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[[caption-width-right:350:[-[[Music/BlackSabbath "Treating people just like pawns in chess..."]]-].]]

->''"Humans aren't chess pieces, they do after all have free will -- to some degree -- but a good player can still use them. In fact, playing humans is harder. Or maybe I should say it simply requires different skills."''
-->-- '''Senna Wales''', ''[[Literature/{{Everworld}} Inside the Illusion]]''
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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]]. The exception to this is 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.

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'''