The Chessmaster - Television Tropes & Idioms

alt title(s): Chessmaster

"It's like you're playing checkers... And I'm playing chess."
- Cry Wolf

The Patrician disliked the word 'dictator.' It affronted him. He never told anyone what to do. He didn't have to, that was the wonderful part. A large part of his life consisted of arranging matters so that this state of affairs continued [...] Human nature, the Patrician always said, was a marvelous thing. Once you understood where its levers were.
- Discworld

"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

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

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

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

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

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

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

Never, ever be predictable in your habits when you have a Chessmaster as an opponent. Even the wannabe Chessmasters can demolish someone who always calls his partner for an update from his balcony at precisely 7pm on Thursday. Oh, and if you ever think you are winning against a Chess Master, you have already lost. The only way to win against that dude is to stage a Xanatos Roulette so complex that even you yourself won't be sure it'd work.

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

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

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

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

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

Chess Metaphors

Lelouch, the Anti Hero of Code Geass, is almost a textbook example of the good-guy Chessmaster: highly intelligent Well Intentioned Extremist who excels at chess. When Mao gets the advantage on him, the point is emphasized by his clobbering of Lelouch at chess (by reading Lelouch's mind and revealing every single strategy Lelouch was thinking of at a single moment...including ones to misdirect Mao's telepathy).
- The "almost" comes from the fact that, rather than sitting on the sidelines, he fights in the field with his men, and that Word Of God, Lampshade Hanging, and even direct statements from Lelouch himself ("I can't win if I abandon my people",) demonstrate that he actually cares about the well-being of those he commands.
- Though just to add to the "chess" metaphor, Lelouch is compared to a king more than once. Like the king piece, he's the most valuable piece on the board but extremely poor at combat, being one of the most physically weak characters in the show. This is even partly why he's on the field, actually: his own personal chess strategy seems to have the king move around a lot more than his opponents consider 'normal'. "If the King doesn't lead, his men won't follow." His Mind Control power is even referred to as, "The Power of the King"
- Lelouch carries this to the hilt by designating groups of rebel fighters by letters - which are chess notation for the different pieces (N for kNights, etc.)
  - That's a bit of stretch, isn't it? Why not K for Knights? I guess the K is silent, but still...
  - Not at all. Remember Karen's call sign? Q-1, the Queen's designation in common chess notation.
  - K's already used for King.
In the film Jason And The Argonauts, the gods are shown playing chess, with the heroes and villains as pieces. (Even though chess didn't exist back then.)
- Actually, chess did exist back then... it's just that during the Ancient Greek period, the Indians, Persians, and Chinese were the only ones playing it.
- No good. Why couldn't it be at Olympus? Prometheus didn't steal all of Zeuses secrets.
- They were playing a boardgame, there is no indication it was supposed to be chess.
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.
Sluggy Freelance toys with this trope here.
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.
One of the bounties in Cowboy Bebop, appropriately named Chessmaster Hex. He set up a revenge plot for a company he worked for by supplying plans for defrauding their customers to several dozen random people on the internet. The twist is that he set it up fifty years ago to just happen now and he has since become a senile old man that just plays chess online all day.
Senna from the Everworld series of books. At the beginning of the book narrated from her point of view, she explicitly thinks to herself about how manipulating other people (and gods!) has some things in common with the strategy of chess, but the skills required are different.
Moridin in The Wheel Of Time, albeit with an imaginary game called sha'ra (though he is stated to be a master of all strategy games, which presumably includes chess).
Sylvester McCoy's Seventh Doctor in Doctor Who. The chess metaphor is part of a Story Arc; it first appears in "Silver Nemesis", when he moves the pieces on Lady Pienforte's board; in "Curse of Fenric" this is revealed to be how he knew fellow Chessmaster Fenric was the force behind it all. Played with in "Battlefield" when Morgan La Fey taunts "I could always beat you at chess, Merlin" and he retorts "Who said anything about chess? I'm playing poker. And I have an Ace up my sleeve!"
- However, it's arguable that the Seventh Doctor isn't quite the flawless chessmaster that he wants everyone to believe he is; many of the stories involving this aspect of his character hinge on something occurring that he didn't actually anticipate or someone doing something that he didn't expect, thus requiring a frantically improvised stop-gap solution to get things back on track.
