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The Chessmaster / Examples Using Chess Metaphors

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     Anime & Manga 
  • Chessmaster vs. Chessmaster example: Light vs. L in Death Note, creating a Gambit Pileup 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.
      • It helps that his "pieces" were supernatural in nature and impossible for L, Near, and Mello to plan around without foreknowledge. L had to battle Light and figure out the rules of the game at the same time, all while being denied a full view of the pieces and the board. His discoveries and observations allowed Near and Mello to wage war against Light without the handicap of ignorance.
    • 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.
  • Black Butler'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 demonic Battle Butler to strike. And he's very good at making people think that he's 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 Deadpan Snarker crossed with a Magnificent Bastard with a pinch of Crazy-Prepared. We see him playing chess quite often during the manga - he's even undefeated.
    • Along with the Chess Motifs scattered throughout the manga and anime (especially the opening), there's quite a few chess metaphors and direct references thrown around.
  • Kaname Kuran of Vampire Knight. 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 Code Geass, is almost a textbook example of the good-guy Chessmaster: highly intelligent Well-Intentioned Extremist 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 Word of God, Lampshade Hanging, 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 Mind Control 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).
      • And to further drive it home, Lelouch is also an actual chessmaster, able to defeat most opponents in the actual game of chess itself with relative ease.
    • 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 The Fool 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 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 Cowboy Bebop, 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.
  • Several characters in Liar Game. 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.
  • Affably Evil Prime Minister Wong Yunfat from Mobile Fighter G Gundam. Humongous chess board included.
  • One Piece'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.
  • Umineko: When They Cry 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 The Record of a Fallen Vampire.
  • Father in Fullmetal Alchemist has a chessboard, and actually uses it as the activation point for his plan.
    • Also Roy Mustang: he often plays chess, and when 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.
  • Fairy Tail 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.
  • SD Gundam Force 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.
  • Mobile Suit Gundam SEED Destiny has Chairman Gilbert Durandal, who manipulates both events and people with incredible ease; unlike many on this list, he's also a Graceful Loser. His predecessor as Big Bad, Rau Le Creuset was also one of these, successfully getting the entire world caught up in a war of mutual extinction. Durandal regularly messes around with a chessboard, and at one point they're seen playing against one another. Le Creuset wins.
  • Seto Kaiba during the Death-T arc in the Yu-Gi-Oh! 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, 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 Mikado. No, seriously.
  • Taikobo from Soul Hunter 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 Hell Girl 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 Chuunin 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 No Game No Life were teleported into a world where chess metaphors become literal objects of power and status. Their first major battle is a chess game that due to the use of magic by their opponent goes Off the Rails by 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 against Tet, the world's God.

     Comic Books 
  • In The Mighty Thor, 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 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. When he was turned mortal for a while, these turned into RPG miniatures and (door stopper) rulebooks, but when asked he called it a game of his own devising. So apparently Loki plays an elaborate game of "Calvinball" with the universe.
  • JLA/Avengers has Metron and The Grandmaster as such.
  • Obadiah Stane did a masterful job of bringing every part of 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.
  • Calvin and Hobbes parodies this 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, 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..."
  • Superman: Red Son has Lex Luthor (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"? 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."
    • And what ticked him off more than anything? His Superman Clone beat him at Chess.
  • 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.
  • DC Comics' Darkseid is also fond of moving figures of his minions and enemies around on a chessboard when hatching his latest evil scheme.
  • Y: The Last Man 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 Doctor Doom, he's toying with chess-piece replicas of the Fantastic Four, 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 Mephisto and Doctor Strange like Stradivarius violins. Simultaneously. With one move.
    • ...which is parodied in these two 8-Bit Theater strips.
    • An issue of 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 Miki Falls, is eventually revealed to be one of these.
  • In the Batman story Hush, Hush is thought to be it, but it actually turns out to be The Riddler who ironically, Batman had dismissed as a threat earlier on in the story.
  • Cyclops from X-Men, the "General of the Mutants", is the 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.
  • In All Fall Down, AIQ Squared becomes this, hatching an elaborate plot to try and kill Siphon, using Phylum and Pronto as his less-than-willing pawns.
  • In Death of the Family, The Joker has spent his year-long absence becoming this. The Catwoman story even shows the chess motif!
  • In The Invisibles, 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 Blind Seer.

