The Chessmaster



"Danny: I don't understand...

Vlad: What? That I used two fourteen-year-old pawns to turn a knight and topple a king? It's chess, Daniel. Of course you don't understand. But then, you never really did."

- Danny Phantom

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 Unwitting Pawns (Who else?) 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.

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. Heroic Chessmasters are very often introduced as a Mysterious Employer. The Svengali, in acting for the (supposed) good of his protégés, will often be this (and if he isn't, he'll pretend).

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. 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 also tend to be overconfident and usually panic when their "perfect" plans fail. The exception to this is when Magnificent Bastard and Chessmaster overlap, since a Magnificent Bastard is quite good at rebounding from defeat. Fond of a Battle of Wits.

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. This is most likely a result of Smart People Play Chess. Compare the Manipulative Bastard who tends to be more personal and controlling in her/his manipulations.

If the chessmaster is the villain, when the hero defeats them it's usually via the one move they didn't plan for.

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

Anime & Manga
"Sebastian: If it's your wish I will follow you everywhere. Even if your throne crumbles, and your shiny crown turns to rust. Even if the bodies pile up endlessly. Above the bottomless pile of corpses beside you as you lie softly down, I will follow you... Until I hear the words "Check mate.""
 * 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.
 * Don't forget Near and Mello.
 * L, Near and Mello are clearer examples of Chessmasters, as all three of them carefully and deliberately set the board in the first few episodes from their introduction. Light had to scramble for pieces to put immediately into play; what saved him was that he was a quick study of his opponent and had powerful and unpredictable gambits.
 * Similarly, in one of the Film adaptations, L and Light actually play a game of chess with each other while having a discussion, with Light winning.
 * 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 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).
 * 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.
 * 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 Wunfat from G Gundam. Humongous chess board included.
 * Umineko no Naku Koro Ni 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.
 * Black Butler's Ciel Phantomhive absolutely 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 quite good at making people think that he's just the 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. (Yes, he is basically a Magnificent Bastard in training, why do you ask?) We see him playing chess quite often during the manga - needless to say, he's good at it!
 * Along with the Chess Motifs scattered throughout the manga and anime (especially the second animation of the opening), there's quite a few chess metaphors and references thrown around.


 * Father in Fullmetal Alchemist has a chessboard, and.
 * 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.
 * 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..
 * 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 . No, seriously.
 * Taikobo from Hoshin Engi 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.

Comic Books
"Calvin: "Ah, you've fallen right into my trap! Perhaps you'd like to take that move over?"
 * 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.
 * 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:

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"?
 * DC Comics' Darkseid is also fond of moving figure of his minions and enemies around on a chessboard when hatching his latest evil scheme.
 * Since everything Countdown to Final Crisis touches turns to fail, when he does it in that series he just winds up looking like Dark Helmet.
 * 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 Eight 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 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,  becomes this, hatching an elaborate plot to try and kill Siphon, using   as his less-than-willing pawns.

Fanfiction

 * In Kyon Big Damn Hero, Kyon is most definitely a Chessmaster, often using chess metaphors as he makes strategies.
 * 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  Trixie's life.

Film
"Red: I like to think the last thing going through head,, was to wonder how the hell Andy Dufresne ever got the best of him."
 * 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.
 * 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.
 * Clint Eastwood's Man With No Name in A Fistfulof Dollars rolls into town, sizes up the situation, and immediately starts playing the two local powerhouses against each other.
 * Inspired in part by Yojimbo and The Glass Key.
 * Don't you mean Red Harvest?
 * Retold in The Coen Brothers' Millers Crossing.
 * 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  The plan shares more than a few aspects of the chess lessons his father gives him, and results in   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.
 * In Star Wars, Emperor Palpatine is SUCH a chessmaster - playing the Old Republic and the Jedi like a cheap fiddle in the culmination of a 2000 year legacy of Chessmasters.
 * You have to give Luke Skywalker props for this as well. At the start of Return of the Jedi, his positioning of Artoo, Threepio, Leia, Han, Chewie and Lando in the rescue of Han is actually quite brilliant, as each of his friends ended up with a very particular role to play.
 * Artoo smuggled in his lightsaber; Threepio's obliviousness to the plan ensured Jabba didn't get wise to the other players, either.
 * Leia brought in Chewie, freed Han from carbonite, and later killed Jabba.
 * Han's subsequent failure to escape ensured Jabba thought he'd won, as well as his part in the sailbarge fight later.
 * Chewbacca...well, when ISN'T a 7-ft tall Wookiee useful in a fight? There's also his role in Leia's cover.
 * And Lando, who infiltrated Jabba's palace before anyone, helped clear the prisoner skiff for their escape by sneak attacking the guards while they distracted by Luke's Force-powered acrobatics.
 * That's quite a few pieces that needed to be in JUST the right places to make the whole thing work.
 * 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 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.


 * 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.
 * is revealed to have been this all along at the end of the 2006 remake of The Pink Panther, having.
 * Cardinal Richelieu's Batman Gambit (bordering on Xanatos Gambit) 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 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.

Literature
"Egwene: They couldn't have done it better if I had told them what to do."
 * 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
 * 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.
 * While Dumbledore and Voldemort are worthy examples of Chessmasters in a metaphorical sense in the Harry Potter series, don't let's forget Ron Weasley as a literal "chessmaster" and his abilities on the wizard's board that lead Harry onto Voldemort's trail in Harry Potter and The Philosopher's Stone.
 * Not least, they both demonstrate an exceptional chess move:
 * 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 from Dashiell Hammett's The Maltese Falcon are both opposing chessmasters who manipulate Sam Spade and an entire cast of minor characters in order to obtain the Maltese Falcon for themselves.
 * 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...

""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.""
 * 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.
 * 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, 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 Xanatos 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.
 * Iain Banks' The Culture: 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,, she sees her relationship with him in terms of a chess game
 * 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 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 the 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 and those aspiring to or dreaming they are one. Off the top of my head:
 * Tywin Lannister - Had control of Westeros since age of 21, manipulated Robert's Rebellion to come out unbloodied and in a dominant position on winning side, orchestrated the destruction of Houses Stark, Tully, and Baratheon, and even in passing he has one son in a very powerful position in Westeros and the other going to probably be in the top 5 lieutenants/advisors if not king of the exiled but rising Targaryen dynasty. Of course he is a straight up Magnificent Bastard after all
 * He didn't plan half of that, and most of it occurred, outside of his control, after his.
 * Varys - Essentially controlled 90% of information to reach or not reach the King and his council, having utterly complete knowledge of everyone's actions, playing at least 3 Kings and 2 dynasties for decades and surviving the transition between them, playing off at least 4 Great Houses against each other for own goals, and in the midst of orchestrating another coup to restore previous dynasty. It is unknown exactly how much of a role Varys played in the events of the novels, but the mere fact he knows about the details of events only a handful of characters even witnessed across the world...says he probably played a big one.
 * Euron Crow's Eye - Returns home at least 2-3 in succession and generally disliked just in time (the day before...with no way to find out) for a 'Kingsmoot', where he manipulates his rivals and their men into making him King, by having spent his time in exile seemingly preparing solely for this day he offered loot and riches far beyond his opponents, countering their promise of conquering some easy but poor lands with the promise of conquering ALL of Westeros. With dragons.
 * Potential: Doran Martell (planning his revenge over about 15 years), Tyrion Lannister
 * Failed: Cersei Lannister
 * 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.
 * YMMV on whether Littlefinger is a Chessmaster or simply a Xanatos Speed Chess master. He doesn't really have an endgame, his only plan is to create chaos which he can then exploit for personal gain. Of course, he's very good at this -
 * 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.
 * 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, and even describes it in chess terms, referring to Pippin as a pawn who was as likely to see as much of the action as the other pieces on the board. If we look at it that way, the whole War of the Ring is a conflict between two spectacularly skillful chessmasters, Gandalf and Sauron. Sauron may be slightly better on the whole, but Gandalf is good enough to take skillful advantage of his one weakness.
 * Gandalf's ulterior motive for organizing the Thirteen Dwarves and Bilbo's expedition in The Hobbit. He needed to do several things: investigate reports of Sauron's rise to power over Mirkwood, defeat a dragon that Sauron could bend to his will and use in the war, re-establish the strong Human and Dwarfish kingdoms of the area, and get everybody allied with each other, so that they could repel an invasion from the east that would allow Sauron to flank and crush Gondor. In the end, . This gambit would work beautifully during the War of the Ring, as the force of Easterlings and Orcs that actually made it through the north alive was much reduced.
 * In Len Deighton's "SS-GB", an Alternate History novel set in a Nazi-occupied Britian, 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 ; then Mayhew betrays the underground and gets the Germans to ; then he gets the underground to and create the myth of  (when in fact ; then he gets the; then he gets the various rivaling Nazi factions in charge of occupied Britian   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 Sixteen Thirty Two 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.
 * 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.


