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The Chessmaster
alt title(s): Chessmaster
You lose.

All warfare is based on deception.
— Sun Tzu, The Art Of War

The victim's security system is down; it was "upgraded" with a version that had a key flaw. (The Chessmaster's flunky sold the new system.) The local cops are all in pursuit of a dangerous criminal on the other side of town. (The Chessmaster made an anonymous tip.) That dangerous criminal actually is on the other side of town, about to visit the house of someone he believes was the person who ratted him out all those years ago. (Now whoever could have given him that idea?). That man has critical evidence against the Chessmaster that only he knows. (The Chessmaster will make sure he takes it to the grave.) A "wild" arsonist is targeting the victim's house that night. (He's the Chessmaster's flunky.)

Chessmasters tug at their strings of influence, patiently move their pieces into places that often seem harmless or pointless until the trap is closed, and get innocent dupes to do all the heavy lifting. The best will also have layers upon layers of misdirection and backup plans in case some unexpected hero appears to gum up the works. They take the (very!) indirect route in order to snake through holes in their opponents' defenses without a trace... assuming they can refrain from boasting of their cleverness near the hero with a triumphant sneer and a raised eyebrow.

One obvious sign you're dealing with a Chessmaster is that, when he's gotten familiar enough with the heroes, he'll start breaking out the Xanatos Gambit. Any sufficiently-complicated cons or capers are also the MO of these types, especially if used regularly. Finally, anyone who successfully executes a Xanatos Roulette is by definition a Chessmaster.

Many chessmasters are Villains With Good Publicity, but they can also be someone no one has ever heard of. Almost all Ancient Conspiracies are led by a collective of chessmasters, silently working toward their goals over generations.

Chessmasters can sometimes be on the side of good, but if so they'll almost certainly be the Anti Hero or the Well Intentioned Extremist, as it's very hard to plan a Chessmaster scheme that doesn't sacrifice a few pawns along the way.

Never, ever be predictable in your habits when you have a Chessmaster as an opponent. Even the wannabe Chessmasters can demolish someone who always calls his partner for an update from his balcony at precisely 7pm on Thursday. Much like the Clock King, who bases his plans on other's predictability but does not outright manipulate them. Oh, and if you ever think you are winning against a Chess Master, you have already lost. The only way to win against that dude is to stage a Xanatos Roulette so complex that even you yourself won't be sure it'd work. Or to act entirely at random, and hope you get lucky.

For some real entertainment, pit two or more Chessmasters against each other and watch the Thirty Xanatos Pileup.

Chessmasters can occasionally be The Strategist, although given the volatility of war, most Strategists will only ply their schemes one campaign at a time, with an emphasis on short-term goals (and an eye towards all possible future contingencies). The Dungeon Master may be a Chessmaster also, but many of them prefer to give their orders more directly.

Of course, actual chess ability is implied, and some Chessmasters take it literally, mapping their plans out with an actual chessboard, occasionally with pieces shaped like the main characters. Don't ask how this works, or where they get pieces.

Chessmasters also tend to be overconfident and usually panic when their "perfect" plans fail. The exception to this is the Magnificent Bastard, an unusual breed of Chessmaster who is quite good at rebounding from defeat.

Also see Smart People Play Chess.

Not to be confused with The Chessmaster, a long-running series of chess videogames.

Examples Actually Using Chess Metaphors:

Anime and Manga
  • Too many to count in Legend Of The Galactic Heroes. Often overlaps with Magnificent Bastard.
  • Light and L in Death Note - the ultimate Chessmasters pit against each other, creating a Xanatos Gambit pileup to no end.
  • Lelouch, the Anti 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 even 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).
    • 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).
  • 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. 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 Liar Game. One of the antagonists, while not playing chess, uses chess pieces to demonstrate headcount in a Minority Rule game. This contributor believes this belongs in this subsection of the category because the three pieces (rook, knight, bishop) all representing the same person are then dramatically replaced with a king, complete with grand sweeping gesture.
  • Inverted in Fullmetal Alchemist when after King Bradley has ordered Riza to be his secretary, and the rest of Mustang's men to be sent to the fronts of the various wars Amestris is fighting, Mustang has noted that he's lost most of his pieces, but he's still not out of the game. The Big Bad Father also uses objects like Chess pieces to simulate all of the things he needs.
    • In the anime version of Fullmetal Alchemist Dante is a text book example of a Chessmaster, creating whole wars by manipulating millions of people with her well placed homunculus minions, all just so she can create a Philosopher Stone and live a few more years herself.
  • Shikamaru Nara in Naruto, exemplified in pretty much any fight he's in, tends to play shogi with Asuma or his father now that the former's dead.
  • Affably Evil Prime Minister Wong Wunfat from G Gundam. Humongous chess board included.
  • Bleach:  spoiler - click to reveal
  • Umineko No Naku Koro Ni: 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.

Comic Books
  • 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:
    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.
    • Lex 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 "to keep my mind occupied". How good is "Luthor good"?  spoiler - click to reveal
  • DC Comics' Darkseid is also fond of moving figure 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, who among other things argue, 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.
  • Rakan's main enemy is actually named ChessMaster.
  • General Wade Eiling definitely fulfills this trope, given the way he manipulates Captain Atom.

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.
  • 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.
  • 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  spoiler - click to reveal.
  • 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.)
  • In Watchmen, Adrian Veidt is a Chessmaster who does not rely especially heavily on Xanatos Roulette.  spoiler - click to reveal.
  • Palpatine in Star Wars. Best quote to summarize this?
    Palpatine: Everything that has transpired has done so according to my design.

Literature
  • A relatively rare female example with Professor Jenna-Jane Mulbridge in Mike Carey's Felix Castor novels: while the series features demons and undead galore, moreover, it is the two human examples, Jenna-Jane and Church Militant leader Father Thomas Gwillam, who draw the most ire from the protagonist.
  • 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  spoiler - click to reveal
  • 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.  spoiler - click to reveal
  • 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.
  • The Continental Op of Dashiell Hammett's Red Harvest.  spoiler - click to reveal Don't forget that the man was the inspiration for the samurai film Yojimbo which was later adapted into a western mentioned just a few paragraphs ago, A Fistful of Dollars. Makes you wonder if Dashiell Hammett had this planned from the start...
  • Moridin in Robert Jordan's The Wheel Of Time, albeit with an imaginary game called sha'ra (though he is stated to be a master of all strategy games, which presumably includes chess).
  • 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 it 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.
  • While Lord Havelock Vetinari, Patrician of Ankh-Morpork and all-around Magnificent Bastard, is mentioned below, in Going Postal he gets his very own not-quite-chess metaphors. More specifically, he gets into a little discussion with Corrupt Corporate Executive Reacher Gilt on the merits of playing the two sides.
  • 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.
  • 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.  spoiler - click to reveal
  • In Eleanor Updale's Montmorency, the titular character has some Chessmaster tendencies, but they are completely trumped by the anarchists in the third and fourth books.
  • In Carrie Vaughn's Kitty Norville series, Mercedes Cook is revealed as this through her manipulation of Arturo and Rick into a vampire war. The fact she in turn is working for/being manipulated by Roman only adds even more delicious levels of convolution...and since he is only stated to be a general in the Long Game, chances are there's an Omniscient Council Of Vagueness out there manipulating everyone, which Kitty will inevitably have to face down.
  • Subverted in "The Twisted Thing" by Mickey Spillane. Private eye Mike Hammer is going crazy trying to sort out who killed a wealthy scientist in the midst of murder and blackmail attempts by all the potential heirs. He eventually realises that there is no Xanatos Gambit going on — the killer murdered the victim out of revenge, knowing that the crime would be obscured by everyone else scrabbling for his money.
  • Jeeves is essentially a Chessmaster who uses his powers for good. His Xanatos Gambit is always the center of the behind-the-scenes plot, and his philosophy of manipulating people based on the "psychology of the individual" throws a little bit of Clock King in there too.
  • 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.
  • John Alpha, the Big Bad of 7th Son, certainly qualifies. It's not until the end of Book One that the Beta clones figure out exactly how long he's been setting up the pieces and just how large and intricate his game is.

