out that the suspect had changed the headstone of his first wife in order to prevent the body from being exhumed]].
** After this, Monk then begins to tell off the chessmaster about how it is such poor form to use chess terms when you're talking about people, ending it with [[Awesome/{{Monk}} "but if you insist... checkmate."]]
* Gideon from ''Series/{{Charmed}}'' relies on the strategy of the Chessmaster, and has forged an alliance with the evil version of himself from the MirrorUniverse. There's even a scene in which the two versions of Gideon are talking strategy over a game of chess.
* In ''Series/{{Heroes}}'' Sylar manipulates Danko into cooperating with him while toying with the pieces on a chessboard.
* Malachi of ''Series/{{Hex}}'', which should be expected since he is more or less the AntiChrist. He gains power over people by tempting them with their deepest desires. This leads some characters to believe they will be fine if they just resist when he tempts him, but unfortunately many people don't even understand what their own desires actually are, nor do they realize when it was Malachi who arranged the opportunities for them to follow them. A couple characters went down because they were actually giving into their desires when they thought they were fighting them.
* In ''Series/{{Leverage}}'', Nate Ford is often referred to as a Black King and in the first episode as a white knight. Hardison comments he often plays online chess and in the episode "Juror #6" he and a opposite Chessmaster both use chess metaphors, an actual chess board and when he wins, he throws her a piece (presumably the king).
** He also enters a chess tournament as part of a heist and beats two grandmasters in the process.
* The Governor from ''Series/{{The Walking Dead}}''. Although he's been a ManipulativeBastard since before his first appearance, this goes full chess-metaphor after [[spoiler: the fall of Woodbury]], when he meets a fatherless family with a little girl and teaches her to play chess. Their conversations reveal how much of a Chessmaster the Governor really is, and the girl paints an eyepatch on the white king to make him look like the Governor. In a later episode, this chess piece is seen [[spoiler: falling to the ground and being stepped on as the Governor dies]].
* On ''Series/LawAndOrderCriminalIntent'' Nicole Wallace plays all sides, steals identities and acts as a recurring archenemy of detective Robert Goren. On top of that she [[spoiler: manages to escape from justice multiple times]].
* ''{{Warehouse 13}}'' has Artie. There is a chessboard just outside the office: he's been playing the same game for months against himself. Good thing he's using these powers for good instead of evil. [[EpilepticTrees Hopefully.]]
** When [[spoiler: Myka]] gets trapped in Lewis Carrol's Mirror, she makes reference to Artie's Chessmaster tendencies, calling themselves chesspieces on his chessboard.
* "Absolute Justice" from ''Series/{{Smallville}}'' features the secret agency Checkmate, with the Chessmaster in question being [[spoiler: Amanda Waller]], orchestrating a series of murders and news leaks in order to [[spoiler: get the older generation of superheroes in the Justice Society of America motivated to get active again, and inspire the new generation of heroes, because the planet will need its heroes in a coming apocalypse.]]
* Considering ''Series/{{Columbo}}'' has been often refered to as a verbal chess match between Columbo and the murderer of the week, it only makes since that he face down an actual Chessmaster at least once in the series run. The second season episode, "The Most Dangerous Match" features a grand master of chess, played by Laurence Harvey, who kills his rival after realizing he has no chance of beating him in an upcoming world championship match.
* Played completely straight with D. Gibbons in ''{{Flash Forward|2009}}'', who is mentioned as having become a grandmaster at the age of fifteen. Although [[spoiler:he appears to have been out-Chessmastered by an as-yet-unidentified faction of villains, it's worth noting that he knew that he would probably die and likely made plans for the event of his death]].
* The [[MeaningfulName appropriately named]] villain Chess in ''Series/TheCape''.
* Literal example in former World Chess Champion Arkady Balagan in ''Series/{{Endgame}}''. He uses his talents to solve crimes.
* In ''Series/RobinHood'', the Sheriff of Nottingham once gave Guy of Gisborne orders while sitting behind a chess board. And then threw one of the pieces at him.
* In ''Series/PowerRangersInSpace'', Astronema is very much the chessmaster. While she doesn't have an actual chessboard, she does have figurines of the rangers on a mat. She also tends to think her plans through very well.
* Bobby Newport's campaign manager Jennifer Barkley on ''Series/ParksAndRecreation'', to the point that she gets bored with the lack of challenge and actually gives her opponent advice to make the "chess game" more challenging for herself.