 * Darren Shan's 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...
 * 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 Chessmaster, though the point of the story seems to be that it's not so much because he knows chess as because he's mastered the one particular strategy that none of the other players are prepared for.
 * While there isn't a chess motif for him, referring to 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. Toohey's masterpiece is described in great detail in the middle part of the book. He wants to destroy the career of the independent minded architect Howard Roark, the book's main protagonist. And a smaller aim - he wants the aging millionaire Hofton Stoddard, who regrds Toohey as a guru, to endow a Home for Retarded Children, while the religiouly-minded Stoddard wants to build a Temple. So, Toohey embarks on a years-long plan, every step planned carefully in advance and carried out precisley as planned. Step One - Toohey tells Stoddard: "Go to Roark, he will build you a wonderful Temple. First he will try to wriggle out of it, he will say he does not believe in God. Tell him 'You are very religious, I can see it in your buildings'". It works perfectly: Roark is shocked, thinks "This old man told something about myself which I never realised". He takes the job. Toohey knew he would. Step Two - Roark builds a Temple with a Classical Greek touch, a statue of a naked woman in its center. Toohey, who studied Roark's earlier works, knew in advnce he would come up with something like that. Step Three - Toohey tells Stoddard "A disaster happened, the Temple is a disgrace and a sacrilage. You are a sinner, unworthy of giving God a Temple. You should start with something more humble, like a Home for Retarded Children". Stoddard is shocked into accepting. Toohey knew he would. Step Four - Toohey writes an article denouncing Roark's Temple as a sacrilegious attack on Established Religion. All the Churches take up the theme and embrak on a huge campaign against Roark, priests and pastors making angry sermons, plus an enormous outburst against Roark in the mass media. Toohey knew this would happen. Step Five - Toohey gets Stoddard to sue Roark for damages. Roark refuses to defend himself, makes a defiant show in court, loses the case and is saddled with paying for transforming his Temple into a Home for Retarded Children. Toohey knew that is how he would act. Step Six - Roark's career takes a plunge, people who want a house look for a more "respectable" architect. Toohey said, when he just started with the whole scheme years before, that this would be the final result. Having accomplished his plan flawlessly, Toohey contrives to be present when Roark comes to see what was done to his Temple - a most painful moment for the architect. Toohey then asks "Tell me, Mr. Roark, what do you think of me?" to which Roark replies "I never think of you" and goes away, thereby completely ruining Toohey's satisafation with the perfectly-exectuted plan.

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 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!"
 * 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, not to mention 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 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 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)
 * 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.
 * 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  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, orchestrating a series of murders and news leaks in order to
 * 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 2009, who is mentioned as having become a grandmaster at the age of fifteen. Although.
 * 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.

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 and 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.

Theatre

 * A prototype for the modern Chessmaster villain is Shakespeare's Iago, from Othello. He uses his influence and his reputation as "honest" to get his pieces into place, and while all of the characters seem to think they act on their own accord, they are actually following Iago's plans. He also often urges others to patience and seems very patient himself. The Handkerchief is the ultimate example of a harmless little thing that closes the trap around his victims. Roderigo and Emilia are the ones who do all of the work for him.
 * In the Oliver Parker film adaptation, Iago (played by Kenneth Branagh) illustrates his plan with an actual chessboard.
 * Interestingly enough, Iago is actually a failed Chessmaster - he allows his own personal hatred (and thus contempt) for Othello and women to screw up his plans -  An example of a chessmaster who really does win is Caesar from Antony and Cleopatra.
 * Shakespeare re-used the theme with Prospero in The Tempest (because Shakespeare re-used, well, everything).
 * Molokov and  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
"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."
 * 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, . 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,
 * Note though, that unlike some of the other examples in this game, 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. This Troper had to paraphrase quite a bit, as he doesn't have the book on-hand, but the way Mengsk puts it is much more eloquent.


 * 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 . 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
 * 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...
 * 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 Adventure Quest subverts this trope; since "there is nothing to be gained in epic struggles", referring to his failed attempts of past, he speaks of playing metaphorical chess randomly, and seeing what happens.
 * Adventure Quest also has The Chessmaster, from The Chessmaster Saga.
 * 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.
 * 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/SecretPolice, 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 Chessmaster or Awesome by Inactivity and dumb luck.

Webcomics

 * Sluggy Freelance toys with this trope here.
 * Eight Bit Theater parodies the trope here.
 * In The Order of the Stick, the three leaders of the Inter-Fiend Cooperation Committee in this strip, which is titled, "Moving the Pieces".
 * 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
 * The chess theme in Homestuck also persists in terms of the game they play-- a checkered battlefield where white fights black,  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.
 * Andrew Hussie himself could count. It's very apparent that everything was Just as Planne, but I think his supposed attitude toward it (huge troll) makes it different from other creators who plan things out. Especially since he interacts with the story.
 * Andrew Hussie himself could count. It's very apparent that everything was Just as Planne, but I think his supposed attitude toward it (huge troll) makes it different from other creators who plan things out. Especially since he interacts with the story.

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.
 * 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.
 * 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.
 * 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.

Other

 * 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 pretty much 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 woman
 * 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.

