[[TheChessmaster Back to the main page]].
----
[[foldercontrol]]

[[folder: Anime & Manga]]
* Creator/AleisterCrowley of ''LightNovel/ACertainMagicalIndex'' is TheManBehindTheMan 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.
* In ''Manga/BlackLagoon'' Rock is getting to this point. Depending on your interpretation of the ''Baille de la meurte'' arc, he is either a budding chessmaster who set up nearly the entire ending with a few choice words and a really accurate prediction of how people would act, or he was a ManipulativeBastard playing on a BatmanGambit. However, considering that he seems to have deduced that [[spoiler: Eda is a CIA agent]] and used that to his advantage to shape the end-game....
* Sousuke Aizen of ''Manga/{{Bleach}}''. Also of the ManipulativeBastard variety and a proven master of the GambitRoulette.
** For that matter [[spoiler: Kisuke Urahara]] fits the role well too, though on the non-villainous side. Aside from being opposed to [[spoiler:Aizen]], it's not really clear what endgame he's playing toward, but that could just be proof of how ''good'' a Chessmaster he is.
** Vandenreich TheEmperor Yhwach fits the role as well also being a ManipulativeBastard.
* Amshel Goldsmith from ''BloodPlus'' is [[TheDragon Diva's chevalier]], but he is the one who organises most of Diva's plan to replace humanity with Chiropterans. To reach that end, he uses everyone, including Diva's other chevaliers who are on his side. In fact, it is completely plausible to argue that he, instead of Diva, is the main villain as [[spoiler:he and the original Joel's experiments on Saya and Diva completely drove Diva insane and made her into a bloodthirsty monster that she is]].
** There are a couple of people who know Amshel's game. [[spoiler:Nathan plays along because he feels like it. Diva just doesn't care, being too insane to focus on anything that takes so much time to develop]].
* In both the manga and the anime versions, Aion of ''ChronoCrusade'' is shown to be a Chessmaster -- in the anime, he manages to manipulate Chrono into giving him exactly what he needs for his plans: [[spoiler:the Holy Maiden, Rosette. He dies in the end, but manages to come back from the dead (and/or become a symbol of evil--it's hard to tell exactly)]]. In the manga, he manipulates not only Chrono and his TrueCompanions, but the ''entire demon society'' to [[spoiler:completely obliterate the entire demon race, and nearly the world along with it, [[UtopiaJustifiesTheMeans so that the world can be rebuilt without the "systems" he despises]]. The only thing that stops him is that Rosette is the living personification of ChaoticGood, and his biases against humans stopped him from realizing what a pain in the ass she'd turn out to be]].
* Dietrich, one of the younger warriors from ''{{Claymore}}'' qualifies. Figuring out Helen and Deneve's identities within seconds was a foretaste of her analytical abilities. Figuring out the only way to defeat the Luciela-Rafaela spawn for good by siccing [[spoiler:the Abyssal Feeders]] on them was a grandmaster move.
* Amber/February from ''Anime/DarkerThanBlack'' is an example of this trope; however, instead of simply using world class intellect to manipulate outcomes in her desired direction, she uses [[spoiler: her ability to rewind time in order to correct failed gambits]].
** She even pulls off a GambitRoulette, managing to [[spoiler: place Hei at the exact place she needs him to be, at the exact right time, in order to allow him to have an epiphany which leads him to the course of action she needed him to make. And all before she ran out of power]] (just).
* [[spoiler:Myotismon]] from ''Anime/DigimonAdventure02''. All the main things that happened in the series were plotted by him in his own designs, both directly and indirectly, and his plans worked so well that the writers were forced to use some half-assed DeusExMachina just to make sure he wouldn't win.
* Rosalie of the Samura Hiroaki oneshot ''Emerald'' plays this astoundingly well. In only sixty odd pages, she saves a young girl from a life of prostitution, orchestrates the death of a legendary criminal, brings an invincible gunfighter out of [[RetiredBadass retirement]] and brings down the local prostitution ring without once firing a gun. Paying for a tombstone for the aforementioned criminal just might bring her into MagnificentBastard territory.
* Other than Father, ''Manga/FullmetalAlchemist'' has a large number of heroic Chessmasters, including [[ColonelBadass Roy Mustang]], [[LadyOfWar Olivier Mira Armstrong]], [[ObfuscatingStupidity General Grumman]], and of all people, [[spoiler:[[CloudCuckoolander Hohenheim]]]], who is revealed to have been planning a counter to Father's moves for years.
** The [[Anime/FullmetalAlchemist 2003 anime version's]] villain, [[spoiler:Dante]], is also a pretty classic example, having manipulated Amestris, its military and above all its alchemists, behind the scenes for centuries.
* ''FushigiYuugi'''s Nakago was not only good at directing his own men, he was a master when it came to misdirecting and manipulating the heroes. (Not that the heroes were any sort of brain trust...)
* Kazundo Gouda from ''GhostInTheShellStandAloneComplex'', who manipulates all of Japan in service of his own convoluted plans.
* In ''{{Gundam 00}}'', Alejandro Corner ''thinks'' he's the Chessmaster, hijacking Aeolia Schenberg's [[spoiler: century-in-the-making]] GambitRoulette and arranging to dispose of the late Aeolia's loyal followers so he can take command of the newly-forming Earth Sphere Federation. [[spoiler:He's wrong. Alejandro was actually being manipulated himself every step of the way by his [[TheManBehindTheMan apparent lackey]], Ribbons Almark. The first hint Alejandro gets of this comes seconds before his death when Ribbons radios him to gloat]].
** Aeolia Schenberg, managed to ''accurately'' predict the events of everything that happened during the first season, and developed effective contingencies for it. What makes him different from all the other different chessmasters? [[spoiler: He's been ''dead'' for ''two hundred years'']].
* Rau Le Creuset of ''GundamSeed'' nearly [[OmnicidalManiac destroyed the world]] by manipulating nations into slaughtering one another. He gains a chess-motif in the sequel.
* Treize Khushreneda of ''GundamWing'', though that's just par for the course when you're that {{magnificent|Bastard}}.
* Nagi Sanzenin's grandfather, Mikado Sanzenin, has proved himself one of these in [[http://img09.tx.us.mangafox.com/store/manga/708/249.0/compressed/n07.jpg chapter 249]] of ''Manga/HayateTheCombatButler''. In past chapters he essentially plays with Nagi, making her a target for people after the inheritance, which is reason enough. In the latest, he forces Hayate, her butler, into deciding her lifestyle, forcing him to choose between protecting a stone which has become the symbol of the Sanzenin inheritance, or breaking it to save his former lover's life. And to make it even worse, [[http://img09.tx.us.mangafox.com/store/manga/708/249.0/compressed/n09.jpg he admits to]] manipulating the boy's life ever since he can remember by posing as innocuous figures. The only good thing about him is the fact that he genuinely loved his daughter, [[MoralityPet favors his granddaughter's maid]], and taught said [[PetTheDog granddaughter how to invest]].. so she's not rendered completely poverty-stricken [[spoiler: [[http://img16.tx.us.mangafox.com/store/manga/708/252.0/compressed/o11.jpg ''when'']]]] the inheritance gets taken away from her.
** He also engineered a plot to steal 'the power of the gods' before the story started. Possibly his first, since it failed and got the three who worked together on it cursed.
* Naraku of ''Manga/InuYasha'' manipulates, schemes, lies, cheats and cons ''every'' member of the cast, pitting hero against hero and tricking them into doing his dirty work. The only time the heroes get to confront him face-to-face is when he wants them to, or when he think he's gotten strong enough to finally finish them off. The heroes spend a lot of time seeking out {{Cosmic Keystone}}s that could weaken him, but by the time they get there he either knows and has destroyed or is about to destroy it, or doesn't care because he's too strong for it to work against him anymore. The pinnacle of Naraku's plans comes when he plans for the heroes to kill him as part of a scheme to exist forever. His schemes ''finally'' fall apart here: [[spoiler: he wanted Kagome to make a selfish wish on the Shikon-no-tama, which would allow him to draw her into the jewel and the two of them would exist inside it in eternal battle. He didn't count on Inuyasha making it to her and convincing her otherwise though, so once Kagome made an unselfish wish]], Naraku's plan was broken and he stayed dead at last.
* ''IrresponsibleCaptainTylor'' may or [[GeniusDitz may not]] be ObfuscatingStupidity, but many both amongst the series characters and the fans believe that he is actually working some master plan of his own, given how he always comes off on top in the end and his opponents invariably find him a SpannerInTheWorks. A {{Fanon}} theory is that Tylor has somehow become enlightened as a boddhistava, and that the beginning and end of the opening trailer showcases both his enlightenment and his plan for the Soyokaze; to lead the RagtagBunchOfMisfits into enlightenment.
* Too many to count in ''LegendOfGalacticHeroes''. Often overlaps with MagnificentBastard.
* ''LiarGame'' is all about games of XanatosSpeedChess between opposing Chessmasters. Akiyama stands out as the first and the most prominent heroic example, [[spoiler: joined later by Fukunaga, though he's not nearly as good]]. Opposing him is Yokoya, and [[spoiler: as of round 4, a cult leader assigned the CodeName "Robes"]].
* Johan Liebert, the titular ''Anime/{{Monster}}''.
* Michio Yuki, the main villain of ''{{MW}}'' plans to use his killings in order to get to the titular chemical warfare and use it to end the world.
* Several people from ''Manga/{{Naruto}}'', such as Shikamaru when [[spoiler: he tricked Hidan into injuring Kakuzu by making Hidan drink Kakuzu's blood, then having him perform his {{Synchronization}} schtick]]. However, [[spoiler: Black Zetsu is the champion of Chess mastery in the series, '''having orchestrated the entire History of Shinobi''' for the purpose of resurrecting Kaguya.]]
* Gendo Ikari from ''Anime/NeonGenesisEvangelion'' even though he was out gambitted in the end [[spoiler: by Rei who also out-gambitted Seele]].
* Toua Tokuchi from ''OneOuts'' (an earlier work by the mangaka of Liar Game) is a baseball player version of this; an adept user of [[GambitIndex gambits]]. He uses so many in the index, andn so well, that he crosses over into MagnificentBastard territory. (And no, he's ''not'' the catcher!)
* ''Manga/OnePiece'' has Sir Crocodile. The country of Arabasta sees him as their greatest protector, while he secretly controls the criminal organization Baroque Works, who likewise do not know his real identity. Anything strange that happens in Arabasta can be traced back to Crocodile's plans: from sandstorms to a countrywide drought to the formation of a rebel army. The final plan of Baroque Works boils down to using the peoples' love for their country to destroy it and allow Crocodile to take over a country that loves him. And that's just the beginning. [[spoiler:Arabasta was in no way picked at random. The World Government (which Crocodile also nominally serves as one of the Seven Warlords of the Sea) takes a dim view of any revolutionary activity, so once his betrayal became known Crocodile would need to control a nation that would give him the power to stand up to them. Like one that hides the secret to finding the [[LostSuperweapon ancient superbattleship Pluton]]. Guess what's encoded onto a tablet in the Arabasta royal tomb]].
** Naturally, Baroque Works' [[HeelFaceTurn former]] [[TheDragon vice president]], Nico Robin, qualifies as well, preferring to manipulate her enemies before resorting to violence. She maintains this trait as a main protagonist and member of the Straw Hat Pirates.
** Dolflamingo (another of the 7 warlords) has a lot of this though his imagery is aimed more at being a puppet master and treating everyone like his toy (which seems to be linked to his ability). He's able to out gambit Law and would have perfectly anticipated the Straw Hats had [[spoiler: Sabo]] not shown up and allowed Luffy to resume his role as SpannerInTheWorks
* The only 2 chapters we see Konata from ''Oto x Maho'' involve her advancing her exceedingly convoluted 7+ year long GambitRoulette to force her son Kanata to become a {{Magical|Girl}} [[GenderBender Girl]], which goes off without a hitch. The fact that she can pull off such a plan can only be explained by her being a Chessmaster.
* Yukihito Tsuge, the BigBad of the second ''{{Patlabor}}'' film nearly drives Tokyo into civil war while operating completely behind the scenes.
* ''PeacemakerKurogane'': In the manga, Suzu becomes one after he goes insane.
* ''Anime/SailorMoon R'' BigBad Wiseman/Death Phantom constructs an elaborate plot that will allow him to destroy the universe of both the past and future which involved him playing the role of the EvilChancellor to the Black Moon Clan, having them attack the earth of the future then in traveling back in time to attack the earth of the past, having the Sailor Senshi foil them, then have the Senshi traveled to the future so he could get his hands on the MacGuffinGirl he needs for his plan, Chibiusa whose power he will feed to his Evil Black Crystal which will then open a gateway of negative energy to to annihilate the universe with.
* Ukyo from ''SamuraiSeven'' constantly manipulates people to serve his own ambitions. Even the shocking news that [[spoiler: he is a clone of the Emperor]] doesn't shock him for long, and he quickly [[spoiler:disposes of the Emperor, possibly causes the death of another of the Emperor's as-yet-unborn clones, and takes over the throne himself]]. The only plan that stops him is a group of samurai who plainly state they ''have'' no plan.
* Hellmaster Fibrizo from ''{{Slayers}}'', who manipulates nearly all the events in ''Next''. He even gets a VillainousBreakdown.
* The Anti-Spiral collective from ''Anime/TengenToppaGurrenLagann'' pull this off quite well; they anticipated every move possible the 'spiral beings' could have made, and intentionally let them achieve almost all of their small victories, for "The greatest despair is brought after the failure of the greatest hope". The only reason they failed was due to a not-so-subjugated mind-puppet herald, Princess Nia Tepperin.
* ''Webcomic/TowerOfGod'': AlmightyJanitor Yu Han-Sung. Few people can actually see he is plotting something and those that do are probably [[KansasCityShuffle looking in the wrong direction]].
* Kurama from ''Manga/YuYuHakusho''. A "good guy" example. Even though he has a GreenThumb (which would [[WhatKindOfLamePowerIsHeartAnyway seem to be useless in normal circumstances]]), you don't ever want to become his enemy or otherwise try to mess with him. '''''Ever'''''.
[[/folder]]

