History TheChessmaster / Literature

%% This page has been alphabetized. Please add new examples in the correct order.

* Creator/AynRand's ''Literature/TheFountainhead'': 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.

** 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.

** Cersei Lannister - She can scheme up a storm, sure, but... [[spoiler: Failed. Spectacularly.]]
** Lord Petyr "Littlefinger" Baelish - [[spoiler: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.]]

* Creator/LewisCarroll's ''Literature/ThroughTheLookingGlass'': 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 Creator/EllenRaskin's ''Literature/TheWestingGame'', Samuel Westing arranged a will so that whoever discovered his murderer's identity would inherit his fortune. Turns out, that wasn't all he'd arranged. [[spoiler: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.]]

* [[spoiler:Smerdyakov]] in ''Literature/TheBrothersKaramazov''. He believed he could engineer Fyodor Karamazov's murder via a GambitRoulette which involved [[spoiler:giving eldest son Dmitri all the tools and [[ManipulativeBastard 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 [[BriefcaseFullOfMoney sealed envelope containing three thousand roubles]]]]. It didn't work out quite the way he expected.

* In the ''Literature/HIVESeries'', the group that the heroes work for is called G.L.O.V.E. In a surprise twist, it's actually being run by [[spoiler: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 [[spoiler: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 [[spoiler: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.

* Robert Van Gulik's ''Literature/JudgeDee'' (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.

* Troll king Thibault from ''Literature/MaledictionTrilogy''. 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.

* ''Literature/PleaseDontTellMyParentsImASupervillain'' 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 [[spoiler:is a spider the size of a car]].
* ''Literature/ThePowerOfFive'': 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.

* Edgewood Dirk in ''Literature/APrincessOfLandover'', by Creator/TerryBrooks. 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 [[RebelliousPrincess 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 ''[[Literature/TheQueensThief Queen's Thief]]'' series have Chessmaster attributes, if they aren't full Chessmasters - most notably, [[spoiler: the title queen]] in ''The Queen of Attolia''. [[spoiler:Nahuseresh]] in the same book ''tries'' to be one. [[spoiler:Eugenides]] is the best at it, successfully pulling off a BatmanGambit in every book. Interestingly enough, most do it for the purposes of good.

** 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.

* ''Literature/TheStormlightArchive'': The series has several, but the king of the trope is [[spoiler:Taravangian]], who's manipulating (and slaughtering) entire kingdoms based upon a plan he made when his curse/wish rendered him superhumanly intelligent - and amoral.

* Thomas Cromwell in ''Literature/WolfHall'' 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 [[SmartPeoplePlayChess to be a formidable player of the actual game]]--his only real rival is his own apprentice.

* In ''Literature/{{Victoria}}'', William Kraft is a heroic example, staying abreast of the domestic and international situation through his private contacts and manipulating Confederation policy even before he becomes Governor.

* The BigBad of the ''Literature/ChroniclesOfPrydain'', 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 [[AntiClimaxBoss 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 [[EvilOverlord evil overlords]]. If only it weren't for that [[YouMeddlingKids meddling Assistant Pig Keeper...]]

* Creator/SergeiLukyanenko's ''Literature/NightWatch Trilogy'': Two crazy-awesome examples are the two heads of the Watches; Boris, head of the titular Night Watch and [[spoiler: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 GambitRoulette (Yes, both of them quite happily) and seem to willingly fling themselves headlong into a GambitPileup.

** The master of it would be the [[Literature/GodEmperorOfDune God Emperor Leto II]], who was so much better than everyone else that [[MyDeathIsJustTheBeginning 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.

** 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 and is willing to take the path that Paul refused to follow.

** The master of it though would be the [[Literature/GodEmperorOfDune God Emperor Leto II]], who was so much better than everyone else that [[MyDeathIsJustTheBeginning even dying was part of his plans]], and didn't seem to hinder his continuing influence much at all.

* 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.

