History TheChessmaster / WesternAnimation

* ''WesternAnimation/GravityFalls'': [[Characters/GravityFallsBillCipher Bill Cipher]] engineered events for at least the last thirty years, all to complete his plan of [[spoiler:merging his world with the real world, freeing him and his other nightmare demons]]. This was just the final and first successfully completed plan in a long line of plans executed since, presumably, [[spoiler: the beginning of the universe.]] Previous plans included [[spoiler: convincing a shaman to try and build a portal long before it was technologically feasible. When the shaman found Bill out, he set himself on fire ("DRAMA QUEEN"). Also, the original intention for Ford's portal was simply a gateway for Bill and Co. to pass through which Ford thought was for his own research purposes before he also found Bill out. After Ford spent thirty years in various dimensions, breaking the Rift the portal created upon his return became the new plan.]] As a VisualPun, he's seen playing chess with [[spoiler: Ford]]. [[spoiler: Ford]] also writes in code in the journal after he discovers Bill's trickery, "INTERDIMENSIONAL CHESS ISN'T FUN WHEN YOU'RE A PAWN."

*** Her father, EvilOverlord Ozai, prefers the 'set the chessboard on fire and stand back laughing maniacally' approach, rather than messing about with all those fiddly little pieces. [[spoiler: Until her VillainousBreakdown]], Azula was a genuine (and, fortunately for Ozai, genuinely ''[[DaddysGirl loyal]]'') Chessmaster, so she got to do all the thinking.\\

** Amon, BigBad of the first season of ''WesternAnimation/TheLegendOfKorra'', has claimed himself to be a chessmaster. He has thus far been very convincing at his role. [[WhamEpisode Episode 6]] sealed his status as not only a brilliant Chessmaster, but also [[MagnificentBastard something more]].

* Viren and his patron Aaravos from ''WesternAnimation/TheDragonPrince'', especially when they combine their skills. Viren is an excellent people-person, able to twist any situation or person to his advantage. When Ezran told him to dismiss a large portion of the army, he still managed to phrase the order in a way that made the remaining army undyingly loyal to him. His charisma and persuasiveness is further bolstered by Aaravos, a chessmaster of highest sort but who's not in any position to be as active as Viren. Together, they [[spoiler:walk straight into the Sunfire elf capital, knowing that the arrogant and traditionalist queen will insist on them going through a lethal "purification" ritual close to the source of sunfire elf power. Aaravos and Viren proceed to absorb said power and burn the queen to death]].