* ''Series/{{Alcatraz}}'' villain Garrett Stillman is an expert at convuluted heists which rely on manipulating others, and was shown discussing chess techniques as a metaphor.
* Windom Earle of ''TwinPeaks'' is in an ongoing chess game with Coop. Every time Coop loses a piece, Earle kills someone.
* ''Series/PersonOfInterest'': In one episode, Elias plays a chess game with Finch.
[[/folder]]

[[folder:Tabletop Games]]
* In ''TabletopGame/OldWorldOfDarkness'', Kindred in ''TabletopGame/VampireTheMasquerade'' makes this about as literal as it gets. Powerful elders are known to play chess against each other; sometimes by themselves, others by Dominating skilled chess masters to play for them. The Jyhad being what it is, few games are actually played for fun. In the more complicated games, each piece has a corresponding real world henchman, location, or valuable resource. When that piece is taken, play is halted so that the attacking player can arrange for the relevant resource to be seized. Should a player advance a pawn, he can promote it to a piece previously taken and the matching objective is restored or released. And according to Camarilla social mores, to quit or forfeit a match should the losses become to severe would result in such a massive loss of status that it becomes less painful for the loser to see it through to the end and lose his stakes rather than quit and become a laughingstock. Such games can become so complex as to be microcosms of the Jyhad and can take years, if not decades, to play out completely, moves being sent to each other through trusted agents, letter drops, burnt into the skin of the ghoul assassin you sent against him whose body is left on your doorstep, etc. Savvy characters can learn much about an elder's political situation and resources just by seeing his chessboard.
* The yugoloths, a race of neutral evil fiends in ''DungeonsAndDragons'', were typically cast as executing secret, evil schemes across time and ''the {{multiverse}}'', particularly in their most fleshed out appearances in the 2nd Edition ''{{Planescape}}'' campaign setting. In one source book, an illustration (by the impeccable hand of Tony DiTerlizzi), a pair of arcanoloths, the most ''AffablyEvil'' of these fiends, are shown playing chess with pieces that resemble other races from the setting.
* BattleTech is ''filled'' with them. among the better known: Julian Tupelo, Myndo Waterly, Hanse Davion, Ulric Kerensky, Sun-Tzu Liao, Jaime Wolf, Thomas Marik (both of them), Katrina Steiner, Morgan Kell, Quintus Allard, and many more. There's a reason so many of the novels involve a ThirtyXanatosPileup.
** Sun-Tzu in particular actually does play chess on what can be safely assumed to be a fairly high level and uses the occasional chess comparison or metaphor, as seen in the novel ''[[BattleTechExpandedUniverse Highlander Gambit]]''.
[[/folder]]

[[folder:Theatre]]
* A prototype for the modern Chessmaster villain is Creator/WilliamShakespeare's Iago, from ''Theatre/{{Othello}}''. He uses his influence and his reputation as "honest" to get his pieces into place, and while all of the characters seem to think they act on their own accord, they are actually following Iago's plans. He also often urges others to patience and seems very patient himself. The Handkerchief is the ultimate example of a harmless little thing that closes the trap around his [[HorribleJudgeOfCharacter victims]]. [[UnwittingPawn Roderigo and Emilia]] are the ones who do all of the work for him.
** In the Oliver Parker film adaptation, Iago (played by KennethBranagh) illustrates his plan with an actual chessboard.
** Interestingly enough, Iago is actually a ''failed'' Chessmaster - he allows his own personal hatred (and thus contempt) for Othello and women to screw up his plans - [[spoiler: for instance, getting Emillia to steal the handkerchief but then thinking he can keep her quiet simply by ordering her to.]] An example of a chessmaster who really does win is [[MagnificentBastard Caesar]] from AntonyAndCleopatra.
* Creator/WilliamShakespeare re-used the theme with Prospero in ''Theatre/TheTempest'' (because Shakespeare re-used, well, ''everything'').
* Molokov and [[spoiler: Walter]] are tag-team Chessmasters who play the protagonists against each other for political purposes in the musical ''Theatre/{{Chess}}''. Ironically, they are the only prominent characters who ''don't'' play chess in the show, and the ones they manipulate are ''international chess grandmasters''.