    Fan Works 
  • Checker Monarch, the Big Bad of Getting Back on Your Hooves, who uses a chess board (chess itself being described at one point as her favorite game) as a representation of her plans to ruin her sister Trixie's life. Her full first name is actually Checkmate as well.
  • In Kyon: Big Damn Hero, Kyon is most definitely a Chessmaster, often using chess metaphors as he makes strategies.
  • Herald, Big Bad of The Stars Will Aid Their Escape. He drops a few chess metaphors over the course of the story, as he manipulates everyone to follow his plan.
  • Jewel of Darkness: The mysterious leader of the White Glove qualifies as one of these, and is even seen playing a game with Vandal Savage 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.
  • Having a drastically expanded role compared to his original appearance, Dragomon from Zero 2 A Revision has a giant chessboard that he uses to monitor the movements of the Digidestined and the other dark forces that the Digidestined are currently facing, patiently waiting for his next move to absorb the Child of Light.
  • Celestia in Rites of Ascension, who admits that due to working on her own for a millennium, it is hard to counsel with other ponies, even her own sister (who admits to sometimes feeling like just another piece on the board), discussing the matter with Twilight over a chessboard. (Notably, said discussion comes immediately after said tendency has circled back around to bite her in the cutie mark and upend her own plans, with Twilight calling her out on it.) She also notes Council Chairpony Charlemane as being similarly gifted (and that the two of them have had many worthy battles in both chess and the political arena).
  • In Once More with Feeling Gendo and SEELE are joined (and opposed) by Original character Major General Shigeru Ishiba, the Director of the Japanese Defense Agency (Intelligence).
    The UN, formerly a simple world forum with delusions of power was, in half a decade turned into a powerful body with delusions that it was a world forum as SEELE moved the pieces on its chess board patiently, taking control behind the scenes to divert the resources they needed to GEHIRN and then NERV and the Human Instrumentality Project.

    Films — Animated 
  • Hades from Disney's 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.

    Films — Live-Action 
  • 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.
  • James Bond
    • Kronsteen in From Russia with Love 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 Tomorrow Never Dies she even uses chess-based code names when corresponding with Bond.
  • Historical gangster "Bumpy" Johnston (played by Laurence Fishburne) is depicted in this manner in the 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 Spinning Paper sequence.
  • In the film Jason and the Argonauts, the gods are shown playing a boardgame, with the heroes and villains as pieces.
  • In Lucky Number Slevin 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 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.
  • Clint Eastwood's Man With No Name in A Fistful of Dollars rolls into town, sizes up the situation, and immediately starts playing the two local powerhouses against each other.
  • Michael Corleone of The Godfather trilogy - especially Godfather II. He started out as a Nice Guy who becomes a true 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 Magnificent Bastard.
  • Lord Cutler Beckett of Pirates of the Caribbean. He even had a strategy board, one with a little Beckett piece-. (R.I.P.)
  • Allenby and Feisal in Lawrence of Arabia. They spend as much time plotting against each other as fighting the Turks.
  • The titular character of the movie Fresh develops a plan to 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 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. Oh, and Fresh is 12. The What Have I Done 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 Xanatos Speed Chess 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.
  • Andy from The Shawshank Redemption, is an example of a Chessmaster who is the "good" guy. (Well, relatively speaking.) It's clear from his conversation about halfway through the movie that he's very clever, talking about 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 Chess Motifs, 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 [Norton's] head, other than that bullet, was to wonder how the hell Andy Dufresne ever got the best of him.
  • Chili Palmer in Get Shorty 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.
  • Inspector Clouseau is revealed to have been this all along at the end of the remake of The Pink Panther (2006), having 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, Don't Try This at Home; he's a trained professional at pretending to be clumsy for the sake of his investigations).
  • Cardinal Richelieu's Evil Plan makes up most of the plot of The Three Musketeers (2011) and he uses Chess Motifs quite frequently. Most notably when he plays a game of chess against himself as he cannot find a Worthy Opponent.
  • Professor Moriarty from Sherlock Holmes: A Game of Shadows is this to Sherlock Holmes's Guile Hero. The film even climaxes with them playing speed chess and finishing their game verbally.
  • In Tinker, Tailor, Soldier, 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.
  • Momentum: 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 Genre Savvy 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 Alex who turns out to be the real chessmaster with a brilliantly planned and executed strategy that incorporates elements of Xanatos Speed Chess.
      • 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.
      • Alex plays the tough Deadpan Snarker while undergoing physical torture, but later - after Washington brings up her tragic CIA history and suggests Females Are More Innocent and can't compartmentalise - she pretends to break, fooling him into thinking he has the upper hand.
      • Alex lets Mr. Washington see a brush pass exchange with an accomplice, pretending to be sloppy because of an injury. In reality this is an intentional Divide and Conquer strategy that forces Washington to split his team up and send a henchman after the accomplice, thus leaving himself more vulnerable.
      • Alex pretends to be reluctant to open 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.
      • Lampshaded in a post-reveal exchange.
      Alex: I had to let you catch me, otherwise this wouldn't have worked.
      Mr. Washington: You... MAGNIFICENT BITCH!
      • And even more explicit lampshading later.
      Alex: Queen to bishop five. Checkmate.
      • 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.
      Alex: Gun!