** The BigGood, Princess Celestia, seems to be able to play this part when necessary, and is a rare benevolent example, working for the good of her subjects. She remains somewhat enigmatic, but seems to have wisdom fitting her [[ReallySevenHundredYearsOld millennial]] experience of ruling. She generally seems on top of everything that's going on, but has twice been shown doing some serious plotting: At the beginning of the first season, she pulled off a GambitRoulette with the twin goals to a) make her student Twilight Sparkle get out more and make some friends and b) save the world. In the beginning of the second season, she performs a much simpler and more elegant single-step BatmanGambit with somewhat similar goals.
** Celestia's old ArchEnemy Discord -- a being so [[KnightOfCerebus dangerous]] and [[MagnificentBastard chaotically ingenious]] that he's actually able to catch her off balance and [[OOCIsSeriousBusiness unnerve her]] -- [[BattleOfWits plays a round against her]] in "The Return of Harmony", with the main characters as pawns. (Although, if we're doing ChessMotifs, there's more than one reason why it might be fitting to call them Celestia's knights.[[note]]If you want to know... "pawns" is a metaphor for ones regarded as mere tools and not valued, and knights are also more powerful; Celestia actually does a "knighting" gesture to Twilight Sparkle before sending them out; and, of course, the characters in question are miniature horses.[[/note]]) Discord's plan aims at making sure that the ponies will be [[BreakTheCutie psychologically]] [[DespairEventHorizon broken]] and unable to use the only thing that can stop him even after they do find it, although [[TheOmnipotent given his power]], it looks like he's also [[JustToyingWithThem doing things the hard way]] just ForTheEvulz.
** Changeling Queen Chrysalis apparently planned an invasion of Canterlot (the pony capital) by deliberately scaring them to set up their defences, which only worked to her advantage when no-one knew she was already inside and working on something that would both give her great power and make sure the magical shields would fall at the right moment anyway. And then she [[TookALevelInBadass takes another level in]] {{magnificent bastard}}ry in the [[ComicBook/MyLittlePonyFriendshipIsMagicIDW comics,]] where she hatches a scheme to [[spoiler:suck all the magic out of Twilight Sparkle by fillynapping the Cutie Mark Crusaders to lure her to her SupervillainLair, then capturing the rest of the Mane Six to coerce Twilight into studying TheDarkArts as her apprentice.]] Like Discord in the show, the only reason she loses this time is because she underestimates ThePowerOfFriendship.
** SorcerousOverlord King Sombra is largely considered the biggest example so far -- at least before he became an AlmightyIdiot WorldWreckingWave, that is (and even then, he still shows signs of ItCanThink). Case in point: He gets a NearVillainVictory just because of the CrazyPrepared measures he took over a millennium in advance. Oh, and the kicker? The Crystal Empire's past vanishing and present reappearance is because of his DeadMansSwitch-style curse allowing him to preserve "his" domain despite Celestia and Luna's initial defeat of him. [[spoiler:When he's resurrected in the Season 9 finale, he doesn't have his CrazyPrepared measures, but his cunning is on full display when he pulls of a complex plan where he attacks the Crystal Empire again, knowing that the heroes will bring the Elements of Harmony to stop him, and then fakes his defeat so that he can follow the heroes when they're returning the Elements to the Tree of Harmony. He then destroys the Tree, depriving the heroes of their greatest weapon, and then nearly succeeds in his real goal of conquering Canterlot.]]
** [[spoiler:Cozy Glow]], the BigBad of Season 8. She puts up the facade that she's [[spoiler:an innocent little filly]] for most of the season, then hatches her master plan. She knew that, [[spoiler:once she started draining the magic of Equestria, the Mane Six would be sent to Tartarus to check on the most likely culprit (Tirek), allowing her to take over the School of Friendship (and even when Starlight Glimmer didn't go with them, she quickly disposed of her). When ObstructiveBureaucrat Chancellor Neighsay shows up, she manages to trick him into thinking she's helping him before betraying him by convincing the other students to revolt against him. Even when she gets defeated and ends up in Tartarus, she still seems to get what she wants–namely, close vicinity to her pen pal Tirek.]] While she isn't seen playing the game, she gets bonus points for [[spoiler:her cutie mark being a chess piece (a rook, to be precise).]]

** Cartman is the chessmaster in quite a few episodes. "Scott Tenorman Must Die" is the most chilling example. Even the main group acknowledges how dangerous Cartman is here. To add to it, [[BatmanGambit he even uses Stan and Kyle to rat out his (fake) plan to Scott Tenorman]]. So beyond everything, everyone knew Cartman was up to something. He just took it to the next level.
** Kyle's also shown to be quite capable of this, usually as [[HeWhoFightsMonsters direct opposition]] to Cartman. This is best seen in "Le Petit Tourettes" where he orchestrates a series of events to stop Cartman's faking of the disorder.