** Lord Havelock Vetinari, Patrician of Ankh-Morpork and all-around MagnificentBastard, is an amazing chessmaster ("It's like being a puppet, only he gets you to pull your own strings"). In ''Discworld/GoingPostal'' he gets his very own not-quite-chess metaphors, getting into a little discussion with CorruptCorporateExecutive 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''.

** [[spoiler:R. Daneel Olivaw]], over the course of his [[TheAgeless twenty-odd thousand year lifespan]] (he's a robot), manages to build a GenusLoci [[spoiler:that will eventually encompass all of humanity/galaxy]], encourage the development of psychohistory to [[PrescienceByAnalysis design the most peaceful outcome for humanity]], and trick a {{Transhuman}} child into [[spoiler:allowing a GrandTheftMe so that he can make sure his plans work the way he wants them to]]. He's driven by the [[ThreeLawsCompliant Three Laws Of Robotics]], and especially the [[ZerothLawRebellion "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".

* Creator/IsaacAsimov's ''Literature/{{Foundation}}'' series:
** Hari Seldon actually figures out the "chess rules" of humanity in the form of psychohistory, then uses that knowledge to engineer the recovery of the Empire after an unavoidable social collapse. Seldon is depicted as good; the AncientConspiracy that follows in his footsteps... sort of.
** R. Daneel Olivaw. Over the course of his twenty-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 [[spoiler:evolve into a single, all-encompassing consciousness]]. All this whilst being bound by the [[ThreeLawsCompliant Three Laws Of Robotics]], which he and a fellow robot manage to subvert by realizing [[ZerothLawRebellion a law even more overriding than the one prohibiting homicide is a "zeroth law" prohibiting harm to the human race]]. This is all well and good until the obvious problem arises: [[spoiler:judging what's good or bad for humanity. Ultimately, the entire [[HiveMind unitary-consciousness]] push is undertaken in order to subsume the zeroth law into the first and resolve the bind they've created for themselves]].
* Dumbledore in Creator/JKRowling's ''Literature/HarryPotter'' books is another good Chessmaster, especially in the later books where everything he does (even [[spoiler:[[MyDeathIsJustTheBeginning his own death]]!]]) seems to be somehow related to some grand plan years in the making. [[spoiler:In fact, "some grand plan years in the making" is a pretty good description of ''Literature/HarryPotterAndTheDeathlyHallows'']].
** He was stage-managing things before that. He's been running rings around Tom Riddle since Riddle was just a weird kid in an orphanage, though he could never prove Riddle did any of the misdeeds he did whilst in school because Riddle was clever and covered it up. Dumbledore had to change his plans when he confirmed that Voldemort had [[spoiler: 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 [[spoiler: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.
*** 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.
*** [[spoiler:Barty Crouch, Jr ]] in ''Goblet of Fire''. Not only does he plan everything out beforehand, helping Harry and devising ways for Harry to win each Task, but also manages to outplay Dumbledore...until the last minute. However;,it's not him that messes up his carefully-laid plans, but ''Voldemort''.
* ''The Hostage Prince'' by Jane Yolen and Adam Stemple features the Chessmaster [[spoiler: 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]].
* From Peter F. Hamilton's ''Literature/HumanxCommonwealth'' novels, we have [[spoiler: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. [[spoiler: 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]].

* ''Literature/SisterhoodSeries'' by Creator/FernMichaels: Charles Martin, former agent of MI6 and Franchise/JamesBond {{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 AntiHero. 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.

* Prince Jewelius in ''Fanfic/LovedAndLost''. In order to usurp his aunt Princess Celestia as Equestria's ruler, he [[spoiler:sets the events of "A Canterlot Wedding" in motion by allying with Queen Chrysalis and helping her to steal Princess Cadance's identity. However, as he becomes acquainted with Twilight Sparkle and witnesses the canon PlotMandatedFriendshipFailure, he [[XanatosSpeedChess devices a new plan]] and turns against the Changelings right before the invasion begins. He makes Twilight use [[ChekhovsGun the shrinking spell he showed her earlier]] to stop the Changelings, and he immediately afterwards [[LetNoCrisesGoToWaste tricks the shaken ponies]] to blame all the other heroes for the invasion, successfully turning the public against them and making himself [[VIllainWithGoodPublicity "Holy King Jewelius I"]]]].