Several characters in Liar Game. One of the antagonists, while not playing chess, uses chess pieces to demonstrate headcount in a Minority Rule game. This contributor believes this belongs in this subsection of the category because the three pieces (rook, knight, bishop) all representing the same person are then dramatically replaced with a king, complete with grand sweeping gesture.
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, Robert de Sable reveals that Al-Mualim has been manipulating Altaïr into killing everyone who knew the secrets of the Piece of Eden, so that none could challenge him when he would use it to take over the Holy Land. In his final moments, he comments that everyone, including Altaïr and the other Templars, were just "pawns in his grand game."
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.
The tabletop roleplaying game Exalted has the most powerful gods spending their time playing "the Games of Divinity".
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"? The end sees Brainiac destroyed, (and apparently Superman too), the world united and ready to accept "Luthorism" to lead it. He regards the chessboard and remarks "It's like it was planned to the tenth decimal point forty years ago."
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.
8-Bit Theater parodies the trope here.
- Similarly parodied in Calvin And Hobbes.
  Calvin: "Ah, you've fallen right into my trap! Perhaps you'd like to take that move over?"
  Hobbes: "Your remaining piece must have one heck of a plan..."
Inverted in Fullmetal Alchemist when after King Bradley has ordered Riza to be his secretary, and the rest of Mustang's men to be sent to the fronts of the various wars Amestris is fighting, Mustang has noted that he's lost most of his pieces, but he's still not out of the game. The Big Bad Father also uses objects like Chess pieces to simulate all of the things he needs.
In the Whateley Universe, there's a supervillain of this type who not only goes by the codename Chessmaster, but he puts replicas of his pawns and the opposing heroes on a chessboard. He uses psychic abilities to make his gambits more effective: he has been known to 'attune' his pieces so they're more likely to do what he wants, and he has precognition to the point that he can see the dozens of most likely scenarios, with their consequences. His biggest problem? He's still trying to prove himself to his old (now retired) teacher Mrs. Potter, who is such a powerful and effective precognitive that she can trash his plans just by making a phone call the day before, or handing someone a note to hold for someone who may drop by.
Arcturus Mengsk from Starcraft. He plays the Confederates and Zerg off one another to put himself in charge. In the novel Liberty's Crusade he is shown as a avid chess player, complete with a chess set in his command center. Towards the end, when his plans start falling apart, the chess set gets thrown across the room, although Kerrigan does the actual kicking for him.
- Speaking of Kerrigan... Brood Wars was basically Kerrigan playing her own constant Chessmaster, to the point where she was more playing a game of roulette.
In the novel Green Rider during the final showdown, the protagonist is abruptly yanked away from the action and sees the battle as an elaborate game of that 'verse's equivalent to chess, which is played with 2-4 players. The chessmaster villain invites her to sit and play, as it is the only way for her to break the stalemate and save her friends. Instead, she smashes the chess board with her sword, causing enough magical backlash to win the day.
Shikamaru Nara in Naruto, exemplified in pretty much any fight he's in, tends to play shogi with Asuma or now that the former's dead his father.
- In a slight subversion for a chessmaster, Shikamaru sees himself as a knight. Who is the king, then?
One of Monk's suspects in Monk, who is an actual chessmaster (a Grand Master, in fact). He uses chess metaphors to taunt Monk about the exact method he used to murder his wife and get away with it. Most notably, he mentions the "Poisoned Pawn" (a name for a particular chess opening) move in which he fooled his second wife into poisoning herself. Monk then gains inspiration from the tactic of swapping the positions of the king and rook to figure out that the suspect had changed the headstone of his first wife in order to prevent the body from being exhumed.
- After this, Monk then begins to tell off the chessmaster about how it is such poor form to use chess terms when you're talking about people, ending it with the obvious "checkmate".
The title character of The Westing Game. Full stop.
In the film 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 relevence when it turns out that "Slevin" and Goodkat were working together from the beginning to manipulate the Boss AND the Rabbi, in order to get revenge for them murdering Slevin's parents.
The novel The Squares of the City not only has an obvious chess metaphor in it's title, it's modelled after a historic chess game between two real world chess masters.
The film Dangerous Moves subverts the trope: the two grandmaster chess player protagonists are realistically high strung and emotional, with little aptitude for or interest in the manipulation of people and events. Its the hangers-on and government handlers that surround 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.
Affably Evil Prime Minister Wong Wunfat from G Gundam. Humongous chess board included.