Anime & Manga

 * Amber/February from Darker Than Black is an example of this trope; however, instead of simply using world class intellect to manipulate outcomes in her desired direction, she uses.
 * She even pulls off a Xanatos Roulette, managing to  (just).
 * Kazundo Gouda from Ghost in The Shell Stand Alone Complex, who manipulates all of Japan in service of his own convoluted plans.
 * Yukihito Tsuge, the Big Bad of the second Patlabor film nearly drives Tokyo into civil war while operating completely behind the scenes.
 * Too many to count in Legend of Galactic Heroes. Often overlaps with Magnificent Bastard.
 * Peacemaker Kurogane: In the manga, Suzu becomes one after he goes insane.
 * Johan Liebert, the titular Monster.
 * Michio Yuki, the main villain of MW plans to use his killings in order to get to the titular chemical warfare and use it to end the world.
 * Sousuke Aizen of Bleach. Also of the Manipulative Bastard variety and a proven master of the Xanatos Roulette.
 * For that matter  fits the role well too, though on the non-villainous side. Aside from being opposed to, 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  doesn't shock him for long, and he quickly  The only plan that stops him is a group of samurai who plainly state they have no plan.
 * Sailor Moon R 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 MacGuffin 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  Xanatos Roulette and arranging to dispose of the late Aeolia's loyal followers so he can take command of the newly-forming Earth Sphere Federation.
 * 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?
 * 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, enigmatic Celestial Being backer , or ? 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
 * The Anti-Spiral collective 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 Arabasta 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 Arabasta 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. And that's just the beginning.
 * 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
 * There are a couple of people who know Amshel's game.
 * Other than Father, Fullmetal Alchemist has a large number of heroic Chessmasters, including Roy Mustang, Olivia Mira Armstrong, General Grumman, and of all people,, who is revealed to have been planning a counter to Father's moves for years.
 * The 2003 anime version's villain,, is also a pretty classic example, having manipulated Amestris, its military and above all its alchemists, behind the scenes for centuries.
 * 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: In the manga, he manipulates not only Chrono and his True Companions, but the entire demon society to
 * 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 Spanner in The Works. A Fanon theory is that Tylor has somehow become enlightened as a boddhistava, and that the beginning and end of the opening trailer showcases both his enlightenment and his plan for the Soyokaze; to lead the Ragtag Bunch of Misfits into enlightenment.
 * Rosalie of the Samura Hiroaki oneshot Emerald plays this astoundingly well. In only sixty odd pages, she saves a young girl from a life of prostitution, orchestrates the death of a legendary criminal, brings an invincible gunfighter out of retirement and brings down the local prostitution ring without once firing a gun. Paying for a tombstone for the aforementioned criminal just might bring her into Magnificent Bastard territory.
 * Nagi Sanzenin's grandfather, Mikado Sanzenin, has proved himself one of these in chapter 249 of Hayate the Combat Butler. In past chapters he essentially plays with Nagi, making her a target for people after the inheritance, which is reason enough. In the latest, he forces Hayate, her butler, into deciding her lifestyle, forcing him to choose between protecting a stone which has become the symbol of the Sanzenin inheritance, or breaking it to save his former lover's life. And to make it even worse, he admits to manipulating the boy's life ever since he can remember by posing as innocuous figures. The only thing that keeps him from being a Complete Monster is the fact that he genuinely loved his daughter, favors his granddaughter's maid, and taught said granddaughter how to invest.. so she's not rendered completely poverty-stricken  the inheritance gets taken away from her.
 * He also engineered a plot to steal 'the power of the gods' before the story started. Possibly his first, since it failed and got the three who worked together on it cursed.
 * Dietrich, one of the younger warriors from Claymore qualifies. Figuring out Helen and Deneve's identities within seconds was a foretaste of her analytical abilities. Figuring out the only way to defeat the Luciela-Rafaela spawn for good by siccing on them was a grandmaster move.
 * Liar Game is all about games of Xanatos Speed Chess between opposing Chessmasters. Akiyama stands out as the first and the most prominent heroic example, . Opposing him is Yokoya, and
 * Toua Tokuchi from One Outs (an earlier work by the mangaka of Liar Game) is a baseball player version of this; an adept user of gambits. He uses so many in the index, andn so well, that he crosses over into Magnificent Bastard territory. (And no, he's not the catcher!)
 * In Black Lagoon Rock is getting to this point. Depending on your interpretation of the Baille de la meurte arc, he is either a budding chessmaster who set up nearly the entire ending with a few choice words and a really accurate prediction of how people would act, or he was a Manipulative Bastard playing on a Batman Gambit. However, considering that he seems to have deduced that  and used that to his advantage to shape the end-game...
 * Hellmaster Fibrizo from Slayers, who manipulates nearly all the events in Next. He even gets a Villainous Breakdown.
 * Naraku of Inuyasha manipulates, schemes, lies, cheats and cons pretty much every member of the cast, pitting hero against hero and tricking them into doing his dirty work. Pretty much the only time the heroes get to confront him face-to-face is when he wants them to, or when he think he's gotten strong enough to finally finish them off. The heroes spend a lot of time seeking out Cosmic Keystones that could weaken him, but by the time they get there he either knows and has destroyed or is about to destroy it, or doesn't care because he's too strong for it to work against him anymore. The pinnacle of Naraku's plans comes when he plans for the heroes to kill him as part of a scheme to exist forever. His schemes finally fall apart here:, Naraku's plan was broken and he stayed dead at last.
 * Treize Khushreneda of Gundam Wing, though that's just par for the course when you're that Magnificent Bastard.
 * Rau Le Creuset of Gundam Seed nearly destroyed the world by manipulating nations into slaughtering one another. He gains a chess-motif in the sequel.
 * The only 2 chapters we see Konata from Oto x Maho involve her advancing her exceedingly convoluted 7+ year long Xanatos Roulette to force her son Kanata to become a Magical Girl Girl, which of course, goes off without a hitch. The fact that she can pull off such a plan can only be explained by her being a Chessmaster.
 * Aleister Crowley of To Aru Majutsu no Index is The Man Behind the Man to all of Academy City. He executes several plans at once, some of which are designed to fail in order to further another, and even then it's not sure whether the failed plan is an actual failure. A character comments that, for Aleister, even the entire planet could just be a resource waiting to be used and discarded.
 * Anyone from Naruto, especially Shikamaru when
 * Gendo Ikari from Neon Genesis Evangelion even though he was out gambitted in the end
 * from Digimon Adventure 02. All the main things that happened in the series were plotted by him in his own designs, both directly and indirectly, and his plans worked so well that the writers were forced to use some half-assed Deus Ex Machina just to make sure he wouldn't win.

Comic Books
""I told you once, Superman, if you would not be my knight, you would be my pawn.""
 * Metron of New Gods, who is an Ensemble Darkhorse thanks to his unemotional, bipartisan manipulation of events.
 * 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
 * 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
 * The Black Panther of the Marvel Universe is a rare example of this trope who's a traditional superhero, albeit one that is occasionally under fire from his more-idealistic peers, for obvious reasons.
 * An example more along the vein of the standard Anti Hero would be Adam Warlock, who is often the foil to Thanos.
 * Batman is the Alternate Company Equivalent for The DCU.
 * 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 he loses the support of the US government.
 * The goddess Athena in the Marvel Universe series The Incredible Hercules is another heroic version of this trope; one of the series' major ongoing threads is a(and, as yet, largely unknown) Batman 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 Medousa'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 written by Alan Moore or Ed Brubaker.
 * Alex Wilder of Runaways.
 * Bruce Banner is this, at least under Greg Pak's pen. As we learn in Fall of the Hulks, Banner's just as dangerous as his savage green alter-ego - if not more so.
 * General Wade Eiling definitely fulfills this trope, given the way he manipulates Captain Atom.
 * Batman villain, The Riddler is an accomplished chessmaster, notably for smooth sway over the media, especially post-reformation (a quality of Villain With Good Publicity), and for his previous yet strategically subtle maneuverings of other well-known manipulators and dangerous personas.
 * Two-Face can also be a Chessmaster, usually having two plans in motion at once, one often entirely different (but also in some way linked) to the other.
 * You can't say Batman, chessmaster, and villain in the same sentence without talking about Bane. He managed to beat fellow Chessmaster, Ra's al Ghul, at a game of Chess even though he's never seen a chessboard before.
 * Hell, Batman himself is this trope as well. He is the namesake of the Batman Gambit after all and he is pretty skilled in chess.
 * Superman enemy Brainiac has often been this, in contrast to Magnificent Bastard Lex Luthor. Brainiac has frequently set up incredibly complex plans, using every character as a chesspiece in his efforts to steal cities/become a god/absorb the sum total of all knowledge in the universe (his motive keeps on changing), but has trouble changing them once something goes wrong.
 * While mentioned and kind of mocked above, Darkseid is definitely a very competent and dangerous Chessmaster when he's written correctly. This is perfectly invoked in Superman the Animated Series.
 * While mentioned and kind of mocked above, Darkseid is definitely a very competent and dangerous Chessmaster when he's written correctly. This is perfectly invoked in Superman the Animated Series.


 * The Phantom Blot is (often) at least as close to a Chessmaster as the writers of Disney Mouse and Duck Comics can manage. If there's an unseen mastermind affecting the events and leaving Mickey Mouse baffled for most of the story, it's probably the Blot.

Fanfiction

 * In the Mass Effect fanfic The Council Era, the advisor to the Krogan Overlord, Halak Marr, definitely qualifies as a Chessmaster. In order to bolster his army in preparation for the war with the Citadel, As mentioned on the Unwitting Pawn page, he usurped his superior in order to enact his dreams of the krogan as a Master Race. He successfully forced Tyrin Lieph to allow his people to take a majority in the Citadel military and give the krogan a Council seat through an excellently-executed plan. He also antagonized the already fragile relationship between the manaba people and the Citadel by faking an attempt on his life by manaban extremists.
 * in With Strings Attached.
 * Soul Chess used to focus on Lelouch and Aizen trying to fight for control over the Soul Society.
 * Calvin slowly develops into this over the course of Calvin and Hobbes The Series.