Live Action TV
  • Sylvester McCoy's Seventh Doctor in Doctor Who. The chess metaphor is part of a Story Arc; it first appears in "Silver Nemesis", when he moves the pieces on Lady Pienforte'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!"
    • However, the Seventh Doctor may not be quite the flawless chessmaster that he wants everyone to believe he is; many of the stories involving this aspect of his character hinge on something occurring that he didn't actually anticipate or someone doing something that he didn't expect, thus requiring a frantically improvised stop-gap solution to get things back on track.
  • 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. 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 I suppose must 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 refered 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)
  • On Law and 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.

Theatre
  • An old and perhaps prototypical Chessmaster is Shakespeare's Iago, from Othello.
    • In the Kenneth Branagh film adaptation, Iago (also played by Branagh) illustrates his plan with an actual chessboard.
  • 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 world champion chess masters.

Video Games
  • One of the Nod mission briefings in the original Command And 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,  spoiler - click to reveal. 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.
    • Speaking of Kerrigan... Brood Wars was basically Kerrigan playing her own constant Chessmaster, to the point where she was more playing a game of roulette.
      • Both Starcraft and Broodwars actually have several of them. The Overmind definitely counts, maybe also Dugall. Alan Shezar and Ulrezaj also count, if you take Blizzard's bonus campaigns as canon. Oh, and of course Duran (who also qualifies as a Magnificent Bastard).
  • The Prophet of Truth from Halo. In Halo 2 he is the epitome of the Chessmaster, going as far as to eliminate the Sangheili without them even knowing it, kills off his two co-leaders with no mercy or regret (hahaha...), and having the Arbiter run a wild goose chase, culminating in the latter's "demise" at the hands of Tartarus.
  • 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.
  • Belthasar in Chrono Cross plays this role as it is revealed he manipulated 10,000 years of history across multiple parallel dimensions to make sure the protagonist would acquire the (eponymous) ultimate item needed to completely destroy the Big Bad.
  • 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 of course, Kain

Web Comics

Web Original
  • In the Whateley Universe, a supervillain of this type not only goes by the codename Chessmaster, but puts replicas of his pawns and the opposing heroes on a chessboard. He uses psychic abilities to make his gambits more effective: he has been known to 'attune' his pieces so they're more likely to do what he wants, and he has precognition to the point that he can see the dozens of most likely scenarios, with their consequences. His biggest problem? He's still trying to prove himself to his old (now retired) teacher Mrs. Potter, who is such a powerful and effective precognitive that she can trash his plans just by making a phone call the day before, or handing someone a note to hold for someone who may drop by.

Western Animation
  • 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 literally part of a special game of chess. This is done literally with the couple competing using a chessboard with board pieces representing each of the people they manipulating; The Pack for Xanatos and the Manhattan Clan for Fox.
  • The Brain from Teen Titans literally 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.
  • Vlad Masters of Danny Phantom is fond of using chess metaphors to describe his Evil Plan.

Non-Chess Motif Examples:

Anime
  • Peacemaker Kurogane: In the manga, Suzu becomes one after he goes insane.
  • Johan Liebert, the titular Monster.
  • Chessmaster vs. Chessmaster example: Light vs. L in Death Note. 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.
    • Death Note later features a Chessmaster moving figurines of the dramatis personae around a chess board. Bonus Points!
  • Sousuke Aizen of Bleach. Also of the Magnificent Bastard variety and a proven master of the Xanatos Roulette.
    • For that matter Kisuke Urahara fits the role well too, though on the non-villainous side. Aside from being opposed to Aizen, it's not really clear what endgame he's playing toward, but that could just be proof of how good a Chessmaster he is.
  • Fushigi Yuugi's Nakago was not only good at directing his own men, he was a master when it came to misdirecting and manipulating the heroes. (Not that the heroes were any sort of brain trust, mind you...)
  • Ukyo from Samurai Seven constantly manipulates people to serve his own ambitions. Even the shocking news that he is a clone of the Emperor doesn't shock him for long, and he quickly  spoiler - click to reveal The only plan that stops him is a group of samurai who plainly state they have no plan.
  • Sailor Moon Big Bad Wiseman/Death Phantom constructs an elaborate plot that will allow him to destroy the universe of both the past and future which involved him playing the role of the Evil Chancellor to the Black Moon Clan, having them attack the earth of the future then in traveling back in time to attack the earth of the past, having the Sailor Senshi foil them, then have the Senshi traveled to the future so he could get his hands on the Mac Guffin Girl he needs for his plan, Chibiusa whose power he will feed to his Evil Black Crystal which will then open a gateway of negative energy to to annihilate the universe with.
  • Kurama from Yu Yu Hakusho. A "good guy" example. Even though he has a Green Thumb (which would seem to be useless in normal circumstances), you don't ever want to become his enemy or otherwise try to mess with him. EVER.
  • In Gundam 00, Alejandro Corner thinks he's The Chessmaster, hijacking Aeolia Schenberg's century-in-the-making Xanatos Gambit and arranging to dispose of the late Aeolia's loyal followers so he can take command of the newly-forming Earth Sphere Federation.  spoiler - click to reveal
    • Let's give credit to Aeolia Schenberg too, please? He managed to accurately predict the events of pretty much everything that happened during the first season, and developed effective contingencies for it. What makes him different from all the other different chessmasters? He's been dead for two hundred years.
    • In season two, there are at least three possible Chessmasters, and it's not yet clear which one is winning. Is it season 1 Chessmaster Ribbons, enigmatic Celestial Being backer Wang Liu Mei, or Ribbons' own apparent lackey Regene Regetta, who happens to also be Gundam Meister Tieria Erde's Evil Twin? Each has already had more than one occasion of seeming to manipulate the others, and it's only eight episodes into the season. And just to make things more confusing, all three claim to still be following Schenberg's true plan. At least two must be lying or mistaken, but which ones? As it turns out  spoiler - click to reveal
  • The Anti-spirals from Tengen Toppa Gurren Lagann pull this off quite well; they anticipated every move possible the 'spiral beings' could have made, and intentionally let them achieve almost all of their small victories, for "The greatest despair is brought after the failure of the greatest hope". The only reason they failed was due to a not-so-subjugated mind-puppet herald, Princess Nia Tepperin.
  • One Piece has Sir Crocodile. The country of Alabasta sees him as their greatest protector, while he secretly controls the criminal organization Baroque Works, who likewise do not know his real identity. Anything strange that happens in Alabasta can be traced back to Crocodile's plans: from sandstorms to a countrywide drought to the formation of a rebel army. The final plan of Baroque Works boils down to using the peoples' love for their country to destroy it and allow Crocodile to take over a country that loves him.
  • Amshel Goldsmith from Blood Plus is Diva's chevalier, but he is the one who organises most of Diva's plan to replace humanity with Chiropterans. To reach that end, he uses everyone, including Diva's other chevaliers who are on his side. In fact, it is completely plausible to argue that he, instead of Diva, is the main villain as  spoiler - click to reveal
  • Dante in the Fullmetal Alchemist anime. It is revealed that  spoiler - click to reveal
    • Also, Founder Cornello. His craftiness turned the citizens of Lior into pawns that would give up their very lives for him. Since, of course, his "miracles" made him a messenger from God and all.
  • In both the manga and the anime versions, Aion of Chrono Crusade is shown to be a Chessmaster — in the anime, he manages to manipulate Chrono into giving him exactly what he needs for his plans:  spoiler - click to reveal In the manga, he manipulates not only Chrono and his nakama, but the entire demon society to  spoiler - click to reveal
  • Irresponsible Captain Tylor may or may not be Obfuscating Stupidity, but many both amongst the series characters and the fans believe that he is actually working some master plan of his own, given how he always comes off on top in the end and his opponents invariably find him a Wrench In The Works. A Fanon theory is that Tylor has somehow become enlightened as a boddhistava, and that the begininng and end of the opening trailer showcases both his enlightenment and his plan for the Soyokaze; to lead the Ragtag Bunch Of Misfits into enlightnment.