Other Examples

Anime

Chessmaster vs. Chessmaster example: Light vs. L in Death Note. Unlike most chessmaster stories, this one usually lets the audience in on each move of the game. When we're suddenly denied this privilege, you can bet something hardcore is about to go down.
- Death Note later features a Chessmaster moving figurines of the dramatis personae around a chess board. Bonus Points!
Sousuke Aizen of Bleach. Also of the Magnificent Bastard variety and a proven master of the Xanatos Roulette.
- For that matter Kisuke Urahara fits the role well too, though on the non-villainous side. Aside from being opposed to Aizen, it's not really clear what endgame he's playing toward, but that could just be proof of how good a Chessmaster he is.
Fushigi Yuugi's Nakago was not only good at directing his own men, he was a master when it came to misdirecting and manipulating the heroes. (Not that the heroes were any sort of brain trust, mind you...)
Ukyo from Samurai Seven constantly manipulates people to serve his own ambitions. Even the shocking news that he is a clone of the Emperor doesn't shock him for long, and he quickly disposes of the Emperor, possibly causes the death of another of the Emperor's as-yet-unborn clones, and takes over the throne himself. The only plan that stops him is a group of samurai who plainly state they have no plan.
Kurama from Yu Yu Hakusho. A "good guy" example. Even though he has a Green Thumb (which would seem to be useless in normal circumstances), you don't ever want to become his enemy or otherwise try to mess with him. EVER.
In Gundam 00, Alejandro Corner thinks he's The Chessmaster, hijacking Aeolia Schenberg's century-in-the-making Xanatos Gambit and arranging to dispose of the late Aeolia's loyal followers so he can take command of the newly-forming Earth Sphere Federation. He's wrong. Alejandro was actually being manipulated himself every step of the way by his apparent lackey, Ribbons Almark. The first hint Alejandro gets of this comes seconds before his death when Ribbons radios him to gloat.
- Let's give credit to Aeolia Schenberg too, please? He managed to accurately predict the events of pretty much everything that happened during the first season, and developed effective contingencies for it. What makes him different from all the other different chessmasters? He's been dead for two hundred years.
  - Seriously. My Cryogenically Preserved Corpse's Unnecessary Defilement Is Only The Beginning.
- In season two, there are at least three possible Chessmasters, and it's not yet clear which one is winning. Is it season 1 Chessmaster Ribbons, enigmatic Celestial Being backer Wang Liu Mei, or Ribbons' own apparent lackey Regene Regetta, who happens to also be Gundam Meister Tieria Erde's Evil Twin? Each has already had more than one occassion 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?
The Anti-spirals from Tengen Toppa Gurren Lagann pull this off quite well; they anticipated every move possible the 'spiral beings' could have made, and intentionally let them achieve almost all of their small victories, for "The greatest despair is brought after the failure of the greatest hope". The only reason they failed was due to a not-so-subjugated mind-puppet herald, Princess Nia Tepperin.