[[folder: Comic Books]]
* ''Comicbook/TheAvengers'' villain Immortus was always a Chessmaster in a big way, but in the ''ComicBook/AvengersForever'' series it turned out he was a Chessmaster on a far greater scale than anyone had imagined, he [[spoiler:had manipulated virtually every event in the history of the Avengers simply to prevent the human race from becoming dangerous enough that the malevolent Time Keepers would wipe them out to preserve their own existence]].
* Franchise/{{Batman}} villain ComicBook/TheRiddler is an accomplished chessmaster, notably for smooth sway over the media, especially post-reformation (a quality of VillainWithGoodPublicity), and for his previous yet strategically subtle maneuverings of other well-known manipulators and dangerous personas.
** [[spoiler: In Hush: The Riddler discovers Batman's secret identity and manipulates Bat's oldest friend and his old mechanic, Poison Ivy (who in turn uses Catwoman and SUPERMAN), Killer Croc, Harley Quinn, Clayface, Scarecrow, Ra's Al Ghul. Even the Joker was talked in to going along with his scheme. However, Batman ensures his confidentiality when he exploits the Riddler's compulsion: he can't expose Batman because it would be like giving away the answer to a riddle]].
** ComicBook/TwoFace can also be a ChessMaster, usually having two plans in motion at once, one often entirely different (but also in some way linked) to the other.
** You can't say Franchise/{{Batman}}, chessmaster, and villain in the same sentence without talking about ComicBook/{{Bane}}. He managed to beat fellow {{Chessmaster}}, ComicBook/RasAlGhul, at a game of Chess even though he's never seen a chessboard before.
** The daughter of Ra's Al Ghul, Talia, [[GrantMorrisonsBatman has recently proven to be far more cunning than anyone could have suspected]]. It helps that she's just as CrazyPrepared as the Bat himself, and fueled by [[WomanScorned a lot more]] [[WellDoneSonGuy malice than]] [[VisionaryVillain Ra's ever was]]. Talia and her agents have proven so dangerous that [[spoiler: it turns out that the mysterious organization Batman thought dangerous enough to create a massive, worldwide organization of Batmen, Leviathan, [[TheReveal is controlled directly by Talia herself]]]].
** Franchise/{{Batman}} himself. He ''is'' the namesake of the BatmanGambit after all and he is pretty skilled in chess.
* The ComicBook/BlackPanther of the MarvelUniverse is a rare example of this trope who's a traditional superhero, albeit one that is occasionally under fire from his more-idealistic peers, for obvious reasons.
** An example more along the vein of the standard AntiHero would be Adam Warlock, who is often the foil to Thanos.
** Franchise/{{Batman}} is the AlternateCompanyEquivalent for TheDCU.
* While mentioned and kind of mocked on the '[[ExamplesUsingChessMetaphors using chess metaphors]]' page, ''{{Darkseid}}'' is definitely a very competent and dangerous Chessmaster when he's written correctly. This is perfectly invoked in ''WesternAnimation/SupermanTheAnimatedSeries''.
--> ''"I told you once, {{Superman}}, if you would not be my knight, you would be my pawn."''
* TheKingpin is another Chessmaster, especially where ''Comicbook/{{Daredevil}}'' is concerned. (Daredevil seems to attract them -- even the two-bit villain Mysterio became one when he took on DD.)
* Metron of ''Comicbook/NewGods'', who is an EnsembleDarkHorse thanks to his unemotional, bipartisan manipulation of events.
* [[UltimateMarvel General Nick Fury]] is a heroic (well, anti-heroic) version of this trope with the full sanction of the United States Government. And also, total {{badass}}ery.
** The regular MarvelUniverse's Colonel NickFury is no slouch either, even when he loses the support of the US government.
* Destiny Ajaye from Top Cow's ''[[http://www.newsarama.com/php/multimedia/album.php?gid=590 Genius]]''
* Marvel's Grandmaster can come up with some really complicated schemes. Luckily for the heroes he really doesn't care about losing, he just does it for fun. And when he really wants something he's [[UnwittingPawn nice enough to let them think they won]].
* The goddess Athena in the MarvelUniverse series ''TheIncredibleHercules'' is another heroic version of this trope; one of the series' major ongoing threads is a(and, as yet, largely unknown) BatmanGambit she is in the process of executing. Her brother Hercules, a frequent key piece on her chessboard, finds her refusal to be upfront with her plans annoying.
** The goddess Athena in DC is possibly an even bigger version. Her scheme to bring down Zeus required the resurrection of Medousa; the death, by Medousa's stone gaze, of a child of one of WonderWoman's embassy workers (to incense Diana into killing), and then a duel to the death between Medousa and Wonder Woman that culminated in Wonder Woman's blindness and the decapitation of Medousa. This entire chain of events was simply her way of obtaining a fresh gorgon's head (Medousa's previous head having rotted away to uselessness) to use on Zeus's champion, the hecatoncheires Briareos. And that doesn't even count the plot that she undergoes to consolidate her power once Zeus, Poseidon, and Hades try to rebel...
* ''Comicbook/IncredibleHulk'': Bruce Banner is this, at least under Greg Pak's pen. As we learn in ''FallOfTheHulks'', Banner's just as dangerous as his savage green alter-ego - if not more so.
* Alex Wilder of ''ComicBook/{{Runaways}}''. [[spoiler: It turns out that, not only did he learn the truth about his parents a full year before the other kids, but he set up virtually every single event in the first volume of the series]].
* General Wade Eiling definitely fulfills this trope, given the way he manipulates CaptainAtom.
* While the comic series ''{{Sleepwalker}}'' is relatively obscure and ran for only 33 issues, its BigBad Cobweb is a brilliant Chessmaster, [[EvilPlan using Sleepwalker as a way to invade Earth while framing him as the demonic invasion's leader]].
* NormanOsborn of ''{{Spider-Man}}'' is another contender in this category. Brought BackFromTheDead when Marvel needed a "[[AuthorsSavingThrow Get Out Of Clone Saga Free]]" card, Osborn has more than made up for lost time. For a while, every other Comicbook/{{Spider-Man}} story was turning out to be some sub-sub-plan of Osborn's.
* Franchise/{{Superman}} enemy {{Brainiac}} has often been this, in contrast to MagnificentBastard SelfDemonstrating/LexLuthor. Brainiac has frequently set up incredibly complex plans, using every character as a chesspiece in his efforts to [[PlanetLooters steal cities]] / [[AGodAmI become a god]]/absorb the sum total of all knowledge in the universe (his motive keeps on changing), but has trouble changing them once something goes wrong.
* The Phantom Blot is ([[DependingOnTheWriter often]]) at least as close to a Chessmaster as the writers of ComicBook/DisneyMouseAndDuckComics can manage. If there's an [[TheManBehindTheMan unseen mastermind]] affecting the events and leaving Mickey Mouse baffled for most of the story, it's probably the Blot.
* {{Thanos}} is a staple Chessmaster in many cosmic [[CrisisCrossover crossovers]] in the MarvelUniverse. It's frequently [[LampshadeHanging lampshaded]] how other characters (especially heroes) exist solely to be manipulated by him for whatever agenda he might have at the moment.
* V, AntiHero of ''ComicBook/VForVendetta''. In the film, Finch actually figures out part of the plan, but can't do much to stop it by that point.
** In the graphic novel, Finch [[spoiler:goes as far as to almost stumble upon V's lair, but decides his ordeal is over when he fatally shoots V. This was all part of V's plan...]].
** V also uses a Domino motif for his plan.
* Tao from the ''Wildstorm'' comics universe, especially as written by Creator/AlanMoore or Ed Brubaker.
[[/folder]]

[[folder:Fanfiction]]
* The WesternAnimation/MyLittlePonyFriendshipIsMagic crossover story FanFic/AHollowInEquestria portrays Princess Celestia as attempting to be this, and failing miserably at every turn.
* [[http://www.fimfiction.net/user/Jordan179 Jordan179]]'s "The Shadow Wars" WesternAnimation/MyLittlePonyFriendshipIsMagic verse depicts ''both'' Major Alicorn Princesses of Equestria as this, especially Celestia. In FanFic/NightmaresAreTragic, a rewrite of ''The Elements of Harmony'' from Nightmare Moon's perspective, Princess Luna is well aware of her sister's cunning and as Nightmare Moon plays (and loses) a very complicated game of XanatosSpeedChess with Celestia playing by proxy through the Mane Six; the final act of which sees Princess Luna [[spoiler:realizing that she's a ''slave'' to the [[AlwaysChaoticEvil Night]] [[DemonicPossession Shadows]] and fighting and a [[FightingFromTheInside battle within]] against the Shadow, paralyzing Nightmare Moon long enough for the Mane Six to destroy the Shadow with the [[CareBearStare Elements of Harmony]]]]. In FanFic/AnExtendedPerformance, we get to see the same Longest Night from the perspective of ''Celestia'', who not only had the Apples found Ponyville a century ago just to have a place to breed potential Element-Bearers, but has complex contingency plans for the event of the Mane Six ''failing.'' Celestia even describes herself in her own thoughts as a "smiling schemer."
* Calvin slowly develops into this over the course of ''Fanfic/CalvinAndHobbesTheSeries''.
* In ''Fanfic/HarryPotterAndTheMethodsOfRationality'', we have.. everyone, really. The adult chessmasters are Lucius Malfoy, Dumbledore, and Quirrel, while the kid ones are Draco and Harry, but everyone has at least some elements. The adults also give a good view on different ways this trope can be played: [[CharacterAlignment Lawful]] Lucius prefers the XanatosGambit approach, controlling events until the only possible outcomes are one or two he predicted, which will benefit him. The more chaotic Dumbledore and Quirrel, however, prefer to just stack dominoes in their favor, and when everything starts to fall apart, [[XanatosSpeedChess move quickly to take advantage]]. Draco takes after his father, while Harry is learning from Dumbledore and Quirrel.
-->'''Quirrell:''' In your future career, Mr. Zabini, I do not suggest trying any plots that complicated. They have a tendency to fail.
-->'''Blaise:''' Um, I said that to the Headmaster, actually, and he said that was why it was important to have more than one plot going at a time.
* In the ''Franchise/MassEffect'' fanfic ''The Council Era'', the advisor to the Krogan Overlord, Halak Marr, definitely qualifies as a Chessmaster. In order to bolster his army in preparation for the war with the Citadel, [[spoiler:Marr preserved specimens of the dezba (who would naturally have retained a major grudge against the Citadel over their people's genocide) and began a project to resurrect a dezban chieftain, a la Project Lazarus in ''VideoGame/MassEffect2'']]. As mentioned on the UnwittingPawn page, he usurped his superior in order to enact his dreams of the krogan as a MasterRace. He successfully forced Tyrin Lieph to allow his people to take a majority in the Citadel military and give the krogan a Council seat through an excellently-executed plan. He also antagonized the already fragile relationship between the manaba people and the Citadel by faking an attempt on his life by manaban extremists.
* ''Fanfic/SoulChess'' used to focus on [[MagnificentBastard Lelouch]] and [[GodModeSue Aizen]] trying to [[UltimateShowdownOfUltimateDestiny fight for control over the Soul Society]]. [[spoiler: Lelouch wins, but Aizen comes back from Hell for Round 2]].
* [[spoiler: Jeft]] in ''Fanfic/WithStringsAttached''. [[spoiler: He maneuvered three of the four into getting their major magic, set up the entire Vasyn quest, fooled the other Fans into thinking it was real by having an AI play the Dalns gods, and moved the Vasyn pieces into “entertaining” places for the four to struggle with. He was so overconfident that during the quest for the third piece, he openly forced the four to travel with his best character, the Hunter, which finally clued Varx and Shag into his duplicity]].
* A number of characters in ''FanFic/TheInfiniteLoops'' can outwit nonlooping characters easily, but this trope really comes into play when the loopers have some form of competition with each other.
* Camillo and August seem to be this in the Hunger Games fanfic ''FanFic/SinkOrSwim''. Camillo rather fails at this, though.
* In ''[[FanFic/TheVinylAndOctaviaSeries Vinyl and Octavia Duel Destiny]]'', [[spoiler: Winter Snow]] reveals at the end that they were behind the events of the last two stories, with nopony realising so.
[[/folder]]