Comic Books
  • V, Anti Hero of V For Vendetta. In the film, Finch actually figures out part of the plan, but can't do much to stop it by that point.
    • In the graphic novel, Finch  spoiler - click to reveal
    • V also uses a Domino motif for his plan.
  • Norman Osborn of ''Spider-Man'' is another contender in this category. Brought Back From The Dead when Marvel needed a "Get Out Of Clone Saga Free" card, Osborn has more than made up for lost time. For a while, every other Spider-Man story was turning out to be some sub-sub-plan of Osborn's.
  • The Kingpin is another Chessmaster, especially where Daredevil is concerned. (Daredevil seems to attract them — even the two-bit villain Mysterio became one when he took on DD.)
  • Thanos is a staple Chessmaster in many cosmic crossovers in the Marvel Universe. It's frequently lampshaded how other characters (especially heroes) exist solely to be manipulated by him for whatever agenda he might have at the moment.
  • While the comic series Sleepwalker is relatively obscure and ran for only 33 issues, its Big Bad Cobweb is a brilliant Chessmaster, using Sleepwalker as a way to invade Earth while framing him as the demonic invasion's leader.
  • The Avengers villain Immortus was always a Chessmaster in a big way, but in the Avengers Forever series it turned out he was a Chessmaster on a far greater scale than anyone had imagined, he  spoiler - click to reveal
  • The Black Panther of the Marvel Universe is rare example of this trope that is a traditional superhero, albeit one that is occasionally under fire from his more-idealistic peers, for obvious reasons.
  • General Nick Fury is a heroic (well, anti-heroic) version of this trope with the full sanction of the United States Government. And also, total badassery.
    • The regular Marvel Universe's Colonel Nick Fury is no slouch either, even when loses the support of the US government.
  • For a character who claims to hate the convoluted plans, The Dark Knight's Joker manages to pull off a doozy of one. Unless he's making it up as he goes along, which is quite possible. The Joker's sadism also leads him to pull off some nasty (although thwarted) Xanatos Gambits.
  • The Riddler is depicted as The Chessmaster in the Batman: Hush storyline, having manipulated all of Batman's villains in his master plan and having learned Batman's secret identity. However, Batman thwarts the scheme when he exploits the Riddler's compulsion. He can't expose Batman because it would be like giving away the answer to a riddle.
    • You can't say Batman, chessmaster, and villain in the same sentence without talking about Bane.
  • The goddess Athena in the Marvel Universe series Incredible Hercules is another heroic version of this trope; one of the series' major ongoing threads is a colossal (and, as yet, largely unknown) Xanatos Gambit she is in the process of executing. Her brother Hercules, a frequent key piece on her chessboard, finds her refusal to be upfront with her plans annoying.
    • The goddess Athena in DC is possibly an even bigger version. Her scheme to bring down Zeus required the resurrection of Medousa; the death, by Medusa's stone gaze, of a child of one of Wonder Woman's embassy workers (to incense Diana into killing), and then a duel to the death between Medousa and Wonder Woman that culminated in Wonder Woman's blindness and the decapitation of Medousa. This entire chain of events was simply her way of obtaining a fresh gorgon's head (Medousa's previous head having rotted away to uselessness) to use on Zeus's champion, the hecatoncheires Briareos. And that doesn't even count the plot that she undergoes to consolidate her power once Zeus, Poseidon, and Hades try to rebel...
  • Marvel's Grandmaster can come up with some really complicated schemes. Luckily for the heroes he really doesn't care about losing, he just does it for fun. And when he really wants something he's nice enough to let them think they won.
  • Destiny Ajaye from Top Cow's Genius
  • Tao from the Wildstorm comics universe, especially as writen by Alan Moore or Ed Brubaker.

Film
  • In Death Race, the Warden is clearly The Chessmaster, with the way she manipulates the convicts to play in the Game Show race. In view of the fact that the audience is made not to like her she's also the Anti Hero, and she's a Manipulative Bastard.
  • CRS in The Game.
  • Vito Corleone in The Godfather would serve well as the very definition of a Chessmaster. In the book and the movie, he planned out every detail of every part of the story perhaps even his own death.
    • Except that he never wanted Michael to become a part of the family business.
  • The Oracle from The Matrix is a sentient computer program capable of predicting Neo's reactions so well that she essentially made Neo the One. All of Neo's heroics are all essentially part of her chessmaster plan, even Agent Smith.
  • Rotti Largo from Repo! The Genetic Opera is so good at these, it sometimes gets hard to find things that aren't orchestrated by him.
  • Both Michael Caine and Laurence Olivier are chessmasters in the 1972 version of Sleuth. The chessmaster in the 2007 version was whoever got me to watch it.
  • Senator/Chancellor/Supreme Chancellor/Emperor Palpatine in the Star Wars prequel trilogy. Got a less-than-scrupulous faction to blockade/invade his backwater homeworld just to get the old leader kicked out and himself elected in the process. Then gets his apprentice to start a war to increase his authority under "wartime powers". Then gets his sworn antitheses to attempt to thwart him so he can declare them enemies of the state and use his "severely disfigured in an attempt on my life" sob story to get enough sympathy to be named dictator for life.
    • Also Grand Admiral Thrawn from the Expanded Universe.
    • From KOTOR II, the character Kreia could be seen as Palpatine from four millenia previously. She manipulates both the jedi and the sith to such a degree that even at the end of the game, it's hard to tell what side she was on, or even if she was on anybody's side. At one point, she even calls one of the other characters a "pawn".
  • Wild Things peels back layer after layer of deception until the real Chessmaster is revealed. The studio must have liked this idea, because they did it two more times with direct-to-video sequels.