* In the musical Rudolf - Affaire Mayerling - the ClassicVillain Graf Taaffe is playing chess throughout the story, sets TheHero Rudolf Checkmate during a song with Rudolf's lover Mary Vetsera and is actually revealed to be the one behind everything by having everyone including Rudolf's father Franz Joseph be his pawns.
[[/folder]]

[[folder: Video Games]]
* One of the Nod mission briefings in the original ''VideoGame/CommandAndConquer'' has Kane, the series' quintessential Chessmaster, actually playing a game of chess while explaining the upcoming mission to the player. He even ends the briefing, and starts up the operation, with a smile and a simple "Your move."
* In the final assassination mission of ''VideoGame/AssassinsCreedI'', [[spoiler:Robert de Sable reveals that Al-Mualim has been manipulating Alta´r into killing everyone who knew the secrets of the Piece of Eden, so that none could challenge him when he would use it to take over the Holy Land]]. In his final moments, he comments that everyone, including Alta´r and the other Templars, were just "pawns in his grand game."
* Arcturus Mengsk from ''{{Starcraft}}''. He plays the Confederates and Zerg off one another to put himself in charge. In the novel ''Liberty's Crusade'' he is shown as a avid chess player, complete with a chess set in his command center. Towards the end, when his plans start falling apart, the chess set gets thrown across the room, [[spoiler: although Kerrigan does the actual kicking for him.]]
** He did not subscribe to the notion of comparing war to Chess with a pretty convincing argument. Such as how war is very rarely ever fought in a scenario where both sides are evenly matched, or that there are never only ever two forces active on the board and not all of them share the same goal of capturing the King.
--->'''Mengsk:''' First, the opponents are hardly ever truly even. The Confederacy of Man had Apocalypse-class missiles and my homeworld did not; the Confederacy played that card until Korhal IV was a blackened glass sphere hanging in space. Hardly even. ... Second is the idea of equal forces. The truth is that a better gun inspires a chemical counterweapon, which then inspires a telepathic strike, which then brings about an artificial intelligence guiding the weapon. The pressure of war does bring about growth, but it is never the neat, linear growth that you learn about in the classroom. Third is the idea of a level playing field. The chessboard is limited to an eight-by-eight grid. There is nothing beyond this little universe. No ninth rank. No green pieces that suddenly sweep onto the board to attack both black and white. No pawns that suddenly become bishops.
* A character called 'A Friend' in ''VampireTheMasqueradeBloodlines'', who sends the main character e-mail containing chess metaphors on how the plot is turning, is very likely the man behind the plot; namely [[spoiler: the taxi driver]]. Fans have written everything short of academic essays on this guy.
* ''LegacyOfKain'' has enough of these to make one think it was a required step in character design. Most notably are [[spoiler: Moebius, the hylden, Elder God, and Kain]]
* ''KnightsOfTheOldRepublic''. Revan, who dazzled even the Mandalorians with his battle strategy, using feints, sacrificing non-productive targets (regardless of population), and flanks. It's even implied that Revan deliberately fell to the Dark Side to serve the greater good in a complicated BatmanGambit.
** And then there's Kreia from the sequel... words do not begin to describe...
* Sandro, the Necromancer Lich, in [[VideoGame/HeroesOfMightAndMagic HoMM3: SoD]] tricks several heroes into finding certain artifacts for him that help him almost conquer the whole continent, and perhaps more. And after that fails he comes up with a plan that causes the events of the original campaign.
* Ryuusei Cartwright of ''Videogame/AdventureQuest'' subverts this trope; since "there is nothing to be gained in epic struggles", referring to his failed attempts of past, he speaks of playing metaphorical chess randomly, and seeing what happens.
** Adventure Quest also has [[ExactlyWhatItSaysOnTheTin The Chessmaster, from The Chessmaster Saga.]]
* Gaia from ''VideoGame/GodOfWar''. Everything Kratos does in the second game and the beginning of the third game was manipulated by her, in her effort to overthrow the Olympians and replace their rule with that of the Titans. She sent him to find the Sisters of Fate, kill them and use their time-powers to wound Zeus, take his Sword of Olympus, bring the Titans from the past to the present time and attack Olympus in stronger force. When Gaia [[spoiler:though Kratos was of no use no more, she told him right out he was "a simple pawn, nothing more". In the endgame, there things have turned really ugly, Zeus told her that her "pawn had failed you (her)" and that she should had used the "other one"]].