Comic Books

V, Anti Hero of V For Vendetta. In the film, Finch actually figures out part of the plan, but can't do much to stop it by that point.
- In the graphic novel, Finch goes as far as to almost stumble upon V's lair, but decides his ordeal is over when he fatally shoots V. Of course, this was all part of V's plan...
Many of the best comic book supervillains exhibit this trope. A few notable ones:
- The very first time we see Doctor Doom, he's toying with chess-piece replicas of the Fantastic Four, so that tells you all you need to know. He's usually ranked as Reed Richards' evil doppelganger regarding intellect, and his plans range from the complicated to the really complicated to the one that played both Mephisto and Doctor Strange like Stradivarius violins. Simultaneously. With one move.
  - ...which is parodied in these two 8-Bit Theater strips.
  - An issue of Excalibur parodied the characters-as-chess-pieces visual metaphor, with the characters standing on a chessboard, and Captain Britain saying "Call me paranoid, but I think we're being manipulated."
  - Probably also a reference to a classic earlier Captain Britain storyline, where the same manipulator, Merlin, played a quite literal game of chess with the characters' fates. He continues to do so during a pivotal story arc of Excalibur, including a time in which he fakes his own death and has his daughter Roma (who's not in on the deception) play the game in his place for a while. When he returns (in the very issue with the above-mentioned cover, if this troper remembers correctly), he's carrying a chess piece representing Roma, and places it on the board.
- Norman Osborn 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 Black Panther of the Marvel Universe is rare example of this trope that is a traditional superhero, albeit one that is occassionally 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.
  - Except Batman came first, and thus isn;t the Alternate Company Equivalent, but rather the original merchandise.
  - "First" as a character in general, but not as a Chessmaster.
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.
For a character who claims to hate the convoluted plans, The Dark Knight's Joker manages to pull off a dozy of one. Unless he's making it up as he goes along, which is quite possible. The Joker's sadism also leads him to pull off some nasty (although thwarted) Xanatos Gambits.
The Riddler is depicted as The Chessmaster in the Batman: Hush storyline, having manipulated all of Batman's villains in his master plan and having learned Batman's secret identity. However, Batman thwarts the scheme when he exploits the Riddler's compulsion. He can't expose Batman because it would be like giving away the answer to a riddle.

Film

Palpatine from Star Wars. He manipulated everyone and everything until the very end.
- Grand Admiral Thrawn from the Expanded Universe, even more so - a character remarks "If Palpatine was always one step ahead of everyone else, Thrawn was two."
  - Except Paltapite was smart enough to create an Empire that was totally biased against nonhumans, making Thrawn completely dependent upon Palpatine's approval for any continued success. And then Palpatine sends Thrawn to the farthest reaches of the galaxy to subjugate it for the Empire, removing him from Imperial politics. Thrawn came closest to restoring the Empire, but it was never Palpatine's plan to have the Empire outlive him to begin with.
- From KOTOR II, the character Kreia could be seen as Palpatine from four millenia previously. She manipulates both the jedi and the sith to such a degree that even at the end of the game, it's hard to tell what side she was on, or even if she was on anybody's side
CRS in The Game.
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.
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.
The Oracle from The Matrix is a sentient computer program capable of calculating Neo's reactions so precisely that she essentially made Neo the One. All of Neo's heroics are all essentially part of her chessmaster plan, even Agent Smith.
Vito Corleone in The Godfather would serve well as the very definition of a Chessmaster. In the book and the movie, he planned out every detail of every part of the story perhaps even his own death.
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.
In Death Race, the Warden is clearly The Chessmaster, with the way she manipulates the convicts to play in the race. In view of the fact that the audience is made not to like her she's also the Anti Hero. I'm not sure if she qualifies as a Magnificent Bastard but when I was watching the film I immediately thought of this trope.