[[folder:Film]]
* The RedSkull, as portrayed in ''Film/CaptainAmericaTheFirstAvenger'', was so DangerouslyGenreSavvy in [[spoiler:dispersing his resources throughout Europe]] that he was able to make his DoomsdayDevice. [[spoiler:Captain America and his allies were only able to stop his final plan at the last possible moment]].
* [[spoiler: Miles Axlerod]] from ''WesternAnimation/{{Cars 2}}''. In order to turn all the cars in the world away from alternative energy, [[spoiler: Axlerod]] actually invents an explosive chemical called Allinol which he pretends is actually a safe alternative fuel, and he promotes Allinol with the World Grand Prix, a series of races where the world's fastest racecars must compete in three races taking place in different parts of the world. [[spoiler: Axlerod]] then order his [[TheDragon Dragon]], Professor Z and his army of [[{{Mooks}} Lemons]] to use a powerful radiation cannon to blast away said racecars once the race is in session, then makes everyone think that Z is the one behind the evil plot and not him. After the second race, which takes place in Italy, [[spoiler: Axlerod]] tells everyone that Allinol is actually dangerous and forces the racecars to use ordinary fuel, because since [[spoiler: Axlerod]] secretly owns the largest oil supply in the entire world, he and the Lemons will become unstoppable once alternative energy has been shunned from society, but tricks Lightning [=McQueen=] into still using Allinol so that the Lemons can blow him up. Unfortunately for [[spoiler: Axlerod]], Sarge secretly removed the Allinol from [=McQueen=]'s body and instead replaces it with [[TheOtherDarrin Fillmore's]], and as a result he has no other choice but to install a detonator onto Mater's body as a last-minute attempt to kill that racecar.
** Unfortunately for him makes a mistake by leaking oil which allows Mater to move up the board and eventually force him into checkmate.
* For a character who ''claims'' to hate the convoluted plans, ''Film/TheDarkKnight'''s Joker is skilled at making them. Unless he's [[IndyPloy making it up as he goes along]], [[ChaoticEvil which is quite possible]]. [[AxCrazy The Joker's sadism]] also leads him to pull off some [[ShootTheDog nasty]] (although thwarted) {{Evil Plan}}s.
* In ''DeathRace'', the Warden is clearly the Chessmaster, with the way she manipulates the convicts to play in the GameShow race. In view of the fact that the audience is made not to like her she's also the AntiHero, and she's a ManipulativeBastard.
* CRS in ''Film/TheGame''.
* Vito Corleone in ''Film/TheGodfather'' would serve well as the very definition of a Chessmaster. In the book and the movie, he planned out every detail of every part of the story [[spoiler: perhaps even his own death]].
** Except that he never wanted Michael to become a part of the family business.
* Scar from ''Disney/TheLionKing''
* In ''Film/LittleSweetheart'' nine year old Thelma (8 and 364 days at the start of the movie) manipulates her new and only friend, her mother, her uncle, the police, the new neighbors who happen to be bank robbers on the run and everyone else she meets throughout the movie. [[spoiler: Only one thing goes wrong: her friend doesn't die after going face down in the ocean after an arm shot and what was either a torso or '''headshot''' for several minutes. The friend is also nine]].
* The Oracle from ''Film/TheMatrix'' is a [[spoiler: sentient computer program]] capable of predicting Neo's reactions so well that she essentially made Neo the One. All of Neo's heroics are all essentially part of her chessmaster plan, even Agent Smith.
** The Architect, who managed to [[spoiler: manipulate all previous "Ones" into his plan by threatening them with the extinction of the human race]].
* Tommy from ''Film/MillersCrossing'' is a very prolific anti-heroic example. Nearly every character in the movie is deceived by him in some capacity. In fact, he manages to [[spoiler: take down Casper's gang]] simply by sowing seeds of mistrust. Even his closest friends are lied to and manipulated, albeit for their own safety. By the resolution of the movie, even the people he saved are are unaware of the entirety of his schemes.
* [[spoiler: Dylan]] in ''Film/NowYouSeeMe''.
* Rotti Largo from ''Film/RepoTheGeneticOpera'' is so good at these, it sometimes gets hard to find things that ''aren't'' orchestrated by him.
* Both MichaelCaine and LaurenceOlivier are chessmasters in the 1972 version of ''{{Sleuth}}''. The chessmaster in the 2007 version was whoever got me to watch it.
* Senator/Chancellor/Supreme Chancellor/Emperor Palpatine in the ''Franchise/StarWars'' prequel trilogy. Got a less-than-scrupulous faction to blockade/invade his backwater homeworld just to get the old leader kicked out and himself elected in the process. Then gets his apprentice to start a war to increase his authority under "wartime powers". Then gets his sworn antitheses to attempt to thwart him so he can declare them enemies of the state and use his "severely disfigured in an attempt on my life" sob story to get enough sympathy to be named dictator for life. While [[PlayingBothSides playing both sides of the board]], so as to have a backup plan if something went wrong (presumably, just sabotage the clones from the Republic side and conquer the galaxy with droids. Not that he ever needed to.)
** Also Grand Admiral Thrawn from the ExpandedUniverse. One character (who knew them both rather well) notes that if Palpatine was always one step ahead of all the would-be players, Thrawn was two steps ahead.
** From [[KnightsOfTheOldRepublic KOTOR II]], the character Kreia could be seen as Palpatine from four millenia previously. She manipulates both the jedi and the sith to such a degree that even at the end of the game, it's hard to tell what side she was on, [[spoiler: or even if she was on anybody's side]]. At one point, she even calls one of the other characters a "pawn".
*** The true Palpatine of that era was the Sith Emperor, who was essentially the ManBehindTheMan for all of the events of the KnightsOfTheOldRepublic series. He played Revan and Malak as pawns to find the Star Forge for him (which only failed due to Revan's memory loss and subsequent redemption), orchestrated the Mandalorian Wars, made puppet governments on a number of Outer Rim Republic worlds, infiltrated the Republic and the Jedi Order, and came closer to conquering the Republic than anyone would until Palpatine himself, almost 3,500 years later.
** [[spoiler: [[WesternAnimation/RobotChicken "Suuuuure, Palpatine. ''You-sa'' manipulated ''me'']]. [[EvilLaugh Mwahahahahaha!"]]]]
* ''Film/WildThings'' peels back layer after layer of deception until the real Chessmaster is revealed. The studio must have liked this idea, because they did it ''two more times'' with direct-to-video sequels.
* Ichirō Yashida was behind most of ''Film/TheWolverine'''s events, directly or indirectly.
* In ''Film/TheWrongArmOfTheLaw'', Pearly Gates develops into this over the course of the war against the IPO mob. This was played up in advertising.
[[/folder]]

[[folder:Literature]]
* Edgewood Dirk in ''A Princess of Landover'', 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.
* [[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.
* The title character of Creator/AlexandreDumas's ''Literature/TheCountOfMonteCristo''.
* Frank Herbert's ''Literature/{{Dune}}'' is filled with them, each with varying levels of skill and subtlety.
** 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.
** The master of it though would be the 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.
** The Bene Tleilax also get a lot of this in Heretics of Dune and Chapterhouse: 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.
* Hari Seldon of Creator/IsaacAsimov's ''{{Foundation}}'' series, who 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.
** Even more so than him, 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 [[Creator/IsaacAsimov Three Laws Of Robotics]], which he and a fellow robot manage to subvert by realizing that [[spoiler:a law even more overriding than the one prohibiting homicide is one "the 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 unitary-consciousness push is undertaken in order to subsume the zeroth law into the first and resolve the bind they've created for themselves]].
* [[Literature/JeevesAndWooster Jeeves]] is essentially a Chessmaster who uses his powers for good. His BatmanGambit 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 ClockKing in there too.
* Sauron in ''Literature/TheLordOfTheRings''.
* Zhuge Liang (styled Kongming) is portrayed as a Chessmaster (who skirts into MagnificentBastard territory quite often) throughout most of ''Literature/RomanceOfTheThreeKingdoms'' (and [[DynastyWarriors subsequently in Koei's adaptations]]), 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.)
** Cao Cao counts as well (especially in real life), but he's given the IdiotBall when confronting Zhuge Liang
* 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.
* In the ''Literature/SherlockHolmes'' 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 [[NoodleIncident alluded to by Holmes]].
* Literature/TheContinentalOp of Creator/DashiellHammett's ''Literature/RedHarvest''. [[spoiler: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 ''Film/{{Yojimbo}}'' which was later adapted into a western, ''Film/AFistfulOfDollars''. Makes you wonder if Dashiell Hammett had this planned from the start...
* Radio/TheShadow 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.
* Essentially, the murderer in ''any'' Creator/AgathaChristie novel. One of her most manipulative murderers would undoubtedly have to be [[spoiler: the judge]] from ''Literature/AndThenThereWereNone'', who plays off the psychology of each victim [[spoiler: especially Vera Claythorne]].
* 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.
* 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.
* Subverted in "The Twisted Thing" by Mickey Spillane. Private eye Literature/MikeHammer 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 EvilPlan 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.
* ''The Judge and His Executioner'' by Friedrich Dürrenmatt. Commissar Bärlach [[spoiler: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]].
* 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...]].
* ''[[Literature/{{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, [[spoiler: turns into a rich-but somewhat crazy-man living in Italy]].
* In Eleanor Updale's ''Literature/{{Montmorency}}'', the titular character has some Chessmaster tendencies, but they are completely trumped by the anarchists in the third and fourth books.
* In Carrie Vaughn's Literature/KittyNorville series, Mercedes Cook is revealed as this through her manipulation of Arturo and Rick into a vampire war. The fact she in turn is [[TheManBehindTheMan working for/being manipulated by]] [[spoiler:Roman]] only adds even more delicious levels of convolution...and since ''he'' is only stated to be a general in [[AncientConspiracy the Long Game]], chances are there's an OmniscientCouncilOfVagueness out there manipulating ''everyone'', which Kitty will [[TheChosenOne inevitably have to face down]].
* John Alpha, the BigBad of ''Literature/SeventhSon'', 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.
* A relatively rare female example with Professor Jenna-Jane Mulbridge in Mike Carey's ''Literature/FelixCastor'' novels: while the series features demons and undead galore, moreover, it is the two human examples, Jenna-Jane and ChurchMilitant leader Father Thomas Gwillam, who draw the most ire from the protagonist.
* Steven Brust's ''[[Literature/{{Dragaera}} Yendi]]''. [[PlanetOfHats 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.
* Arguably Gentleman John Marcone, from Jim Butcher's ''Literature/TheDresdenFiles''. 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, [[spoiler: 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 Knight'', talked his way into [[spoiler: becoming a freeholding lord in the supernatural world. There are twenty such legal entities; Marcone is the only mortal]].
** Also Nicodemus, Daddy Raith and Lara, any of the Sidhe by default, the 'Black Council' (assuming it exists), possibly Cowl, Uriel, Harry himself (after CharacterDevelopment) and many more . . . really, Jim Butcher seems to love these.
* 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''.
* Makina Seval of ''Literature/TheAssassinsOfTamurin'', whose GambitRoulette 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 title character of the ''Literature/ArtemisFowl'' series (being a TeenGenius 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 GambitPileup, with Artemis [[OutGambitted coming out on top]].
* ''[[Literature/EndersGame Shadows of the Hegemon]]'' by Creator/OrsonScottCard is a [[GambitPileup 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 subtlety guiding their kids.
* Saint Dane from ''Literature/ThePendragonAdventure''. VoluntaryShapeshifting 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.
* The Puppeteers from Larry Niven's ''Literature/{{Ringworld}}''.
* The Duke of Wellington, as depicted in the Literature/{{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 MagnificentBastard 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'': [[spoiler: 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'': [[spoiler: 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:''' [[spoiler: 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]]. ''[[spoiler: 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.
* ''Literature/ThePiloFamilyCircus'' 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 [[ManchurianAgent brainwashing her customers]] into committing [[ForWantOfANail seemingly unrelated events in the real world]] and therefore actually pull off one successful GambitRoulette after another.
* Kelsier, the main character from the first book of Brandon Sanderson's Literature/{{Mistborn}} series, is a nice inversion as a ''heroic'' Chessmaster. He demonstrates his talent through a multi-layered BatmanGambit.
** It's not just him. [[EvilOverlord The Lord Ruler]], [[AristocratsAreEvil Straff]], [[DungeonMaster Preservation]], [[OmnicidalManiac 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 GambitPileup.
* Human/alien merger Mademoiselle in Creator/AlastairReynolds' ''Literature/RevelationSpace'' 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."
* Waleran Bigod from ''Literature/ThePillarsOfTheEarth''.
* Emperor Ezar in Creator/LoisMcMasterBujold's ''[[Literature/VorkosiganSaga 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 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.))
* 'Sticky Eye' Kawakami in ''Literature/CloudOfSparrows'' wants to be one, but he isn't very good at it. He compensates by being a truly fearsome ManipulativeBastard.
* 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.
* Ardneh, from Creator/FredSaberhagen'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 TheEmpire. In the second volume, he manipulates two of the villains from the first volume into {{Heel Face Turn}}s 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 TheEmpire, and most of the world's most powerful demons, [[ThanatosGambit in a single stroke]].
* Paladine, in the ''Literature/{{Dragonlance}} Chronicles'', but especially in the ''Legends''. In the former, he recruits and manipulates the RagtagBunchOfMisfits into saving the world, while [[spoiler:disguised as the [[ObfuscatingStupidity senile pyromaniac Fizban]]]]. In the latter, he actually lets [[spoiler:Raistlin [[ThanatosGambit 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.
* Both The Ellimist and Crayak in ''Literature/{{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 it
** The Ellimist is a classic one, though. At one point he 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...
* ''Literature/TheObsidianTrilogy'' 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... [[KlingonPromotion 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 [[TheMagocracy 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 [[TheManBehindTheMan effective control]] of Armethalieh and come within moments of [[spoiler: handing the whole thing over to Savilla]].
* Gaius Sextus in ''Literature/CodexAlera'' is one of these, though the limitations of trying to do this without inexplicable perfect knowledge of all events is clear. A lot of people became extremely angry at these tendencies, and many people considered him less "masterful" than "feeble" and blamed him for the situation of Alera.
** 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 [[spoiler: when he conspires with the [[{{Wolfman}} 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]].
* Admiral Sun Ji Guoming from the Creator/DaleBrown novel ''Fatal Terrain'' carries out an unconventional warfare plan that succeeds in getting the rest of the world to see China as a VillainWithGoodPublicity even as it [[NukeEm 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.
** [[spoiler: National Security Adviser Robert Chamberlain]] from ''Act of War'' plays everyone in his quest to kill [[CorruptCorporateExecutive Harold Kingman]].
* Lisbeth Salander of Stieg Larsson's ''Literature/MillenniumTrilogy'', if she doesn't start as a chessmaster, certainly ''becomes'' one by the end of the third book. As an example, [[spoiler: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]].
* "Mister X" in the third ''Literature/EmpireFromTheAshes'' 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 [[YouHaveOutlivedYourUsefulness they inevitably die]]).
* Merlin from ''Literature/TheWarlordChronicles'' makes sure that plenty of powerful people on all sides he has influence on owe him favours, and that everybody fears his [[MaybeMagicMaybeMundane 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.
* 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]].
* ''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]].
* Discussed in Lord Chesterfield's ''Literature/LettersToHisSon''. "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)
* Viviane in ''Literature/TheMistsOfAvalon''. Ultimately to little avail and the general detriment of everyone involved.
* ''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.
** 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.
* ''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.
* ''Literature/SongAtDawn'': Moving pieces and outgambitting are required skills for anyone in this setting: nobles, merchants, bishops, bodyguards, etc. The greatest of them is [[spoiler: al-Hisba who plays everyone to accomplish his own objective while placating his enemies and helping a friend]].
* Prince Vassily Kuragin in ''Literature/WarAndPeace''. ItRunsInTheFamily too, as Anatole and Elena (not [[UpperClassTwit 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 ''TabletopGame/{{Warhammer 40000}} Literature/BloodAngels'' novels rather masterfully steers the titular Space Marine Chapter towards [[spoiler: Chaos]], though as we are reminded several times, he's still a pawn to a greater power.
* Jonathan Stonagal is made to be this in the Literature/LeftBehind series, particularly in the prequel books where he funds the DesignerBabies project that creates Nicolae Carpathia, with the intention that he would be Jonathan's puppet to rule the world with. Unfortunately, Jonathan gets an EtTuBrute 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.
* In S.A. Swann's Literature/TerranConfederacy, elements of the composite AI called Random Walk[[spoiler:/Tjaele Mosasa/Mike Kelly/Ambrose/Adam]] have been manipulating human society to its own ends and that of its alien creators for centuries.
* Aly, the protagonist of ''Literature/DaughterOfTheLioness'', 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.
* ''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]].