Literature
  • Hari Seldon of Isaac Asimov's Foundation series, who actually figures out the "chess rules" of humanity in the form of psychohistory, then uses that knowledge to engineer the recovery of the Empire after an unavoidable social Gotterdammerung. Seldon is depicted as good; the Ancient Conspiracy that follows in his footsteps... sort of.
    • Even more so than him, R. Daneel Olivaw. Over the course of his thirty-odd thousand year lifespan (he's a robot) he manages to: Engineer humanity's final exodus to the stars, set up the First Galactic Empire, manipulate Hari Seldon into developing his psychohistory in the first place, make sure the plan goes off as it should, and finally set the universe on track to evolve into a single, all-encompassing consciousness. All this whilst being bound by the Three Laws Of Robotics, which he and a fellow robot manage to subvert by realizing that a law even more overriding than the one prohibiting homicide is one - the zeroth law - prohibiting harm to the human race. This is all well and good until the obvious problem arises:  spoiler - click to reveal.
  • Steven Brust's Yendi. Members of House Yendi are famed for their machinations that sometimes take centuries to bear fruit (they live for a couple millennia, so they can be patient). It's a saying in the Empire that the only one who can decipher a Yendi's scheme is another Yendi.
  • Arguably Gentleman John Marcone, from Jim Butcher's The Dresden Files. While neither an antagonist (most of the time) nor a main character, Marcone in eleven books has brought the Chicago criminal underworld under his reasonably organized command, become aware of the supernatural world, hired a Valkyrie, stole the freaking Shroud of Turin, saved Harry's bacon several times and collected a large payment for it, and, in White Knight, talked his way into becoming a freeholding lord in the supernatural world. There are twenty such legal entities; Marcone is the only mortal.
  • The title character of Alexandre Dumas' The Count Of Monte Cristo.
  • Frank Herbert's Dune is filled with them, each with varying levels of skill and subtlety.
    • The Bene Gesserit tried to execute all their schemes through Chessmaster ploys, many of which spanned generations, to prevent people from realizing how much power their organization really had.
    • The master of it though would be the God Emperor Leto II, who was so much better than everyone else that even dying was part of his plans, and didn't seem to hinder his continuing influence much at all.
    • The Bene Tleilax also get a lot of this in Heretics of Dune and Chapterhouse: Dune.
      • They build an intrinsic subversion into their own Chessmastery: it's no fun unless the victim has a possible way out. The thing which fascinates the Tleilaxu is seeing whether said victim can find it.
  • The Patrician of Ankh-Morpork, Lord Havelock Vetinari, in Discworld. See the quote at the top. In Going Postal, Moist von Lipwig describes talking to Vetinari as "...like being a puppet. The difference is, he arranges for you to pull your own strings."
    • It is said that Vetinari only cares about the functioning of the city. (All right, and about his dog Wuffles.) It is said he founded most of the secret conspiracies against him himself, so that he would always know where his enemies are. He encouraged the formation of the Thieves Guild, complete with annual quotas, because "If we have crime, let it at least be organized crime." Technically he is a Machiavellian autocrat, but he is intelligent and smart enough not to become a brutal overlord or to interfere in people's everyday lives unless their actions somehow threaten the city. He has managed to balance out the various powerhungry Guilds and factions against each other so that somehow his enemies never get around to toppling him. Even the Assassins Guild does not accept contracts on the Patrician's life anymore, partly due to the fact that he was educated at the Assassins Guild and has survived a number of assassination attempts, and partly due to the fact that everyone recognizes that the city with Vetinari in power is preferable to a city without Vetinari and the chaos that would result. Or as it was put, (paraphrased) "The Assassins have no problem with people trying to rock the boat, but they will not allow people to smash a hole in the bottom." Everyone remembers paranoid Lord Winder and neurotic Lord Snapcase, two previous Patricians (as well as Deranged Lord Harmoni and Laughing Lord Scapula - Ankh-Morpork has had bad luck when it comes to Patricians), and no-one wants to go back to that.
      • They also took The Commander of the City Watch, His Grace, The Duke of Ankh, Commander Sir Samuel Vimes off the registry, the official excuse being it would destabilize the city but the truth being that the guild was fed up with its members returning from attempts beaten up, sent to foreign lands, burnt by dragons or just dead.
  • Dumbledore in JK Rowling's Harry Potter books is another good Chessmaster, especially in the later books where everything he does (even his own death!) seems to be somehow related to some grand plan years in the making.  spoiler - click to reveal.
    • Not just the later books. After you've read all the books and you know all the reveals, re-read the series. Dumbledore's been manipulating everyone and everything since his first appearance in chapter 1 of book 1, when he leaves Harry with the Dursleys while lying to McGonagall about the reason. And he was obviously stage-managing things before that. He's been running rings around Tom Riddle since Riddle was just a weird kid in an orphanage.
      • Riddle was as smart as Dumbledore (who described him as "probably the most brilliant student Hogwarts has ever seen.") He just let his arrogance get in the way of his genius.
  • Makina Seval of The Assassins Of Tamurin, whose Xanatos Roulette has been years in the making, spanning across an empire but never hitting a snag, and using players in the most obscure and unpredictable roles, who know absolutely nothing about what they're being used for.
  • The Talented Mr Ripley is an interesting variation: he can create elaborate plans on the spur of the moment, then discard then with equal ease and start again. He starts out as a New York City valet and, through fate and quick thinking, turns into a rich-but somewhat crazy-man living in Italy.
  • The titular character of the Artemis Fowl series (being a Teen Genius he is naturally a literal chessmaster as well, though this gets only a passing mention). Opal Koboi also counts.
  • Smerdyakov in The Brothers Karamazov. He believed he could engineer Fyodor Karamazov's murder via a Xanatos Roulette which involved giving eldest son Dmitri all the tools and motivational nudges necessary to murder the old man - a set of signals to gain entry into the house, certain dates on which Fyodor's servants would be incapable of interfering, and the (later revealed to be false) location in the house of a sealed envelope containing three thousand roubles. It didn't work out quite the way he expected.
  • Shadows of the Hegemon by Orson Scott Card is a Chessmaster free-for-all, with Achilles betraying everyone, Peter playing his own games behind the mask of Locke, Petra working to screw Achilles from underneath him, and Bean formulating his own tactics and webs. The plot is so complex with betrayals, it's like reading a game of risk.
    • The opening chapter of Ender In Exile showcases the Wiggins' chessmaster talents, as used on each other, except for Ender, who doesn't appear in that chapter, though when he does show up, he gets to show off his ability to manilpulate others as well, abiet to a slightly lesser extent. Also: Hyrum Graff.
  • Prince Vassily Kuragin in War And Peace. It Runs In The Family too, as Anatole and Hélène (not Ippolit) exhibit traits of The Chessmaster, just not to the degree their father does.
    "According to his circumstances and his intimacy with people, he constantly formed various plans and schemes which he himself was not quite aware of, but which constituted all the interest of his life. He would have not one or two or these plans and schemes going, but dozens, of which some were only beginning to take shape for him, while others were coming to completion, and still others were abolished."
  • In the Sherlock Holmes stories, both Professor Moriarty (Holmes's nemesis) and Sherlock Holmes himself demonstrate considerable Chessmaster talents, most notably in "The Final Problem." Unfortunately, most of the actual plays and counterplays take place offscreen and are merely alluded to by Holmes.
  • Littlefinger of A Song Of Ice And Fire. Tyrion does very well, Cersei stumbles about thinking she's smarter than she is, Walder Frey is too obvious, Varys knows a lot but can't act on it, Tywin Lannister and Olenna Tyrell are no slouches...but none of them hold a candle to Littlefinger.
  • Zhuge Liang (styled Kongming) is portrayed as a Chessmaster (who skirts into Magnificent Bastard territory quite often) throughout most of Romance of the Three Kingdoms (and subsequently in Koei's adaptations), and probably would have remained one if not for the inevitable weight of history: he dies in the middle of a campaign against his rival Sima Yi, still planning for the future and implementing plans. (Notably however, he has no association whatsoever with chess; his feather fan is far more iconic of him than any board game.)
  • Saint Dane from The Pendragon Adventure. Voluntary Shapeshifting abilities and a full knowledge of how to work the Flumes allow him to manipulate everything to work to his whims across Halla. The actual metaphor he uses is dominoes, saying that if one Territory falls, the rest will follow.
  • Robert Van Gulik's Judge Dee, (based on traditional Chinese mysteries) is a subversion of this trope as he is constantly going up against Chessmasters and defeating them because life is NOT predictable - but chessmasters are, at least to Judge Dee! In his final case Dee is trapped by a chessmaster opponent but because he knows how such villains think manages to turn the trap on his rival.
  • The Puppeteers from Larry Niven's Ringworld.
  • Though he is seldom thought of that way, Gandalf of The Lord Of The Rings 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.
  • Chessmasters are common in Korean historical epics. Or at least Strategists. Perhaps it comes of the old Far Eastern tradition of cloak-and-dagger stories that goes back to the likes of Sun Tzu.
  • The Duke of Wellington, as depicted in Sharpe. To give just one example, he summons Sharpe out of retirement to see him with no explanation, tells him he wants Sharpe to rescue an unnamed missing agent in India, lets Sharpe refuse and walk out... only to find his best friend's wife sitting outside the office. "Oh, didn't I tell you? Mrs. Harper's husband is our missing man."
  • The Pilo Family Circus exhibits the fortune teller, Shalice, as the hired planner behind most of the Pilo brothers' schemes for worldwide chaos. Since she's a genuine psychic, she can manipulate entire timelines via brainwashing her customers into committing seemingly unrelated events in the real world and therefore actually pull off one successful Xanatos Roulette after another.
  • U Po Kyin of Orwell's Burmese Days quickly establishes himself as a chessmaster as well. He states his plan to worm himself a way into the European Club by libelling the town doctor in the first chapter of the book, but it isn't until later that the sheer brilliance of his plan becomes apparent.
  • Kelsier, the main character from the first book of Brandon Sanderson's Mistborn series, is a nice inversion as a heroic Chessmaster. He demonstrates his talent through a multi-layered Batman Gambit.
  • Essentially, the murderer in any Agatha Christie novel. One of her most manipulative murderers would undoubtedly have to be the judge from And Then There Were None, who plays off the psychology of each victim especially Vera Claythorne.
  • Human/alien merger Mademoiselle in Reynolds' Revelation Space and Redemption Ark "saw information flows with the clarity most people lack". Ironically, she was destroyed by H, a formidable but ordinarily inferior Chessmaster, because she got so wrapped up in what was essentially a science project, she stopped paying attention to her webs.
    H: "she was a very powerful influence in Chasm City for many years, without anyone realising it. She was the perfect dictator. He control was so pervasive that no one noticed they were in her thrall. Her wealth, as estimated by usual indices, was practically zero. She did not 'own' anything in the usual sense. Yet she had webs of coercion that enabled her to achieve whatever she wanted silently, invisibly. When people acted out on what they imagined was pure self-interest, they were often following Mademoiselle's hidden script."
  • Waleran Bigod from The Pillars Of The Earth.
  • The Big Bad of the Prydain Chronicles, Arawn the Death Lord, is such a noted master of deception and cunning among the people of Prydain that he is feared by all despite being spectacularly weak. Instead of force, he relies on shrewd manipulation of the lesser lords of Prydain into doing his bidding, and in fact comes much devistatingly closer to toal victory than most evil overlords. If only it weren't for that meddling Assistant Pig Keeper...
  • Emperor Ezar in Lois McMaster Bujold's Shards of Honor. He starts a war that he knows he's going to lose, in order to: 1) Kill off his psychopathic son, 2) Discredit his political opponents, 3) Set up Aral Vorkosigan to become regent for his grandson. (Vorkosigan is only man he trusts to a) hold power for 13 years, and b) turn that power over to an 18 year old emperor who will no doubt be an idiot (since everyone is an idiot at 18.))
  • 'Sticky Eye' Kawakami in Cloud Of Sparrows wants to be one, but he isn't very good at it. He compensates by being a truly fearsome Manipulative Bastard.
  • The 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.
  • Several characters in Megan Whalen Turner's Queen's Thief series have Chessmaster attributes, if they aren't full Chessmasters - most notably, the title queen in The Queen of Attolia. Nahuseresh in the same book tries to be one. Eugenides is the best at it, successfully pulling off a Xanatos Gambit in every book. Interestingly enough, most do it for the purposes of good.
  • The Judge and His Executioner by Friedrich Dürrenmatt. Commissar Bärlach  spoiler - click to reveal
  • Ardneh, from Fred Saberhagen's Empire of the East. In the first volume, he actually quotes an ancient (especially by that time) real-world Hindu myth to the villain in order to tell him exactly how he's going to kill him. He then lets said villain get control of the invincible super-weapon in order to kill him in exactly the manner he said he would (with foam, of all things). In the process, he liberates the entire west coast from The Empire. In the second volume, he manipulates two of the villains from the first volume into HeelFaceTurns in order to defeat the demon, using the very fact that the main villain of that volume has moved his one vulnerability to a more secure location. And then, in the third volume, he wipes out The Empire, and most of the world's most powerful demons, in a single stroke.
  • Paladine, in the Dragonlance Chronicles, but especially in the Legends. In the former, he recruits and manipulates the Ragtag Bunch Of Misfits into saving the world, while disguised as the senile pyromaniac Fizban. In the latter, he actually lets Raistlin kill him and destroy the world in an alternate future, so that when Caramon travels back in time and shows Raistlin said future, Raist finally repents.
  • Sun Tzu wrote a good guide on how to be The Chessmaster called The Art Of War. Although the primary focus groups are generals and monarchs, nearly all of it can be generalized to any chessmaster activity.
  • Both The Ellimist and Crayak are Chessmasters by necessity (though The Ellimist has been one since his space bird gamer days), because a direct fight between them could destroy the fabric of reality and themselves along with it
    • The Ellimist is a classic one, though. At one point he reveals the location of the Kandrona (a strategically important target, since it generates the rays Yeerks need to periodically absorb to survive) via a vision of a future where the Yeerks won...
  • The Obsidian Trilogy presents us with Queen Savilla of Shadow Mountain. She saw her father make certain that all the Races of the Light lived in fear of the demonic creatures called the Endarkened, and was forced to retreat alongside him after all who feared the Endarkened forged an alliance that nearly destroyed them. After... inheriting... the leadership of demonkind, Savilla literally spent centuries insuring that most of the surface world more-or-less dismissed Demons as something from the distant past, kept the various races distracted with thier own issues, and most importantly keeping the High Mages of Armethalieh and the Wild Mages scattered elsewhere from making common cause for any reason. All the while using agents, catspaws, and even breeding programs to set up the next war to her advantage.
    • Chired Anigrel only seems an understudy compared to the Demon Queen he worshipped since childhood. Managing to both attain effective control of Armethalieh and come within moments of handing the whole thing over to Savilla.
  • 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.