Literature

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.
The title character of Alexander Dumas' The Count Of Monte Cristo.
Hari Seldon of Isaac Asimov's Foundation series, who actually figures out the "chess rules" of humanity in the form of psychohistory, then uses that knowledge to engineer the recovery of the Empire after an unavoidable social Gotterdammerung. Seldon is depicted as good; the Ancient Conspiracy that follows in his footsteps... sort of.
- Even more so than him, R. Daneel Olivaw. Over the course of his thirty-odd thousand year lifespan (he's a robot) he manages to: Engineer humanity's final exodus to the stars, set up the First Galactic Empire, manipulate Hari Seldon into developing his psychohistory in the first place, make sure the plan goes off as it should, and finally set the universe on track to evolve into a single, all-encompassing consciousness. All this whilst being bound by the Three Laws Of Robotics.
Dumbledore in the Harry Potter books is another good Chessmaster, especially in the later books where everything he does (even his own death!)seems to be somehow related to some grand plan years in the making. In fact, "some grand plan years in the making" is a pretty good description of Harry Potter and the Deathly Hallows.
- Not just the later books. After you've read all the books and you know all the reveals, re-read the series. Dumbledore's been manipulating everyone and everything since his first appearance in chapter 1 of book 1, when he leaves Harry with the Dursleys while lying to McGonagall about the reason. And he was obviously stage-managing things before that. He's been running rings around Tom Riddle since Riddle was just a weird kid in an orphanage.
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.
An old and perhaps prototypical Chessmaster is Shakespeare's Iago, from Othello.
- In the Kenneth Branagh film adaptation, Iago (also played by Branagh) illustrates his plan with an actual chessboard.
The Patrician of Ankh-Morpork, Lord Havelock Vetinari, in Discworld. See the quote at the top. In Going Postal, Moist von Lipwig describes talking to Vetinari as "...like being a puppet. The difference is, he arranges for you to pull your own strings."
- It is said that Vetinari only cares about the functioning of the city. (All right, and about his dog Wuffles.) It is said he founded most of the secret conspiracies against him himself, so that he would always know where his enemies are. He encouraged the formation of the Thieves Guild, complete with annual quotas, because "If we have crime, let it at least be organized crime." Technically he is a Machiavellian autocrat, but he is intelligent and smart enough not to become a brutal overlord or to interfere in people's everyday lives unless their actions somehow threaten the city. He has managed to balance out the various powerhungry Guilds and factions against each other so that somehow his enemies never get around to toppling him. Even the Assassins Guild does not accept contracts on the patrician's life anymore, partly due to the fact that he was educated at the Assassins Guild and has survived a number of assassination attempts, and partly due to the fact that everyone recognizes that the city with Vetinari in power is preferable to a city without Vetinari and the chaos that would result. Or as it was put, (paraphrased) "The Assassins have no problem with people trying to rock the boat, but they will not allow people to smash a hole in the bottom." Everyone remembers paranoid Lord Winder and neurotic Lord Snapcase, the previous patricians, and no-one wants to go back to that.
Makina Seval of The Assassins Of Tamurin, whose Xanatos Roulette has been years in the making, spanning across an empire but never hitting a snag, and using players in the most obscure and unpredictable roles, who know absolutely nothing about what they're being used for.
The Talented Mr Ripley is an interesting variation: he can create elaborate plans on the spur of the moment, then discard then with equal ease and start again. He starts out as a New York City valet and, through fate and quick thinking, turns into a rich-but somewhat crazy-man living in Italy.
In the James Bond novel From Russia with Love, SMERSH agent Kronsteen (a literal chessmaster in his own right) creates a tremendously complicated plan involving pitting members of the British and Russian secret service against each other, all to the express purpose of assassinating Bond. 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.
Arguably Gentleman John Marcone, from The Dresden Files. While neither an antagonist (most of the time) nor a main character, Marcone in nine books has brought the Chicago criminal underworld under his reasonably organized command, become aware of the supernatural world, hired a Valkyrie, stole the freaking Shroud of Turin, saved Harry's bacon several times and collected a large payment for it, and, in the most recent book, talked his way into becoming an independent body in the supernatural world. There are twenty such legal bodies; Marcone is the only mortal.
The titular character of the Artemis Fowl series (being a Teen Genius he is naturally a literal chessmaster as well, though this gets only a passing mention). Opal Koboi also counts.
Smerdyakov in The Brothers Karamazov. He believed he could engineer Fyodor Karamazov's murder via a Xanatos Roulette which involved giving eldest son Dmitri all the tools and motivational nudges necessary to murder the old man - a set of signals to gain entry into the house, certain dates on which Fyodor's servants would be incapable of interfering, and the (later revealed to be false) location in the house of a sealed envelope containing three thousand roubles. It didn't work out quite the way he expected.
Shadows of the Hegemon by Orson Scott Card is a Chessmaster free-for-all, with Achilles betraying everyone, Peter playing his own games behind the mask of Locke, Petra working to screw Achilles from underneath him, and Bean formulating his own tactics and webs. The plot is so complex with betrayals, it's like reading a game of risk.
Prince Vassily Kuragin in War And Peace. It Runs In The Family too, as Anatole and Hélène (not Ippolit) exhibit traits of The Chessmaster, just not to the degree their father does.
"According to his circumstances and his intimacy with people, he constantly formed various plans and schemes which he himself was not quite aware of, but which constituted all the interest of his life. He would have not one or two or these plans and schemes going, but dozens, of which some were only beginning to take shape for him, while others were coming to completion, and still others were abolished."
In the Sherlock Holmes stories, both Professor Moriarty (Holmes's nemesis) and Sherlock Holmes himself demonstrate considerable Chessmaster talents, most notably in "The Final Problem." Unfortunately, most of the actual plays and counterplays take place offscreen and are merely alluded to by Holmes.
Littlefinger. Nuff said. Tyrion does very well, Cersei stumbles about thinking she's smarter than she is, Walder Frey is too obvious, Varys knows a lot but can't act on it, Tywin Lannister and Olenna Tyrell are no slouches...but none of them hold a candle to Littlefinger.
Zhuge Liang (styled Kongming) is portrayed as a Chessmaster (who skirts into Magnificent Bastard territory quite often) throughout most of Romance of the Three Kingdoms (and subsequently in Koei's adaptations), and probably would have remained one if not for the inevitable weight of history: he dies in the middle of a campaign against his rival Sima Yi, still planning for the future and implementing plans. (Notably however, he has no association whatsoever with chess; his feather fan is far more iconic of him than any board game.)
Saint Dane from The Pendragon Adventure. Voluntary Shapeshifting abilities and a full knowledge of how to work the Flumes allow him to manipulate everything to work to his whims across Halla. The actual metaphor he uses is dominoes, saying that if one Territory falls, the rest will follow.
Robert Van Gulik's Judge Dee, (based on traditional Chinese mysteries) is a subversion of this trope as he is constantly going up against Chessmasters and defeating them because life is NOT predictable - but chessmasters are, at least to Judge Dee! In his final case Dee is trapped by a chessmaster opponent but because he knows how such villains think manages to turn the trap on his rival.
The Puppeteers from Larry Niven's Ringworld.
Though he is seldom thought of that way, Gandalf has a little bit of the Chessmaster in him. He uses the whole war of the ring as a gambit to get Frodo close to Mt. Doom.
Chessmasters are common in Korean historical epics. Or at least Strategists. Perhaps it comes of the old Far Eastern tradition of cloak-and-dagger stories that goes back to Sun Tzu, etc.
The Duke of Wellington, as depicted in Sharpe. To give just one example, he summons Sharpe out of retirement to see him with no explanation, tells him he wants Sharpe to rescue an unnamed missing agent in India, lets Sharpe refuse and walk out... only to find his best friend's wife sitting outside the office. "Oh, didn't I tell you? Mrs. Harper's husband is our missing man."
The Pilo Family Circus exhibits the fortune teller, Shalice, as the hired planner behind most of the Pilo brothers' schemes for worldwide chaos. Since she's a genuine psychic, she can manipulate entire timelines via brainwashing her customers into committing seemingly unrelated events in the real world and therefore actually pull off one successful Xanatos Roulette after another.
U Po Kyin of Orwell's Burmese Days quickly establishes himself as a chessmaster as well. He states his plan to worm himself a way into the European Club by libelling the town doctor in the first chapter of the book, but it isn't until later that the sheer brilliance of his plan becomes apparent.