[[/folder]]

[[folder: Live Action TV]]
* The Shadows and the Vorlons in ''Series/BabylonFive'' are two entire ''races'' of Chessmasters.
** Londo Mollari also has some serious game.
* Number One/Brother Cavil/John in ''Series/{{Battlestar Galactica|Reimagined}}'' is ultimately revealed to be the mastermind behind "the Plan" that encompassed the near-annihilation of the human race and the subsequent pursuit of the survivors halfway across the galaxy for the next five years. The point of this plan? [[spoiler: ''To prove to Ellen Tigh that humans suck'']].
* ''Series/BlakesSeven''. This is the job of the 'psychostrategist', a Federation officer whose role is to predict and manipulate people. Unfortunately he's informed too late about a random element and, realising his plan will therefore collapse, smartly decides to vanish before Servalan finds out. Servalan, a bit of a ManipulativeBastard herself, seems amused rather than incensed over his cunning.
** And the Puppeteer in question, Carnell, is also [[SmartPeoplePlayChess very good]] at chess.
--> '''Carnell:''' ''I'm very good, Supreme Commander, believe me. I've taken everyone and everything into consideration. It's all as predictable as... that very expensive chess machine''.
* In later seasons of ''Series/BreakingBad'' Walter White becomes a Chessmaster, manipulating Jesse into [[spoiler: killing Gustavo Fring by poisoning Brock, the 9 year old son of Jesse's girlfriend, and making him believe that it was Gus who poisoned him]].
* J.R. Ewing in ''{{Dallas}}''.
* Adelle [=DeWitt=] of ''{{Dollhouse}}'', especially if you believe the WildMassGuessing that [[spoiler:"speaks-through-Echo" was a deliberate false mole to manipulate Ballard into leaving the FBI and "letting the Dollhouse win" to get him off their backs and feed him whatever information they wanted to]].
* Likewise the team of ''Series/HawaiiFiveO''.
* Linderman of ''Series/{{Heroes}}'' seems to have his hooks in everything, especially DL and Niki. His apparent omniscience is helped along by being a collector of art... particularly art made by a guy who paints the future.
** Rebel/[[spoiler:Micah]] is showing signs of this. He certainly prefers to operate by proxy [[spoiler:given that he's a 12-year-old kid with no combat powers]]. He's a {{Technopath}}, which enables him to covertly communicate with his "pieces" and listen in on government communications. However, he hasn't done much in the way of manipulation - he prefers to give direct instructions, and his plans tend to be short term. Then again, you don't need to be much of a chessmaster to outsmart the federal government.
* Silas Blisset from ''Series/{{Hollyoaks}}'' of all shows. "You'd better raise your game or I may grow weary of such a dull opponent."
* On the subject of Chessmasters using their powers for good... [[LoveableRogue sorta]]... Mickey from ''{{Hustle}}'' is a pretty good example. For example, he (at the time of writing) [[spoiler:stole from a corrupt banker turned financial consultant and, when arrested, bluffed his way out of it by pretending he'd actually been consulting him on pension schemes - vindicated when the briefcase full of money was opened to show... pension plan leaflets. He does similarly '''every episode''']].
* Clayton Webb in ''Series/{{JAG}}''. A cold blooded CIA officer who is skilled and subtle in manipulating operations all over the world.
* Benjamin Linus from ''Series/{{Lost}}'' has pulled off at least one GambitRoulette, as well as quite a few plans that are so roundabout and convoluted one has to wonder if he's actually omniscient. Case in point, [[spoiler:in the season 3 finale, he gave advance orders to some of his men to pretend to shoot their captives over an intercom so that he could manipulate Jack, knowing that Jack would assume Ben was bluffing, and having to survive with the guilt of killing three people by not giving into Ben's demands]].
** Ben Linus also fits in the ManipulativeBastard trope, seeing as most of his schemes have to do with toying with people's emotions.
** Ben always has a plan, but his plan pales in comparison to that of [[spoiler:Jacob's Enemy, [[BigBad The Man In Black]]]]. As of the Season 5 finale, we know that [[spoiler:The Man In Black]] is the true Chessmaster of ''Lost''. The guy's [[ThePlan scheme]] includes everything in Ben's plans, plus some extra behind-the-scenes manipulation of both Locke and Ben to get them in position to execute [[spoiler:The Man In Black]]'s master plan.
*** The Man In Black may be the show's master in terms of raw skill and speed. In The Candidate, we see him discover one of his enemies's plots to kill him, subvert it and then with only minutes to spare [[spoiler: rebuild a bomb that was intended for him into a device that appears active but will only actually activate when someone tries to disarm it, get the main characters he needs to kill to go where he wants them to, slips the bomb into one of their backpacks, and then relies on the fact he knows they will double cross him to keep him clear of the trap he's just set up. The end result: three main characters die at the hands of a master XanatosSpeedChess player]].
** According to [[spoiler:Jacob's enemy]], Jacob has manipulated the main characters' lives so that they would get on Ocean 815 and crash on the island. He proves this by showing [[spoiler:several familiar names written on on a wall in a cliffside cave]].
* The ''MissionImpossible'' series is a rare but well-executed example of non-villain, non-AntiHero chessmastery.
* Michael Scofield from ''PrisonBreak'' is a chessmaster on par with people like [[Manga/DeathNote Light Yagami]]. You can be sure that, no matter how short the time is or how hard the creation of a plan is, he ''will'' come up with something. And if his plan fails he ''will'' have a backup-plan ''or'' it was supposed to fail all along. Adding to that, he's sometimes CrazyPrepared.
* On ''{{Smallville}}'', Lex has used the quote at least once to describe the comparison of his scheming to that of his MagnificentBastard father. Then there's Brainiac who usually sets his plans in motion months in advance, and Waller of the appropriately named Checkmate.
* Captain Benjamin Sisko manages to be one on ''Series/StarTrekDeepSpaceNine'', episode "In the Pale Moonlight". In truth, he [[spoiler: asks for Garak's help, who, in the end, proves to be the real chessmaster]].
* Seska on ''Series/StarTrekVoyager''. (Especially when she showed up to torment the crew [[spoiler: three years after her death.)]]
* John Connor of ''{{Terminator}}: TheSarahConnorChronicles''. Specifically, John Connor from the future, where one of the resistance fighters even comments on "his chess game with Skynet." Current John Connor seems to be headed that way, too.
* Most ''Series/TwentyFour'' {{Big Bad}}s. Though most of them are even better at [[GambitRoulette roulette]].
* Wyndham Earl from ''TwinPeaks''.
* CJ Cregg, press secretary on ''TheWestWing'', manages to manipulate both the press and the House of Representatives into making the HR be the one handling the investigation of the president, instead of the Special Prosecutor, because she feels they'll bungle it. And she does it entirely by complimenting the Special Prosecutor and talking up his credentials too!
* ''VeronicaMars'' pulls off several of these to catch criminals. The plan she uses to allow Duncan to escape the USA with his child crosses into roulette territory.
** There's also the epic scheming of [[spoiler:Cassidy Casablancas]]. Not only did he kill a dozen people, keep any attention off him for months, manipulate and blackmail his way through the stock market, he's also the only person I can ''ever'' remember lying to Veronica's face and not having her suspect at ''all''. [[spoiler:And he's just 16]]. He's ''good'' dammit.
* Stringer Bell of ''Series/TheWire'' is a cunning and ruthless player in Baltimore's drug game who manipulates and betrays those around him to advance his own goals. That said, he's not quite as good at it as he thinks, and is eventually conned out of a lot of money by the even more shrewd Clay Davis. [[spoiler:His plan to set Omar Little and Brother Mouzone against each other backfires on him fatally]].
** Stringer has more flash, but he can't hold a candle to Prop Joe [[spoiler:who is the actually the one who came up with the idea of putting Omar on Mouzone, but was smart enough to route the plan through Stringer, and thus avoided all of the blowback. When we first meet Joe, plays Avon and Stringer by getting them to double-down on their basketball bet (by holding back a ringer on his team). Later, runs a fairly brilliant gambit to bring Marlo into the co-op (earning himself a nice little payday in the process). Ultimately, he was too slow in getting out of Marlo's way, but unlike Stringer, he saw his doom coming and managed to die with some dignity]].
** Lester Freamon also deserves a mention. Lester, like any good chessmaster, understands that "all of the pieces matter" (as he tells Prez). Though he's obviously a part of a team effort, Freamon plays a huge role in bringing in the victories for his side; like Jimmy and Kima, he contributes good detective work, but beyond that his big picture view, political savvy, and capacity for deception and subtle manipulation (sometimes of his allies and coworkers) are what really allow his investigations to (sometimes) break through the wall; there's a reason why Daniels says to Lester, "as far as I'm concerned, you ARE the Major Crimes Unit."
** Interestingly, when the trope is made explicit by D'Angelo, he, unlike many others who talk about chess metaphors, does not believe he is a Chessmaster. He is fully aware that he is only a pawn, and his growing bitterness with this role, and the callous actions of the "kings" and "queens," fuels much of his growth as a character.
* Sir Humphrey Appleby in ''YesMinister'' and ''Yes, Prime Minister'' pulls off several devious yet intricately devised gambits designed to flummox the far-less intellectually cunning (Prime) Minister Jim Hacker, in order to thwart Hacker's agenda, cement his power and influence over the department and government, and to feather his own nest. However, Hacker - whilst nowhere near Humphrey's level of ability - is not without some low cunning himself, and is occasionally able to pull a fast one on Humphrey, and events occasionally conspire to leave Humphrey spluttering in astonishment as his plan collapses around him.
* Zora, from ''SonnyWithAChance'' does this once in the episode where she makes Chad believe he's the host of a TV program that plays pranks on celebrity stars. After she has all the characters together, she herself explained that she was manipulating everyone around the whole time, as she is the true host of the program and their true victim was Chad himself from the beginning. Then they stick Chad's feet on the floor, his face on the window and they spill manure over his new car. Chad was not happy. PlayedForLaughs.
* Molly Hardy, in ''Series/TheAdventuresOfShirleyHolmes''. Many of her plots involve blackmailing, buying and manipulating other people, or using their circumstances to her advantage.
* Katherine Pierce in ''TheVampireDiaries''. If everyone just accepted that she is always playing them no matter how vulnerable or uncertain she seems, then it probably wouldn't change the actual outcome, but they wouldn't waste time and energy trying to beat her at her own game.
* ''Series/TheShadowLine'' has several:
** Gatehouse, who's very skilled at planning events in his favour, to the point where the BBC website actually calls him a puppetmaster. [[spoiler:Indeed, it's his skill at this that ensures his ultimate victory]].
** Glickman, who actually manages to [[OutGambitted out-plan]] Gatehouse in his first appearance and ultimately proves at least as good at planning as Gatehouse.
** Joseph Bede, who, while not as good at it as the two above, successfully manages to dupe Customs into looking the other way while he carries out his deal.
* ''Series/{{Sherlock}}'': [[ManipulativeBastard Moriarty]] and [[BigBrotherIsWatching Mycroft]] both. Possibly [[TheVamp Irene]].
** Moriarty exploits what matters most to people to get whatever he wants - which, often, is just to prove that he ''can'' do whatever he wants. He even [[spoiler: drives Sherlock to suicide]] by framing him for kidnapping and threatening to kill [[BadAssNormal John]]. He manages to ruin Sherlock's reputation by convincing everyone that [[spoiler: Sherlock's a fraud]], which they want to believe anyway because of Sherlock's [[InsufferableGenius annoying personality]].
** Mycroft even admits to having more-or-less-intentionally driven Sherlock into harm's way as a result of a failed attempt to win his (metaphorical) chess game with Moriarty.
** Irene [[spoiler: fakes her death]] twice, in part to mess with Sherlock's head. Her fatal flaw is that she lets her heart rule her head, and actually is [[spoiler: in love with Sherlock]].
* In ''Series/{{Justified}}'', Limehouse is constantly manipulating the various criminals and other violent elements in Harlan County to keep his own community safe.
* Ruby in ''Series/{{Supernatural}}''. Though there is always suspicion amongst the rest of the characters that she is playing Sam, the enormous scale of her plans aren't revealed until [[spoiler:Sam kills Lilith and it is revealed that Lilith was the last seal all along, and Ruby has been working towards Lucifer's release since the very beginning]].
* ''Series/OnceUponATime'': Mr. Gold/Rumplestiltskin. It seems that everything in the show was done by him.
-->'''Regina (The Evil Queen):''' I assume this was all ''your'' doing.
-->'''Gold:''' Most things are.
%% (No context) * ''Series/{{Scandal}}'': Olivia.
* "Series/DoctorWho", the Doctor himself is a Chessmaster, though often puts on ObfuscatingStupidity. In "The Evil of the Daleks" when the Daleks force him to work on their latest plan he is able to manipulate events and start a Dalek Civil War.
** "The Impossible Astronaut/The Day of the Moon" has the Doctor trick the Silents into brainwashing the human race to kill them on sight.
[[/folder]]

