The Chessmaster / Literature

Chessmasters in literature.

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• The 1632 series is bursting at the seams with these. Mention must be made of Cardinal Richelieu, who is just as good in the new history as he was in the old, and Mike Stearns, who is on the record as trying to set up a more long-term-successful series of gambits than Otto von Bismarck, the Real Life guy who created the modern state of Germany almost entirely with use of gambits and chessmastery.
• The Snake in Above Ground is a prime example, particularly because he can use magic to enslave others into doing his will.
• Regine in Addergoole — the school, and the students, exist to fulfill her plans.
• Kurt Vonnegut's All The Kings 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.
• Angel of Death:
  • Bavandersloth in pulled a pretty impressive gambit when he set fire to a police station to free Cody and kill detective Williams.
  • He's since been revealed to be planning something much bigger, though little is known about his new plan, save that it's objective is to turn the partial breaking of The Masquerade to the community of liches' advantage.
• Both The Ellimist and Crayak in Animorphs 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. At one point, the Ellimist 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 title 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.
• Makina Seval of The Assassins of Tamurin, whose Gambit 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 Balanced Sword has dueling chessmasters: the Big Bad is running an elaborate scheme with many moving parts, and the good guys' response is being guided by their Mysterious Backer, the wizard Khoros. Both are described at least once as playing battlesquares with human pieces.
• F. in Beautiful Losers is a master of political schemes and manipulation, and implies that he arranged major aspects of the narrator's life, such as his relationship with Edith.
• The Beginning After the End:
  • The leaders of both sides of the Divine Conflict, Agrona and Kezess, are dueling examples. Agrona is established to be a Manipulative Bastard who, in preparation for his invasion of Dicathen (a stepping stone in his war against Epheotus), established a comprehensive spy network that sowed the seeds of corruption among the Dicathian nobility which in turn would create a string of Les Collaborateurs once the invasion began. In particular, the dwarven kingdom of Darv had been so heavily compromised by his manipulations that it became effectively a puppet state of his even before the war ended. He is also able to take advantage of some of Arthur's own decisions and turn them against him in the long run. In particular, he takes advantage of the Beast Will Arthur gave Tessia, which came from a failed experiment of his, to control whether she lives or dies. He uses this knowledge to blackmail her parents into a Sadistic Choice where he lets Tessia die or they let in his forces into the Council Castle to kill Virion. They choose the latter, but Agrona has them both executed in the aftermath along with the Glayders to mark the end of his conquest. In addition, he was able to hide from Kezess his true plans in investigating the Djinn ruins using his mortal servants (not that Kezess could have easily done anything as it could have led the fact he committed genocide upon the Djinn being exposed in one way or another). In turn, this tied into his research into fate and reincarnation, which culminated in him summoning the Legacy, a Person of Mass Destruction whom he intends as his ace in the hole in his war against Epheotus, using two other reincarnates that he already summoned as anchor points.
    Arthur: I don't think you know half as much as you pretend to. If you'd understood any of this before Cecilia's reincarnation, you would have had Windsom kill Tessia, or Nico, or even me. How has Agrona gotten so far ahead of you?
  • As for Kezess, while he ends up being taken aback and outmaneuvered by Agrona's schemes (as indicated by the above quote), he does have his moments. Case in point, after orchestrating the destruction of Elenoir in a futile bid to prevent the Legacy from being summoned, he reestablishes contact with the Dicathian resistance. He gives them a new set of magical artifacts that he claims will help them defeat the Agrona and Vritra, but in truth would enslave them to his will. On top of that, he forces Virion, the former King of Elenoir and the leader of the resistance, to lie to his people about what is really going on. When Kezess's scheme is exposed and Virion turns against him, Kezess decides to wipe the slate clean by having Aldir kill off the Lances separately while Taci exterminates the rest. However, thanks to Aldir's wavering loyalties and Arthur's timely intervention, his gambit fails. Later on, he summons Arthur to Epheotus to negotiate with him regarding his place in the impending war. In the process, he attempts to use a Magically-Binding Contract on Arthur to extract what he knows about aether in return for securing Epheotus's protection against Agrona and the Vritra, but Arthur is able to reverse the deal so that Kezess is beholden to keep his word rather than vice versa. However, Kezess does take advantage of their deal to send his forces to occupy Dicathen while Arthur was stuck in the aether realm for two months trying to resurrect Sylvie. While this does mean Dicathen is secure from Agrona launching a counter-offensive for the time being, Arthur knows that Kezess's tyranny is no better than Agrona's. On top of that, Kezess's intervention makes it harder for him to openly ally with either Seris or Mordain against Agrona, the former for being Vritra-blooded and the latter for being Kezess's former friend whom he had exiled for going against the genocide of the Djinn. Both Agrona and Kezess, in their game of chess against each other, reveal themselves to be callous manipulators with little regard for the lives of mortals whom they view as completely expendable.
    Mordain: Kezess is ancient, and he has played this game many times before in Epheotus, with much greater stakes than now. Or, at least that is the case so far as he is concerned.
  • Seris Vritra turns out to be one of these, on top of being a Bastard Understudy. She was never loyal to Agrona and the Vritra as she realized they viewed their Alacryan subjects as completely expendable in their war against Epheotus. As such, when Arthur, whom she had taken an interest in during the war as a potential wild card, ends up in Alacrya, she begins acting as an Anonymous Benefactor to him. She gets him acquitted of the Kangaroo Court he was stuck in, gives him asylum in her domain of Sehz-Clar, and grants him favors that allow him to navigate the Alacryan social hierarchy. After Arthur proceeds to humiliate Agrona and the Vritra at the Victoriad, Seris begins setting in motion a rebellion against the Vritra. She captures the Sovereign Orlaeth and holds him hostage to drain his power. Once Arthur foils the Siege of Vildorial and destroys a secret encampment in Vechor, she openly launches her revolt. She even has her protégé Caera travel to Dicathen in order to reestablish contact with Arthur and secure Dicathen's aid in the revolt. When Agrona sends the Legacy after her, she humiliates her by tricking her into overloading her mana core and destroying it, on top of executing Orlaeth and broadcasting the deed to all of Alacrya to show that they can make the Vritra bleed. Afterwards, she goes into hiding in the Relictombs, where it is revealed she prepared for such a possibility by not only making sure she had enough supplies and infrastructure down there, but by cutting off all possible entrance points that Agrona could use to enter the Relictombs and discover where she is hiding.
• Cobinian, the villain from Dave-Brendon de Burgh's Betrayal's Shadow, is a good example. He's adept with using people as pawn in his mind games and strategies but is also skilled with Xanatos Speed Chess and Batman Gambits. His "father" is also seems to have a knack for it.
• Mr. Guppy of Bleak House WANTS to be a chessmaster, but his plains fail due to lack of opposition.