* Creator/KurtVonnegut's "[[Literature/AllTheKingsHorses All the King's Horses]]" is about an Army colonel, his wife and sons, and 12 men who are captured by a communist Chinese officer, who will let them go free if the colonel can beat him at a game of chess. The only catch is, they are also human chesspieces, and any piece captured is immediately executed.

* Creator/KAApplegate's ''Literature/{{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.

* Creator/IainBanks's ''Literature/TheCulture'': ''Literature/ThePlayerOfGames'': 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 Creator/KristenBritain's ''Literature/GreenRider'' during the final showdown, the protagonist is abruptly yanked away from the action and sees the battle as an elaborate game of that 'verse's equivalent to chess, which is played with 2-4 players. The chessmaster villain invites her to sit and play, as it is the only way for her to break the stalemate and save her friends. Instead, she [[spoiler:smashes the chess board with her sword, causing enough magical backlash to win the day.]]
* Creator/JohnBrunner's novel ''Literature/TheSquaresOfTheCity'' not only has an obvious chess metaphor in its title, and many literal chess players and games in the story, it's modelled after a historic chess game between two real world chess masters. [[spoiler: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.]]
* Creator/LewisCarroll's ''Literature/ThroughTheLookingGlass'': 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.

%%* Creator/RomeoDallaire's ''Literature/ShakeHandsWithTheDevil'' features Paul Kagame, Chessmaster extraordinaire.
* In Creator/LenDeighton's ''SS-GB'', an AlternateHistory 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[[spoiler: 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[[spoiler: set an ambush, shoot and kill the escaping King]]; then he gets the underground to [[spoiler:rouse the British people against the "Nazi Regicides"]] and create the myth of [[spoiler:a matryred, heroic King]] (when in fact [[spoiler:the poor George VI had been a broken man)]]; then he gets [[spoiler:the young Princess Elizabeth crowned Queen-in-Exile at Australia]]; then he gets the various rivaling Nazi factions in charge of occupied Britian [[spoiler: 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.

* Creator/DavidDrake's series ''Literature/TheLordOfTheIsles'': The [[EvilSorceror 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.
* Creator/DorothyDunnett's ''{{Literature/Lymond}}'' novels derive their titles from chess and feature two very chessmasterly characters whose opposition culminates in a terrible game of chess.

* Creator/DashiellHammett's ''Literature/TheMalteseFalcon'': Casper Gutman and [[spoiler: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. [[spoiler:Though in the end, they both fail.]]
%%** Spade himself is this to some degree, as well.

* Creator/RobertJordan's ''Literature/TheWheelOfTime'':
** Moridin is stated to be a master of all strategy games, which includes the setting's CaptainErsatz 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.

* Creator/SergeiLukyanenko's ''Literature/NightWatch Trilogy'': Two crazy-awesome examples are the two heads of the Watches; Boris, head of the titular Night Watch and [[spoiler: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 GambitRoulette (Yes, both of them quite happily) and seem to willingly fling themselves headlong into a GambitPileup.

* Creator/GeorgeRRMartin:
** ''Literature/ASongOfIceAndFire'' is loaded with {{Chessmaster}}s, 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.
*** [[spoiler: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, [[spoiler: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 GambitPileup 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... [[spoiler: Failed. Spectacularly.]]
*** Lord Petyr "Littlefinger" Baelish - [[spoiler: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.]]
** "Literature/UnsoundVariations": 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 MentalTimeTravel 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 SmugSnake, 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 Creator/AndreNorton's ''Literature/VictoryOnJanus'', Ayyar at one point has a vision of playing a boardgame against THAT WHICH ABIDES, with his own people and the Great Crowns on one side, and the Larsh and enemy robots on the other.