Live Action TV
  • Most 24 Big Bads. Though most of them are even better at roulette.
  • The Mission Impossible series is a rare but well-executed example of non-villain, non-Anti Hero chessmastery.
  • Linderman of Heroes seems to have his hooks in everything, especially DL and Niki. His apparent omniscience is helped along by being a collector of art... particularly art made by a guy who paints the future.
    • Rebel/Micah is showing signs of this. He certainly prefers to operate by proxy given that he's a 12-year-old kid with no combat powers. He's a Technopath, which enables him to covertly communicate with his "pieces" and listen in on government communications. However, he hasn't done much in the way of manipulation or XanatosGambits - he prefers to give direct instructions, and his plans tend to be short term. Then again, you don't need to be much of a chessmaster to outsmart the federal government.
  • On Smallville, Lex has used the quote at least once to describe the comparison of his scheming to that of his Magnificent Bastard father.
  • Benjamin Linus from Lost has pulled off at least one Xanatos Roulette, as well as quite a few plans that are so roundabout and convoluted one has to wonder if he's actually omniscient. Case in point,  spoiler - click to reveal
    • Ben Linus also fits in the Manipulative Bastard trope, seeing as most of his schemes have to do with toying with people's emotions.
  • CJ Cregg, press secretary on The West Wing, manages to manipulate both the press and the House of Representatives into making the HR be the one handling the investigation of the president, instead of the Special Prosecutor, because she feels they'll bungle it. And she does it entirely by complimenting the Special Prosecutor and talking up his credentials too!
  • J.R. Ewing in Dallas.
  • Seska on Star Trek Voyager. (Especially when she showed up to torment the crew three years after her death.
  • Veronica Mars pulls off several of these to catch criminals. The plan she uses to allow Duncan to escape the USA with his child crosses into roulette territory.
    • There's also the epic scheming of Cassidy Casablancas. Not only did he kill a dozen people, keep any attention off him for months, manipulate and blackmail his way through the stockmarket, he's also the only person I can ever remember lying to Veronica's face and not having her suspect at all. And he's just 16. He's good dammit.
  • Clayton Webb in JAG. A cold blooded CIA agent who is skilled and subtle in manipulating operations all over the world.
  • Michael Scofield from Prison Break is a chessmaster on par with people like Light Yagami. You can be sure that, no matter how short the time is or how hard the creation of a plan is, he will come up with something. And if his plan fails he will have a backup-plan or it was supposed to fail all along. Adding to that, he's sometimes Crazy Prepared.
  • Sir Humphrey Appleby in Yes Minister and Yes Prime Minister pulls off several devious yet intricately devised gambits designed to flummox the far-less intellectually cunning (Prime) Minister Jim Hacker, in order to thwart Hacker's agenda, cement his power and influence over the department and government, and to feather his own nest. However, Hacker - whilst nowhere near Humphrey's level of ability - is not without some low cunning himself, and is occasionally able to pull a fast one on Humphrey, and events occasionally conspire to leave Humphrey spluttering in astonishment as his plan collapses around him.
  • Blakes Seven. This is the job of the 'psychostrategist', a Federation officer whose role is to predict and manipulate people. Unfortunately he's informed too late about a random element and, realising his plan will therefore collapse, smartly decides to vanish before Servalan finds out. Servalan, a bit of a Manipulative Bastard herself, seems amused rather than incensed over his cunning.
  • Number One/Brother Cavil/John in Battlestar Galactica is ultimately revealed to be the mastermind behind "the Plan" that encompassed the near-annihilation of the human race and the subsequent pursuit of the survivors halfway across the galaxy for the next five years. The point of this plan? To prove to Ellen Tigh that humans suck.
  • Adelle DeWitt of Dollhouse, especially if you believe the Wild Mass Guessing that  spoiler - click to reveal
  • John Connor of Terminator: The Sarah Connor Chronicles''. Specifically, John Connor from the future, where one of the resistance fighters even comments on "his chess game with Skynet." Current John Connor seems to be headed that way, too.
  • The Shadows and the Vorlons in Babylon 5 are two entire races of Chessmasters.
  • Warehouse 13 has Artie, who this troper is almost 100% positive is just plain not human. Every episode includes some sort of Xanatos Gambit, not to mention the whole plot seems to be him with a weighted ball in Xanatos Roulette, and he is so good at Speed Chess that he'd be leaving Lelouch Lamperouge reeling and wondering what just happened. Good thing he's using these powers for good instead of evil. Hopefully. While it doesn't have a chess motif yet, I expect an artifact to be a chess board sometime later in the series.