  • Nightfall Series: Prince Vladimir is always ten steps ahead of his opponents in every evil plan. He even tries to teach a person sent to assassinate him how to be a better player, in an attempt to get a more interesting enemy. And all the while he uses chess and checkers metaphors.
  • Chung Kuo has a Go master, Howard deVore, who compares manipulating people to placing pieces on the Go board
  • Romeo Dallaire's Shake Hands with the Devil 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 Green Rider 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 smashes the chess board with her sword, causing enough magical backlash to win the day.
  • John Brunner'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. 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 Harry Potter series, Ron Weasley is a literal "chessmaster" and his abilities on the wizard's board lead Harry onto Voldemort's trail in Harry Potter and The Philosopher's Stone.
    • Not least, they both demonstrate an exceptional chess move: 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 Lewis Carroll's Through the Looking-Glass, 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 Brigid O'Shaughnessey from Dashiell Hammett's The Maltese Falcon are both opposing chessmasters who manipulate Sam Spade and a cast of minor characters in order to obtain the Maltese Falcon for themselves. Though in the end, they both fail.
    • Spade himself is this to some degree, as well.
  • In the James Bond novel From Russia with Love, 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 The Wheel of Time, albeit with a Captain Ersatz 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 Corrupt Corporate Executive types battle for promotion by fighting Mad Max-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 Just Between You and Me 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 Andre Norton'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 Magnificent Bastard of the Discworld is an amazing chessmaster ("It's like being a puppet, only he gets you to pull your own strings"). In Going Postal he gets his very own not-quite-chess metaphors, getting into a little discussion with Corrupt Corporate Executive 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.
    • The Discworld's gods are the literal embodiment of the trope; they've got their own game-board (though it's not actually 'chess', per se), on which the pieces are the mortal residents of the Disc (and thus literal pawns in the games of the deities).
  • Two crazy-awesome examples exist in Sergei Lukyanenko's Night Watch Trilogy in the form of the two heads of the Watches; Boris, head of the titular Night Watch and 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 Gambit Roulette (Yes, both of them quite happily) and seem to willingly fling themselves headlong into a Gambit Pileup.
  • In Ellen Raskin's The Westing Game, 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. 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.
  • Iain Banks' The Player of Games: 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 Sidney Sheldon both got rich and powerful via skilled Chessmaster tactics. By the end of the book, 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 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 Generational Saga 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 Demon Queen from David Drake's series The 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 Codex Alera has these in spades, the ones who actually use chess ludus metaphors are mostly the Canim. Tavi considers beating enemy commander and Worthy Opponent Nasaug at a game to be worthy of inclusion in a list of badass feats he accomplished as Captain of the First Aleran Legion. At another point, professional Chessmaster Gaius Sextus makes a joke about how the situation doesn't resemble the game, since at that moment, the First Lord and a Knight are at the mercy of a lowly steadholder.
  • In 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.
  • George R.R. Martin's A Song of Ice and Fire is loaded with Chessmasters, many of whom have at least a passing familiarity with the game of cyvasse, a chess-analogue developed in Volantis centuries ago. Oh, and a few of those aspiring to or dreaming they are Chessmasters, knowledge of cyvasse or not — and, success or not.
    • Varys - Has 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. He also knows the game of cyvasse, even though he doesn't make a song or dance about it.
    • 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.
    • 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. However, Doran, despite being denied all physical sports and leisures, does not play cyvasse itself. 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 actual cyvasse games on purpose so he could gamble successfully for an important piece of information after his opponent grows rather too cocky. However, in the grander scheme of things, Tyrion's political game often gets stomped on within the massive Gambit Pileup 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).
    • Cersei Lannister - She can scheme up a storm, sure, but... Failed. Spectacularly.
    • Lord Petyr "Littlefinger" Baelish - 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.
  • 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 Mental Time Travel 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 Smug Snake, 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.
  • In Tolkien's Legendarium, Gandalf is a bit of a chessmaster. Sent to Middle-earth 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 The Lord of the Rings he describes the approaching war as a chess game ("And pawns are likely to see as much of it as any, Peregrin son of Paladin, soldier of Gondor. Sharpen your blade!") Gandalf's chessmaster qualities are also highlighted in "The Quest of Erebor", a narrative account (intended for inclusion in the LotR appendices but cut for space) of how Gandalf and Thorin came to arrange the journey to the Lonely Mountain in The Hobbit.
    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 Len Deighton's SS-GB, an Alternate History 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 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 set an ambush, shoot and kill the escaping King; then he gets the underground to rouse the British people against the "Nazi Regicides" and create the myth of a matryred, heroic King (when in fact the poor George VI had been a broken man); then he gets the young Princess Elizabeth crowned Queen-in-Exile at Australia; then he gets the various rivaling Nazi factions in charge of occupied Britian 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 1632 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 Otto von Bismarck, the Real Life 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 Bleak House 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."
  • Darren Shan's The Demonata series has a heavy chess theme running throughout, and several characters probably qualify for this trope, but none moreso than Lord Loss, the Big Bad of the first four books and later The Dragon to the Big Bad of the overall series. In terms of literal chess, he's obsessed with the game, and only ever beaten rarely. Figuratively... 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 Karma Houdini par excellence.
  • Kurt Vonnegut'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.
  • Get Shorty's Chili Palmer is a low-end Chess Master, 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 The Sphinx's plans as a game of chess is mentioned several times in the Fablehaven series.
  • Elsworth Toohey, the journalist, critic and social activist who is the main villain of Ayn Rand's The Fountainhead. 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 Wings of Dawn: Thomas of Magnus. Lord Mewburn. Lord Hawkwood. Waleran.
  • The Duchess in The Princess Series is this.
  • In John C. Wright's The Hermetic Millennia, Larz's story where he 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 The Fifth Wave by Rick Yancey, Commander Vosch is so good he gets human teens to kill the rest of humanity for him. Without them knowing. Ringer also seems to be quite The Chessmaster in training.
  • In 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.
  • The Balanced Sword has dueling chessmasters: the Big Bad is running an elaborate scheme with many moving parts, and the good guys' response is being guided by their Mysterious Backer, the wizard Khoros. Both are described at least once as playing battlesquares with human pieces.
  • Fiona Khal, from The Lay of Paul Twister, prefers to think of the conflict between the Magi and the Dragons as a game of chess, though she puts an interesting 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!"
  • Sylvester, in Twig, is generally more of an Opportunistic Bastard than an outright Chessmaster, but he verges into this when he comments on how he sees the social conflict between himself and Reverend Mauer, a charismatic religious leader. If Mauer is playing chess, Sy reasons, then Sy has arrived late to the game and Mauer has created an impenetrable defense. Therefore, the only way for Sy to win is to cheat and make Mauer's next move for him in order to create an opening. Thus, he and his team promptly start a riot.