[[folder:Music]]
* The song ''You're Gonna Go Far Kid'' by The Offspring talks about a chessmaster. ''Another clever word/sets off an unsuspecting herd/And as you step back into line/a mob jumps to their feet...''.
** Regrettably, people mistake it for a song about fighting by taking the line "hit 'em right between the eyes"
** There are many theories that the chessmaster from the song is none other then Jack from ''Literature/LordOfTheFlies''. "Turning all against the one" is the best evidence of this, referring to how Jack turned everyone against Ralph. Other parts of the song refer to Simon, "and no one even knew, it was really only you" referring to his death at the hands of Jack and the other boys, thinking he was a monster.
* OingoBoingo's song (released as a single under DannyElfman's name) "Gratitude."
[[/folder]]

[[folder: Professional Wrestling]]
* Puerto Rican Wrestler Ray Gonzalez's gimmick is that he's a chessmaster (and a good one at that).
* WWE Wrestler Wrestling/WadeBarrett had this as his gimmick as the leader of the PowerStable called Wrestling/TheNexus, his "endgame" being winning the WWE Championship. He planned situations masterfully, even exploiting BoringInvincibleHero JohnCena's HonorBeforeReason and HotBlooded nature alongside the occasional NoHoldsBarredBeatdown
* MickFoley of all people was revealed to be one in {{TNA}}. He worked his way silently up into the Network as an executive behind Immortal's back, using his position to make them ScrewedByTheNetwork at every turn. When he finally reveals this, they're dumbstruck because he was the last person they'd expect. On May 26th, Hogan believes he's outsmarted Foley and got the Network to give him control again during a meeting the previous week. However, while Hogan is celebrating both that and Eric destroying the X Division, Foley comes out and reveals that after Hogan left, Foley took over the meeting. The end result was the Network furious at Immortal again and giving Foley the authority to revive the X Division. He even found a loophole to give him control of the PPV because the Network funds them.
[[/folder]]

[[folder: Tabletop Games]]
* ''{{Exalted}}'' has the most powerful gods spending their time playing "the Games of Divinity".
** These games explicitly don't have anything to do with manipulating anyone - that's the job of the Sidereal Exalted, who constantly act as Chessmasters to ensure Fate follows its proper course. MemeticMutation has cast the Games of Divinity as a cosmic {{Xbox}}.
** Meanwhile, the Deathlords are plotting and scheming against Creation (and each others), dragging the world into Oblivion one Shadowland at a time. And sometimes their grand scheme works, too: just ask the people who died of Great Contagion.
** The Ebon Dragon on the other hand, are playing a speed chess variant of the game, what's with his new 50 Infernal pawns and his marriage to a certain prominent woman.
* In ''TabletopGame/{{Warhammer}}'' and ''TabletopGame/{{Warhammer 40000}}'', the Chaos entity Tzeentch is the god of Chessmasters. His followers commonly favour such tactics, but considering that Tzeentch tends to use them as his own pawns in his own schemes, which are both plentiful and occasionally contradicting, it all just comes back to him eventually. It's rumored that Tzeentch is the only force stopping the [[HyperspaceIsAScaryPlace Immaterium]] and universe from merging as part of an elaborate plan roughly forty-six thousand years in the making.
** Other grand schemers of the forty-first millennium include the Eldar's Laughing God and the C'Tan known as The Deceiver, prompting fan debates over [[GambitRoulette who is responsible for any given plot]], [[GambitPileup what happens when they work against each other]], or [[MindScrew who is simply a guise of another]]. There are also the Eldar Farseers, who use their prescient abilities to manipulate galactic events in their favor, and the Chaos Space Marines of the Alpha Legion, renowned for using sabotage, propaganda, or infiltration when their colleagues would just charge in with weapons blazing.
** Possibly also the Emperor - it is hinted that not only did he anticipate the [[GreatOffscreenWar Heresy]] but also plans to be reborn when his phsycial form dies (which may well be soon)
** Cypher. But with a name like that...
** Asdrubael Vect? No mention of him? He's the guy in charge of the largest Dark Eldar kabal in the galaxy, but he actually started out as a lowly slave. How did he manage to do it? He manipulated and backstabbed thousands, including one of his own consorts [[WomanScorned Aurelia Malys]], to climb his way up into a position of power as a lowly Archon of a lowly kabal, the Kabal of the Black Heart, then he set his plan in motion. First, he focused his piracy efforts in one part of space known as the Desaderian Gulf, simultaneously adding to his wealth and power while also provoking the Imperium. Eventually, the Imperium sent a [[SuperSoldier Space Marine]] cruiser, the ''Forgehammer'' to investigate, which he ordered crippled with haywire bombs and transported to Commorragh. Vect then manipulated rival Archon Xelion into trying to claim the contents of the ''Forgehammer'' for himself, knowing that his forces would be woefully under-equipped to take on the Space Marines waiting inside. Vect also allowed a Librarian on board to send a psychic beacon, attracting a huge Space Marine force to reclaim the cruiser. During the following battle between Dark Eldar and Space Marine forces which razed most of upper Commorragh and caused ridiculous casualties on both sides, Vect manipulated battlefield communications, battle strategies and reinforcement allocations in such a way that the city would defeat the Space Marine attackers and also leave the leadership of ''every single noble house and major kabal in Commorragh dead''. This created a power vacuum and left Vect's kabal the most powerful in Commorragh, allowing him to easily seize ''de facto'' rule over the entire dark city. JustAsPlanned.
* [[http://www.wizards.com/default.asp?x=dnd/rl/20050713a This article]] outlines typical manipulators' methods in ForgottenRealms. Some even legal.
* In ''TabletopGame/VampireTheMasquerade'', the elders are like this. Their schemes unfold over ''centuries''.
* ''TabletopGame/ChangelingTheLost'' has the Contracts of the Board, which allow the user, by utilising some form of strategic game, whether it's chess or cards or Candyland, to read opponents, send orders, and tweak fate through correspondences and the odd bit of cheating.
* The ''DungeonsAndDragons'' rulebook ''Fiendish Codex II: Tyrants of the Nine Hells'' explicitly compares Asmodeus' plans to a game of chess. Supposedly his plan to topple heaven is a few centuries ahead of schedule.
** Also, the rulebook ''Lords of Madness: The Book of Aberations'' describes mind flayers - a.k.a "[[{{Cthulhumanoid}} illithids]]" - and their leaders the Elder Brains as often being this. They are manipulating politics and slowly working towards reestablishing the illithid empire that was lost long ago.
** The Illumians, introduced in ''Races of Destiny'', are a species of humanoids organized into cabals where they study and manipulate the world around them, ultimately hoping to accumulate enough power and knowledge to ascend to godhood.
** Dragons play ''xorvintaal'', the Great Game in which they use mortal servants as chess pieces to compete for each others' hoards. The game itself is [[CalvinBall far too complex for mortals to understand]] (a dragon that is killed as a result loses, of course, but seeing as only the most powerful dragons play it, that rarely happens), but in the small term can shape entire lives. In the long term, it shapes ''continents'' - UsefulNotes/WorldWarI would have been a particularly complex ''xorvintaal'' maneuver, with UsefulNotes/WorldWarII being a good counter-move. Just as a consequence of powerful creatures to who WeAreAsMayflies getting bored.
*** An example: Dragon A uses his magic to cause a volcano to erupt, wiping out a town but forcing Dragon B to evacuate her hoard and leaving her vulnerable to attack by PC mercenaries hired by Dragon A. This would be considered a crude, noobish maneuver. A master of ''xorvintaal'', such as Dragon C, would rush to the volcano, see a family trapped in a burning house, and use just enough magic to save the boy. Over the coming years Dragon C supports the boy as he hones his skills as an adventurer, nurturing his hatred of Dragon A until he's ready to form a party to avenge his parents, afterward continuing as a loyal supporter of Dragon C. That's a character whose entire life was played like a chess piece in a game he may never become fully aware of. And Dragon B? The mercenaries that would have attacked her were instead wiped out by a party sent by Dragon D, a young vassal of Dragon C who is now owed a favor by a powerful rival, who Dragon C only wants around as a buffer against Dragon E...
* The rilmani, introduced in the ''{{Planescape}}'' setting, are like this on a cosmic scale. A TrueNeutral race who seeks to preserve what they refer to as [[BalanceBetweenGoodAndEvil The Balance]], they make sure no side of a philosophical conflict (such as Good versus Evil, Law versus Chaos, and other minor ones) ever dominates the other. They usually don't act directly in this goal, however; usually throughout history they use disguise, subterfuge, and covert skills to infiltrate governments and empires, posing as advisors or military leaders to either help or sabotage them in order to aid whichever side of the overall conflict is losing until it evens out. They honestly believe that if there was any definite winner in any of these conflicts, the state of the universe would be broken and it wouldn't work.
** One rilmani of note is Jemorille the Exile, the rilmani assigned to Sigil. He's supposed to be a chessmaster, but if what he says is true, all of his attempts to preserve the Balance have caused [[EpicFail Epic Fails]], causing disasters and cataclysms. (For example, he claims he taught the halfling Rajaat magic, which if true, means he's indirectly responsible for [[DarkSun Athas]] becoming [[DeathWorld the place it is today]], although he insists it [[NeverMyFault wasn't his fault]]. He was assigned to Sigil because the other rilmani thought that would be an easy job, [[spoiler:but he even managed to mess that up, starting the chain of events that led to the Faction War]].
* SeventhSea has [[spoiler: a whole team of them--Novus Ordum Mundi--]]and the biggest and baddest of them all is none other than [[spoiler: Alvara Arciniega]].
* ''{{Traveller}}'': Cleon Zhunastu, founder of the Third Imperium manipulated thousands of planets and countless individuals into forming an empire that stood for over a thousand years. The Hivers are arguably an entire race of these, "Manipulator" is a title they all strive to achieve, though many of their manipulations seem benevolent.
* In the storyline of ''TabletopGame/MagicTheGathering'', Urza is this. After witnessing the might and horror of Phyrexia as it slowly corrupted his brother Mishra, Urza uses his newfound [[PhysicalGod nigh-godhood]] to concoct a 4,000 year plan to defeat the Phyrexian invasion of Dominaria. Most notable among his machinations is the creation of the Legacy, a collection of artifacts that, when fully utilized, created a burst of white mana so intense that it vaporized the demonic god of Phyrexia, Yawgmoth, along with the entire northern half of Dominaria itself.
[[/folder]]

[[folder:Theatre]]
* Theatre/ThePhantomOfTheOpera is initially the {{Chessmaster}} until [[spoiler: the part where Christine rips his [[TheUnmasking mask off]] and the theatre burns down]]. He even has a model of Il Muto where the characters have interchangeable heads to help him in his plans.
* Lucy is this in ''Theatre/{{Thirteen}}''. She [[MindScrew tells Kendra she shouldn't kiss Brett because she's a good girl]]. Then all she has to do is turn Brett's head for [[spoiler: an AccidentalKiss between [[HoYay Brett and Archie]] ]] then when [[spoiler: Evan reunites Brett and Kendra]] Lucy [[spoiler: [[GossipEvolution starts a rumor]] about Kendra and Evan]]
* Edmund, Regan, and Goneril from Shakespeare's Theatre/KingLear. They all fully take advantage of their fathers' weaknesses.
* Oberon from ''AMidsummerNightsDream''. He had only planned on a few simple maneuvers, but things get complicated when you let [[TheTrickster Puck]] handle the AppliedPhlebotinum.
* Iago from ''Theatre/{{Othello}}'' plays off of Barbantio's [[FantasticRacism racism]], Othello's [[ClingyJealousGuy jealousy]] and [[IfICantHaveYou distrust]] in [[MarySue Desdemona]], and [[CasanovaWannabe Roderigo's]] love for Desdemona all to destroy a man he hates - but for whom he has no good reason to hate.
* Prince Hal in ''HenryIV'' part one monologues about how he's using his time drinking, whoring and stealing with the lowest of ruffians as part of a public image long game. He's manipulating perceptions and expectations of him so that when he becomes the glorious, reformed king he knows he will be, it will appear that he has risen even higher by starting so very low. He plays everyone, from the Eastcheap rascals to his father the king. It's up to interpretation whether this makes him super cool or a total bastard.
* In ''Theatre/PokemonLive'', Giovanni orchestrates the entire plot and manipulates just about everyone.
[[/folder]]