Music
  • The song You're Gonna Go Far Kid by The Offspring talks about a chessmaster. Another clever word/sets off an unsuspecting herd/And as you step back into line/a mob jumps to their feet....
  • This trouper always though that the song No Leaf Clover by Metallica was talking about a Chessmaster, possibly one who failed, or a pawn in a Chessmaster's game because of the lyrics All the pieces fall to his wish/Sucker for that quick reward boy/Sucker for that quick reward they say/Then it comes to be that the soothing light at the end of your tunnel/Was just a freight train coming your way..

Professional Wrestling
  • Puerto Rican Wrestler Ray Gonzalez's gimmick is that he's a chessmaster (and a good one at that).

Tabletop Games
  • Exalted has the most powerful gods spending their time playing "the Games of Divinity".
    • These games explicitly don't have anything to do with manipulating anyone - that's the job of the Sidereal Exalted, who constantly act as Chessmasters to ensure Fate follows its proper course. Memetic Mutation has cast the Games of Divinity as a cosmic Xbox.
  • In Warhammer 40000, the Chaos Space Marines of the Alpha Legion are infamous for their utilization of these sorts of tactics; while most other Chaos Legions simply slaughter all the defenders of a planet they invade, the Alpha Legion uses everything from sabotage to propaganda to well-placed cults of infiltrators to undermine their opponents' ability to fight, with the slaughtering of defenders coming in only at the very end.
    • And let's not forget Tzeentch, the Warhammer god (literally) of Chessmasters. His followers commonly favour such tactics as a matter of course, but considering Tzeentch tends to use them as his own pawns, it all just comes back to him eventually.
      • Best example of Tzeentch's Chessmastering? It is said that only he stops the Immaterium and Materium from merging, an act that could be very bad to all living things, as part of an elaborate plan roughly 46 thousand years in the making.
    • The C'tan god known as the Deceiver has been doing his own Chessmastering for quite some time, and there are fan debates about exactly how long and to what extent Tzeentch and the Deceiver have been Playing Chess against each other.
      • There are even some fans who speculate that Tzeentch and the Deciever are one in the same , for what reason, no one knows.
    • The Eldar Farseers use this as their primary modus operandi, helpful when you can see the manifold outcomes of the future.
  • This article outlines typical manipulators' methods in Forgotten Realms. Some even legal.
  • In Vampire The Masquerade, the elders are like this. Their schemes unfold over centuries.