  "Mr. Guppy suspects everybody who enters on the occupation of a stool in Kenge and Carboy's office, of entertaining, as a matter of course, sinister designs upon him. [. . .] he in the most ingenious manner takes infinite pains to counterplot, when there is no plot; and plays the deepest games of chess without any adversary."
• Abbess Glass from Book of the Ancestor is a heroic example: her ultimate goal seems to be to root out corruption from the church and the empire she lives in. Examples of her scheming include turning her own trial for heresy into an opportunity to expose the misdeeds and impeach the sister of the emperor in her own home. She does this in part by her superior knowledge of church laws, allies she has set up years in advance and even tricking the the emperor's sister herself to submit herself to the trial.
• Breaking Providence: Volupa, a Dark General who worked for the previous Dark Lord, spends a decade working as the Pope's loyal Shadow. In that time, she assassinates several troublesome nobles and clergymen (on the Pope's orders no less), ensures a specific letter reaches another Dark General, arranges for the current Destined Hero (who's also the Dark Lord) to overhear the Dark General has been sentenced to be raped to death, and aids the crown princess in obtaining her independence while also cementing herself as the girl's one true ally. In the end, she helps the princess force her mother to Ascend to a Higher Plane of Existence and dispose of the Pope so the princess can become queen. All of it done so that the Dark Lord could easily take control of the Empire now that the only person in power left is a girl madly in love with him.
• Smerdyakov in The Brothers Karamazov. He believed he could engineer Fyodor Karamazov's murder via a Gambit 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.
• 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.
• Hannegan from A Canticle for Leibowitz played everyone and their dog to do exactly what he wanted them to do, leading to his complete hegemony. It's strongly implied the empire he built is one of the two world superpowers from Fiat Voluntas Tua.
• Aleister Crowley of A Certain Magical 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 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.
• Essentially, the murderer in any Agatha Christie novel. One of her most manipulative murderers would undoubtedly have to be the judge from And Then There Were None, who plays off the psychology of each victim especially Vera Claythorne.
• The Chronicles of Amber: In The Chronicles of Merlin, Merlin in his travels encounters Dworkin and Suhuy playing chess, and during their game making commentary on current events in the timeline using chess metaphors.
• The Chronicles of Prydain: Arawn the Death Lord, is such a 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...
• Chung Kuo has a Go master, Howard deVore, who compares manipulating people to placing pieces on the Go board.
• '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.
• Though Codex Alera has these in spades, the ones who actually use 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. 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 when he conspires with the Cane to raid Alera to distract attention from his rebellion. He expects them to bring a few hundred raiders. They bring thousands and have no intention of leaving.
• The Continental Op of Dashiell Hammett's Red Harvest. He is hired by a man who is killed before he can give The Op the case, and to deal with this fact, the Op joins every gang in town, convinces each one that the others are playing against them. He almost gets killed, gets everyone else killed, and ends up framed for murder in a way that works out for him. The man was the inspiration for the samurai film Yojimbo which was later adapted into a western, A Fistful of Dollars. Makes you wonder if Dashiell Hammett had this planned from the start...
• John C. Wright's Count to the Eschaton: In The Hermetic Millennia, Larz's story where he claims to have seen Menelaus confront D'Arago has D'Arago argue that he's got the same enhancement as Menelaus, and Menelaus countering that he's still sloppy, while Menelaus plans out checkmate twenty moves ahead.
• Iain Banks's The Culture: The Player of Games: A very complex strategy game is both a metaphor for the conflict of two civilizations, and crucial to a real-life struggle; the protagonist is being manipulated, though the identity of those pulling the strings remains shadowy.
• 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.
• The Dark Forest: Zhang Beihai who, along with his father, predicts the future development of human society under sophon lockdown and successfully executes a centuries long plot to ensure that at least some humans escape.
• Rahze el'Dax in Dark Heart, despite his impassive, detached manner, is disturbingly good at manipulating people into doing his bidding. He nudges Shial and Kail into falling in love to fulfill a prophecy, although Kail is certain it would have happened even without his interference.
• Darren Shan's The Demonata series has a heavy chess theme running throughout, and several characters probably qualify for this trope, but none more so than Lord Loss, the Big Bad of the first four books and later The Dragon to the Big Bad of the overall series. In terms of literal chess, he's obsessed with the game, and only ever beaten rarely. Figuratively... he shines most in the very last book, where he manages to trick Death itself by conspiring with Bec, one of the heroes. The result? Every other demon master except him is wiped from existence, whereas he is allowed to remain 'till the end of time, unmolested by the Kah-Gash, doing what he loved doing all along. Which also makes him a Karma Houdini par excellence.
• Discworld:
  • Lord Havelock Vetinari, Patrician of Ankh-Morpork and all-around Magnificent Bastard, is an amazing chessmaster ("It's like being a puppet, only he gets you to pull your own strings"). In Going Postal he gets his very own not-quite-chess metaphors, getting into a little discussion with Corrupt Corporate Executive Reacher Gilt on the merits of playing the two sides in Thud. According to The Discworld Companion, Vetinari, in addition to being a Thudmeister, is also a Grandmaster at Stealth Chess, where some pieces are not necessarily where they appear to be.
  • The Discworld's gods have got their own game-board (though it's not actually 'chess', per se), on which the pieces are the mortal residents of the Disc (and thus literal pawns in the games of the deities). That said, they also suffer from Immortal Immaturity, leading to one book sayin g the gods' preferred type of game is Snakes & Ladders with greased rungs.
• Rosenmaester, the Big Bad of the eponymous novel in the Distortionverse series. Not only he prepares a Plan-A and B to take into account interferences from the protagonists, but also incorporates them in his plans. When he openly confronts Vortag Schlieber and ONE, he shoots and kill the girl believing she is a gynoid to prevent her from recording his face. Then, he succeeds in setting up a strategy to kill four million people and direct all the blame on Vortag. He's actually able to exterminate a whole city, but gets killed as well, after being infected by his own blood-sucking flowers. The reason of his failure? A counter-trick enacted by the real ONE, who completely outsmarts him.
• Steven Brust's Dragaera: The 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.
• Paladine, in the Dragonlance Chronicles, but especially in the Legends. In the former, he recruits and manipulates the Ragtag Bunch of Misfits into saving the world, while disguised as the senile pyromaniac Fizban. In the latter, he actually lets Raistlin kill him and destroy the world in an alternate future, so that when Caramon travels back in time and shows Raistlin said future, Raist finally repents.
• In the Dred Chronicles, Tameron, chief advisor to prison gang boss Dred, is always consciously trying to manipulate the people around him, including Dred. He prefers to work that way over trying to gain open control of the gang himself, and helped Dred taking over from the previous boss for that reason. Tam claims to have been a spymaster for a royal dynasty before getting shipped to the Prison Ship they're all on.