[[folder: Video Games]]
* ''VideoGame/FableII'' has Theresa whose also a [[ManipulativeBastard Manipulative Bitch]] the DLC reveals [[spoiler: That she was the one who gave the music box to murgo, then convinced Sparrow to buy it while manipulating Lucien to become obsessed with the spire and possibly convincing him to kill Rose and try to kill Sparrow. So she could guide Sparrow to become a hero and gather the heroes of legends to claim the spire for her own. May also constitute as a GambitRoulette]]
* ''FinalFantasyTactics'' was completely filled with [[GambitPileup Chessmaster-on-Chessmaster action]]. [[spoiler:The Galbados Church was trying to manipulate commoner legends to set themselves up as faux-saviors in the Lion War. The church's new "Zodiac Braves" were actually the demonic Lucavi, playing the church for fools and using the bloodshed of the Lion War to revive their leader. Both Prince Larg and Goltana were using the recent death of the King to try and place their preferred puppet candidates on the throne, setting themselves up as Regent. Dycedarg was using Larg, hoping to kill him and take his place in the whole plot. And Delita was outmaneuvering them all, using the church and Goltana to set himself as the new king by marrying Ovelia (The fact that he seemed to genuinely like her was almost problematic for him), and using the protagonist to stop the Lucavi, as he couldn't deal with them personally without screwing up the rest of his plans. Delita succeeded, and every other contender was dead when the dust settled]]. About the only people ''not'' trying to screw everyone else like a two-dicked billygoat was the protagonist and his crew, but his actions definitely were manipulated for other peoples' gain.
* Rufus Shinra, of ''FinalFantasyVIIAdventChildren'', was a very sneaky, wheelchair-bound chessmaster who, with only four hired goons and his wits about him, manages to fool Kadaj for the entire movie. While suffering from a ''fatal disease'', no less.
** Not as though this is his first act of such. He's been doing this for years as revealed in ''VideoGame/BeforeCrisis'' wherein [[spoiler:he was shown to be the financial backer and chessmaster behind the second incarnation of the ecoterrorist group AVALANCHE, simply because he wanted his father out of the way. Though, the whole thing does come back to bite him on the ass with the third incarnation of the group in ''VideoGame/FinalFantasyVII'' proper]].
** Though, this trait runs in the family as we see in ''VideoGame/CrisisCore'' with [[spoiler:Rufus' all-bastard half-brother Lazard is revealed to be effectively using both SOLDIER and the Genesis Army to play chess ''with himself'' in his efforts to topple the company. But again, it all comes back to bite him in the ass when people start investigating him too closely and he ends up a victim of the very same SendInTheClones style plot he had been orchestrating. It proves though that only by having his ''DNA rewritten'' will he ever stop being a Shinra. Which he absolutely hates being, but in trying to destroy his family, he proves how much of a Shinra he really is]].
* ''FrozenSynapse'''s Charon's Palm can be seen as a chessmaster with a perhaps unique twist; [[spoiler:it splintered itself in two to create Tactics and assist Graham Nix with his coup, creating more destruction and death of innocent and guilty lives than was necessary. Why? Because it was ''bored'']]
* Zexion from ''KingdomHearts'', complete with VillainousBreakdown when he DidntSeeThatComing.
** Everything that has happened in the ''KingdomHearts'' saga from ''Birth by Sleep'' onwards can be traced back to Master Xehanort, although [[spoiler: his future incarnations kind of drifted away from his original plan]]. Sheer [[ThePowerOfFriendship Power Of Friendship]] is the only reason his plan to restart the Keyblade War didn't succeed at the Keyblade Graveyard, [[spoiler: and after losing all his memories, he's able to continue his plans in some form thanks to Braig]].
* [[TheVoice The Administrator]] from VideoGame/TeamFortress2 could certainly qualify: though it's never specified why, it's clear that she's been deliberately prolonging and encouraging the conflict between RED and BLU for years.
** [[spoiler: Gray Mann]] also qualifies as one. He patiently waited over a century to solidify his power and weaken both his brothers enough, and when they are both old ([[DeathIsCheap to the point of dying mid - conversation occasionally]])he tricks them into negotiating a truce, and then he kills them both, taking their assets. Then in order to take over Mann Co.'s [[MemeticBadass Saxton Hale]], he steps down from his position, makes his little daughter the CEO, then takes over Mann Co. by playing off Hale's refusal to fight a child. The most recent comics are hinting at a chess match between the Administrator and [[spoiler: Gray Mann]].
* ''VideoGame/{{Xenogears}}'' could feature a football team full of chessmasters. Just to name a few who were playing (and they were each manipulating each other): [[spoiler:Miang, Krelian, Grahf]].
* [[spoiler: Wilhelm]] in the ''VideoGame/{{Xenosaga}}'' series manipulates most, if not all, the protagonists and antagonists in the story in some way as well as the overarching flow of events, often by [[spoiler: assuming leadership of companies and organizations (where all positions appear to be held by different individuals)]].
* In ''VideoGame/SuperRobotWars'' (in various timelines), Shu Shirakawa and Ingram Prisken often act as chessmasters, manipulating the protagonists into doing their bidding unwittingly, and with unparalleled amounts of panache (Shu has even garnered an unwanted harem in the past). Interestingly, they take to the field of battle quite often, but this is perhaps solely to show off their (incredibly cool) Humongous Mecha. Due to the crossover nature of the series, Shu and Ingram have butted heads with each other, [[Anime/NeonGenesisEvangelion Gendo Ikari]], [[ZetaGundam The Titans]], [[GiantRobo Big Fire]], and various other factions and have generally come out on top. They could also be considered a subversion of this trope,[[spoiler:because they themselves are being forced to do the bidding of higher powers, and actually fall under direct control of them on several occasions. The protagonists generally end up killing them, or being unable to prevent their deaths. Ironically, after noting just before dying that he was now free of all the chains that bound him, Shu is actually brought back from the dead to resume his previous role. Perhaps proving what a magnificent bastard he is, Shu is actually -released- from his bonds upon his resurrection. Whether or not this was intentional is up in the air, but if it was, it most definitely counts as a GambitRoulette]].
* ''VideoGame/SuperPaperMario'' has [[spoiler: Dimentio]]. [[spoiler:Not only did he pull all the strings behind the plan to cause [[TheEndOfTheWorldAsWeKnowIt the end of all worlds]] with a damned great EvilPlan he tried to get Mario and crew to join him by saying that [[UtopiaJustifiesTheMeans he was doing the right thing for a perfect world]]]].
* Grand Master of the Order, Jacques de Aldersberg in ''TheWitcher'' computer game, who [[spoiler:used crime group ''Salamandra'' along with mad wizard under his power, sparked full-scale racial war and manipulated the whole bunch of people to solidify the power of his Order - and all this just to save humanity from his vision of terrible future, which makes him into WellIntentionedExtremist as well]].
* Freed from the constraints of StupidityIsTheOnlyOption in ''ApolloJusticeAceAttorney'', Phoenix Wright becomes one of the most capable Chessmasters not only of that game, but of the entire VisualNovel/AceAttorney series. He manipulates every important event towards his own ends, and any major errors on his part are made only when [[spoiler:[[StupidityIsTheOnlyOption he's being controlled by the player during the fourth case]]]].
** The prosecutors of the original trilogy, (excluding Winston Payne) also seem to have Chessmaster-ish qualities, Edgeworth even has a chess set in his office with a suspiciously spiky blue pawn.
** In ''AceAttorneyInvestigations 2'', the chess motif becomes literal, with Edgeworth engaging in "Logic Chess" to get people to talk. There's also a witness who is obsessed with chess, and another who plays long-distance chess with the former. [[spoiler:The real {{Chessmaster}} of the game is the former's best friend and the latter's protege, and the one acting as courier for their games. Amusingly, he himself doesn't particularly like chess. He does, however, take the grandmaster title for the role, masterminding every murder in the game save one and manipulating most of the cast to do his bidding]].
* [[CityOfHeroes Lord Nemesis]]. Anyone who can convince you that ''you're'' a BetaBaddie deserves a nod. Take a gander at his GambitRoulette entry if you don't believe me.
* This is the whole point of the text adventure ''Varicella'', with the player competing for the role of regent with a whole slew of Chessmasters [[spoiler: which ends up in a magnificent GambitPileup]]
* [[MagnificentBastard Revolver Ocelot]] of ''Videogame/MetalGearSolid'' was described in one FanFic as "the only person ever to successfully pull off an octuple cross". Said octuple cross must have been a pretty small operation by his standards. [[spoiler:Actually, the worst he manages ''is'' a octuple cross, betraying Colonel Gurlucovitch, Richard Ames, James Johnson, Olga Gurlucovitch, Fortune, George Sears, the Patriots and [[MindScrew the player himself. Let's put it this way, by the end of MGS4, you discover the entire series was about two competing chessmasters...both of them are Ocelot]]]].
* Hikawa from ''VideoGame/ShinMegamiTenseiIIINocturne'' manipulates people and events from the shadows, never taking any unnecessary actions and always moving towards his goal.
** [[spoiler:Lucifer]] arguably counts as well, attempting to maneuver the player into [[spoiler:unmaking reality and spearheading Armageddon]]. Granted, he more or less admits this upfront and gives the player a choice in the matter. However, failing to follow his plan means the player will miss out on most of the game's backstory and some nice rewards...
* A non-villain example is Sereph Lamington from ''VideoGame/{{Disgaea|HourOfDarkness}}''. His BatmanGambit was so well executed that he qualifies for this trope. Sending his most loyal angel on a false assassination mission (knowing that she'll take the change in mission he was expecting), turning the ambitions of his 2nd in command to his advantage (humans, angels, and demons had to share in it) which causes said traitor to be exposed to him (and punished). Even his battle with Laharl was part of the plan. There's a reason why he's the Seraph, and this is it. Far more intelligent than he looks.
* Kil'jaeden [[NamesToRunAwayFromReallyFast the Deceiver]] from the VideoGame/{{Warcraft}} Universe. His motto is "There are more ways to destroy one's enemy than with an army. Sometimes those ways are better." He corrupts the race of orcs by posing as the spirits of their ancestors and makes them think the Draenei are evil and should be destroyed, because if he used his personal demon army to raid the planet the Draenei are living on, they would simply run away (or so he thought, they were actually stranded).
** [[{{WMG/Warcraft}} One interpretation]] of the events of ''Warcraft III'' is that Kil'jaeden created the Lich King knowing that it would betray Archimonde (his counterpart and co-leader of the Burning Legion), leading in Archimonde's death and Kil'jaeden becoming the absolute ruler of the demons.
** He also managed to enslave a race of demons known for their clever trickery.
** [[EldritchAbomination The Old Gods]] take the cake, though. First they infest the Titans' newly-created world with "the curse of flesh", causing their mechanical creations to become organic. Then they rig it so that the Titans can't actually destroy them without destroying the world alongside them, forcing them to just [[SealedEvilInACan seal the Old Gods away]]. Even that doesn't do the job so well for C'thun and Yogg-Saron...[[DidYouJustPunchOutCthulhu which is where the players step in]]. In fact, the latter could be counted a Chessmaster among Chessmasters - even after being sealed away he manages to corrupt the wardens of his prison into loyal, if batshit insane, servants. [[spoiler:When you do fight him, he takes you on a brief guided tour of the events throughout Warcraft's history he has been responsible for, including the assassination of a king and the creation of an important MacGuffin]].
** Lich King Ner'zhul deserves special mention. He was the mastermind behind the Scourge Invasion and plotted successfully against his masters. He even succeded to deceive his guardians, the Dreadlords... who are considered to be chessmasters themselves.
* The player in this game of ''GalacticCivilizations 2'', who ended the existence of his galaxy's then greatest military power in a single turn. When his race specialized in cultural influence and entertainment programming, and had ''zero military power whatsoever''. Via a combo of diplomatic, financial, and cultural maneuvering that... seriously, just read it. * g* (The relevant parts are at Day 9 and 10.)
---> '''Player:''' I don't care that my foreign intel reports rate you as the most powerful race in the galaxy. I don't care that I come dead last on that same list. I don't care that I couldn't even fight back if I ''had'' any gunships because of a pledge to spread peace throughout the galaxy. In fact, you know what? That's it. Your race ends this week. When I next click that 'Turn' button, you're out of the game.
** At the end of that same game, He exploited his own cultural influence technologies and a law ''he passed'' at the beginning of the game to override the normal limitations on ship movement in order to place the final starbase he needed in order to wipe out his remaining rivals and end the game. [[http://computerandvideogames.com/article.php?id=198344 Day 30]]. I cried at the beauty of the move:
---> '''Player:''' I'd catapulted the slowest unit in the galaxy 600 trillion kilometers in an instant: right to the sun it was built to destroy.
** He's come a long way since his [[http://www.computerandvideogames.com/article.php?id=161570&site=pcg last GalCiv II game]], then. In that attempt, [[spoiler:it took him the entire game to realize that all of his strategies and tactics were merely a sideshow to some byzantine maneuvering between the [=AI=] opponents, and the only reason he hadn't been exterminated by one faction long ago was because they knew it would allow another faction to win]].
* ''VideoGame/ChronoCross'' has a rare example of the Chessmaster actually being a good guy. [[spoiler:Belthasar]] manipulated 10,000 years of history across multiple parallel dimensions to make sure the protagonist would acquire the (eponymous) ultimate item needed to completely destroy the Big Bad.
* ''VideoGame/FinalFantasyX'' has a heroic Chessmaster tag-team of Jecht and Auron, who spend the game (and the 10 years prior to it) preparing Tidus so he'll someday kill Sin, instead of letting it get sealed back into its can.
** One of Auron's moves in the game was [[spoiler:getting Tidus and Yuna alone together in one of the most romantic spots in Spira long enough for the inevitable to happen, ensuring that Tidus would not allow the Grand Summoning to happen as scheduled]]. Bonus points for [[spoiler: sending ''Kimahri'' along as chaperone, the ''only member'' of the party who wouldn't have stopped them]].
** On the villain's side, there is [[spoiler: Yu Yevon and Yunalesca]]. The former sacrifices an entire city so that the latter can build a cycle of SenselessSacrifice in his name.
** Not quite as bad as the former entry, but [[spoiler: The Maesters]] have a bit of this going too. The whole of Operation Mi'hen was to make the Crusaders look like they were ignoring scriptures and doctrine to strike off on their own, while in fact, [[spoiler: the Church of Yevon]] was the driving force behind it all along. Hell, even if the Operation ''worked'' the group could claim credit, which turns the Operation into a XanatosGambit.
* ''Franchise/{{Halo}}'s'' Gravemind displays the traits of a chessmaster throughout parts two and three in the series. Gravemind, as the collection of Flood intelligence, managed to turn an AI that had been specifically designed to destroy the Flood over to his side milennia ago, manages to in five seconds convince the [[ChurchMilitant Arbiter]] to prevent the rings from firing, takes over the flood's ruling ship, and uses the Chief and Arby to stop Truth from activating the Ark and destroying all life in the galaxy, just so that he could infest all life in the galaxy. When the Halo was about to fire and destroy the flood yet again, Gravemind says that all it'll do is delay the inevitable.
** On the subject of ''Franchise/{{Halo}}'', there's also the Prophet of Truth. In ''Halo 2'' he is the epitome of the Chessmaster, going as far as to eliminate the Sangheili without them even knowing it, kills off his two co-leaders with no mercy or regret ([[IncrediblyLamePun hahaha...]]), and having the Arbiter run a wild goose chase, culminating in the latter's "demise" at the hands of Tartarus.
* ''{{Tsukihime}}'' has, of all people, [[spoiler:Kohaku - the cheerful and seemingly carefree maid who ends up single-handedly killing off the entire Tohno family in Hisui's True Ending (and comes close in the other paths too). She gives Akiha her blood to awaken the Tohno blood in her, as well as being responsible for the resultant insanity of the real SHIKI. On top of that, she leads Shiki into believing HE'S the one responsible for all the murders and that it won't stop until SHIKI dies. Oh, and during the final battle, she deliberately gets herself attacked knowing there's a good chance that Akiha will jump in the way and sacrifice herself to save her. All this while [[StepfordSmiler never letting go of that cheerful smile]], even up to her eventual suicide after her revenge is complete]].