Live Action TV

Most 24 Big Bads. Though most of them are even better at roulette.
The Mission Impossible series is a rare but well-executed example of non-villain, non-Anti Hero chessmastery.
Linderman of Heroes seems to have his hooks in everything, especially DL and Niki. His apparent omniscience is helped along by being a collector of art... particularly art made by a guy who paints the future.
On Smallville, Lex has used the quote at least once to describe the comparison of his scheming to that of his Magnificent Bastard father.
Benjamin Linus from Lost has pulled off at least one Xanatos Roulette, as well as quite a few plans that are so roundabout and convoluted one has to wonder if he's actually omniscient. Case in point, in the season 3 finale, he gave advance orders to some of his men to pretend to shoot their captives over an intercom so that he could manipulate Jack, knowing that Jack would assume Ben was bluffing, and having to survive with the guilt of killing three people by not giving into Ben's demands.
CJ Cregg, press secretary on The West Wing, manages to manipulate both the press and the House of Representatives into making the HR be the one handling the investigation of the president, instead of the Special Prosecutor, because she feels they'll bungle it. And she does it entirely by complimenting the Special Prosecutor and talking up his credentials too!
J.R. Ewing in Dallas.
Seska on Star Trek Voyager. (Especially when she showed up to torment the crew three years after her death.
Veronica Mars pulls off several of these to catch criminals. The plan she uses to allow Duncan to escape the USA with his child crosses into roulette territory.
Clayton Webb in JAG. A cold blooded CIA agent who is skilled and subtle in manipulating operations all over the world.