• Jim Butcher's The Dresden Files has many of these, as befits a mystery series. Of note:
  • Gentleman John Marcone. While neither an antagonist (most of the time) nor a main character, Marcone in eleven books has brought the Chicago criminal underworld under his reasonably organized command, become aware of the supernatural world, hired a Valkyrie, stole the freaking Shroud of Turin, saved Harry's bacon several times and collected a large payment for it, and, in White Night, talked his way into becoming a freeholding lord in the supernatural world, a singular entity not beholden to some greater nation or group. There are twenty such legal entities; Marcone is the only mortal.
  • Archangel Uriel, the ultimate spymaster compared to Archangel Michael's frontline general motif, has been known to get involved in things, make a tiny nudge and with one stone hit well more than two birds. Harry is his current stone. In the short story "The Warrior", Uriel gets Harry to save a child from being hit by a car, and Harry's questioning of a bruise heightened the mother to realize her husband is abusing her daughter, and the mother moved out the next morning, then Harry stopped a man from working at a construction site while intoxicated (by using magic to break the equipment for a short while) which saved the man from an accident his intoxication would have led him to and eventually the death of his daughter by leukemia and the father the only viable donor, inspired a girl with low self-esteem that by being there and listening one can make people better and now she will become a counselor to help others, and lastly, Harry's good friend Michael was saved because Harry stopped him from killing a man in his rage after the man strapped a bomb to Michael's daughter to obtain holy swords in Harry's custody, and justified his action as it being God's will.
  • Nicodemus Archleone, host of Anduriel, Uriel's Evil Counterpart. His plans are the focus of multiple books. He almost always has a backup plan or makes one up on the fly. Even if his plans are thwarted, he usually has a winning outcome.
  • Mab, Queen of Air and Darkness always plays the long game, manipulates Harry multiple times, and often comes out on top in the end, even if it takes multiple books to do so.
  • Norse god Odin is still around and is still the powerful knowledge broker. He successfully manipulates Harry into destroying the ancient evil empire of the Red Court, which held Harry's daughter (whom he only learned existed a day or two prior to this meeting). It is only after Harry does that, did he realize Odin gave him all the knowledge he needed and pointed him in the direction to attack.
  • The White Court of vampires prides itself on being this. They loathe direct confrontation, so they fight by manipulating others into combat. During White Night, Lara Raith doesn't have any direct hand in House Skavis, one of the great houses of the Court, killing weak female practitioners as she notes the leader of that house had that idea for several centuries nor does she encourage the other House from trying to steal their thunder, but she uses it and Harry Dresden to wreck the plan and bringing it to the open, which destroys all credibility the plan has.
  • In later novels, Harry himself, despite being more of a Guile Hero, proves that he's capable of Chessmastering with the best of them. In Turn Coat, he lets it be known that he's got Morgan (currently with a price on his head) on the island Demonreach. This draws the Wardens to the island to arrest Morgan, but it also lures in the other supernatural forces moving to collect on Morgan's bounty, including the skinwalker that's been stalking him, and thus forces the Wardens (who think Harry is bad news) to team up with him to fight all the others off. But then it turns out that even that was just part of Harry's real plan, which was to identify the mole within the White Council of Magic. Harry knew the mole would show up as well, to make sure that Morgan took the fall, and was able to get indisputable evidence to present to the Council to clear his name, Morgan's name, and flush out the mole. "Wile E. Coyote, suuuper genius," indeed.
• Frank Herbert's Dune is filled with them, each with varying levels of skill and subtlety.
  • The Emperor and Great Houses are constantly attempting this to build their power base.
  • 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.
  • Paul Atreides through the first three novels fits this trope to the point that even when he's blinded half-way through the second book, he is still able to "see" because he has so perfectly predicted the future that he is essentially just going through the motions. His plans are ultimately upset by his son, Leto II, who shares his father's prescient abilities but is willing to take the path that Paul refused to follow.
  • God Emperor Leto II 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. In fact, he was so good at the "game" that he grew bored and craved surprises.
  • The Bene Tleilax also get a lot of this in Dune Messiah and Heretics of 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.
• 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. In the real world, he deliberately singles out specific individuals in order to manipulate them and create chaos for everyone involved- all for the sake of his amusement. This is illustrated by the fact that he represents the events around him through an odd mix of of board games (including chess, among many, many others). Meaning he sees the characters as literal pawns. Not helped by the fact that he also happens to be a Psychopathic Man Child with a habit of setting his pieces on fire.
• "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).
• 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). 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.
• The Empirium Trilogy: The Prophet has been manipulating events behind the scenes for years. They were the ones who orchestrated Simon becoming Corien's right hand man, Eliana being captured by Corien who they knew would use mind-speak to break her, and that her metophorical rebirth would allow Simon to create a portal into the past for Eliana to travel through.
• In the Erebus Sequence, the Majordomo lacks the resources of a noble House, but is sufficiently good at politics (and has sufficiently numerous spies) that he holds authority anyway. In the second book, he continues to be good at manipulation despite supposedly being dead.
• 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.
• Fablehaven: Referring to The Sphinx's plans as a game of chess is mentioned several times in the series.
• 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. National Security Adviser Robert Chamberlain from Act of War plays everyone in his quest to kill Harold Kingman.
• 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.
• In The 5th Wave by Rick Yancey, Commander Vosch is so good he gets human teens to kill the rest of humanity for him. Without them knowing. Ringer also seems to be quite The Chessmaster in training.
• The Folk of the Air: General Madoc is skilled at manipulating events in his favour, such as planting ideas to trick opponents into acting in a certain manner that he wants or secretly plotting against them for his own ends.
• Isaac Asimov's Foundation Series:
  • Hari Seldon figures out the "chess rules" of humanity in the form of psychohistory, equations that describe humanity's responses to stimuli, making him able to predict the future. He then realizes that the Galactic Empire is facing an unavoidable social collapse, so he uses psychohistory to engineer civilization's recovery within only one thousand years. His skill at manipulating people is shown improving over the course of Forward the Foundation, he maneuvers Chief Commissioner Linge Chen into giving him exactly what he wants during "The Psychohistorians", and for most of the subsequent stories, he's left a recording where he explains what he's predicted would happen. The one time his predictions go wrong creates In-Universe panic.
  • The Second Foundation, an Ancient Conspiracy that inherits Seldon's psychohistorical tools, continues to refine and expand the Seldon Plan, enacting a series of Xanatos Speed Chess moves to reassert The Plan when the events of "The Mule" disrupt it.
  • R. Daneel Olivaw, over the course of his twenty-odd thousand year lifespan (he's a robot), manages to build a Genuis Loci that will eventually encompass all of humanity/galaxy, encourage the development of psychohistory to design the most peaceful outcome for humanity, and trick a Transhuman child into allowing a Grand Theft Me so that he can make sure his plans work the way he wants them to. He's driven by the Three Laws Of Robotics, and especially the "zeroth law", which forces him to judge individual human life against harm to humanity. Most of his work can be summarized as trying to prepare a method of objectively determining the currently nebulous concept of "harm to humanity".
