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[[quoteright:350:[[ComicBook/{{Cyclops}} http://static.tvtropes.org/pmwiki/pub/images/chessmaster_new_mutants2_8004.jpg]]]]
[[caption-width-right:350:[-[[Music/BlackSabbath "Treating people just like pawns in chess…"]]-]]]

->''"They say it's the game of kings. That chess teaches one to think strategically. What a load of rubbish! Both sides have identical pieces, the rules stay invariably the same. How does this mirror real life? …pawns see only their comrades at their sides and their foes across the field. A king has a different view of the chessboard. His greatest foes surround him. His own chessmen might trap him. And that is check--and death. You see, witcher, chess is the art of sacrificing your own pieces. Now do you see?"''
-->-- '''Radovid V the Stern''', ''VideoGame/TheWitcher3WildHunt''
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The Chessmaster gets their name from his ability to manipulate people and events as if they were pieces on a chessboard as well as their ability to "think three moves ahead." Chessmasters tug at their strings of influence, patiently move their pieces into places that often seem harmless or pointless until the trap is closed, and get [[HorribleJudgeOfCharacter innocent]] {{Unwitting Pawn}}s ([[ChessMotifs who else?]]) to do all the heavy lifting. The best will also have [[KansasCityShuffle layers upon layers of misdirection]] [[XanatosGambit and backup plans]] in case some unexpected hero appears to [[SpannerInTheWorks gum up the works]].

Chessmasters can [[GuileHero sometimes be on the side of good]], but if so they'll almost certainly be the AntiHero (the PragmaticHero variation) at best or the WellIntentionedExtremist at worst, as it's very hard to plan a Chessmaster scheme that doesn't [[WeHaveReserves sacrifice a few pawns along the way]]. Heroic Chessmasters are very often introduced as a MysteriousEmployer. TheSvengali, in acting for the (supposed) good of his protégés, will often be this (and if he isn't, he'll pretend).

Chessmasters can occasionally be TheStrategist, although given the volatility of war, most Strategists will only ply their schemes one campaign at a time, with an emphasis on short-term goals (and an eye towards all possible future contingencies). The GameMaster may be a Chessmaster also, but many of them prefer to give their orders more directly. Many chessmasters are [[VillainWithGoodPublicity Villains With Good Publicity]], but they can also be [[MilkmanConspiracy someone no one has ever heard of]]. Almost all [[AncientConspiracy Ancient Conspiracies]] are led by a [[TheOmniscientCouncilOfVagueness collective of chessmasters]], silently working toward their goals over generations. Chessmasters also tend to be [[SmugSnake overconfident]] and usually [[VillainousBreakdown panic]] when their [[DidntSeeThatComing "perfect" plans fail]]--unless they [[OminousAdversarialAmusement just start laughing]] instead. This is also usually averted when MagnificentBastard and Chessmaster overlap, since a MagnificentBastard is quite good at [[XanatosSpeedChess rebounding]] [[LetNoCrisisGoToWaste from defeat]]. Fond of a BattleOfWits.

Of course, actual TabletopGame/{{chess}} ability is implied, and some Chessmasters [[ChessMotifs take it literally]], mapping their plans out with an actual chessboard, occasionally with pieces shaped like the main characters. [[BellisariosMaxim Don't ask how this works, or where they get pieces]]. This is most likely a result of SmartPeoplePlayChess. Compare the ManipulativeBastard who tends to be more personal and controlling in her/his manipulations. Compare/contrast OpportunisticBastard as well. Contrast SpannerInTheWorks, though it's possible for a character to be both of these.

Chessmasters are usually [[BadassBookworm (but not]] [[GeniusBruiser always)]] [[NonActionBigBad non-physical and unsuitable for action]] due to age, infirm, or simply being a thinker, not a fighter.

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

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

* '''TheChessmaster/ExamplesUsingChessMetaphors'''
* '''TheChessmaster/NonChessMotifExamples'''