Theatre
  • The titular Phantom Of The Opera is initially the Chessmaster until the part where Christine rips his mask off and the theatre burns down. He even has a model of Il Muto where the characters have interchangable heads to help him in his plans.

Video Games
  • Final Fantasy Tactics was completely filled with Chessmaster-on-Chessmaster action.  spoiler - click to reveal About the only people not trying to screw everyone else like a two-dicked billygoat was the protagonist and his crew, but his actions definitely were manipulated for other peoples' gain.
  • Rufus Shinra, of Final Fantasy VII: Advent Children, was a very sneaky, wheelchair-bound chessmaster who, with only four hired goons and his wits about him, manages to fool White Haired Pretty Boy Kadaj for the entire movie. While suffering from a fatal disease, no less.
    • Not as though this is his first act of such. He's been doing this for years as revealed in Before Crisis wherein  spoiler - click to reveal
    • Though, it should be noted that this trait runs in the family as we see in Crisis Core with  spoiler - click to reveal
  • Zexion from Kingdom Hearts, complete with Villainous Breakdown when he Didnt See That Coming.
  • Xenogears could feature a football team full of chessmasters. Just to name a few who were playing (and they were each manipulating each other): Miang, Krelian, Grahf
  • Wilhelm in the Xenosaga series manipulates most, if not all, the protagonists and antagonists in the story in some way as well as the overarching flow of events, often by assuming leadership of companies and organizations (where all positions appear to be held by different individuals).
  • In Super Robot Wars (in various timelines), Shu Shirakawa and Ingram Prisken often act as chessmasters, manipulating the protagonists into doing their bidding unwittingly, and with unparalleled amounts of panache (Shu has even garnered an unwanted harem in the past). Interestingly, they take to the field of battle quite often, but this is perhaps solely to show off their (incredibly cool) Humongous Mecha. Due to the crossover nature of the series, Shu and Ingram have butted heads with each other, Gendo Ikari, the Titans, Big Fire, and various other factions and have generally come out on top. They could also be considered a subversion of this trope,  spoiler - click to reveal
  • Super Paper Mario has Dimentio.  spoiler - click to reveal
  • Grand Master of the Order, Jacques de Aldersberg in The Witcher computer game, who  spoiler - click to reveal
  • Freed from the constraints of Stupidity Is The Only Option in Apollo Justice: Ace Attorney, Phoenix Wright becomes one of the most capable Chessmasters not only of that game, but of the entire Ace Attorney series. He manipulates every important event towards his own ends, and any major errors on his part are made only when he's being controlled by the player during the fourth case.
  • Lord Nemesis. Anyone who can convince you that you're a Beta Baddie deserves a nod. Take a gander at his Xanatos Roulette entry if you don't believe me.
  • This is the whole point of the text adventure Varicella, with the player competing for the role of regent with a whole slew of Chessmasters which ends up in a magnificent Thirty Xanatos Pileup
  • Revolver Ocelot of Metal Gear Solid was described in one Fan Fic as "the only person ever to successfully pull off an octuple cross". Said octuple cross must have been a pretty small operation by his standards.  spoiler - click to reveal
  • Hikawa from Shin Megami Tensei: Nocturne manipulates people and events from the shadows, never taking any unnecessary actions and always moving towards his goal.
    • Lucifer arguably counts as well, attempting to maneuver the player into unmaking reality and spearheading Armageddon. Granted, he more or less admits this upfront and gives the player a choice in the matter. However, failing to follow his plan means the player will miss out on most of the game's backstory and some nice rewards...
  • A non-villain example is Sereph Lamington from Disgaea. His Xanatos Gambit was so well executed that he qualifies for this trope. Sending his most loyal angel on a false assasination mission (knowing that she'll take the change in mission he was expecting), turning the ambitions of his 2nd in command to his advantage (humans, angels, and demons had to share in it) which causes said traitor to be exposed to him (and punished). Even his battle with Laharl was part of the plan. There's a reason why he's the Seraph, and this is it. Far more intelligent than he looks.
  • Kil'Jaeden the Deceiver from the Warcraft Universe. His motto is "There are more ways to destroy one's enemy than with an army. Some times those ways are better." He corrupts the race of orcs by posing as the spirits of their ancestors and makes them think the Draenei are evil and should be destroyed, because if he used his personal demon army to raid the planet the Draenei are living on, they would simply run away.
    • One interpretation of the events of Warcraft III is that Kil'Jaeden created the Lich King knowing that it would betray Archimonde (his counterpart and co-leader of the Burning Legion), leading in Archimonde's death and Kil'Jaeden becoming the absolute ruler of the demons.
      • The Old Gods take the cake, though. First they infest the Titans' newly-created world with "the curse of flesh", causing their mechanical creations to become organic. Then they rig it so that the Titans can't actually destroy them without destroying the world alongside them, forcing them to just seal the Old Gods away. Even that doesn't do the job so well for C'thun and Yogg-Saron...which is where the players step in. In fact, the latter could be counted a Chessmaster among Chessmasters - even after being sealed away he manages to corrupt the wardens of his prison into loyal, if batshit insane, servants.  spoiler - click to reveal.
  • The player in this game of Galactic Civilizations 2, who ended the existence of his galaxy's then greatest military power in a single turn. When his race specialized in cultural influence and entertainment programming, and had zero military power whatsoever. Via a combo of diplomatic, financial, and cultural maneuvering that... seriously, just read it. *g* (The relevant parts are at Day 9 and 10.)
    Player: I don't care that my foreign intel reports rate you as the most powerful race in the galaxy. I don't care that I come dead last on that same list. I don't care that I couldn't even fight back if I had any gunships because of a pledge to spread peace throughout the galaxy. In fact, you know what? That's it. Your race ends this week. When I next click that 'Turn' button, you're out of the game.
    • He's come a long way since his last GalCiv II game, then. In that attempt,  spoiler - click to reveal
  • Chrono Cross has a rare example of the Chessmaster actually being a good guy.
  • Final Fantasy X has a heroic Chessmaster tag-team of Jecht and Auron, who pretty much spend the entire game (and the ten years prior to it) preparing Tidus so he'll someday kill Sin, instead of letting it get sealed back into its can.
    • One of Auron's moves in the game was  spoiler - click to reveal. Bonus points for sending Kimahri along as chaperone, the only member of the party who wouldn't have stopped them.
  • Halo's Gravemind displays the traits of a chessmaster throughout parts two and three in the series. Gravemind, as the collection of Flood intelligence, managed to turn an AI that had been specifically designed to destroy the Flood over to his side milennia ago, manages to in five seconds convince the Arbiter to prevent the rings from firing, takes over the flood's ruling ship, and pretty much uses the Chief and Arby to stop Truth from activating the Ark and destroying all life in the galaxy, just so that he could infest all life in the galaxy. And even when the Halo was about to fire and destroy the flood yet again, Gravemind says that all it'll do is delay the inevitable.
  • Tsukihime has, of all people,  spoiler - click to reveal
  • If you are in a Suikoden game and your last name is Silverberg, chances are you're a Chessmaster. If your name is Lucretia Merces, you are a crazy, crazy chessmaster.
  • The World Ends With You, has around three -  spoiler - click to reveal. This is hardly surprising, coming from a game with a Thirty Xanatos Pileup.
  • A somewhat odd version occurs in Sanitarium. It initially appears that the Big Bad has an incredibly elaborate plan to stop the hero. However, it later turns out that there are two versions of the villain: one in the real world and one in a parallel world. Each was attacking the hero independently of the other, meaning that the elaborate plan was actually two simpler plans. Although both versions still fit this trope, the fact that the plan wasn't as elaborate as initially thought makes them somewhat diminished variations.