• Ayn Rand's The Fountainhead: Ellsworth Toohey, the journalist, critic, and social activist, is also the main villain. 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.
• Get Shorty's Chili Palmer is a low-end Chess Master, though the point of the story seems to be that it's not so much because he knows chess as because he's mastered the one particular strategy that none of the other players are prepared for.
• The Great Greene Heist: For most of the book it seems that Jackson is plotting to rig the voting machines. Actually, he's running a Long Game to manipulate Keith into getting caught trying to counter Jackson's supposed tampering.
• In Kristen Britain's Green Rider during the final showdown, the protagonist is abruptly yanked away from the action and sees the battle as an elaborate game of that 'verse's equivalent to chess, which is played with 2-4 players. The chessmaster villain invites her to sit and play, as it is the only way for her to break the stalemate and save her friends. Instead, she smashes the chess board with her sword, causing enough magical backlash to win the day.
• Harry Potter:
  • Ron Weasley is a literal "chessmaster" and his abilities on the wizard's board leads Harry onto Voldemort's trail in Harry Potter and the Philosopher's Stone. Not least, they both demonstrate an exceptional chess move: they realize that the best way to win the game is to sacrifice themselves like a pawn, so that the hero can win.
  • Dumbledore's Back Story includes being the most powerful wizard in England and Europe, but it is his tactical abilities that drive most of the series' plot. 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. Dumbledore had to change his plans when he confirmed that Voldemort had created horcruxes, and this was at the end of the second book. Despite already having theories years in the making prior to that discovery, he only made confirmed active moves to find the horcruxes in the sixth book. While he was uncertain of what Voldemort had done in years prior, he did a lot of research on his history and personality to finally vanquish him. Some state that Dumbledore manipulated Harry, however, other argue that he did not. They believe he gave Harry a choice to live or die, and only put Harry with the Dursleys to protect him with the blood connection, rather than having ulterior motives. Dumbledore also suspected Harry was truly safe from Voldemort at the end of the fourth book when Voldemort took Harry's blood. In book six, 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.
  • 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 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 disregarding the prophecy.
  • The primary antagonist of Goblet of Fire, Barty Crouch, Jr., manages to plan everything out beforehand, helping Harry and devising ways for Harry to win each Task, but also manages to outplay Dumbledore. The only factor that thwarted his ability to kill Harry is Voldemort, who loses badly enough that Harry manages to return to Hogwarts and the safety of Dumbledore.
• Hive Mind (2016):
  • Keith's plans to make Amber and her team miserable involve a large amount of planning and preparation with multiple plans going on at once.
  • Amber specifically thinks of Ryne with those words, after seeing how he has manipulated both Adversary Aura and Hive England to get what he wants out of the investigation.
• In the H.I.V.E. Series, the group that the heroes work for is called G.L.O.V.E. In a surprise twist, it's actually being run by Overlord. Rival faction H.O.P.E. takes some of our main characters hostage, and it's revealed that this group is also being run by Overlord. Then, a new group of villains emerges — the Disciples! They seem to be completely different and new — until it's revealed that they are also working for Overlord. Every character who appears for more than three pages and is alive at the beginning of the series works for him at some point.
• The Hostage Prince by Jane Yolen and Adam Stemple features the Chessmaster Jack Daw, who is the only one kind to the hostage prince, Aspen, for many years, and then convinces him that he's about to be assassinated. Aspen runs back to his home kingdom, only to discover that he was actually safe, Jack Daw had lied, and now the two realms of Seelie and Unseelie must go to war because he ran away.
• A few examples in How a Realist Hero Rebuilt the Kingdom:
  • King Souma and Prime Minister Hakuya usually work together as one, trying to manipulate situations behind the scenes to get people with an advantage over them to fall for traps. This allows them to relatively easily end the rebellion by the Dukes, consolidating power in the Kingdom of Elfrieden, and win the war against neighboring Amidonia.
  • Princess Roroa of Amidonia outplays Souma and Hakuya, setting up a complicated trap in the aftermath of said war that they're forced to annex the entire country of Amidonia, which just a few weeks earlier considered Elfrieden mortal enemies.
• From Peter F. Hamilton's Humanx Commonwealth novels, we have The Starflyer. 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 everywhere you look. It takes most of two books for all of the good guys to become convinced that the Starflyer even exists. It doesn't appear on stage until near the end of the second book... the only clues to its existence are the behavior of its agents.
• Illuminatus!: Hagbard Celine.
  "You are the Beethoven, the Rockefeller, the Michelangelo of deception. The Shakespeare of the gypsy switch, the two-headed nickel, and the rabbit in the hat. What little liver pills are to Carter, lies are to you. You dwell in a world of trapdoors, sliding panels, and Hindu ropetricks. Do I suspect you? Since I met you, I suspect everybody."
• Lady Cassandra Blackthorne from the Inferno Series is shaping up to be this. When she argues her case before the Elder Council she implies that House Blackthorne is full of chessmasters.
• 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.
• Jeeves and Wooster: 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.
• Journey to Chaos:
  • A Mage's Power: Everything went as Tasio directed. He arranged for Eric to meet Annala and join the Dragon's Lair. He worked with Basilard to engineer a Darkest Hour that would force Eric into action. He removed the sound-proof runes from Tahart's apartment so Eric would hear Annala's cry. Even Selen's Evil Plan only unfolded as it did because Tasio incorporated it into his own.
  • Looming Shadow: Tasio hijacks the Evil Plan of the Big Bad Duumvirate to elevate themselves and kill Team Four into his own plan to continue forging Eric into the weapon of chaos that he needs while at the same time forcing Basilard to confront his heretical past.
• The Judge and His Executioner by Friedrich Dürrenmatt. Commissar Bärlach knew that his colleague Inspector Tschanz was a murderer, and manipulated Tschanz into pinning his own crime on a master criminal who couldn't be convicted by legal means, ultimately disposing of both of them.
• Judge Dee: Discussed in Murder In Canton, where the judge talks with the Big Bad suffering from this mindset. The judge realized he wasn't dealing with a player of Chinese chess (Go) where all the pieces are of the same importance, but the Indian-imported variant where pieces have different roles. He also points out that unlike chess, pawns have their own desires that wreak havoc on plans (in this case, the "queen" falling in love).
• In Carrie Vaughn's Kitty Norville series, Mercedes Cook is revealed as this through her manipulation of Arturo and Rick into a vampire war. The fact she in turn is working for/being manipulated by Roman only adds even more delicious levels of convolution...and since he is only stated to be a general in the Long Game, chances are there's an Omniscient Council of Vagueness out there manipulating everyone, which Kitty will inevitably have to face down.
• Fiona Khal, from The Lay of Paul Twister, prefers to think of the conflict between the Magi and the Dragons as a game of chess, though she puts an interesting twist on it...