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.
 * Except that he never wanted Michael to become a part of the family business.
 * The Oracle from The Matrix is a  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.
 * Also notable is The Architect, who managed to
 * Scar from The Lion King
 * 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. While playing both sides of the board, so as to have a backup plan if something went wrong (presumably, just sabotage the clones from the Republic side and conquer the galaxy with droids. Not that he ever needed to.)
 * Also Grand Admiral Thrawn from the Expanded Universe. One character (who knew them both rather well) notes that if Palpatine was always one step ahead of all the would-be players, Thrawn was two steps ahead.
 * 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, . At one point, she even calls one of the other characters a "pawn".
 * The true Palpatine of that era was the Sith Emperor, who was essentially the Man Behind the Man for all of the events of the Knights of the Old Republic series. He played Revan and Malak as pawns to find the Star Forge for him (which only failed due to Revan's memory loss and subsequent redemption), orchestrated the Mandalorian Wars, made puppet governments on a number of Outer Rim Republic worlds, infiltrated the Republic and the Jedi Order, and came closer to conquering the Republic than anyone would until Palpatine himself, almost 3,500 years later.
 * 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.
 * For a character who claims to hate the convoluted plans, The Dark Knight Saga's Joker is skilled at making them. 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) Evil Plans.
 * from Cars 2. In order to turn all the cars in the world away from alternative energy,  actually invents an explosive chemical called Allinol which he pretends is actually a safe alternative fuel, and he promotes Allinol with the World Grand Prix, a series of races where the world's fastest racecars must compete in three races taking place in different parts of the world.   then order his Dragon, Professor Z and his army of Lemons to use a powerful radiation cannon to blast away said racecars once the race is in session, then makes everyone think that Z is the one behind the evil plot and not him. After the second race, which takes place in Italy,   tells everyone that Allinol is actually dangerous and forces the racecars to use ordinary fuel, because since   secretly owns the largest oil supply in the entire world, he and the Lemons will become unstoppable once alternative energy has been shunned from society, but tricks Lightning Mc Queen into still using Allinol so that the Lemons can blow him up. Unfortunately for , Sarge secretly removed the Allinol from Mc Queen's body and instead replaces it with Fillmore's, and as a result he has no other choice but to install a detonator onto Mater's body as a last-minute attempt to kill that racecar.
 * Unfortunately for him makes a mistake by leaking oil which allows Mater to move up the board and eventually force him into checkmate
 * Unfortunately for him makes a mistake by leaking oil which allows Mater to move up the board and eventually force him into checkmate

Literature
""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.""
 * 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, since chess is after all not Chinese; his feather fan is far more iconic of him than any board game.)
 * Cao Cao counts as well (especially in real life), but he's given the Idiot Ball when confronting Zhuge Liang
 * 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 title character of Alexandre Dumas' The Count of Monte Cristo.
 * in The Brothers Karamazov. He believed he could engineer Fyodor Karamazov's murder via a Xanatos Roulette which involved . It didn't work out quite the way he expected.
 * Prince Vassily Kuragin in War and Peace. It Runs in The Family too, as Anatole and Elena (not Ippolit) exhibit traits of the Chessmaster, just not to the degree their father does.

"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.""
 * 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.
 * The Continental Op of Dashiell Hammett's Red Harvest. 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...
 * Jeeves is essentially a Chessmaster who uses his powers for good. His Batman 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.
 * The Shadow spends most of his stories manipulating both the cops and the criminals until they are brought to a final confrontation where he will finally get involved personally.
 * Essentially, the murderer in any Agatha Christie novel. One of her most manipulative murderers would undoubtedly have to be  from And Then There Were None, who plays off the psychology of each victim
 * 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.
 * 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.
 * 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 money grubbing Evil Plan but a different motive -- the killer murdered the victim out of revenge, knowing that the crime would be obscured by everyone else scrabbling for his money.
 * The Judge and His Executioner by Friedrich DÃ¼rrenmatt. Commissar BÃ¤rlach
 * 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 collapse. 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 All this whilst being bound by the Three Laws Of Robotics, which he and a fellow robot manage to subvert by realizing that  This is all well and good until the obvious problem arises:.
 * 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 Big Bad of the Chronicles of Prydain, 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 devastatingly closer to total victory than most evil overlords. If only it weren't for that meddling Assistant Pig Keeper...
 * 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,
 * 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 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.
 * John Alpha, the Big Bad of Seventh 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.
 * 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.
 * 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,  saved Harry's bacon several times and collected a large payment for it, and, in White Knight, talked his way into
 * Also Nicodemus, Daddy Raith and Lara, any of the Sidhe by default, the 'Black Council' (assuming it exists), possibly Cowl, and many more . . . really, Jim Butcher seems to love these.
 * Dumbledore in JK Rowling's Harry Potter books is another good Chessmaster, especially in the later books where everything he does (even ) seems to be somehow related to some grand plan years in the making..
 * 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, though he could never prove Riddle did any of the misdeeds he did whilst in school because Riddle was clever and covered it up.
 * Riddle was as smart as Dumbledore (who described him as "probably the most brilliant student Hogwarts has ever seen.") He just let his arrogance and impatience get in the way of his genius. He didn't seem to fully grasp that if he was just as smart as Dumbledore, the reverse by definition was also true, or that Dumbledore's apparently reactionary policy might be masking a plan longer than Riddle's year-by-year plots. However, Riddle DID take over the ministry in a silent coup that slowly took place during both the 6th and 7th books. We do not know of Riddle's actions during the first war, however, we DO know that when the time was right, he would give the order for Lucius Malfoy to slip the Horcrux Diary into Hogwarts, and basically bring Hogwarts down from the inside. This is Chessmaster worthy thinking on Riddle's part, as he was patiently waiting for the right time to strike, and the plan would have succeeded because there would be no parseltongue-speaking Harry to hear the snake in the walls. This is of course disregarding the prophecy.
 * 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 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.
 * And several others. In fact, most of the books end up as Gambit Pileup, with Artemis coming out on top.
 * 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 manipulate others as well, albeit to a slightly lesser extent. Also: Hyrum Graff.
 * And it's not just Younger Wiggins... Mom and Dad have been working the Long Game and subtlety guiding their kids.
 * 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.
 * The Puppeteers from Larry Niven's Ring World.
 * 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."
 * In fairness, that's from the TV adaptation, and it isn't Nosey's idea, but rather the East India Company mandarin's (Wellington is quite uncomfortable the whole idea). A better example from the Sharpe books would be Magnificent Bastard Lord Pumphrey in Sharpe's Prey, Sharpe's Fury and Sharpe's Havoc, who is the only Chessmaster whose schemes can survive Richard Sharpe:
 * Sharpe's Prey:
 * Sharpe's Havoc:
 * Sharpe's Fury:'   
 * Pierre Ducos is a sublime Chessmaster. His problem is that Sharpe has a cockroach-like refusal to die at the right time, which means he inevitably survives to muck everything up.
 * 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.
 * 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.
 * It's not just him. The Lord Ruler, Straff, Preservation, Ruin, and others all have more than a little Chessmaster in them (of varying degrees of skill), and indeed the whole trilogy can best be described as a bunch of peoples' (and gods') plans running roughshod over each other, with the ending arguably amounting to a Gambit Pileup.
 * 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.