* Steve Gardner and John Parker from ''VideoGame/MetalGearGhostBabel''. Snake comments in the ending that he plans to make them pay for playing chess with peoples lives and hearts.
* Nemesis in ''CityOfHeroes'' is all about this.
* Gwyndolin of ''VideoGame/DarkSouls''. The guy is secretly ruling the capital city through the use of an incredibly powerful illusion. He runs his own religion/SecretPolice, and he is working with an AncientKeeper to manipulate an undead into sacrificing themselves to fuel the First Flame, which is the source of all fire and light in the world. The [[TheGhost Furtive Pygmy]] might be one of these as well, though it isn't sure if he is a ChessMaster or Awesome by Inactivity and dumb luck.
[[/folder]]

[[folder:Webcomics]]
* ''Webcomic/EightBitTheater'' parodies the trope [[http://www.nuklearpower.com/2004/11/20/episode-484-midfighter-vs-thiefollo/ here]].
* Thaco from ''Webcomic/{{Goblins}}''. [[http://www.goblinscomic.com/09032008/ "You keep playing your little game of chess or whatever you think you're doing."]]
* In ''Webcomic/{{Homestuck}}'', Doc Scratch and Vriska are implied to play long-distance games of a variation on chess using cubic and spherical boards. Doc Scratch, who has near-omniscience, playfully reminds Vriska of her consistent failure to defeat him, even when he tells her his next 100 moves in advance. Even when she cheats using [[spoiler: her own omniscient oracle, of which he is unaware.]] Paralleled in his later schemes, where he is able to manipulate several of the cast into doing exactly what he wants, despite being completely honest about his motives as a CardCarryingVillian who exists solely to [[TheDragon bring about the rise of an Indestructible Demon]].
** The chess theme in Homestuck also persists in terms of the game they play-- a checkered battlefield where white fights black, [[spoiler: and inevitably loses.]] However, manipulating this game of chess is unnecessary, and ultimately futile, unless someone decides to [[GameBreaker smash the board.]]
** In addition to the chess motifs, Doc Scratch's overall theme (and the theme of Lord English and the Felt in general) is of another strategic game: American eight-ball pool.
** Dirk is rapidly becoming one of these, which fits with his puppet theme. He assured Jane early on that he would be "the one pulling the strings here," and [[BatmanGambit he]] [[GeniusBruiser has]] [[TeenGenius yet]] [[XanatosSpeedChess to]] [[ThanatosGambit disappoint]].
*** Ultimately subverted, as [[spoiler: Dirk eventually points out that the Auto-Responder was doing much of the planning during [s] Dirk: Synchronize and [s] Dirk: Unite, to the point that Dirk only realized the full extent of everything afterwords. Granted, the Auto-responder is a hyper-intelligent AI with a personality copied from his thirteen year old self, so in a way it still fits.]]
* In ''Webcomic/TheOrderOfTheStick'', the three leaders of the [[CelestialBureaucracy Inter-Fiend Cooperation Committee]] in [[http://www.giantitp.com/comics/oots0668.html this strip]], which is titled, "Moving the Pieces".
* ''Webcomic/SluggyFreelance'' toys with this trope [[http://www.sluggy.com/daily.php?date=990213 here]].
** [[spoiler:Although ''Torg'', of all people, seems to be developing some of these tendencies, {{Out Gambit}}ting one villain after another ever since he joined up with the Minion Master. Perhaps this comes from being GenreSavvy enough to know that [[EnemyMine teaming up with villains]] [[ReliableTraitor will inevitably lead to being double-crossed]].]]
* Billy Thatcher from ''[[{{Webcomic/Morphe}} morphE]]'' is a chess grandmaster on his way to the World Chess Championship. Then he awakens as a Obrimos mage. He's arrogant enough to think that his chess expertise can translate in to real world situations.
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[[folder: Web Original]]
* Fiona Khal, from Literature/TheLayOfPaulTwister, prefers to think of the conflict between the Magi and the Dragons as a game of chess, though she puts an interesting [[IncrediblyLamePun twist]] on it...
--> "And now you want me to work for you, against [the dragon who had hired Paul to steal from her]?" I asked, trying not to look too bemused. "It's a strange game, where Black and White both move the same pawn!"