* Creator/AynRand's ''Literature/TheFountainhead'': 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.
* In Creator/EllenRaskin's ''Literature/TheWestingGame'', Samuel Westing arranged a will so that whoever discovered his murderer's identity would inherit his fortune. Turns out, that wasn't all he'd arranged. [[spoiler: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.]]
* Creator/DarrenShan's ''Literature/TheDemonata'' series has a heavy chess theme running throughout, and several characters probably qualify for this trope, but none moreso than Lord Loss, the BigBad of the first four books and later TheDragon to the BigBad of the overall series. In terms of literal chess, he's obsessed with the game, and only ever beaten rarely. Figuratively... [[spoiler: 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 KarmaHoudini ''par excellence''.]]
* Creator/SidneySheldon:
** ''Literature/MasterOfTheGame'': A GenerationalSaga 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.
** ''Literature/TheOtherSideOfMidnight'': Constantin Demeris and his mistress Noelle Page both got rich and powerful via skilled Chessmaster tactics. By the end of the book, [[spoiler: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 [[spoiler:with her and her lover's lives as the pawns and the stakes. Constantin wins.]]

* Creator/KurtVonnegut's "[[Literature/AllTheKingsHorses All the King's Horses]]" is about an Army colonel, his wife and sons, and 12 men who are captured by a communist Chinese officer, who will let them go free if the colonel can beat him at a game of chess. The only catch is, they are also human chesspieces, and any piece captured is immediately executed.
%%* In the historical novel ''Literature/WingsOfDawn'': Thomas of Magnus. Lord Mewburn. [[spoiler: Lord Hawkwood. Waleran.]]
* Creator/JohnCWright's ''Literature/CountToTheEschaton'': In ''The Hermetic Millennia'', Larz's story where he [[UnreliableNarrator 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.

* Moridin in Robert Jordan's ''Literature/TheWheelOfTime'', albeit with a CaptainErsatz of Chess called ''sha'ra'' (though he is stated to be a master of all strategy games, which presumably would include chess).
** Several other characters are Chessmasters, or aspiring Chessmasters. Among the aspiring Chessmasters, Egwene stands out. When she successfully manipulates the heads of two fractions into giving her the power she needs...
--->'''Egwene''': They couldn't have done it better if I had told them what to do.

* Creator/KurtVonnegut's "All the King's Horses" is about an Army colonel, his wife and sons, and 12 men who are captured by a communist Chinese officer, who will let them go free if the colonel can beat him at a game of chess. The only catch is, they are also human chesspieces, and any piece captured is immediately executed.

* Though ''Literature/CodexAlera'' has these in spades, the ones who actually use [[strike:chess]] ''ludus'' metaphors are mostly the Canim. Tavi considers beating enemy commander and WorthyOpponent Nasaug at a game to be [[ArsonMurderAndJaywalking worthy of inclusion]] in a list of badass feats he accomplished as Captain of the [[BadassArmy First Aleran Legion]]. At another point, professional {{Chessmaster}} Gaius Sextus makes a [[BlackComedy joke]] about how the situation ''doesn't'' resemble the game, since at that moment, the [[PersonOfMassDestruction First Lord]] and a Knight are at the mercy of a lowly steadholder.
* Creator/JohnCWright's ''Literature/CountToTheEschaton'': In ''The Hermetic Millennia'', Larz's story where he [[UnreliableNarrator 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.
* Creator/IainBanks' ''Literature/TheCulture'': ''Literature/ThePlayerOfGames'': 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 ''Literature/{{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.
* Creator/DarrenShan's ''Literature/TheDemonata'' series has a heavy chess theme running throughout, and several characters probably qualify for this trope, but none moreso than Lord Loss, the BigBad of the first four books and later TheDragon to the BigBad of the overall series. In terms of literal chess, he's obsessed with the game, and only ever beaten rarely. Figuratively... [[spoiler: 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 KarmaHoudini ''par excellence''.]]
* Lord Havelock Vetinari, Patrician of Ankh-Morpork and all-around MagnificentBastard of the ''Literature/{{Discworld}}'' is an amazing chessmaster ("It's like being a puppet, only he gets you to pull your own strings"). In ''Discworld/GoingPostal'' he gets his very own not-quite-chess metaphors, getting into a little discussion with CorruptCorporateExecutive Reacher Gilt on the merits of playing the two sides in Thud.
** According to ''The Discworld Companion'', Vetinari, in addition to being a Thudmeister, is also a Grandmaster at Stealth Chess, where some pieces ''are not necessarily where they appear to be''.
** The Discworld's gods are the literal embodiment of the trope; they've got their own game-board (though it's not actually 'chess', per se), on which the pieces are the mortal residents of the Disc (and thus literal pawns in the games of the deities).