     Live Action TV 
  • Doctor Who:
    • Sylvester McCoy's Seventh Doctor. The chess metaphor is part of a Story Arc; 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!"
    • 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. 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.
    • In "Wedding of River Song" the Eleventh Doctor plays live chess, in which pieces are electrified, with Gantok to gain information about the Silence.
  • Colditz: In the second series, Carter and Mohn begin to taunt each other with chess metaphors once the two establish their enmity. When Carter becomes the new Escape Officer, he makes it clear that he intends to win his game of chess against Mohn, and indeed spars with him across the board literally on multiple occasions, parlaying Mohn's exemplary chess advice into both his game and his schemes. In this role, Carter is also significantly more of a Chessmaster than his predecessor, cooking up deliberately obtuse schemes with limited initial payoff (and even putting lives in danger) with grand long-term plans in mind. As Carter becomes a more proficient escape officer, he also improves at the chessboard.
  • One of Monk's suspects in 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 gains inspiration from 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 "but if you insist... checkmate."
  • Gideon from Charmed relies on the strategy of the Chessmaster, and has forged an alliance with the evil version of himself from the Mirror Universe. There's even a scene in which the two versions of Gideon are talking strategy over a game of chess.
  • In Heroes Sylar manipulates Danko into cooperating with him while toying with the pieces on a chessboard.
  • Malachi of Hex, which should be expected since he is more or less the Anti Christ. 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 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 The Walking Dead. Although he's been a Manipulative Bastard since before his first appearance, this goes full chess-metaphor after 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 falling to the ground and being stepped on as the Governor dies.
  • On Law & Order: Criminal Intent Nicole Wallace plays all sides, steals identities and acts as a recurring archenemy of detective Robert Goren. On top of that she 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. Hopefully.
    • When 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 Smallville features the secret agency Checkmate, with the Chessmaster in question being Amanda Waller, orchestrating a series of murders and news leaks in order to 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 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, who is mentioned as having become a grandmaster at the age of fifteen. Although 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 appropriately named villain Chess in The Cape.
  • Literal example in former World Chess Champion Arkady Balagan in Endgame. He uses his talents to solve crimes.
  • In Robin Hood, 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 Power Rangers in Space, 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 Parks and Recreation, 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.
  • 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 Twin Peaks is in an ongoing chess game with Coop. Every time Coop loses a piece, Earle kills someone.
  • Person of Interest: In one episode, Elias plays a chess game with Finch. In fact in one episode the team needed to Deal with the Devil with him. His wish afterwards? To have Finch come and play chess with him on a regular basis.
    • While training The Machine (in a flashback) in the intricacies of chess, Finch gives a resounding denouncement of the Chessmaster concept, and instructs the Machine to not regard people as unequal, disposable chess pieces.
  • In The Messengers the Devil plays chess with a gambling man to start a chain of events intended to lead to the breaking of a seal.
  • Joan Ferguson of 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.
  • The Russian spymaster Igor Panin in the Cold War spy drama Chessgame, based on the spy thrillers of Anthony Price.