  "And now you want me to work for you, against [the dragon who had hired Paul to steal from her]?" I asked, trying not to look too bemused. "It's a strange game, where Black and White both move the same pawn!"
  She laughed. "I've always lamented the lack of mercenaries on the chessboard. It would bring whole new levels of strategy to the game!"
• Knaves on Waves has both Sheridan and Jacques, who manipulate those around them through a combination of guile, seduction and fear. Jacques is a particularly interesting example, whose charisma pushes him towards Magnificent Bastard territory.
• Jonathan Stonagal is made to be this in the Left Behind series, particularly in the prequel books where he funds the Designer Babies project that creates Nicolae Carpathia, with the intention that he would be Jonathan's puppet to rule the world with. Unfortunately, Jonathan gets an Et Tu, Brute? moment when Nicolae murders both him and Joshua Todd-Cothran in a secret meeting where he appoints the ten subpotentates for the coming Global Community.
• Lester Leith delights in engaging in seemingly bizarre actions that throw off the cops who are spying on him, even when they are trying to think ahead of him. Every little move he makes helps ensure that he ends up with the loot and the police don't get any evidence.
  • In "Thieves Kitchen," he hires several ex-cons, supposedly for a get-rich scheme meant to disguise his latest theft, but really because he's gambling on them stealing the evidence the police could use to arrest him.
  • In "Put It in Writing," he insists on the police signing a letter giving him the right to sell two seemingly worthless items. He then uses those items for some Bluffing the Murderer Blackmail while producing the letter to make it seem as if the police are working with him and are willing to let the murderer go if they get paid. Then he tells the police to arrest the killer while the man is nearby with access to poison, causing him to commit suicide. When the police threaten to arrest Leith, he reveals that he's summoned a reporter who will arrive within minutes, and they can either take credit for solving the case or be humiliated when he waves around the letter they signed.
• Discussed in Lord Chesterfield's Letters to His Son. "A man who hath studied the world knows when to time, and where to place them; he hath analyzed the characters he applies to, and adapted his address and his arguments to them" (letter 163)
• The Lord of the Isles: The Demon Queen 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.
• 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.
• The Machineries of Empire: Shuos Jedao's brilliance comes from his uncanny ability to manipulate everyone on every side of the conflict into acting the way he wants them to.
• Magical Girl Raising Project has Pfle in Restart, who has experience in manipulating people and in fact manipulated 98 different magical girls to kill each other to protect Shadow Gale and herself.
• The Malazan Book of the Fallen begins when Shadowthrone sets his revenge plans in motion, and he keeps the position of resident reigning champion of long-term plans up to the end of the series, culminating in the freeing of the Crippled God, which needed decades, if not centuries to plan and involved a big chunk of the pantheon and the mortal players of the world.
• Troll king Thibault from Malediction Trilogy. He manipulates everyone around him, even his own son Tristan, he easily sees through his son's plots — and he has managed to keep power in the highly competitive troll society.
  Tristan: He'll [Thibault] have predicted that this conversation would occur. He'll know I'm down here by now, and he will be expecting us to take certain actions.
  Tips: Which actions?
  Tristan: I don't know. But I do know he will have planned for all contingencies.
• Dashiell Hammett's The Maltese Falcon: Casper Gutman and Brigid O'Shaughnessey are both opposing chessmasters who manipulate Sam Spade and a cast of minor characters in order to obtain the Maltese Falcon for themselves. Though in the end, they both fail.
• 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.
• Master Of The Game: 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 Mental State has the main character, Zack State. He has an uncanny ability to turn any situation to his advantage. He skilfully manipulates the prison system using blackmail and extortion. One by one, he identifies people who pose a threat to him and destroys whatever it is that makes them such a threat. He frames people, stages coups, lures his enemies into traps and constantly strengthens his own position, winning every time. By the end, he can comfortably go head-to-head with a criminal genius and eventually deconstructs his entire criminal network. It is only in the penultimate chapter that one realises just how far ahead he has planned.
• Lisbeth Salander of Stieg Larsson's Millennium Series, if she doesn't start as a chessmaster, certainly becomes one by the end of the third book. As an example, she encounters her half-brother Roland Niedemann, who has repeatedly tried to kill her. Now, she could just kill him, and thereby give the authorities cause to start pursuing her again. So, she doesn't do this. She makes an anonymous tip to the gangster scum who previously employed him, and now want to kill him. Then she makes an anonymous tip to the police that said gangster scum have likely murdered Niedemann. In doing so, she manages to wipe out three of her enemies without any of them knowing she is responsible for doing so.
• 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.
• Viviane in The Mists of Avalon. Ultimately to little avail and the general detriment of everyone involved.
• 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.
• The espionage thriller Mr. Standfast, set during World War I, develops into a chess match between Graf von Schwabing for the German side and John S. Blenkiron for the Allied side. Near the end, von Schwabing captures the protagonist, one of Blenkiron's agents, and gives him a lengthy Just Between You and Me speech about how he's been ahead of them the whole way, seeing and counteracting all their moves while allowing them to believe they were undetected. A couple of chapters later, he tries to give the same speech to Blenkiron, only for Blenkiron to cut him off and demonstrate that actually Blenkiron has been doing the same thing to him.
• My Next Life as a Villainess: All Routes Lead to Doom!:
  • While Sophia Ascart appears to be the least aggressive person in Catarina's harem, she's not being passive. She's just being sly. For starters, it's hinted by Anne that her interest in playing The Matchmaker for her brother Nicol and Catarina is is a ploy to have both for herself. While Sorcier society frowns upon both incestuous and same-sex relationships (which is the primary barrier the aggressive Keith and Mary each face), Sophia is planning to have a very forbidden harem that's completely under the radar. Due to being a "cursed child", people expect Sophia to never marry anyone and be a "burden" on her big brother for the rest of her life. So if she just happens to live with her brother while he's married to her best friend...what happens at home stays at home.
  • On Catarina's fifteenth birthday, she is the reason why Nicol is the only person who can get Catarina to accept a thing as girly as a necklace—she reasons that Catarina won't reject it if it looks like one wore by the protagonist from one of the romance novels she reads.^{Modern analogy} The "monkey girl" won't reject an item if it happens to be Fortune Lover merchandise, despite the fact that it's a bit too girly for her taste.
  • In a story in the fifth novel, she introduces Nicol to romance novels, in particular recommending the "stolen love" genre (where a woman betrothed or promised to another man instead falls in love with someone else—exactly the thing she wants to happen between Nicol and Catarina). She gleefully tells him to read them in order to "gain confidence" and become more willing to ignore societal expectations. It's blatantly transparent that she's trying to get him to more actively pursue Catarina and, at the very least (as in the anime), succeeds in helping the two of them bond over the books they read. In the novels, this goes even further—Nicol ends up abandoning his plan to forget Catarina and be more active in pursuing Catarina.