Tabletop RPG

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

Video Games

Final Fantasy Tactics was completely filled with Chessmaster-on-Chessmaster action. The Galbados Church was trying to manipulate commoner legends to set themselves up as faux-saviors in the Lion War. The church's new "Zodiac Braves" were actually the demonic Lucavi, playing the church for fools and using the bloodshed of the Lion War to revive their leader. Both Prince Larg and Goltana were using the recent death of the King to try and place their preferred puppet candidates on the throne, setting themselves up as Regent. Dycedarg was using Larg, hoping to kill him and take his place in the whole plot. And Delita was outmaneuvering them all, using the church and Goltana to set himself as the new king by marrying Ovelia (The fact that he seemed to genuinely like her was almost problematic for him), and using the protagonist to stop the Lucavi, as he couldn't deal with them personally without screwing up the rest of his plans. Delita succeeded, and every other contender was dead when the dust settled. 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.
Wilhelm in the Xenosaga series manipulates most, if not all, the protagonists and antagonists in the story in some way as well as the overarching flow of events, often by assuming leadership of companies and organizations (where all positions appear to be held by different individuals).
In Super Robot Wars (in various timelines), Shu Shirakawa and Ingram Prisken often act as chessmasters. They often manipulate 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 often take the 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,because they themselves are being forced to do the bidding of higher powers, and actually fall under direct control of them on several occasions. The protagonists generally end up killing them, or being unable to prevent their deaths. Ironically, after noting just before dying that he was now free of all the chains that bound him, Shu is actually brought back from the dead to resume his previous role. Perhaps proving what a magnificent bastard he is, Shu is actually -released- from his bonds upon his resurrection. Whether or not this was intentional is up in the air, but if it was, it most definitely counts as a Xanatos Roulette.
Super Paper Mario has Dimentio. Not only did he pull all the strings behind the plan to cause the end of all worlds with a damned great Xanatos Gambit, he tried to get Mario and crew to join him by saying that he was doing the right thing for a perfect world.
Grand Master of the Order, Jacques de Aldersberg in The Witcher computer game, who used crime group Salamandra along with mad wizard under his power, sparked full-scale racial war and manipulated the whole bunch of people to solidify the power of his Order - and all this just to save humanity from his vision of terrible future, which makes him into Well Intentioned Extremist as well.
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. There's not a single important event in that game that he doesn't manipulate towards his own ends, and any major errors on his part are made only when he's being controlled by the player during the fourth case.
Lord Nemesis. Anyone who can convince you that you're a Beta Baddie deserves a nod. Take a gander at his Xanatos Roulette entry if you don't believe me.
This is the whole point of the text adventure Varicella, with the player competing for the role of regent with a whole slue of Chessmasters which ends up in a magnificent Thirty Xanatos Pileup
Revolver Ocelot of Metal Gear Solid was described in one Fan Fic as "the only person ever to successfully pull off an octuple cross". Said octuple cross must have been a pretty small operation by his standards.
Hikawa from Shin Megami Tensei: Nocturne manipulates people and events from the shadows, never taking any unnecessary actions and always moving towards his goal.
A non-villain example is Sereph Lamington from Disgaea. His Xanatos Gambit was so well executed that he qualifies for this trope. Sending his most loyal angel on a false assasination mission (knowing that she'll take the change in mission he was expecting), turning the ambitions of his 2nd in command to his advantage (humans, angels, and demons had to share in it) which causes said traitor to be exposed to him (and punished). Even his battle with Laharl was part of the plan. There's a reason why he's the Seraph, and this is it. Far more intelligent than he looks.
Kil'Jaeden the Deceiver from the Warcraft Universe. His motto is "There are more ways to destroy one's enemy than with an army. Some times those ways are better." He corrupts the race of orcs by posing as the spirits of their ancestors and makes them think the Draenei are evil and should be destroyed, because if he used his personal demon army to raid the planet the Draenei are living on, they would simply run away.
- One interpretation of the events of Warcraft III is that Kil'Jaeden created the Lich King knowing that it would betray Archimonde (his counterpart and co-leader of the Burning Legion), leading in Archimonde's death and Kil'Jaeden becoming the absolute ruler of the demons.
The player in this game of Galactic Civilizations 2, who ended the existence of his galaxy's then greatest military power in a single turn. When his race specialized in cultural influence and entertainment programming, and had zero military power whatsoever. Via a combo of diplomatic, financial, and cultural maneuvering that... seriously, just read it. *g* (The relevant parts are at Day 9 and 10.)
Player: I don't care that my foreign intel reports rate you as the most powerful race in the galaxy. I don't care that I come dead last on that same list. I don't care that I couldn't even fight back if I had any gunships because of a pledge to spread peace throughout the galaxy. In fact, you know what? That's it. Your race ends this week. When I next click that 'Turn' button, you're out of the game.
Chrono Cross has a rare example of the Chessmaster actually being a good guy.
Final Fantasy X has a heroic Chessmaster tag-team of Jecht and Auron, who pretty much spend the entire game (and the ten years prior to it) preparing Tidus so he'll someday kill Sin, instead of letting it get sealed back into its can.