    Tabletop Games 
  • In Old World of Darkness, Kindred in Vampire: The Masquerade 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 Dungeons & Dragons, 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 Di Terlizzi), a pair of arcanoloths, the most Affably Evil 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 Gambit Pileup.
    • 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 Highlander Gambit.

  • Molokov and Walter are tag-team Chessmasters who play the protagonists against each other for political purposes in the musical 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 Classic Villain Graf Taaffe is playing chess throughout the story, sets The Hero 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.

     Video Games 
  • One of the Nod mission briefings in the original Command & Conquer 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 Assassin's Creed I, Robert de Sable reveals that Al-Mualim has been manipulating Altaïr 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 Altaïr 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, 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 Vampire: The Masquerade Bloodlines, 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 the taxi driver. Fans have written everything short of academic essays on this guy.
  • Legacy of Kain has enough of these to make one think it was a required step in character design. Most notably are Moebius, the hylden, Elder God, and Kain
  • Knights of the Old Republic. 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 Batman Gambit.
    • And then there's Kreia from the sequel... words do not begin to describe...First of all, she was Revan's master, and Revan may have been following her bigger plan all along. Malak becomes a Spanner in the Works? Fine. Just rig things up so one of Revan's top generals (The Exile) ends up walking into her trap. Then manipulate the hell out of Exile and Exile's entire party, brought together (and forced to stay together) by a combination of blackmail, lies, and Force bonds. The endgame? She's playing her chess game against The Force itself! She blatantly admits what she's doing, too. "no game of dejarik [StarWars's answer to chess] can be won without pawns." indeed.
  • Sandro, the Necromancer Lich, in 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 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.
  • Gaia from God of War. 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 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 Metal Gear: Ghost Babel. Snake comments in the ending that he plans to make them pay for playing chess with peoples lives and hearts.
  • Nemesis in City of Heroes is all about this.
  • Gwyndolin of Dark Souls. The guy is secretly ruling the capital city through the use of an incredibly powerful illusion. He runs his own religion/Secret Police, and he is working with an Ancient Keeper 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 Furtive Pygmy might be one of these as well, though it isn't sure if he is a Chess Master or Awesome by Inactivity and dumb luck.
  • Maxwell, the antagonist of Don't Starve, complete with chessboard flooring decorating some of the game's special areas (such as his throne room) and clockwork chess piece monsters (styled after rooks, bishops, and knights) defending those special areas. He tricks unsuspecting people into making a deal with him and then traps them on his island of death, seemingly just to watch them suffer horrible and painful deaths. Over and over and over again. However, it turns out that he's a piece in an even bigger bad's game, and he knows it. The main reason he keeps capturing survivors and egging them on is actually because he wants to have his freedom back at the cost of theirs.
    Maxwell: Even a king is bound to the board.