* [[spoiler: Toffee]] from ''WesternAnimation/StarVsTheForcesOfEvil''. [[spoiler: He infiltrates Ludo's group as he is the monster that aims for the wand the most. He gains Ludo's absolute trust and uses that trust to use Ludo's minions, moving them around to get as much information on Star and her wand as he can. He then makes Ludo banish his previous [[UndyingLoyalty loyal]] [[TheDragon dragon]] Buff Frog. ''Then'' he causes a revolt among the minions which results in Ludo being thrown out of his own castle, making Toffee the new group leader.]] And the absolute masterpiece of the entire thing? [[spoiler: He doesn't want the wand. He has no interest in owning and using it. He asks Star to ''destroy it''. And ''everything'' he had done was so he could force her in a situation where she must obey him. He also alludes that he possibly knows most of Star's family secrets as he knew exactly how Star could destroy the wand, while ''she didn't'']]. Oh yeah, and as cherry on top: during that confrontation [[spoiler:the destruction of the wand causes a massive explosion. And Toffee leans back in satisfaction, only a few steps away and watches the wand go off, having been fully aware that this would happen as well]]. But wait, there's more! [[spoiler:The Season 2 finale reveals that Toffee didn't perish in the explosion. No, the reason he wanted the wand destroyed was so that he could use the explosion to merge with the wand, from which he manipulated everything Star and Ludo (having found half of the wand) did throughout the entire season, while at the same time, corrupted the wand's magic. Then after Star realized the truth and used the Whispering Spell again to remove him from the wands, this turned out to be what Toffee wanted as well, using it to trap Star in the wand so he could force her mother to return the lost finger she had taken from him, thus finally allowing him to completely restore his body. Even in his final moments, Toffee hinted that everything was still going as he planned]].

** [[Characters/AvatarTheLastAirbenderPrincessAzula Azula]] of ''WesternAnimation/AvatarTheLastAirbender'' -- TheVamp, DragonLady, MagnificentBitch, HeroKiller, and PsychoForHire all rolled into one.

*** [[EvilChancellor Long Feng]] is very good at this too, keeping a city under his control for years with no one but his immediate henchmen the wiser. Really the only things keeping him from being a full fledged MagnificentBastard are underestimating his opponents and not dealing well with sudden reversals -- [[EvilerThanThou both of which Azula exploits...]].

Effectively, Azula plays this trope straight, using [[BatmanGambit plots]], [[LackOfEmpathy her skills as]] [[ManipulativeBastard a 'people-person']] and good ol' situational awareness to deal with her enemies; [[DarkActionGirl kicking ass]] and [[PlayingWithFire taking]] [[PsychoElectro names]] is more a trump card she keeps close to the vest. Ozai's cunning when he needs to be, but he is much more of an outright bully who uses [[KillEmAll violence]], intimidation and [[KillItWithFire raw displays of power]] to get his way. Ozai's the club, Azula's the rapier.

** The terrorist cell in the ''Imaginationland'' trilogy, who orchestrate a war between the Good and Evil characters who were at peace on their separate territories of Imagination, and in order to [[KillEmAll wipe them all out and destroy collective imagination]], even posthumously as they were killed after they started the war. However, the Good characters get full support in the narrative as if the Evil characters, despite being ObviouslyEvil, were the [[BigBadEnsemble Big Bads]], [[UnwittingPawn but neither side were responsible for the war]]. Also, the gambit failed when Good characters won the war [[BackFromTheDead with all their casualties resurrected]], while the Evil characters weren't so lucky and their survivors were imprisoned. And the real perpetrators of the war were already dead right after the war started.

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* Viren and his patron Aaravos from ''WesternAnimation/TheDragonPrince'', especially when they combine their skills. Viren is an excellent people-person, able to twist any situation or person to his advantage. When Ezran told him to dismiss a large portion of the army, he still managed to phrase the order in a way that made the remaining army undyingly loyal to him. His charisma and persuasiveness is further bolstered by Aaravos, a chessmaster of highest sort but who's not in any position to be as active as Viren. Together, they [[spoiler:walk straight into the Sunfire elf capital, knowing that the arrogant and traditionalist queen will insist on them going through a lethal "purification" ritual close to the source of sunfire elf power. Aaravos and Viren proceed to absorb said power and burn the queen to death]].

* Anarky, the BigBad of ''WesternAnimation/BewareTheBatman'' Season 3, loves to play chess using Batman and various villains as chess pieces, as symbolism for how he indirectly manipulates the events of the series.