 * Waleran Bigod from The Pillars of the Earth.
 * 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.
 * Several characters in Megan Whalen Turner's Queen's Thief series have Chessmaster attributes, if they aren't full Chessmasters - most notably,  in The Queen of Attolia.  in the same book tries to be one.  is the best at it, successfully pulling off a Batman Gambit in every book. Interestingly enough, most do it for the purposes of good.
 * 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 Heel Face Turns 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 . In the latter, he actually lets in an alternate future, so that when Caramon travels back in time and shows Raistlin said future, Raist finally repents.
 * 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 their 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
 * Inquisitor Ramius Stele from the Warhammer 40000 Blood Angels novels rather masterfully steers the titular Space Marine Chapter towards, though as we are reminded several times, he's still a pawn to a greater power.
 * Gaius Sextus in the Codex Alera is one of these, though the limitations of trying to do this without inexplicable perfect knowledge of all events is clear. A lot of people became extremely angry at these tendencies, and many people considered him less "masterful" than "feeble" and blamed him for the situation of Alera.
 * Lord Kalarus tries to be one of these, but while he has a few tricks, he's not nearly in control as he thinks he is. A good example of this is
 * Admiral Sun Ji Guoming from the Dale Brown novel Fatal Terrain carries out an unconventional warfare plan that succeeds in getting the rest of the world to see China as a Villain With Good Publicity even as it nukes Taiwan. This plan also makes Taiwan and the US look like aggressors, at least twice fooling them into misusing their military might. He comes quite close to his goal of retaking Taiwan.
 * from Act of War plays pretty much everyone in his quest to kill Harold Kingman.
 * Lisbeth Salander of Stieg Larsson's Millennium Trilogy, if she doesn't start as a chessmaster, certainly becomes one by the end of the third book. As an example,.
 * "Mister X" in the third Empire From the Ashes book, whose elaborate plans stretch back ten years or more and involve minions buried everywhere in the government, military, and largest terrorist organization (until they serve their function, at which point they inevitably die).
 * Merlin from The Warlord Chronicles makes sure that plenty of powerful people on all sides he has influence on owe him favours, and that everybody fears his questionable magical powers, simply to ensure that he can always recruit people for his personal quest for the Treasures of Britain. If his goals were less abstract and religious, he could have probably controlled the entire island from behind the various thrones.
 * From Peter F. Hamilton's Commonwealth novels, we have . The action starts with this Chessmaster funding an astronomical observation that indirectly kicks off a genocidal war, has minions working at the highest levels of the military (helping humanity just enough so that the two sides can destroy each other), has another minion hosting one of the highest rated news shows, with more minions just about everywhere you look..
 * Viviane in The Mists of Avalon. Ultimately to little avail and the general detriment of pretty much everyone involved.
 * Sisterhood series by Fern Michaels: Charles Martin, former agent of MI 6 and James Bond Expy is definitely this. He works for the Vigilantes and it could be argued that he uses this trope for good, but he is basically an Anti Hero. He tries his hardest to come up with foolproof plans for the Vigilantes to use in order to succeed in their missions. However, there have been times when those plans go awry, and he really hates it when that happens. Under The Radar reveals that he has a large network of contacts and agents who are well-funded and good at their job, which helps to explain how his plans are effective. By Vanishing Act, however, the Vigilantes pretty much make it clear to Charles that they call the shots and not him, and that he had best stop lording over them or he will get the boot.

Live Action TV
"Carnell: I'm very good, Supreme Commander, believe me. I've taken everyone and everything into consideration. It's all as predictable as... that very expensive chess machine."
 * Most Twenty Four 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.
 * Likewise the team of Hawaii Five O.
 * 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/ is showing signs of this. He certainly prefers to operate by proxy . 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 - 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. Then there's Brainiac who usually sets his plans in motion months in advance, and Waller of the appropriately named Checkmate.
 * In later seasons of "Breaking Bad" Walter White becomes a Chessmaster, manipulating Jesse into
 * 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,
 * Ben Linus also fits in the Manipulative Bastard trope, seeing as most of his schemes have to do with toying with people's emotions.
 * Ben always has a plan, but his plan pales in comparison to that of . As of the Season 5 finale, we know that is the true Chessmaster of Lost. The guy's scheme includes everything in Ben's plans, plus some extra behind-the-scenes manipulation of both Locke and Ben to get them in position to execute  master plan.
 * The Man In Black may be the show's master in terms of raw skill and speed. In The Candidate, we see him discover one of his enemies's plots to kill him, subvert it and then with only minutes to spare.
 * According to, Jacob has manipulated the main characters' lives so that they would get on Ocean 815 and crash on the island. He proves this by showing.
 * 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.
 * Captain Benjamin Sisko manages to be one on Star Trek Deep Space Nine, episode "In the Pale Moonlight". In truth, he
 * Seska on Star Trek Voyager. (Especially when she showed up to torment the crew
 * 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 Not only did he kill a dozen people, keep any attention off him for months, manipulate and blackmail his way through the stock market, he's also the only person I can ever remember lying to Veronica's face and not having her suspect at all.  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.
 * And the Puppeteer in question, Carnell, is also very good at chess.


 * 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?
 * Adelle DeWitt of Dollhouse, especially if you believe the Wild Mass Guessing that
 * 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.
 * Londo Mollari also has some serious game.
 * On the subject of Chessmasters using their powers for good... sorta... Mickey from Hustle is a pretty good example. For example, he recently (at time of writing, anyway)
 * Stringer Bell of The Wire is a cunning and ruthless player in Baltimore's drug game who manipulates and betrays those around him to advance his own goals. That said, he's not quite as good at it as he thinks, and is eventually conned out of a lot of money by the even more shrewd Clay Davis. Not to mention that
 * Stringer has more flash, but he can't hold a candle to Prop Joe
 * Lester Freamon also deserves a mention. Lester, like any good chessmaster, understands that "all of the pieces matter" (as he tells Prez). Though he's obviously a part of a team effort, Freamon plays a huge role in bringing in the victories for his side; like Jimmy and Kima, he contributes good detective work, but beyond that his big picture view, political savvy, and capacity for deception and subtle manipulation (sometimes of his allies and coworkers) are what really allow his investigations to (sometimes) break through the wall; there's a reason why Daniels says to Lester, "as far as I'm concerned, you ARE the Major Crimes Unit."
 * Interestingly, when the trope is made explicit by D'Angelo, he, unlike many others who talk about chess metaphors, does not believe he is a Chessmaster. He is fully aware that he is only a pawn, and his growing bitterness with this role, and the callous actions of the "kings" and "queens," fuels much of his growth as a character.
 * Zora, from Sonny With a Chance does this once in the episode where she makes Chad believe he's the host of a TV program that plays pranks on celebrity stars. After she has all the characters together, she herself explained that she was manipulating everyone around the whole time, as she is the true host of the program and their true victim was Chad himself from the beginning. Then they stick Chad's feet on the floor, his face on the window and they spill manure over his new car. Chad was not happy. Played for Laughs, of course.
 * Molly Hardy, in The Adventures of Shirley Holmes. Many of her plots involve blackmailing, buying and manipulating other people, or using their circumstances to her advantage.
 * Katherine Pierce in The Vampire Diaries. If everyone just accepted that she is always playing them no matter how vulnerable or uncertain she seems, then it probably wouldn't change the actual outcome, but they wouldn't waste time and energy trying to beat her at her own game.
 * The Shadow Line has several:
 * Gatehouse, who's very skilled at planning events in his favour, to the point where the BBC website actually calls him a puppetmaster.
 * Glickman, who actually manages to out-plan Gatehouse in his first appearance and ultimately proves at least as good at planning as Gatehouse.
 * Joseph Bede, who, while not as good at it as the two above, successfully manages to dupe Customs into looking the other way while he carries out his deal.
 * Sherlock: Moriarty and Mycroft both. Possibly Irene.
 * Moriarty exploits what matters most to people to get whatever he wants - which, often, is just to prove that he can do whatever he wants. He even  by framing him for kidnapping and threatening to kill John. He manages to ruin Sherlock's reputation by convincing everyone that , which they want to believe anyway because of Sherlock's annoying personality.
 * Mycroft even admits to purposefully driving Sherlock into harm's way.
 * Irene  twice, in part to mess with Sherlock's head. Her fatal flaw is that she lets her heart rule her head, and actually is.
 * In Justified, Limehouse is constantly manipulating the various criminals and other violent elements in Harlan County to keep his own community safe.

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....
 * Regrettably, people mistake it for a song about fighting by taking the line "hit 'em right between the eyes" literally
 * This troper has heard many theories that the chessmaster from the song is none other then Jack from Lord of the Flies. "Turning all against the one" is the best evidence of this, referring to how Jack turned everyone against Ralph. Other parts of the song refer to Simon, "and no one even knew, it was really only you" referring to his death at the hands of Jack and the other boys, thinking he was a monster.
 * Oingo Boingo's song (released as a single under Danny Elfman's name) "Gratitude."

Professional Wrestling

 * Puerto Rican Wrestler Ray Gonzalez's gimmick is that he's a chessmaster (and a good one at that).
 * WWE Wrestler Wade Barrett had this as his gimmick as the leader of the Power Stable "Nexus", his "endgame" being winning the WWE Championship. He planned situations masterfully, even exploiting Boring Invincible Hero John Cena's Honor Before Reason and Hot Blooded nature alongside the occasional No Holds Barred Beatdown
 * Mick Foley of all people was revealed to be one in TNA. He worked his way silently up into the Network as an executive behind Immortal's back, using his position to make them literally Screwed By the Network at every turn. When he finally reveals this, they're dumbstruck because he was the last person they'd expect. On May 26th, Hogan believes he's outsmarted Foley and got the Network to give him control again during a meeting the previous week. However, while Hogan is celebrating both that and Eric destroying the X Division, Foley comes out and reveals that after Hogan left, Foley took over the meeting. The end result was the Network furious at Immortal again and giving Foley the authority to revive the X Division. He even found a loophole to give him control of the PPV because the Network funds them.