• In Kim Newman's works, the recurring villain Derek Leech is a Corrupt Corporate Executive with a multinational business empire, and the Devil in multiple Deals With the Devil. He always gets out of any story he appears in scot-free, and usually having achieved whatever goal he set out to gain. In The Quorum, he argues that he never coerces anybody to accept his deals, but is also shown to research his targets thoroughly and it's suggested that he never offers anyone a deal if he's not already certain they'll be unable to resist.
• Nightfall (Series): Prince Vladimir is always ten steps ahead of his opponents in every evil plan. He even tries to teach a person sent to assassinate him how to be a better player, in an attempt to get a more interesting enemy. And all the while he uses chess and checkers metaphors.
• Sergei Lukyanenko's Night Watch (Series): Two crazy-awesome examples are the two heads of the Watches; Boris, head of the titular Night Watch and Zabulon, head of the Day Watch. At one point they are even described as two people playing chess with their agencies as the pieces. They often steer towards Gambit Roulette (Yes, both of them quite happily) and seem to willingly fling themselves headlong into a Gambit Pileup.
• Sora and Shiro in No Game No Life were teleported into a world where chess metaphors become literal objects of power and status. Their first major battle is a chess game that due to the use of magic by their opponent goes Off the Rails by the players directly addressing the pieces, appealing to their humanity, logic or fear, foregoing the game's typical rules. All of this becomes the first game against 15 other enemies who hold symbolic chess pieces in a meta-tournament to qualify squaring off against Tet, the world's God.
• 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 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 breeding programs to set up the next war to her advantage.
  • Chired Anigrel only seems an understudy compared to the Demon Queen he worshipped since childhood. Managing to both attain effective control of Armethalieh and come within moments of handing the whole thing over to Savilla.
• The Other Side Of Midnight: Constantin Demeris and his mistress Noelle Page both got rich and powerful via skilled Chessmaster tactics. By the end of the book, when she's on trial for the murder of her lover's wife, she sees her relationship with him in terms of a chess game with her and her lover's lives as the pawns and the stakes. Constantin wins.
• 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.
• Peril at End House:
  • The killer fakes several attempts on her life and brings them up in a causal and unconcerned way to get Poirot involved as a Detective Patsy so that she can kill her intended victim and make it look like a failed attempt on her life.
  • In a lower-stakes example, Jim offers to buy one of Nick's paintings for far more than it's worth, knowing that she'll be utterly confused and baffled by this. The next time he asks to buy one of her paintings, she'll assume that he's offering too much again when the inverse is true and sell it without an appraisal.

• 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 Gambit Roulette after another.
• Please Don't Tell My Parents I'm a Supervillain gives us Spider, a supervillain who uses spider imagery. She's the lord of Chinatown, controlling the entire area to such an extent that heroes are not allowed to patrol there — which they allow since they know they don't need to, with her in charge. She also wrote the treaty that governs hero/villain interactions, and is a spider the size of a car.
• The Power of Five:
  • The Chairman of the Nightrise Corporation is a pretty impressive example of this — he rigs a US presidential election, manages to capture two of the Five, takes over Hong Kong and already has a business empire that controls most of South East Asia.
  • Matt Freeman is perhaps the best example in the series, outwitting both the King of the Old Ones and the aforementioned Chairman.
  • The Master of the Mountain is another heroic example.
• In Anthony Price's spy thrillers, Professor Nikolai Panin of the KGB has a knack for tricking his enemies into doing his work for him while trying to prevent what they think he's up to. Lampshaded in The Old Vengeful, where Paul Mitchell becomes convinced about halfway through that the trail they're following is a garden path the Russians are leading them up yet again.
• Edgewood Dirk in A Princess of Landover, by Terry Brooks. After Princess Mistaya gets expelled from school, her father King Benjamin decides to send her to Libiris, a place she is so desperate not to go that she runs away from home instead. Along the way, she meets Edgewood Dirk, who, for reasons of his own, offers to help hide her from her father. He explains to her, the only way to hide her from the King, who, after all, has a magic device that lets him scry on almost any place within the kingdom, is for her to go to the absolutely last place where her father would think to look for her: Libiris — where, it turns out, Dirk wanted her to go for those aforementioned reasons of his own.

• Several characters in Megan Whalen Turner's Queen's Thief series have Chessmaster attributes, if they aren't full Chessmasters — most notably, the title queen in The Queen of Attolia. Nahuseresh in the same book tries to be one. Eugenides is the best at it, successfully pulling off a Batman Gambit in every book. Interestingly enough, most do it for the purposes of good.
• Human/alien merger Mademoiselle in Alastair Reynolds' Revelation Space and Redemption Ark "saw information flows with the clarity most people lack". Ironically, she was destroyed by H, a formidable but ordinarily inferior Chessmaster, because she got so wrapped up in what was essentially a science project, she stopped paying attention to her webs.
  H: She was a very powerful influence in Chasm City for many years, without anyone realising it. She was the perfect dictator. He control was so pervasive that no one noticed they were in her thrall. Her wealth, as estimated by usual indices, was practically zero. She did not 'own' anything in the usual sense. Yet she had webs of coercion that enabled her to achieve whatever she wanted silently, invisibly. When people acted out on what they imagined was pure self-interest, they were often following Mademoiselle's hidden script.

• Ripliad: 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.
• Romance of the Three Kingdoms
  • Zhuge Liang (styled Kongming) is portrayed as a Chessmaster (who skirts into Magnificent Bastard territory quite often) throughout most of the story 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.)
  • Sima Yi himself counts, holding the distinction of the only character in the entire novel to go up against Zhuge Liang and come out even. Indeed, in the end, he comes out ahead thanks to Kongming's death — and it's even implied that said death came prematurely thanks to the strain of trying to secure victory against Sima Yi before his kingdom's inferior resources ran out.
  • Cao Cao counts as well (especially in real life), but he's given the Idiot Ball when confronting Zhuge Liang.
• Scavenge the Stars: Boon plays everyone in the story as pieces in his game of chess, such as using Amaya as a way to get to the children of his enemy and to have her deliver poisoned coins to the city's elite.
• John Alpha, the Big Bad of 7th Son, certainly qualifies. It's not until the end of Book One that the Beta clones figure out exactly how long he's been setting up the pieces and just how large and intricate his game is.
• 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.
• Shadow 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 subtly guiding their kids.
• Shadows of the Empire: Prince Xizor is constantly formulating plots and pulling strings (largely against Vader) so he'll be brought down by losing favor with the Emperor throughout the story. It eventually catches up to him, and he dies for it at Vader's orders.
• The Duke of Wellington, as depicted in the Sharpe novels. 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: Sends Sharpe with John Lavisser with tonnes of gold in order to bribe the Danish Crown Prince, as he doesn't trust Lavisser. Blackmails Sharpe into helping him for free, and then uses him to secure Britain's massive spy ring in the Baltic. Goes behind Admiral Gambier's back and sends a team of Navy men into the city to secure the Danish war fleet for Britain. Sends Sharpe into the city to kill Lavisser and recover the gold. Uses the failure of the Lavisser expedition (not his idea) to remove the rivals for his job. Cleans up the whole thing by murdering and replacing his Danish contacts.