--> She laughed. "I've always lamented the lack of mercenaries on the chessboard. It would bring whole new levels of strategy to the game!"
[[/folder]]


[[folder: Western Animation]]
* Lawrence Limburger had a couple of episodes playing several factions against each other in ''BikerMiceFromMars''. This had to involve a chessboard with the people involved and a lot of {{Evil Laugh}}ter.
* Vlad Masters of ''WesternAnimation/DannyPhantom'' is fond of using chess metaphors to describe his EvilPlan.
* David Xanatos of ''WesternAnimation/{{Gargoyles}}'', king of the eponymous XanatosGambit. His girlfriend/wife Fox is no slouch at it to the point where almost all the events outside of the Trio's promotion competition in the episode, "Upgrade" is part of a special game of chess. This is done with the couple competing using a chessboard with board pieces representing each of the people they are manipulating; The Pack for Xanatos and the Manhattan Clan for Fox.
* Hades from Disney's ''Disney/{{Hercules}}'' has a large chessboard at his place in the Underworld, with pieces representing the Olympians and his forces. He usually uses this chessboard in order to think out strategy how to kill Hercules or to attack Olympus.
* Hilariously averted in an episode of ''TheSimpsons'' where Mr. Burns hires an assassin to kill Grandpa. After two botched attempts, the assassin suggests a [[RuleOfThree third option]] which he describes "as complex and precise as a well-played game of chess." [[GilliganCut Cut]] to him bursting into the retirement home with a machine gun and [[ATeamFiring firing wildly in all directions.]]
* The Brain from ''WesternAnimation/TeenTitans'' plans out all of his moves like a chess game and he even LOOKS like a giant chesspiece!
** The final battle against the Brain's Brotherhood of Evil actually takes place in a large room that resembles a gigantic chessboard.
* Spoofed in ''{{Futurama}}'' by Zapp Brannigan, who sees himself as a brilliant strategist and refers to chess to prove this, but keeps mixing it up with other games: "In the game of chess, you can never let your adversary see your pieces."
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[[folder:Other]]
* OttoVonBismarck is depicted in [[http://germanhistorydocs.ghi-dc.org/sub_image.cfm?image_id=1341 a contemporary political cartoon]] playing against the Pope in chess and winning. He didn't get the nickname "Iron Chancellor" for ''nothing''; he will be attached to the term ''Realpolitik'' for a long time to come. (Since he didn't exactly operate in the shadows, he has MagnificentBastard status, though).
** This may count as a subversion, as the picture refers to Bismarck's kulturkampf against the Catholic Church's influence in Germany. Which he actually was forced to back down from due to masterful rallying of Catholic middle and working classes by the Church.
* [[http://cheezburger.com/5305000704 This woman]]. Don't swipe her dessert.
* Roodaka of ''{{Bionicle}}'' describes how she has "spun a web" in one issue where she speaks to a Visorak underling, complete with a board of miniature figurines of the heroes and villains. While it's not actually a chess board [[CallARabbitASmeerp but an alt-universe equivalent]], the chess motifs are still there.
* BarackObama's administration is often discussed in blogs and the media using chess metaphors. When he appears to exhibit inaction or waffle on an issue, some will feel he is falling short on a campaign promise, while others suspect he is pursuing a Chessmaster resolution. Pundit [[http://www.thedailybeast.com/newsweek/2012/01/15/andrew-sullivan-how-obama-s-long-game-will-outsmart-his-critics.html Andrew Sullivan]] is particularly devoted to the concept.
** For example, the defense authorization act included provisions apparently authorizing the indefinte detention of US citizens. This could be an [[FaceHeelTurn about-face]] on civil liberties, or [[http://www.addictinginfo.org/2012/09/13/ndaa-detention-struck-down/ a "political chess" play to move the issue from the military legal system to the civil system where it may be struck down for good by sympathetic judges Obama himself had appointed]].
* Don't forget [[http://en.wikipedia.org/wiki/Ivan_the_Terrible dear Tsar Ivan]]. Apart from PeterTheGreat he is said to be Russia's most cunning monarch ever, and this ''really'' has its reasons. To be fair, he is actually a gal of a MagnificentBastard, from which even most fictional examples could learn their fair share. Is it even a surprise that he was also a spectacular and passionate Chessplayer?
[[/folder]]

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