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 X Box.
 * In Warhammer and Warhammer 40000, the Chaos entity Tzeentch is literally the god of Chessmasters. His followers commonly favour such tactics as a matter of course, but considering that Tzeentch tends to use them as his own pawns in his own schemes, which are both plentiful and occasionally contradicting, it all just comes back to him eventually. It's rumored that Tzeentch is the only force stopping the Immaterium and universe from merging as part of an elaborate plan roughly forty-six thousand years in the making.
 * Other grand schemers of the forty-first millennium include the Eldar's Laughing God and the C'Tan known as The Deceiver, prompting fan debates over who is responsible for any given plot, what happens when they work against each other, or who is simply a guise of another. There are also the Eldar Farseers, who use their prescient abilities to manipulate galactic events in their favor, and the Chaos Space Marines of the Alpha Legion, renowned for using sabotage, propaganda, or infiltration when their colleagues would just charge in with weapons blazing.
 * Possibly also the Emperor - it is hinted that not only did he anticipate the Heresy but also plans to be reborn when his phsycial form dies (which may well be soon)
 * Cypher. But with a name like that...
 * 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.
 * Changeling: The Lost has the Contracts of the Board, which allow the user, by utilising some form of strategic game, whether it's chess or cards or Candyland, to read opponents, send orders, and tweak fate through correspondences and the odd bit of cheating.
 * The Dungeons and Dragons rulebook Fiendish Codex II: Tyrants of the Nine Hells explicitly compares Asmodeus' plans to a game of chess. Supposedly his plan to topple heaven is a few centuries ahead of schedule.
 * Also, the rulebook Lords of Madness: The Book of Aberations describes mind flayers - a.k.a "illithids" - and their leaders the Elder Brains as often being this. They are manipulating politics and slowly working towards reestablishing the illithid empire that was lost long ago.
 * The Illumians, introduced in Races of Destiny, are a species of humanoids organized into cabals where they study and manipulate the world around them, ultimately hoping to accumulate enough power and knowledge to ascend to godhood.
 * Dragons play xorvintaal, the Great Game in which they use mortal servants as chess pieces to compete for each others' hoards. The game itself is far too complex for mortals to understand, but in the small term can shape entire lives. In the long term, it shapes continents - World War I would have been a particularly complex xorvintaal maneuver, with World War II being a good counter-move. Just as a consequence of powerful creatures to who We Are As Mayflies getting bored.
 * An example: Dragon A uses his magic to cause a volcano to erupt, wiping out an entire town but forcing Dragon B to evacuate her hoard and leaving her vulnerable to attack by PC mercenaries hired by Dragon A. This would be considered a crude, noobish maneuver. A master of xorvintaal, such as Dragon C, would rush to the volcano, see a family trapped in a burning house, and use just enough magic to save the boy. Over the coming years Dragon C supports the boy as he hones his skills as an adventurer, nurturing his hatred of Dragon A until he's ready to form a party to avenge his parents, afterward continuing as a loyal supporter of Dragon C. That's a character whose entire life was played like a chess piece in a game he may never become fully aware of. And Dragon B? The mercenaries that would have attacked her were instead wiped out by a party sent by Dragon D, a young vassal of Dragon C who is now owed a favor by a powerful rival, who Dragon C only wants around as a buffer against Dragon E...
 * Seventh Sea has and the biggest and baddest of them all is none other than.

Theatre

 * The titular Phantom of the Opera is initially the Chessmaster until . He even has a model of Il Muto where the characters have interchangeable heads to help him in his plans.
 * Lucy is this in Thirteen. She tells Kendra she shouldn't kiss Brett because she's a good girl. Then all she has to do is turn Brett's head for  then when   Lucy
 * Edmund, Regan, and Goneril from Shakespeare's King Lear. They all fully take advantage of their fathers' weaknesses.
 * Oberon from A Midsummer Nights Dream. Of course, he had only planned on a few simple maneuvers, but things get complicated when you let Puck handle the Applied Phlebotinum.
 * Iago from Othello plays off of Barbantio's racism, Othello's jealousy and distrust in Desdemona, and Roderigo's love for Desdemona all to destroy a man he hates - but for whom he has no good reason to hate.

Video Games
"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."
 * Fable 2 has Theresa whose also a Manipulative Bitch the DLC reveals
 * Final Fantasy Tactics was completely filled with Chessmaster-on-Chessmaster action. 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
 * Though, it should be noted that this trait runs in the family as we see in Crisis Core with
 * Zexion from Kingdom Hearts, complete with Villainous Breakdown when he Didn't See That Coming.
 * Everything that has happened in the Kingdom Hearts saga from Birth by Sleep onwards can be traced back to Master Xehanort, although . Sheer Power Of Friendship is the only reason his plan to restart the Keyblade War didn't succeed at the Keyblade Graveyard,
 * The Administrator from Team Fortress 2 could certainly qualify: though it's never specified why, it's clear that she's been deliberately prolonging and encouraging the conflict between RED and BLU for years.
 * Xenogears could feature a football team full of chessmasters. Just to name a few who were playing (and they were each manipulating each other):
 * 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.
 * 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,
 * Super Paper Mario has.
 * Grand Master of the Order, Jacques de Aldersberg in The Witcher computer game, who
 * 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.
 * The prosecutors of the original trilogy, (excluding Winston Payne) also seem to have Chessmaster-ish qualities, Edgeworth even has a chess set in his office with a suspiciously spiky blue pawn.
 * In Ace Attorney Investigations 2, the chess motif becomes literal, with Edgeworth engaging in "Logic Chess" to get people to talk. There's also a witness who is obsessed with chess, and another who plays long-distance chess with the former.
 * 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
 * Revolver Ocelot of Metal Gear Solid was described in one Fanfic 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.
 * Hikawa from Shin Megami Tensei: Nocturne manipulates people and events from the shadows, never taking any unnecessary actions and always moving towards his goal.
 * arguably counts as well, attempting to maneuver the player into . 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 Batman Gambit was so well executed that he qualifies for this trope. Sending his most loyal angel on a false assassination 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 War Craft Universe. His motto is "There are more ways to destroy one's enemy than with an army. Sometimes 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 (or so he thought, they were actually stranded).
 * 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.
 * He also managed to enslave an entire race of demons known for their clever trickery.
 * 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..
 * 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'd catapulted the slowest unit in the galaxy 600 trillion kilometers in an instant: right to the sun it was built to destroy."
 * At the end of that same game, He exploited his own cultural influence technologies and a law he passed at the beginning of the game to override the normal limitations on ship movement in order to place the final starbase he needed in order to wipe out his remaining rivals and end the game. Day 30. I cried at the beauty of the move:


 * He's come a long way since his last GalCiv II game, then. In that attempt,
 * Chrono Cross has a rare example of the Chessmaster actually being a good guy. 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.
 * 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 . Bonus points for.
 * 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.
 * On the subject of Halo, there's also the Prophet of Truth. 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.
 * Tsukihime has, of all people,
 * 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 - . This is hardly surprising, coming from a game with a Gambit 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
 * In Modern Warfare 2.
 * Touhou's Yukari Yakumo, especially evident in the official supplementary manga.
 * Half-Life has the G-Man, the mysterious suited man who has been shadowing Gordon Freeman since the beginning of the series. He speaks of his "employers," but it's obvious that the G-Man has been subtly influencing events since the first game and that Gordon is really just his pawn, . The real question is which side the G-Man is on.
 * The Kimono Girls take on a role that could be described as this in Pokémon HeartGold and SoulSilver. I'm as surprised as you. Their actual plan is horribly vague; apparently it involves finding a kindhearted Trainer to summon Ho-oh or Lugia (depending on the game). What purpose this serves is not made clear, and the whole plan seems to be rendered a bit useless by the fact that said kindhearted Trainer proceeds to beat the crap out of the aforementioned Pokémon and, if they're feeling merciful, capture it in a tiny ball and make it their slave.
 * from Pokémon Mystery Dungeon: Explorers of Time/Darkness/Sky, who actually came up with different plans to kill the heroes over the course of the game. During the post game story, he has no less than five backup plans in place!
 * Lenora from Pokémon Black and White has this as her battle style, in the game, Anime, and Manga. In the game, defeating her first Pokemon is a no win situation, as both of her Pokemon know Retaliate, which with the STAB granted by it being a normal type move, which makes it one of the most powerful moves you'll see early in the game. In both the Anime and Manga, her battle style resolves around forcing her opponents to play into her hand. There's a reason she's considered That One Boss.
 * Mass Effect 2 has the leader of Cerberus, the Illusive Man, who pulls string after string to get things to go as he wants them to throughout the game. He does, however, make one flaw- he under-estimates Commander Shepard. Depending on the player's actions,
 * Not to mention Harbinger:
 * The cake must go to . He
 * And he is still Out Gambitted by.
 * Sarah Kerrigan, full stop. Brood Wars was basically Kerrigan playing her own constant Chessmaster, to the point where she was more playing a game of Xanatos Roulette.
 * Both Starcraft and Brood Wars actually have several of them. The Overmind definitely counts, maybe also Dugall. Alan Shezar and Ulrezaj also count, if you take Blizzard Entertainment's bonus campaigns as canon. Oh, and of course  (who also qualifies as a Magnificent Bastard).
 * In Sonic Adventure 2, Shadow the Hedgehog allows Eggman to believe that he is gathering Emeralds as a favor for waking him from a 50 year sleep that his only friend put him in before she is killed, then tells Eggman he can hold the world ransom with the Eclipse Cannon on the Space Colony ARK, when really Shadow has been doing all this just so the Cannon could destroy Earth. Why? Because in SA2, Shadow the Hedgehog really, REALLY hates human beings and just wants them to suffer. So much that even when his plan fails, he is content to watch the Earth be destroyed anyways even if it's by a way that wasn't in his plan.
 * Until  shows up and talks him out of it.
 * Malefor from The Legend of Spyro trilogy is a shining example. He's such a good example, it's hard to tell what WASN'T a part of his plan did he really intend to kill Spyro in the raid or did he want him alive to  Did Spyro really free Cynder or did Malefor let her free so   And to top it all off, the Hannibal Lecture he gives the two when they finally confront them even has them wondering whether they'd done anything but play right into his claws.
 * Soul Nomad and The World Eaters has, amongst others. Those "pointless" side quests you've been doing? Not so much.
 * And in the Blaz Blue corner we have Hazama, also known by his true name, Terumi Yuuki! He may seem unimpressive at first glance, merely 183 cm/6'0" high and weighing in at 61 kg/134 lbs, but make no mistake folks, this guy has outmanouvered his universe's equivalence of Gods! And it only took 1/470000th of a second of them focusing on something else than their omniscience to do so, folks! And that's not even getting into how utterly he has owned the mere mortals (and occasional "shitty vampire") of his universe. Just don't mention squirrels to him.
 * There are two real chessmasters in Eien no Aselia, and in general they don't really show up until the last 15% of the game. is the big bad and set up the whole plot and  interfered so that the game doesn't get a downer ending.
 * Lord Alden in Vanguard Bandits is a literal chessmaster, being the best player on the continent and rumored to be undefeated.  Meanwhile big bad Faulkner, is more of the moving and controlling of wars type of Chessmaster. And he's very, very good at it.
 * The Sith Emperor of Star Warsthe Old Republic managed to be the Man Behind the Man for nearly all of the major events of the galaxy since the Exar Kun War, including all of the events in the Knights of the Old Republic series. He manipulated the Mandalorians into attacking Republic space leading them into the Mandalorian Wars, a devastating war which he orchestrated entirely to lead Revan to him, who he took as his apprentice and sent off to find the Star Forge. When this failed due to Malak's betrayal and Revan's subsequent redemption, he set up puppet leaders on Republic worlds on the Outer Rim, infiltrated the Jedi Order, and rigged the Mandalorian gladiator tournament to place a Sith agent as the new Mandalore. All of this was in preparation for their strike on the Republic border worlds, in which he struck while the Mandalorians (under the leadership of aforementioned Sith agent) blockaded Coruscant and disrupted Core World trade routes. At the time of the first cease-fire, his Sith Empire controlled nearly half of of the known galaxy--the closest any Sith Lord has gotten to conquering the galaxy until Emperor Palpatine himself, nearly four millenia later.
 * Lord Fain of Lusternia. Ostracised by his fellows Gods eons ago for his questionable methods, upon his return to the First World he adopts the guise of a shadowy manipulator, using mortals and even other Gods as tools to carry out his complex plans. Though progress through his service is characterized by chess motifs, it's just flattery designed to ingratiate him to his more competent followers - to Fain, everyone is a pawn.
 * from Jade Empire. They don't call him for nothing.

Visual Novels

 * Maji De Watashi Ni Koi Shinasai refreshingly has the main Protagonist, Yamato, be a Chessmaster. Touma is the 2-S equivalent and the two have a rivalry of sorts.

Webcomics
""When you're working for Charlescomm, you'll learn. We prefer to play games that don't even contain a losing outcome. You see?"
 * MAGISA -- We have an unnamed reptoid (or demon) villain who seems to be calm even though the mind-control experiment has seemingly failed. Is it because... he's got another plan and its all a diversion?
 * In 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.
 * And Nale, especially at the Cliffport arc, gives us the more traditional villainous one.
 * Generally Nale is too unsuccessful to be counted. Tarquin is a better example.
 * The IFCC seems to count, too.
 * And in comic 830,
 * 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 deceive 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.
 * (ironicly the only clue that permit to the AI "Tag" to come to this conclusion was the analysis that the UNS government 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.

"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. :)""

"Marena: Everything she does is layer on layer of sheer deviousness.
 * from DMFA appears to be leaning in this direction. Even his sister, who is well-aware of his deviousness, falls for his tricks.
 * In spite of her misleading middle name, Pandora Chaos Raven of El Goonish Shive is the epitome of this trope. As an Immortal who has lived for millenia, her joy comes from not knowing what will happen next. Despite this, her actions are cold and calculated, and she pulls the strings of everyone she meets. Her tendency to stay behind the scenes is not due to any sort of weakness (Immortals possess near god-like power when on the Spirit Plane, and can use magic without being detected), but rather because the other Immortals get seriously pissed off if one does anything more than empower or guide people on the Physical Plane. That, and doing everything herself would just be boring to her.
 * Sonorous Aria, from Keychain of Creation, is stated to be one. Most of her chessmastery is offscreen, so far.

Aria: Now, a feast! Lavish meals and fine drinks for everyone! Then: Party games!

Marena: She's up to nine layers already.

Aria: Extra drinks for the handsome bearded fellow in the corner!

Marena: ...twelve."


 * Sluggy Freelance has Dr. Schlock, who seems like a harmless coward and Chew Toy with some minor Manipulative Bastard tendencies for a long time until Hereti-Corp finally pushes him too far by becoming a never-ending threat to the one thing he cares the most about (his own well-being). At this point, pushed into a corner, he feels forced to
 * Mitadake Saga:
 * Mojo Nixon from Princess Pi relies entirely on such plans committing evil deeds.
 * Skerry from Fite, who uses a more generic gameboard rather than a chessboard.

Web Original

 * In The Gamers Alliance, quite a few villains such as the Master and Iblis end up being quite good at manipulating events into their liking.
 * The Big Bad and fake-out Big Bad of Broken Saints both fit the bill here, but, naturally, the real Big Bad does more.
 * The Snake in Above Ground is a prime example, particularly because he can use magic to enslave others into doing his will.
 * The Emperor, leader of TAROT, has his fingers in nearly every criminal enterprise on Earth in The Global Guardians PBEM Universe. Of course, he's also got his fingers in nearly every major legitimate business enterprise on Earth as well. But then, what do you expect of a villain who is secretly an immortal Niccolo Machiavelli?
 * in There Will Be Brawl
 * Ice and Ranger are often this in Comic Fury Werewolf
 * Espeh also managed to do this from Beyond The Grave, to throw a Spanner in The Works for the Werewolves' master plan which was just about to succeed.
 * Nick Fury, Charles Xavier, Forge, Tzigone, Vengeance and many others from Marvels RPG.
 * Regine in Addergoole - the entire school, and the students, exist to fulfill her plans.
 * The Architect (no, not that one) is hinted at being this in Shadowhunter Peril. However, he tends to go against the grain of the usual Chessmaster, as he is a genuine hero...he's just hiding a lot.