* The Brain from ''WesternAnimation/TeenTitans'' plans out all of his moves like a chess game and his mobile body even LOOKS like a giant chess piece! The final battle against the Brain's Brotherhood of Evil actually takes place in a large room that resembles a gigantic chessboard.

* The adaptation of Dick Grayson/Robin/Nightwing in ''WesternAnimation/YoungJustice'' is a benevolent form of this. He engineers a [[spoiler: fake mission from Batman to help out the circus he was raised in]] in Season 1, while in Season 2 he makes a complex plan involving a false case of [[FaceHeelTurn teammate gone bad]], a faked death, and more, which ultimately results in [[spoiler:the two factions of bad guy turning against each other]]

!!Examples With Chess Motifs

* ''WesternAnimation/{{Gargoyles}}'': David Xanatos, king of the eponymous XanatosGambit. His girlfriend/wife Fox is no slouch at it to the point where almost all the events outside of the Trio's promotion competition in the episode, "Upgrade" is part of a special game of chess. This is done with the couple competing using a chessboard with board pieces representing each of the people they are manipulating; The Pack for Xanatos and the Manhattan Clan for Fox.

* Hilariously averted in an episode of ''WesternAnimation/TheSimpsons'' where Mr. Burns hires an assassin to kill Grandpa. After two botched attempts, the assassin suggests a [[RuleOfThree third option]] which he describes "as complex and precise as a well-played game of chess." [[GilliganCut Cut]] to him bursting into the retirement home with a machine gun and [[ATeamFiring firing wildly in all directions.]]
* The Brain from ''WesternAnimation/TeenTitans'' plans out all of his moves like a chess game and his mobile body even LOOKS like a giant chess piece! The final battle against the Brain's Brotherhood of Evil actually takes place in a large room that resembles a gigantic chessboard.