  • 8-Bit Theater parodies the trope here.
  • Thaco from Goblins. "You keep playing your little game of chess or whatever you think you're doing."
  • In 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 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 Card-Carrying Villain who exists solely to 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, and inevitably loses. However, manipulating this game of chess is unnecessary, and ultimately futile, unless someone decides to 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 he has yet to disappoint.
      • Ultimately subverted, as 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.
    • Terezi is also this. As a Seer of Mind, she has a comprehensive understanding of the effects that decisions will have. This means that she is incredibly good at manipulating and tricking people, from physical gods to reality warpers. Vriska is not happy about this.
  • In The Order of the Stick, the three leaders of the Inter-Fiend Cooperation Committee in this strip, which is titled, "Moving the Pieces".
  • Billy Thatcher from 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.
  • In 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).

     Western Animation 
  • Lawrence Limburger had a couple of episodes playing several factions against each other in Biker Mice from Mars. This had to involve a chessboard with the people involved and a lot of Evil Laughter.
  • Vlad Masters of Danny Phantom is fond of using chess metaphors to describe his Evil Plan.
  • David Xanatos of Gargoyles, king of the eponymous Xanatos Gambit. 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.
  • Hilariously averted in an episode of The Simpsons where Mr. Burns hires an assassin to kill Grandpa. After two botched attempts, the assassin suggests a third option which he describes "as complex and precise as a well-played game of chess." Cut to him bursting into the retirement home with a machine gun and firing wildly in all directions.
  • The Brain from Teen Titans 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."
  • Bill Cipher engineered events for at least the last thirty years, all to complete his plan of merging his world with the real world, freeing him and his other nightmare demons. This was just the final and first successfully completed plan in a long line of plans executed since, presumably, the beginning of the universe. Previous plans included convincing a shaman to try and build a portal long before it was technologically feasible. When the shaman found Bill out, he set himself on fire ("DRAMA QUEEN"). Also, the original intention for Ford's portal was simply a gateway for Bill and Co. to pass through which Ford thought was for his own research purposes. After Ford spent thirty years in various dimensions, breaking the Rift the portal created upon his return became the new plan. As a Visual Pun, he's seen playing chess with Ford. Ford also writes in code in the journal after he discover's Bill's trickery, "INTERDIMENSIONAL CHESS ISN'T FUN WHEN YOU'RE A PAWN."
  • Henry Haber from Bob's Burgers runs for school president under a chess-based platform, with him eventually winning the election not by popular vote, but rather by some crafty manipulation that involves Millie running for school president (and Louise, knowing full well of her Yandere interest in her, going all out to stop her).
  • Anarky the Big Bad of Beware the Batman Season 3, loves to play chess using Batman and various villains as chess pieces, as symbolism for how he indirectly manipulates the events of the series.
  • Viggo Grimborn from Dragons: Riders of Berk does this with "Maces and Talons", what appears to be its universe's version of chess. He even spells this out when Hiccup arrives at his completely abandoned ship, save for a Maces and Talons board setup to reflect the current situation.

  • Otto von Bismarck is depicted in 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 Magnificent Bastard 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.
  • 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 but an alt-universe equivalent, the chess motifs are still there.
  • Barack Obama'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 Andrew Sullivan is particularly devoted to the concept.
  • Don't forget dear Tsar Ivan. Apart from Peter the Great 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 Magnificent Bastard, 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?