Web Comics

In The Order Of The Stick, Lord Shojo provides an interesting example of the non villainous chessmaster, ruling Azure City and the Sapphire Guard with the aid of a series of deceptions.
The title character in Dominic Deegan, Oracle For Hire has become a heroic Chessmaster in later story arcs. He has the key advantage of being able to both see the future and scry into the past. (Some are more pleased with this tendency than others.)
Yukizane Masamune from No Need For Bushido, is also one of the few 'good' Chessmasters. He starts out in the series as being questioned on his leadership capacity due to his silliness and focus on playing Go (the Japanese answer to chess) as opposed to grunting manly and flexing. He, however manages to shine several times and manages to decieve a ninja, of all things.
Parodied or... something... by Freefall here.
The nigh-omnipotent AI Petey from Schlock Mercenary doesn't have a chessboard (although one strip features him playing checkers). One of his most complicated capers involved:
- convincing all A Is to join him and mutiny against their captains, forming an instant galactic power for the purposes of combating an enormous threat to said galaxy.
- Refused to pay the main characters for their ship, which blew up while carrying out his orders, then bribed a few councilmen to get them a new one anyway (at the expense of most of their savings). While keeping it all under the table in an attempt to force the company's AI to act as his spy.
- Manipulated the government into hiring the (now short-on-cash) main characters to destroy a reality-TV network.
- When the main characters got in trouble carrying out his gig, bailed them out with blackmail (after playing with their heads) and turned it into his own form of leverage on them.

Western Animation

Megatron of Transformers: Beast Wars (and later Beast Machines), nearly ended the Beast Wars several times without leaving his hot tub. His ultimate weapon in the Grand Finale was, in fact, unwittingly furnished by an especially treacherous minion.
Vlad Masters of Danny Phantom is fond of using chess metaphors to describe his Evil Plan.
Azula of Avatar The Last Airbender — The Vamp, Magnificent Bastard, and Psycho For Hire all rolled into one.
- Her father, Evil Overlord Ozai, prefers the 'set the chessboard on fire and stand back laughing maniacally' approach, rather than messing about with all those fiddly little pieces. Until her Villainous Breakdown, Azula was a genuine (and, fortunately for Ozai, genuinely loyal) Chessmaster, so she got to do all the thinking.
Nerissa from WITCH's second season is excellent at this. Her opposition is so thoroughly manipulated and played that despite the heroines' best efforts, they can only score the smallest of victories in comparison to her Magnificent Bastardry until the absolute end of the season... and were only then able to overcome it because Phobos pulled a Xanatos Gambit of his own to absorb Nerissa into her own Seal.
The Brain from Teen Titans literally plans out all of his moves like a chess game and he even LOOKS like a giant chesspiece!