* If you are in a ''{{Suikoden}}'' game and your last name is Silverberg, chances are you're a Chessmaster. If your name is Lucretia Merces, you are a [[GambitRoulette crazy, crazy chessmaster]].
* ''VideoGame/TheWorldEndsWithYou'', has around ''three'' - [[spoiler:Joshua, who initiated the whole thing, and kept it moving whilst on the sidelines for a good portion of the game, Megumi Kitaniji, who carefully made sure that everyone was kept in the dark about his game with Joshua, whilst slowly infiltrating Shibuya with the Red-Skull pins, and finally, (possibly) Sanae Hanekoma, who popped up here and there, never letting on too much, and in the end turned out to be ''an Angel'']]. This is hardly surprising, coming from a game with a GambitPileup.
* A somewhat odd version occurs in ''VideoGame/{{Sanitarium}}''. It initially appears that the BigBad has an incredibly elaborate plan to stop TheHero. However, it later turns out that [[spoiler: there are two versions of the villain: one in the real world and one in a parallel world. Each was attacking the hero independently of the other, meaning that the elaborate plan was actually two simpler plans. Although both versions still fit this trope, the fact that the plan wasn't as elaborate as initially thought makes them somewhat diminished variations]].
* In ''ModernWarfare 2''[[spoiler: General Shepherd sends a CIA agent, Joseph Allen, to infiltrate the terrorist cell of Vladimir Makarov. Makarov reveals he knew Allen was CIA, and kills him after a terrorist attack in a Russian airport; this leads Moscow to declare war on the US and invade the East Coast; which the US manages to repel by the skin of their teeth (and with a little help from Taskforce-141). Anyways, Shepherd is revealed to have planned this all along; after the events of the first ''ModernWarfare'', he felt that the US public hadn't appreciated the sacrifices his men made. So by starting a war with Russia, he's a hero, and the public has rallied behind him]].
* ''VideoGame/{{Touhou}}'''s Yukari Yakumo, especially evident in the official [[AllThereInTheManual supplementary manga]].
* ''VideoGame/{{Half-Life}}'' has the G-Man, the mysterious suited man who [[TheWatcher has been shadowing Gordon Freeman]] since the beginning of the series. He speaks of his "employers," but it's obvious that the G-Man has been subtly influencing events since the first game and that Gordon is really just his pawn, [[spoiler:at least until the Vortigaunts intervene in ''VideoGame/{{Half-Life 2}}: Episode 1'']]. The real question is which side the G-Man is on.
* The Kimono Girls take on a role that could be described as this in ''{{Pokemon}} [=HeartGold=]'' and ''[=SoulSilver=]''. I'm as surprised as you. Their actual plan is horribly vague; apparently it involves finding a kindhearted Trainer to summon Ho-oh or Lugia (depending on the game). What purpose this serves is not made clear, and the whole plan seems to be rendered a bit useless by the fact that said kindhearted Trainer proceeds to beat the crap out of the aforementioned Pokémon and, if they're feeling merciful, capture it in a tiny ball and make it their slave.
** [[spoiler:Darkai]] from ''Pokémon Mystery Dungeon: Explorers of Time/Darkness/Sky'', who actually came up with different plans to kill the heroes over the course of the game. During the post game story, he has no less than ''[[CrazyPrepared five backup plans]]'' in place!
** Lenora from ''VideoGame/PokemonBlackAndWhite'' has this as her battle style, in the game, Anime, and Manga. In the game, defeating her first Pokemon is a no win situation, as both of her Pokemon know Retaliate, which with the STAB granted by it being a normal type move, which makes it one of the most powerful moves you'll see early in the game. In both the Anime and Manga, her battle style resolves around forcing her opponents to play into her hand. There's a reason she's considered ThatOneBoss.
* ''VideoGame/MassEffect2'' has the leader of Cerberus, the Illusive Man, who pulls string after string to get things to go as he wants them to throughout the game. He does, however, make one flaw- he under-estimates Commander Shepard. Depending on the player's actions, [[spoiler:Shepard can disobey the Illusive Man by blowing up a "potential resource", after which possibly telling him to "fall in line or step aside- but don't get in my way", and potentially getting Cerberus' most loyal and intelligent operative to disobey a direct order and quit in the same moment]].
** Harbinger: [[spoiler: Sends Collector's to find and destroy Shepard. Attacks human colonies in order to build Human-Reaper, but eventually decides to use the project to lure Shepard to him. [[XanatosGambit Then he leads the Reapers on a charge to the Alpha Relay, forcing Shepard to either let them through it or destroy it, killing 300,000 batarians and earning the hatred of the whole galaxy]]]].
** The cake must go to [[spoiler: the Shadow Broker]]. He [[spoiler: killed his master and took control of his information network. He uses that network to keep himself in power, playing rivals off against each other and controlling galactic espionage in order to prevent anyone gaining the upper hand, and thus making sure his service are no longer]].
*** And he is still OutGambitted by [[spoiler: his replacement, Liara T'Soni]].
*** ...Who is subsequently OutGambitted by the Illusive Man. He knew that [[spoiler: Liara]] had no hope of finding the Shadow Broker alone, so he sent her data tipping her off to the Broker's location and plans. After she dispatched and replaced the Shadow Broker, the Illusive Man recognized that the new Shadow Broker's organization was at an all time low in power from the recent coup. So he sent a small army of Cerberus soldiers to destroy her main base and splinter her organization. [[spoiler: Liara]] just barely managed to escape.
**** However, [[spoiler: Liara]] DID escape, with the hardware needed to maintain the network while [[spoiler: using her base as a convenient way to take out a chunk of Cerberus troops by blowing it up]].
** The Reapers as a whole are this on a ''galactic'' scale stretching over a billion years. Using an incredibly clever BatmanGambit (mixed with unbelievable firepower and technology), they have successfully waged [[CurbStompBattle completely one-sided wars]] and harvested thousands of advanced and intelligent civilizations over the course of their existence.
* [[StarCraft Sarah Kerrigan]], full stop. ''Brood Wars'' was Kerrigan playing her own constant Chessmaster, to the point where she was more playing a game of {{Gambit|roulette}}.
*** Both Starcraft and Brood Wars actually have several of them. The Overmind definitely counts, maybe also Dugall. Alan Shezar and Ulrezaj also count, if you take {{Blizzard|Entertainment}}'s bonus campaigns as canon. Oh, and [[spoiler: Duran]] (who also qualifies as a MagnificentBastard).
* In ''[[SonicAdventureSeries Sonic Adventure 2]]'', Shadow the Hedgehog allows Eggman to believe that he is gathering Emeralds as a favor for waking him from a [[AndIMustScream 50 year sleep that his only friend put him in before she is killed]], then tells Eggman he can hold the world ransom with the Eclipse Cannon on the Space Colony ARK, when really Shadow has been doing all this just so the Cannon could destroy Earth. Why? Because in [=SA2=], Shadow the Hedgehog really, REALLY hates human beings and just wants them to suffer. So much that even when his plan fails, he is content to watch the Earth be destroyed anyways even if it's by a way that wasn't in his plan.
** Until [[spoiler: Amy]] shows up and talks him out of it.
* Malefor from [[SpyroTheDragon The Legend of Spyro]] trilogy is a shining example. He's such a good example, it's hard to tell what WASN'T a part of his plan did he really intend to kill Spyro in the raid or did he want him alive to [[spoiler: set him free?]] Did Spyro really free Cynder or did Malefor let her free so [[spoiler: he could use her to lure Spyro to the Well of Souls to free him?]] And to top it all off, the HannibalLecture he gives the two when they finally confront them even has them wondering whether they'd done anything but play right into his claws.
* ''SoulNomadAndTheWorldEaters'' has [[spoiler: Levin/Raksha]], [[GambitPileup amongst others]]. Those "pointless" {{side quest}}s you've been doing? Not so much.
* In ''VideoGame/BlazBlue'', we have [[CardCarryingVillain Hazama]] / Yuuki Terumi. While one of the most powerful people in the world, Hazama has manipulated dozens if no hundreds of people into furthering his evil deeds. [[spoiler:He even ends up outwitting an omniscient supercomputer that has three minds and runs reality]]. Just don't mention a [[spoiler:[[SpannerInTheWorks certain]] [[PluckyGirl squirrel girl]]]] to him.
* There are two real chessmasters in EienNoAselia, and in general they don't really show up until the last 15% of the game. [[spoiler:Temuorin]] is the big bad and set up the whole plot and [[spoiler:Tokimi]] interfered so that the game doesn't get a downer ending.
* Lord Alden in ''VideoGame/VanguardBandits'' is a literal chessmaster, being the best player on the continent and rumored to be undefeated. [[spoiler: Then [[LoveInterest Milea]] beats him in her second time playing the game at all]]. Meanwhile [[BigBad big bad Faulkner]], is more of the moving and controlling of wars type of Chessmaster. And he's very, very good at it.
* The Sith Emperor of ''VideoGame/StarWarsTheOldRepublic'' managed to be the ManBehindTheMan for nearly all of the major events of the galaxy since the Exar Kun War, including all of the events in the ''VideoGame/KnightsOfTheOldRepublic'' series. He manipulated [[BloodKnight the]] [[ProudWarriorRaceGuy Mandalorians]] into attacking Republic space leading them into the Mandalorian Wars, a devastating war which he orchestrated entirely to lead Revan to him, who he took as his apprentice and sent off to find the Star Forge. When this failed due to Malak's betrayal and Revan's subsequent redemption, he set up puppet leaders on Republic worlds on the Outer Rim, infiltrated the Jedi Order, and rigged the Mandalorian gladiator tournament to place a Sith agent as the new Mandalore. All of this was in preparation for their strike on the Republic border worlds, in which he struck while the Mandalorians (under the leadership of aforementioned Sith agent) blockaded Coruscant and disrupted Core World trade routes. At the time of the first cease-fire, his Sith Empire controlled nearly half of of the known galaxy--the closest any Sith Lord has gotten to conquering the galaxy until Emperor Palpatine himself, nearly four millenia later.
** Whether played on the [[PragmaticVillainy Light Side]] or the [[MagnificentBastard Dark Side]], the Sith Inquisitor is not too far behind in this department; having risen from [[MadeASlave a Slave]] to [[spoiler: [[FromNobodyToNightmare Dark Councillor]]]] over the course of their storyline and even [[spoiler: leading the entire Empire along with Darth Marr]] as of the end of ''Rise of the Hutt Cartel'' expansion. Only fitting, since the class was inspired by Emperor Palpatine.
* [[ManipulativeBastard Lord Fain]] of ''{{Lusternia}}''. Ostracised by his fellows Gods eons ago for his [[IDidWhatIHadToDo questionable]] [[CannibalismSuperpower methods]], upon his return to the First World he adopts the guise of a shadowy manipulator, using mortals and other Gods as tools to carry out his complex plans. Though progress through his service is characterized by chess motifs, it's just flattery designed to ingratiate him to his more competent followers - to Fain, ''everyone'' is a pawn.
* [[spoiler:Master Li]] from ''JadeEmpire''. They don't call him [[spoiler:the Glorious Strategist]] for nothing.
** [[spoiler:The Water Dragon]] counts too. [[spoiler:She uses Li's entire gambit to ensure the PlayerCharacter will be bringing her back from the dead. How she pulls this off is a combination of MyDeathIsOnlyTheBeginning with the PC as the guy dying and an UnexplainedRecovery with a little dash of RoaringRampageOfRevenge]].
* In ''[[VideoGame/{{Diablo}} Diablo II]]'', most of the plot and background involving apparently fluctuating fortunes for all sides in the conflict between the Burning Hells, the High Heavens, and the humans in between, including significant losses for the [[BigBadDuumvirate Three Prime Evils]] Diablo, Mephisto and Baal along the way, turns out to have been all part of the long-term plan of the Prime Evils themselves. This trend continues in ''VideoGame/DiabloIII''.
* The ending of ''VideoGame/GhostTrick'' reveals that the course of the entire game is orchestrated by [[spoiler:Ray, who is actually Missile from an AlternateTimeline where he did not have the necessary ghost tricks to save anyone, so he goes back in time and waits for ten years for the right moment to come around again, so he could manipulate Sissel's self-interest into saving Lynne and everyone else that could be a lead in Sissel's QuestForIdentity]].
* Ganondorf from ''Franchise/TheLegendOfZelda'' series tends to stay two steps ahead of Zelda and Link, even though he eventually gets defeated in the end. Some of his grand schemes include the following:
** ''VideoGame/TheLegendOfZeldaOcarinaOfTime'': Ganondorf seeks entry into the Sacred Realm so he can claim the Triforce. The entrance is barred by a lock requiring 3 Spiritual Stones and the Ocarina of Time. He allows Link to collect the stones and knew that Zelda would entrust the ocarina to him. Using this to his advantage, he simply waits for Link to bring all of items to the Temple of Time, waits for Link to lift the Master Sword, and then waltz in to steal the Triforce right in front of him after the sword puts Link in a deep sleep. [[spoiler: Ganondorf only obtains the Triforce of Power and he knew Zelda held the Triforce of Wisdom while Link held the Triforce of Courage. Rather than taking Link head on or endlessly search for Zelda, Ganondorf lets Link undo the corruption in the temples so that Zelda could be lured out of hiding, making her believe that Link was making progress. He is proven right and he snatches Zelda away to lure Link to him, having all 3 Triforce pieces in one place]].
** ''VideoGame/TheLegendOfZeldaTheWindWaker'': Ganondorf's powers are sealed by the Master Sword and the sword needs to be removed from its shinre to restore his powers. Already knowing firsthand at what the sword can do to him, [[spoiler: Ganondorf kills the two sages that are praying for the Master Sword, which is the source of its power. By doing so, the Master Sword would be nothing more than a normal sword. He knows Link would go and obtain the sword to strike him down with, so he lets Link go through his trials to reach the sunken Hyrule and unsheathe the sword. Ganondorf gets his power back and Link can't stop him due to the sword having no power left. Knowing that Zelda has the Triforce of Wisdom and Link has the Triforce of Courage, he lets Link go around the Great Sea obtaining the Triforce fragments and waits for him to return to Hyrule to see Zelda. Once Link does so, Ganondorf snatches Zelda away and then he successfully extracts Zelda and Link's triforce pieces to form the complete Triforce. If the King of Hyrule hadn't stepped in to make his wish to the Triforce first, Ganondorf would have succeeded in his plans]].
* ''Super Smash Bros Brawl'' had a single-player mode named the Subspace Emissary that actually had a plot, and a good one too, about the various heroes banding together to stop the world being destroyed. In this mode it turned out that [[spoiler: King Dedede, of all people]] was the one with the best plan: he protected himself by [[spoiler: appearing to be a bad guy]], created a backup reserve so that if the rest of the heroes were wiped out then there could still be some left who were ignored before but could now take up the quest and incapacitated some of the other villains as he did this. He did this with [[spoiler: badges on a timer that could restore the defeated fighters he had collected for safekeeping in his castle back to life, so that they would be safe until the time was right and they were needed]]. No-one saw this coming - not even smart characters like Ganondorf. Read the above entry on legend of Zelda, and know that Ganondorf was OutGambitted by this guy.
* In ''Franchise/TheElderScrolls'' universe:
** Mannimarco. In ''[[VideoGame/TheElderScrollsOnline Online]]'', he successfully plays Varen and the other four companions into getting the Amulet of Kings for him, allowing his Worm Cult to rise to power and kicking off the game's plot. In the same game, Meridia [[spoiler:uses you (her own words) to build up an army and end the Planesmeld that Mannimarco is attempting]].
** The Daedric Prince Mephala, also known as the Webspinner and the Lady of Whispers, is known for her complex, long-reaching plans that are likened to spider webs.
** The giant slug-like beastmen, the Sload, view this as a societal ideal. Sload tales have their heroes sitting around for very long periods of time, consulting wiser Sload and performing subtle actions to further very long goals, while Sload villains are bold and audacious types who always [[LeeroyJenkins rush]] and [[FailureIsTheOnlyOption always lose]] to the hero's careful manipulations. [[TheUnfettered The Sload idea of what is "right" or "wrong"]] [[AlwaysChaoticEvil tends to differ a lot from the other races]].
[[/folder]]