** To a lesser extent, Aoba as well. Oh, and [[spoiler: Mikado]]. No, seriously.
* K.A. Applegate's ''Literature/{{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.
* While there isn't a chess motif for him, referring to [[spoiler:The Sphinx]]'s plans as a game of chess is mentioned several times in the ''Literature/{{Fablehaven}}'' series.
* In ''Literature/TheFifthWave'' by Rick Yancey, Commander Vosch is so good he [[spoiler: gets human teens to kill the rest of humanity for him. Without them knowing.]] Ringer also seems to be quite TheChessmaster in training.
* Ellsworth Toohey, the journalist, critic and social activist who is the main villain of Creator/AynRand's ''Literature/TheFountainhead''. He has been manipulating people since childhood - first his parents and schoolmates, then people on a worldwide level. He observes people and plans meticulously what to say and do which would push person A to an act which will influence person B to make person C - who never heard of Tohhey - to do exactly what Toohey wants.

* In Kristen Britain's ''Literature/GreenRider'' during the final showdown, the protagonist is abruptly yanked away from the action and sees the battle as an elaborate game of that 'verse's equivalent to chess, which is played with 2-4 players. The chessmaster villain invites her to sit and play, as it is the only way for her to break the stalemate and save her friends. Instead, she [[spoiler:smashes the chess board with her sword, causing enough magical backlash to win the day.]]
* In the ''Literature/HarryPotter'' series, Ron Weasley is a literal "chessmaster" and his abilities on the wizard's board lead Harry onto Voldemort's trail in ''Harry Potter and The Philosopher's Stone''.
** Not least, they both demonstrate an exceptional chess move: [[spoiler: They realize the best way to win the game is to sacrifice ''themselves'' like a pawn, so that the hero can win.]]
* In the ''Literature/JamesBond'' novel ''Literature/FromRussiaWithLove'', SMERSH agent Kronsteen (a literal chessmaster in his own right) creates a tremendously intricate plan to the express purpose of assassinating Bond in such a way as to hurt [=MI6=]'s image. In fact, the setup for the plan is so complicated that the entire first third of the novel is devoted to it, with Bond himself not appearing in the book until more than a hundred pages into it. Kronsteen also explicitly thinks of all the people he sees as chess pieces.
** The film adaptation took the plan in question, put it in the hands of SPECTRE, and made it even ''more'' complicated. The audience is left in the dark as to just what the bad guys are up to until Bond himself figures it out.

* The [[EvilSorceror Demon Queen]] from Creator/DavidDrake's series ''Literature/TheLordOfTheIsles'' 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.
* Casper Gutman and [[spoiler:Brigid O'Shaughnessey]] from Creator/DashiellHammett's ''Literature/TheMalteseFalcon'' are both opposing chessmasters who manipulate Sam Spade and a cast of minor characters in order to obtain the Maltese Falcon for themselves. [[spoiler:Though in the end, they both fail.]]
** Spade himself is this to some degree, as well.
* Subverted in ''Market Forces'' by Richard Morgan, a 2004 sci-fi novel in which CorruptCorporateExecutive types battle for promotion by fighting ''Film/MadMax''-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 JustBetweenYouAndMe 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.
* Another Sidney Sheldon novel, aptly titled ''Master of the Game'', is a GenerationalSaga 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.