  • Sharpe's Havoc: Turns up at the end. Sent by the Foreign Office to defeat fellow Chessmaster Colonel Christopher. Sends Sharpe to kill Christopher and his knowledge with him. Again uses Sharpe to murder threats to his job. As a side project, secures communication and financial links with Spanish and Portugese partisans.
  • Sharpe's Fury:' Directing the transfer of money to Spanish partisan operations from Cadiz. Recovers important Foreign Office documents using Sharpe, fights personally for once (he's okay at it). Kills all threats to the Crown. Discredits hostile Spanish politicians. Mocks Sharpe to his face when the latter finds out about his murder of his Danish friends.
  • 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.
• 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.
• Sisterhood Series by Fern Michaels: Charles Martin, former agent of MI6 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 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 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.
• The Sister Verse and the Talons of Ruin has a war between two factions of Eldritch Abominations, using their human followers as pawns as they constantly try and outwit each other.
• Hellmaster Fibrizo from Slayers, who manipulates nearly all the events in Next. He even gets a Villainous Breakdown.
• Song at Dawn: Moving pieces and outgambitting are required skills for anyone in this setting: nobles, merchants, bishops, bodyguards, etc. The greatest of them is al-Hisba who plays everyone to accomplish his own objective while placating his enemies and helping a friend.
• A Song of Ice and Fire is loaded with Chessmasters, many of whom have at least a passing familiarity with the game of cyvasse, a chess-analogue developed in Volantis centuries ago. Oh, and a few of those aspiring to or dreaming they are Chessmasters, knowledge of cyvasse or not — and, success or not.
  • Varys — Has essentially controlled 90% of information to reach or not reach the King and his council, having utterly complete knowledge of everyone's actions, playing at least 3 Kings and 2 dynasties for decades and surviving the transition between them, playing off at least 4 Great Houses against each other for own goals, and in the midst of orchestrating another coup to restore previous dynasty. It is unknown exactly how much of a role Varys played in the events of the novels, but the mere fact he knows about the details of events only a handful of characters even witnessed across the world...says he probably played a big one. He also knows the game of cyvasse, even though he doesn't make a song or dance about it.
  • Euron Crow's Eye — Returns home at least 2-3 in succession and generally disliked just in time (the day before...with no way to find out) for a 'Kingsmoot', where he manipulates his rivals and their men into making him King, by having spent his time in exile seemingly preparing solely for this day he offered loot and riches far beyond his opponents, countering their promise of conquering some easy but poor lands with the promise of conquering ALL of Westeros. With dragons.
  • Doran Martell, the Prince of Dorne, plans his revenge for the atrocities performed against his sister and her children for fifteen years, and is so subtle and low-note about it that his own family insults him to his face about his apparent forgiveness. However, Doran, despite being denied all physical sports and leisures, does not play cyvasse itself. Why? He never plays any game he could potentially lose.
  • Tyrion Lannister is a great cyvasse-player, and has his moments of setting things up, including losing a few weeks' worth of actual cyvasse games on purpose so he could gamble successfully for an important piece of information after his opponent grows rather too cocky. However, in the grander scheme of things, Tyrion's political game often gets stomped on within the massive Gambit Pileup that the Seven Kingdoms becomes. Mostly its not due to his own fault, but sometimes it can be because 1) he couldn't keep his mouth shut and 2) having to trust the wrong people thanks to having few right ones to turn to (despite knowing they're not reliable).
  • Cersei Lannister — She can scheme up a storm, sure, but... Failed. Spectacularly.
  • Lord Petyr "Littlefinger" Baelish — The mastermind responsible for, directly or indirectly, the War of the Five Kings, the Lannister-Stark divide, the betrayal of Ned Stark and the assassination of King Joffrey. He now has plans for the North, using Sansa Stark.
• John Brunner's novel The Squares of the City not only has an obvious chess metaphor in its title, and many literal chess players and games in the story, it's modelled after a historic chess game between two real world chess masters. The president of a fictional Latin American country, and his Minister of the Interior, have a severe disagreement about treatment of the poor, serious enough to lead to civil war. But instead, they play a game of chess against each other, on an actual board and then manipulating real people to enact the moves.
• In Len Deighton's SS-GB, an Alternate History novel set in a Nazi-occupied Britain, the character Mayhew is a formidable Chessmaster who uses the German Nazi occupiers and the British anti-Nazi underground for his pawns, and is described as fond of "playing God and writing the future history books". In his master stroke, unfolding in the later part of the book, Mayhew gets the underground to smuggle King George VI out of the Tower of London where the Germans kept him imprisoned; then Mayhew betrays the underground and gets the Germans to set an ambush, shoot and kill the escaping King; then he gets the underground to rouse the British people against the "Nazi Regicides" and create the myth of a matryred, heroic King (when in fact the poor George VI had been a broken man); then he gets the young Princess Elizabeth crowned Queen-in-Exile at Australia; then he gets the various rivaling Nazi factions in charge of occupied Britian to engage in bitter infighting, blaming each other for the fiasco, and ending with one group of Nazis summarily executing the leader of the other group; and meanwhile, Mayhew's part in all this remains unknown, and he remains on excellent terms with both the Nazis and the underground and free to start working on his next gambit.
• Gary Seven shows shades of this in Star Trek: The Eugenics Wars, playing the superhumans against each other and outwitting Khan in the long run.
• The Stormlight Archive: The series has several, but the king of the trope is Taravangian, who's manipulating (and slaughtering) entire kingdoms based upon a plan he made when his curse/wish rendered him superhumanly intelligent — and amoral.
• In S.A. Swann's Terran Confederacy, elements of the composite AI called Random Walk/Tjaele Mosasa/Mike Kelly/Ambrose/Adam have been manipulating human society to its own ends and that of its alien creators for centuries.
• The Three-Body Problem: This is supposed to be the job of Wallfacers in The Dark Forest, which is set on an Earth that's expecting an invasion from an alien species whose homeworld is dying: they're supposed to maintain a degree of confusion in their attempts to prepare humanity for the Trisolaran strike, ensuring that each plan is locked away in the one thing the sophons cannot interfere with: the human mind. As it goes on, the Trisolarans' agents in the ETO start figuring out their plans, and the Wallfacers start adopting more and more risky and insane plans, with each "Wallbreaker" describing their conclusions to the Wallfacer responsible: the first had settled on a plan to have a swarm of tiny fighters armed with high-yield bombs first betray the human fleet, then take over the swarm as it drew close to the Trisolarans and coordinate the strike; the second had adopted a Mutually Assured Destruction model which would, if he pulled it off, destroy most of the solar system; and the third had sabotaged his mental seal design in order to produce deep-rooted defeatist and Escapist sympathies in their victims. The most effective, bizarrely, is the main character, Luo Ji, who takes years to actually start doing it, preferring to start out by using his virtually unlimited authority to get a fancy retreat and live in peace there, and his actual plan is mostly hidden from the reader as well for a substantial chunk: having concluded that the universe is a Cosmic Horror Story where trust between societies is virtually impossible, and revealing your species' existence is a quick path to oblivion, he sets things up so he can essentially target-paint the Solar System at will, and then extorts the Trisolarans into giving up on the approach lest the system they're working so hard to conquer become just a big target.