Web Comics
  • In The Order Of The Stick, Lord Shojo provides an interesting example of the non villainous chessmaster, ruling Azure City and the Sapphire Guard with the aid of a series of deceptions.
  • The title character in Dominic Deegan, Oracle For Hire has become a heroic Chessmaster in later story arcs. He has the key advantage of being able to both see the future and scry into the past. (Some are more pleased with this tendency than others.)
  • In the SNAFU hosted webcomic The Grimm Tales From Down Below, Grimm's journal reveals that Mandy, had planned a series of events to convince Grimm to give Billy his powers for a day. Then when done, she convinces him to give his powers to her to make it fair. Later, while snooping through her room, Grimm finds plans for initiating the 9/11 attacks on the World Trade Centers and Pentagon. Her plans also included the United State's response: Operation Iraqi Freedom BEFORE it happened.
  • Yukizane Masamune from No Need For Bushido, is also one of the few 'good' Chessmasters. He starts out in the series as being questioned on his leadership capacity due to his silliness and focus on playing Go (the Japanese answer to chess) as opposed to grunting manly and flexing. He, however manages to shine several times and manages to decieve a ninja, of all things.
  • Parodied or... something... by Freefall here.
  • The nigh-omnipotent AI Petey from Schlock Mercenary doesn't have a chessboard (although one strip features him playing checkers). One of his most complicated capers involved:
    • convincing all A Is to join him and mutiny against their captains, forming an instant galactic power for the purposes of combating an enormous threat to said galaxy.
    • Refused to pay the main characters for their ship, which blew up while carrying out his orders, then bribed a few councilmen to get them a new one anyway (at the expense of most of their savings). While keeping it all under the table in an attempt to force the company's AI to act as his spy.
    • Manipulated the government into hiring the (now short-on-cash) main characters to destroy a reality-TV network.
    • When the main characters got in trouble carrying out his gig, bailed them out with blackmail (after playing with their heads) and turned it into his own form of leverage on them.
      • The new ship AI 'Tag" finished to discover his true plan but only revealed the Social Ingenering from the governement to let Petey know that he know he is the one the manipulated them into it. (ironicly the only clue that permit to the AI "Tag" to come to this conclusion was the analysis that the UNS governement leadership is too short-sighted to plan that much.
  • In Erfworld, Charlie manages to manipulate circumstances - WARS - so that he will *always* end up on top. And he gets paid to do it.
    "When you're working for Charlescomm, you'll learn. We prefer to play games that don't even contain a losing outcome. You see?"
    "Yeah, yeah... you turned it into a no-lose situation by rejoining him."
    "Oh no! No, I got paid to turn it into a no-lose situation. :)"
  • Biggs from DMFA appears to be leaning in this direction. Even his sister, who is well-aware of his deviousness, falls for his tricks.

Web Original

Western Animation
  • Megatron of Transformers: Beast Wars (and later Beast Machines), nearly ended the Beast Wars several times without leaving his hot tub. His ultimate weapon in the Grand Finale was, in fact, unwittingly furnished by an especially treacherous minion.
    • This role equally describes Tarantulas - who was a third party in and of himself, only pretending to work with the Predacons. He frequently even pulled one over on Megatron. At one point Megatron was sitting in his throne all impressed with how brilliant he was because he managed to a way to spy on Blackarachnia... and then we cut to Tarantulas spying on 'him.'
    • Tankor, of all characters, became one in Beast Machines after his spark was reawoken.
  • Azula of Avatar The Last Airbender — The Vamp, Magnificent Bastard, and Psycho For Hire all rolled into one.
    • Her father, Evil Overlord Ozai, prefers the 'set the chessboard on fire and stand back laughing maniacally' approach, rather than messing about with all those fiddly little pieces. Until her Villainous Breakdown, Azula was a genuine (and, fortunately for Ozai, genuinely loyal) Chessmaster, so she got to do all the thinking.
    • Long Feng is very good at this too, keeping an entire city under his control for years with no one but his immediate henchmen the wiser. Really the only things keeping him from being a full fledged Magnificent Bastard are underestimating his opponents and not dealing well with sudden reversals- both of which Azula exploits...
  • Nerissa from WITCH's second season is excellent at this. Her opposition is so thoroughly manipulated and played that despite the heroines' best efforts, they can only score the smallest of victories in comparison to her Magnificent Bastardry until the absolute end of the season... and were only then able to overcome it because Phobos pulled a Xanatos Gambit of his own to absorb Nerissa into her own Seal.
  • Anti-Cosmo and HP on The Fairly Oddparents could both qualify, usually tricking Timmy or some other third party into helping with their plans.

Real Life
  • The Athenian politician Themistocles.
  • Had he gotten away with it, Richard Nixon would have been quite the chessmaster.
    • ...so you're saying he wasn't a chessmaster?
  • Tom Scholz.
  • William Pitt the Elder can be credited for founding The British Empire with conquests in the Seven Years War. He was Britain's and maybe the world's greatest Chessmaster of the eighteenth century and at least verges on being a Magnificent Bastard.
  • Mayor Cory Booker, depending on your Alternate Character Interpretation, and invoked indirectly by Ice-T ("Who is playing whom?"). After Conan O'Brian made a joke about Newerk, New Jersey, Mayor Booker banned Conan from Newark Airport as a joke (which, required the TSA to clarify the counter-joke that no, a mayor can not actually do that due to some people believing it to be true and being outraged). This resulted in a back and forth exchange between the two and ended up involving various other mayors of New Jersey (who sided with Conan... probably a trope) as well as Secretary of State, Hilary Clinton (acting as a High Queen and telling the two to works things out as Conan had, she claimed, been acting differently due to a Real Life head injury). It resulted in the two airing out their 'grievances' on air... which involved Mayor Booker and six of his family as well as a few other New Jersey residents getting flown out to California for Conan's show, Conan and Universal giving a 100K donation (half Conan's personal money and half he got Universal to match... cause he's Awesome that way) to his charity, and a Newark joke box in which 500 dollars will be put in whenever Conan makes a Newark joke (which may or may not remain in continuity). To quote Conan, "Boy, that was a really expensive joke!"

Other
  • Makuta (Teridax, specifically) in Bionicle: As he tells one of the heroes in one of the novels: "Even my... setbacks have been planned for." Turns out he's right...
Chekhovs Pun
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