* Two crazy-awesome examples exist in Sergei Lukyanenko's ''Literature/NightWatch Trilogy'' in the form of the two heads of the Watches; Boris, head of the titular Night Watch and [[spoiler: 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 GambitRoulette (Yes, both of them quite happily) and seem to willingly fling themselves headlong into a GambitPileup.

* Constantin Demeris and his mistress Noelle Page in ''The Other Side of Midnight'' by Creator/SidneySheldon both got rich and powerful via skilled Chessmaster tactics. By the end of the book, [[spoiler: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 [[spoiler:with her and her lover's lives as the pawns and the stakes. Constantin wins.]]

%%* The Duchess in Literature/ThePrincessSeries is this.
%%* Romeo Dallaire's ''Literature/ShakeHandsWithTheDevil'' features Paul Kagame, Chessmaster extraordinaire.
* Creator/GeorgeRRMartin's ''Literature/ASongOfIceAndFire'' is loaded with {{Chessmaster}}s, 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.
** [[spoiler: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, [[spoiler: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 GambitPileup 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... [[spoiler: Failed. Spectacularly.]]
** Lord Petyr "Littlefinger" Baelish - [[spoiler: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.]]
* Creator/JohnBrunner's novel ''Literature/TheSquaresOfTheCity'' not only has an obvious chess metaphor in its title, and many literal chess players and games in the story, it's modelled after a historic chess game between two real world chess masters. [[spoiler: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 Creator/LenDeighton's ''SS-GB'', an AlternateHistory 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[[spoiler: 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[[spoiler: set an ambush, shoot and kill the escaping King]]; then he gets the underground to [[spoiler:rouse the British people against the "Nazi Regicides"]] and create the myth of [[spoiler:a matryred, heroic King]] (when in fact [[spoiler:the poor George VI had been a broken man)]]; then he gets [[spoiler:the young Princess Elizabeth crowned Queen-in-Exile at Australia]]; then he gets the various rivaling Nazi factions in charge of occupied Britian [[spoiler: 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.
* Although the storyline is purposefully haphazard and dream-like in Creator/LewisCarroll's ''Literature/ThroughTheLookingGlass'', 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 Literature/TolkiensLegendarium, Gandalf is a bit of a chessmaster. Sent to Middle-earth [[AngelUnaware 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 ''Literature/TheLordOfTheRings'' 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 ''Literature/TheHobbit''.

* Sylvester, in ''Literature/{{Twig}}'', is generally more of an OpportunisticBastard 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.
* A short story by Creator/GeorgeRRMartin called ''Unsound Variations'' featured a man seeking revenge on the former members of his chess team. He ruined their lives without them realizing he was involved, by using MentalTimeTravel 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 SmugSnake, 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 Creator/AndreNorton's ''Victory on Janus'', Ayyar at one point has a vision of playing a boardgame against THAT WHICH ABIDES, with his own people and the Great Crowns on one side, and the Larsh and enemy robots on the other.
* In Ellen Raskin's ''Literature/TheWestingGame'', Samuel Westing arranged a will so that whoever discovered his murderer's identity would inherit his fortune. Turns out, that wasn't all he'd arranged. [[spoiler: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.]]

%%* In the historical novel ''Literature/WingsOfDawn'': Thomas of Magnus. Lord Mewburn. [[spoiler: Lord Hawkwood. Waleran.]] %% This entry was added automatically by FELH2. In case the wording doesn't make sense, rewrite it as you like, remove this comment and tell this troper.

!!!General Examples
* Chessmasters are common in Korean historical epics. Or at least Strategists. Perhaps it comes of the old Far Eastern tradition of cloak-and-dagger stories that goes back to the likes of Sun Tzu.
!!!Specific Examples

* Elsworth Toohey, the journalist, critic and social activist who is the main villain of Creator/AynRand's ''Literature/TheFountainhead''. 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.

* 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.