• Lewis Carroll's Through the Looking Glass: Although the storyline is purposefully haphazard and dream-like, 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.
• In Tolkien's Legendarium, Gandalf is a bit of a chessmaster. Sent to Middle-earth in the form of an old man and forbidden from showing his power openly, he mostly brings about Sauron's downfall by exerting strategic influence on various key players opposed to Mordor. At one point in The Lord of the Rings he describes the approaching war as a chess game ("And pawns are likely to see as much of it as any, Peregrin son of Paladin, soldier of Gondor. Sharpen your blade!") Gandalf's chessmaster qualities are also highlighted in "The Quest of Erebor", a narrative account (intended for inclusion in the LotR appendices but cut for space) of how Gandalf and Thorin came to arrange the journey to the Lonely Mountain in The Hobbit.
  Thorin: You are playing some crooked game of your own, Master Gandalf. I am sure that you have other purposes than helping me.
  Gandalf: You are quite right. If I had no other purposes, I should not be helping you at all. Great as your affairs may seem to you, they are only a small strand in the great web. I am concerned with many strands. But that should make my advice more weighty, not less.
• A rare positive and heroic example in Jean Johnson's Theirs Not to Reason Why. Ia has phenomenal pre-cognitive abilities, to the point that she can see every path of every choice for the entire universe. Unfortunately, virtually all of the choices lead to the death of all life in our galaxy from an invasion of unimaginable proportions. Only by thousands of people doing precisely the right thing (meeting a person whom they marry and produce a child who does something amazing, not meeting a person whom they would have married and produced a child who would have done something bad, etc) can this crisis be averted. Ia enlists the aid of a group of people who are instructed what to do to ensure that things go according to plan (help a person across the street so they are just in time to meet the right person to marry ..., trip another person so they are too late to meet the wrong person to marry ..., etc). Ia is unfortunately and tragically fully aware of the cost of her requests, and often apologizes to the people she is killing or not saving, saying "Your 2,501 deaths will save 768,916 people, would you like me to name each person in both groups for you?" because she sees everything.
• Tortall Universe: Aly, the protagonist of the Trickster's Duet, naturally takes this role because she's the spymaster for the raka rebellion. She's very good at manipulating people and setting up event to weaken the Rittevons and strengthen the raka, like fake evidence of a royal affair and converting enemy spies with carrot-and-stick.
• To Welcome Oblivion has Noah T. Trepaly, who spent the entire story letting Dr. Lilith Madison do all the heavy work while he remained in the background watching. As soon as it was convenient, he subdued Madison and started using his powers to cause chaos around the world, with hardly anyone left to oppose him thanks to Madison's work.
• In the finale of Trail of Lightning the villain claims credit for manipulating events into manifesting and developing Maggie's powers.
• Twig: Sylvester is generally more of an Opportunistic Bastard than an outright Chessmaster, but he verges into this when he comments on how he sees the social conflict between himself and Reverend Mauer, a charismatic religious leader. If Mauer is playing chess, Sy reasons, then Sy has arrived late to the game and Mauer has created an impenetrable defense. Therefore, the only way for Sy to win is to cheat and make Mauer's next move for him in order to create an opening. Thus, he and his team promptly start a riot.
• 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.
• Under Heaven: Shen Tai's brother, Shen Liu. He studied hard for the Civil Service exam, and ends up the primary advisor to the First Minister. When the Emperor allows one of his daughters to be sent north as part of an arranged marriage, Liu manages to have his own sister declared a princess, and made part of the arrangement, so that the family can be supported better; this ends up impacting a conversation Tai has later. And when, at the end of the book, he realizes that being tied to the First Minister is effectively a death sentence, he plans out several actions that Tai could perform to make sure the family survives the civil war, including the fact that Tai had publicly accused Liu of hiring an assassin.
• "Unsound Variations": A short story that features 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.
• In Andre Norton's Victory On Janus, Ayyar at one point has a vision of playing a board game against THAT WHICH ABIDES, with his own people and the Great Crowns on one side, and the Larsh and enemy robots on the other.
• Vorkosigan Saga: Emperor Ezar in 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 the 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].)
• 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.
  "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."
• Inquisitor Ramius Stele from the Warhammer 40,000 Blood Angels novels rather masterfully steers the titular Space Marine Chapter towards Chaos, though as we are reminded several times, he's still a pawn to a greater power.
• 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.
• Mr. Ross from Wars of the Realm. Although he works for the NCS instead of the CIA, he arranges to have Drew recruited as a CIA agent, then contrives an excuse (with the angels' help) to get him booted out of the CIA...all so that he can recruit him as a non-official agent for use in a special mission to save the United States.
• In Ellen Raskin's The Westing Game, Samuel Westing arranged a will so that whoever discovered his murderer's identity would inherit his fortune. Turns out, that wasn't all he'd arranged. The will puzzle was actually an elaborate scheme to get revenge on his wife by framing her for his murder. A murder that never occurred — he faked his death and continued running his company under a different identity. One of three false identities he created post-death — he also posed as an heir and a landlord who brought the heirs together. His heir identity secretly plays long-term chess with another character over the course of the book. Characters refer to Westing as the king, his wife as a queen they're fooled into taking and the rest of them as pawns.
• Robert Jordan's The Wheel of Time:
  • Moridin is stated to be a master of all strategy games, which includes the setting's Captain Ersatz of chess called sha'ra.
  • When Egwene successfully manipulates the heads of two fractions into giving her the power she needs...
    Egwene: They couldn't have done it better if I had told them what to do.
• Thomas Cromwell in Wolf Hall is a master of manipulating people and situations for his desired outcome. He can charm, flatter, and threaten with equal skill, expertly places a network of spies in households whose interests do not align with the kings, can assess situations quickly and adapt quickly, and makes good use of resources that are natural to a common-born man but not to his pedigreed adversaries. While he doesn't think of people in terms of chess pieces, he is shown in several scenes to be a formidable player of the actual game — his only real rival is his own apprentice.

• In the Zodiac Series, Aquarius is this, with a side of Manipulative Bastard. He is The Man Behind the Man of every major villain in the series, and just about everything proceeds according to his plans. Even when the protagonists work out that they're being manipulated, that ends up being a Xanatos Gambit in his favor.

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