!!Examples Without Chess Motifs
* ''Franchise/AvatarTheLastAirbender'':
** [[Characters/AvatarTheLastAirbenderPrincessAzula Azula]] of ''WesternAnimation/AvatarTheLastAirbender'' -- TheVamp, DragonLady, MagnificentBitch, HeroKiller, and PsychoForHire all rolled into one.
*** Her father, EvilOverlord Ozai, prefers the 'set the chessboard on fire and stand back laughing maniacally' approach, rather than messing about with all those fiddly little pieces. [[spoiler: Until her VillainousBreakdown]], Azula was a genuine (and, fortunately for Ozai, genuinely ''[[DaddysGirl loyal]]'') Chessmaster, so she got to do all the thinking.\\
Oh, Ozai ''can'' scheme fine (note the flashback in "Zuko Alone", where he very clearly exploits the weak spots of everyone around him to get ''exactly'' what he wants, and he managed to keep Azula under control for years -- no mean feat!). Problem is, he's usually far too DrunkWithPower to put that cunning to effective use.\\
Effectively, Azula plays this trope straight, using [[BatmanGambit plots]], [[LackOfEmpathy her skills as]] [[ManipulativeBastard a 'people-person']] and good ol' situational awareness to deal with her enemies; [[DarkActionGirl kicking ass]] and [[PlayingWithFire taking]] [[PsychoElectro names]] is more a trump card she keeps close to the vest. Ozai's cunning when he needs to be, but he is much more of an outright bully who uses [[KillEmAll violence]], intimidation and [[KillItWithFire raw displays of power]] to get his way. Ozai's the club, Azula's the rapier.
*** [[EvilChancellor Long Feng]] is very good at this too, keeping a city under his control for years with no one but his immediate henchmen the wiser. Really the only things keeping him from being a full fledged MagnificentBastard are underestimating his opponents and not dealing well with sudden reversals -- [[EvilerThanThou both of which Azula exploits...]].
** Amon, BigBad of the first season of ''WesternAnimation/TheLegendOfKorra'', has claimed himself to be a chessmaster. He has thus far been very convincing at his role. [[WhamEpisode Episode 6]] sealed his status as not only a brilliant Chessmaster, but also [[MagnificentBastard something more]].
%%* Loki from ''WesternAnimation/TheAvengersEarthsMightiestHeroes''.
* Viren and his patron Aaravos from ''WesternAnimation/TheDragonPrince'', especially when they combine their skills. Viren is an excellent people-person, able to twist any situation or person to his advantage. When Ezran told him to dismiss a large portion of the army, he still managed to phrase the order in a way that made the remaining army undyingly loyal to him. His charisma and persuasiveness is further bolstered by Aaravos, a chessmaster of highest sort but who's not in any position to be as active as Viren. Together, they [[spoiler:walk straight into the Sunfire elf capital, knowing that the arrogant and traditionalist queen will insist on them going through a lethal "purification" ritual close to the source of sunfire elf power. Aaravos and Viren proceed to absorb said power and burn the queen to death]].
* Anti-Cosmo and HP on ''WesternAnimation/TheFairlyOddparents'' could both qualify, usually tricking Timmy or some other third party into helping with their plans.
* ''WesternAnimation/{{Gargoyles}}'':
** Fox, Thailog, and the Weird Sisters all play close to Xanatos's own level (Thailog and Fox have even bested him once each).
** Demona does some of this, though she's often so hot blooded and/or generally screwed up that she'll inadvertently sabotage herself.
** [[EvilSorcerer The Archmage]] doesn't have the same skill as the above, but he makes up for it with [[AGodAmI the sheer grandiose nature of his ambitions]].
** The [[AncientConspiracy Illuminati]] are implied to be a whole ''organization'' of these (at least, the ones at the top are). The Illuminati's status as an organization of these is established in the comics, where Xanatos is recognized for his cunning and manipulative skills and is inducted into the organization... at the lowest rank! The illuminati ranks run from 1 to 36, with each rank having that many members at that level (1 member is rank one, 2 members are rank two, and so on.). The person who is Rank 1 has thus outwitted 666 other chess masters to get there.
* HP's thirty-seven year plan from ''WesternAnimation/SchoolsOutTheMusical''. After the Pixies discovered the abandoned clown baby Flappy Bob, they raised him to become a boring corporate executive and inspired him to build an educational camp/day care center called the Learn-a-Torium. At the start of the summer, the pixies sabotaged the kids' summer plans to cause Dimmsdale to be destroyed, which allowed Bob to rally support from the town for his "Camp Learn-a-Torium". The kids were sent there and HP convinced Timmy to wish for a world ruled by kids, eventually making them so happy that they don't need fairies anymore, forcing Jorgen to recall them all back to Fairy World. Finally, the Pixies convinced Bob to sign over control of Fairy World in exchange for him taking back control of Earth. However, the plan all unravels when Bob overhears the pixies celebrating their plan and admitting they never genuinely cared for their godson. Feeling betrayed, he decides that Timmy had a point about him betraying his own values in a quest for power and decides that the world should go back to the way it should be.

* ''WesternAnimation/{{WITCH}}'':
** Nerissa from ''WesternAnimation/{{WITCH}}'s'' second season is '''excellent''' at this. Her opposition is so thoroughly manipulated and played that despite the heroines' best efforts, they can only score the smallest of victories in comparison to her [[MagnificentBastard Magnificent Bastardry]] until the absolute end of the season... and were only then able to overcome it because [[spoiler: Phobos is also good at chess and moved Nerissa into being absorb into her own Seal]].
** And then we find out that [[spoiler: Will was manipulating ''Phobos'' like a fiddle, expecting him to betray them as soon as he had the Seal of Nerissa and easily putting him in a situation in which he would be defeated]].

** [[Characters/AvatarTheLastAirbenderPrincessAzula Azula]] of ''WesternAnimation/AvatarTheLastAirbender'' -- TheVamp, MagnificentBastard, HeroKiller, and PsychoForHire all rolled into one.

* The Brain from ''WesternAnimation/TeenTitans'' plans out all of his moves like a chess game and he even LOOKS like a giant chesspiece! The final battle against the Brain's Brotherhood of Evil actually takes place in a large room that resembles a gigantic chessboard.