Western Animation

 * Megatron of 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 almost 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.  Azula was a genuine (and, fortunately for Ozai, genuinely loyal) Chessmaster, so she got to do all the thinking.
 * Oh, Ozai can scheme fine (note the flashback in "Zuko Alone", where he very clearly exploits the weak spots of everyone around him to get exactly what he wants, and he managed to keep Azula under control for years- no mean feat!). Problem is, he's usually far too Drunk With Power to put that cunning to effective use.
 * Effectively, Azula plays this trope straight, using plots, her skills as a 'people-person' and good ol' situational awareness to deal with her enemies; kicking ass and taking names is more a trump card she keeps close to the vest. Ozai's cunning when he needs to be, but he is much more of an outright bully who uses violence, intimidation and raw displays of power to get his way. Ozai's the club, Azula's the rapier.
 * 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...
 * Amon, Big Bad of The Legend of Korra, has claimed himself to be a chessmaster. He has thus far been very convincing at his role.
 * Episode 6 sealed his status as not only a brilliant Chessmaster, but also something more.
 * Loki from "Avengers: Earth's Mightiest Heroes".
 * 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.
 * Cartman from South Park is the chessmaster in quite a few episodes.
 * Scott Tenorman Must Die is the most chilling example. Even the main group acknowledges how dangerous Cartman is here. To add to it, he even uses Stan and Kyle to rat out his (fake) plan to Scott Tenorman. So beyond everything, everyone knew Cartman was up to something. He just took it to the next level.
 * Kyle's also shown to be quite capable of this, usually as direct opposition to Cartman's elaborate Complete Monster moments. This is best seen in Le Petit Tourettes where he orchestrates an entire series of events to stop Cartman's faking of the disorder.
 * Anti-Cosmo and HP on The Fairly Odd Parents could both qualify, usually tricking Timmy or some other third party into helping with their plans.
 * Xanatos isn't the only one Gargoyles has to offer. Fox, Thailog, and the Weird Sisters all play close to Xanatos's own level (Thailog even bested him once). Demona does some of this, though she's often so hot blooded and/or generally screwed up that she'll inadvertently sabotage herself. The Archmage doesn't have the same skill as the above, but he makes up for it with the sheer grandiose nature of his ambitions. Also, the Illuminati are implied to be a whole organization of these (at least, the ones at the top are).
 * James McCullen makes a good attempt at being this in the G.I. Joe Renegades episodes, playing the Joes and Cobra against each-other
 * My Little Pony Friendship Is Magic:
 * The Big Good, Princess Celestia, seems to be able to play this part when necessary, and is a rare benevolent example, working for the good of her subjects. She remains somewhat enigmatic, but seems to have wisdom fitting her millennial experience of ruling. She generally seems on top of everything that's going on, but has twice been shown doing some serious plotting: At the beginning of the first season, she pulled off a Gambit Roulette with the twin goals to a) make her student Twilight Sparkle get out more and make some friends and b) save the world. In the beginning of the second season, she performs a much simpler and more elegant single-step Batman Gambit with somewhat similar goals.
 * Celestia's old Arch Enemy Discord -- a being so dangerous and chaotically ingenious that he's actually able to catch her off balance and unnerve her -- plays a round against her in "The Return of Harmony", with the main characters as pawns. (Although, if we're doing Chess Motifs, there's more than one reason why it might be fitting to call them Celestia's knights. ) Discord's plan aims at making sure that the ponies will be psychologically broken and unable to use the only thing that can stop him even after they do find it, although given his power, it looks like he's also doing things the hard way just For the Evulz.
 * Then we have
 * The supercomputer from Phineas and Ferb is a rare benevolent example.

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."
 * A list of tongue-in-cheek predictions for 2010 included the revelation that Taylor Swift has been moonlighting as a Chessmaster-for-hire, having orchestrated not only Kanye West's outburst at the 2009 MTV Video Music Awards, but other celebrity scandals.

Real Life

 * The Athenian politician Themistocles.
 * Richard Nixon was quite the chessmaster; he just forgot what happens when you let a minor pawn get up the board.
 * John F Kennedy as well, based on his expert handling of the Cuban Missile Crisis.
 * Bill Clinton fits this trope in his handling of the Monica Lewinsky scandal and his subsequent impeachment. What was intended to be Clinton's downfall instead lead to the downfall of his main political rival, Newt Gingrich.
 * 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.
 * Although that was more a case of exploiting a situation created by other politicians and rulers, a simple matter of shoring up one continental ally (Prussia) and concentrating Britain's own military efforts against France and her overseas empire. As a chessmaster, Pitt actually was outshone by Count Kaunitz, Maria Theresia's chief minister, who with a little help from the ineptitude of Frederick the Great (who managed to alienate France by an somewhat rash alliance with Britain) brought about the "Reversal of Alliances" before the Seven Years War and managed to preserve the anti-Prussian alliance of several powers with greatly divergent interests (for starters, France had continually been at war with the Habsburgs for literally centuries) throughout most of the duration.
 * 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 Newark, 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 cannot 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 Hillary Clinton (acting as The 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!"
 * 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.
 * Ironically, Sun Tzu's theories were almost all entirely influenced by Go, which emphasizes misdirection and maneuvering, while de-emphasizing direct contact.
 * Niccolo Machiavelli's book The Prince is another guide to this trope (or else a parody of such politicians). While Sun Tzu focused more on military strategy, Machiavelli focused more on political strategy and how to use them in order to gain power and how to keep it for a long time.
 * The I Ching is a great book for Chessmasters.
 * Louis XI, King of France. Began his reign with a weak and small kingdom and a really powerful neighborhood (Charles le Téméraire, duke of Burgundy). He never fought Charles directly, hiring other countries (Switzerland, Flanders...) to finally kill him. When he died, Burgundy was a part of his kingdom.
 * Although to be fair his kingdom was a bit stronger and more powerful than it had been under his predecessors (it was only his father who saw the English presence in France reduced to just Calais) and that Louis was helped to a large degree by Charles of Burgundy being his own worst enemy ("téméraire" means "reckless, rash" as well as "bold"). Also, the larger half of the duchy of Burgundy ended up in the possession of the another powerful neighbor, the Habsburgs.
 * Otto Von Bismarck, who orchestrated several wars among Europe to manipulate the populace and political power to unite the German states into the nation that exists today.
 * Ruben Amaro Jr., general manager of the Philadelphia Phillies, just might be one of these- now that a one-year process of trades and signings has left him with four of the best pitchers in baseball on his squad.
 * But it's not like there isn't a team that hasn't beaten all of them in the playoffs.
 * You could say that Sabean was a chessmaster during 2010. He made all the right moves during 2010 to win the World Series.
 * Red Auerbach, legendary coach and general manager of the Boston Celtics, was notorious for his Chessmaster tendencies (particularly in the form of elaborate trades with other teams). So much so that the process by which he acquired Larry Bird for the team was later banned by the NBA.
 * Stalin, at least in the way he orchestrated his rise to absolute power within the party apparat against rivals considered a great deal more brilliant or popular than himself, by forming various alliances against one rival, and then turning on his erstwhile ally after that rival had been eliminated.
 * Before his rise to power, Stalin was viewed as a petty clerk attending to meaningless paperwork, but nobody stopped to think of the extreme command he was developing of obscure laws. In some ways, his most potent ability was actually to Rules Lawyer his opponents.
 * Barack Obama could be one with his nature of handling Osama Bin Laden. He kept completely quiet about while he organized a team to attack while making jokes the night before. The move caused his approval rating to shoot up.
 * Cardinal Richelieu of France was a startling example of this trope. The man was the world's first Prime Minister, and raised up alliance after alliance during the Thirty Years War. He's the main reason that France became as powerful as it did.
 * Hitler started out as one, getting the people of Germany to give him the power, and the nations of Europe to just give him several nations before the war even started, but his ability to control the board quickly vanished after making one horrible choice after another. The British actually stopped their plans to kill Hitler because they figured out somebody who was competent would take his place.

Checkmate, troper. You've read through the article just as I planned. You lose.