[[folder: Visual Novels]]
* ''VisualNovel/MajiDeWatashiNiKoiShinasai'' refreshingly has the main {{protagonist}}, Yamato, be a {{Chessmaster}}. Touma is the 2-S equivalent and the two have a [[TheRival rivalry]] of sorts.
[[/folder]]

[[folder:Webcomics]]
* {{MAG ISA}} -- We have an [[http://mag-isa.thecomicseries.com/comics/pl/119735 unnamed reptoid]] (or demon) villain who seems to be calm even though the mind-control experiment has seemingly failed. Is it because... he's got another plan and its all a diversion?
* In ''Webcomic/TheOrderOfTheStick'', Lord Shojo provides an interesting example of the non-villainous chessmaster, ruling Azure City and the Sapphire Guard with the aid of a series of deceptions.
** And Nale, especially at the Cliffport arc, gives us the more traditional villainous one.
** Generally [[BigBadWannabe Nale is too unsuccessful to be counted]]. [[LukeIAmYourFather Tarquin is a better example]].
** The IFCC seems to count, too.
** And in comic 830, [[spoiler: Red Cloak is revealed to be one who's manipulating Xykon]].
* The title character in ''DominicDeegan, Oracle For Hire'' has become a heroic Chessmaster in later story arcs. He has the key advantage of being able to both see the future and scry into the past. ([[http://www.dominic-deegan.com/view.php?date=2007-08-13 Some are more pleased with this tendency than others]].)
* In the SNAFU hosted webcomic GrimTalesFromDownBelow, Grimm's journal reveals that Mandy, had planned a series of events to convince Grimm to give Billy his powers for a day. Then when done, she convinces him to give his powers to her to make it fair. Later, while snooping through her room, Grimm finds plans for initiating the 9/11 attacks on the World Trade Centers and Pentagon. Her plans also included the United State's response: Operation Iraqi Freedom BEFORE it happened.
* Yukizane Masamune from ''NoNeedForBushido'', is also one of the few 'good' Chessmasters. He starts out in the series as being questioned on his leadership capacity due to his silliness and focus on playing Go (the Japanese answer to chess) as opposed to grunting manly and flexing. He, however manages to shine several times and manages to ''deceive a ninja''.
* Parodied or... something... by ''Webcomic/{{Freefall}}'' [[http://freefall.purrsia.com/ff400/fv00397.htm here]].
* The [[AGodAmI nigh-omnipotent]] AI Petey from ''Webcomic/SchlockMercenary'' doesn't have a chessboard (although one strip features him playing checkers). One of his most complicated capers involved:
** convincing all AIs to join him and mutiny against their captains, forming an instant galactic power for the purposes of combating an enormous threat to said galaxy.
** Refused to pay the main characters for their ship, which blew up while carrying out his orders, then bribed a few councilmen to get them a new one anyway (at the expense of most of their savings). While keeping it all under the table in an attempt to force the company's AI to act as his spy.
** Manipulated the government into hiring the (now short-on-cash) main characters to destroy a reality-TV network.
** When the main characters got in trouble carrying out his gig, bailed them out with blackmail (after playing with their heads) and turned it into his own form of leverage on them.
*** [[spoiler:The new ship AI 'Tag" finished to discover his true plan but only revealed the Social Ingenering from the government to let Petey know that he know he is the one the manipulated them into it]]. (ironicly the only clue that permit to the AI "Tag" to come to this conclusion was the analysis that the UNS government leadership is too short-sighted to plan that much.
* In ''{{Erfworld}}'', Charlie manages to manipulate circumstances - WARS - so that he will * always* end up on top. And he gets paid to do it.
-->"When you're working for Charlescomm, you'll learn. We prefer to play games that don't even ''contain'' a losing outcome. You see?"
-->"Yeah, yeah... you turned it into a no-lose situation by rejoining him."
-->"Oh no! No, I got ''paid'' to turn it into a no-lose situation. :)"
* [[spoiler: Biggs]] from ''Webcomic/DanAndMabsFurryAdventures'' appears to be leaning in this direction. Even his sister, who is well-aware of his deviousness, falls for his tricks.
* In spite of her misleading middle name, Pandora Chaos Raven of ''Webcomic/ElGoonishShive'' is the ''epitome'' of this trope. As an Immortal who has lived for millenia, her joy comes from ''not'' [[PrescienceIsPredictable knowing what will happen next]]. Despite this, her actions are cold and calculated, and she pulls the strings of everyone she meets. Her tendency to stay behind the scenes is not due to any sort of weakness (Immortals possess near god-like power when on the Spirit Plane, and can use magic without being detected), but rather because the ''other'' Immortals get seriously pissed off if one does anything more than empower or guide people on the Physical Plane. That, and doing everything herself would just be boring to her.
* Sonorous Aria, from ''KeychainOfCreation'', is stated to be one. Most of her chessmastery is offscreen, so far.
-->'''Marena: ''' Everything she does is layer on layer of sheer '''deviousness'''.
-->'''Aria: ''' Now, a feast! Lavish meals and fine drinks for everyone! Then: Party games!
-->'''Marena: ''' She's up to nine layers already.
-->'''Aria:''' Extra drinks for the handsome bearded fellow in the corner!
-->'''Marena:''' ...twelve.
* ''Webcomic/SluggyFreelance'' has Dr. Schlock, who seems like a harmless coward and ChewToy with some minor ManipulativeBastard tendencies for a long time until Hereti-Corp finally pushes him too far by becoming a never-ending threat to the one thing he cares the most about (his own well-being). At this point, pushed into a corner, he feels forced to [[spoiler: execute a plot to take over H-C and become the new DiabolicalMastermind behind its schemes, taking everyone by surprise and becoming the closest active character to a BigBad in the comic]].
* MitadakeSaga: [[spoiler: Keiichi Hideki]].
* Mojo Nixon from ''Webcomic/PrincessPi'' relies entirely on such plans committing evil deeds.
* Skerry from ''{{Fite}}'', who uses a more generic gameboard rather than a chessboard. [[spoiler:And really, he's just a doctor trying to wake Lucco from his coma]].
[[/folder]]

[[folder: Web Original]]
* In ''Roleplay/TheGamersAlliance'', quite a few villains such as the Master and Iblis end up being quite good at manipulating events into their liking.
* Bavandersloth in ''Literature/AngelOfDeath'' pulled a pretty impressive gambit when he [[spoiler: 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 [[spoiler:the partial breaking of TheMasquerade]] to the community of liches' advantage.
* The BigBad and fake-out BigBad of ''BrokenSaints'' both fit the bill here, but, naturally, the real BigBad does ''more''.
* The Snake in ''AboveGround'' is a prime example, particularly because he can use magic to enslave others into doing his will.
* The Emperor, leader of [[NebulousEvilOrganization TAROT]], has his fingers in nearly every criminal enterprise on Earth in The GlobalGuardiansPBEMUniverse. He's also got his fingers in nearly every major legitimate business enterprise on Earth as well. But then, what do you expect of a villain who is secretly an immortal [[ManipulativeBastard Niccolo Machiavelli]]?
* [[spoiler: Ganondorf and Kirby even moreso]] in ''ThereWillBeBrawl''
* Ice and Ranger are often this in ComicFuryWerewolf
** Espeh also managed to do this from [[MyDeathIsJustTheBeginning Beyond The Grave]], to throw a SpannerInTheWorks for the Werewolves' master plan which was going to succeed.
* Nick Fury, Charles Xavier [[spoiler:Sr.]], Forge, Tzigone, Vengeance and many others from MarvelsRPG.
* Regine in ''Literature/{{Addergoole}}'' - the school, and the students, exist to fulfill her plans.
* The Architect ([[Film/TheMatrix no, not that one]]) is hinted at being this in ShadowhunterPeril. However, he tends to go against the grain of the usual Chessmaster, as he is a genuine hero...he's just hiding a lot. [[spoiler: He's actually a dimension hopper who has visited multiple universes and seen how events will play out depending on the choices made, so he's just really knowledgeable because of his experience]].
* A downplayed version gets subverted in ''Series/{{Noob}}'' Season 2 finale. Two of the protagonists arrive at the only place where they can destroy an item that can put them in big trouble with the game authorities if discovered in their possession. Their former Guild Master, who wants them kicked out of the game, suddenly shows up, claims to have requested one of the {{MMORPG}}'s Game Masters and plans to fight them while waiting for its arrival. When asked if he had been planning this all along, the former Guild Master replies that had just been spying on them and had come up with the plan on the spot.
[[/folder]]

[[folder: Western Animation]]
* Megatron of ''WesternAnimation/BeastWars'' (and later ''WesternAnimation/BeastMachines''), nearly ended the Beast Wars several times without leaving his hot tub. His ultimate weapon in the GrandFinale was, in fact, unwittingly furnished by an especially treacherous minion.
** This role almost equally describes Tarantulas - who was a third party in and of himself, only pretending to work with the Predacons. He frequently even pulled one over on Megatron. At one point Megatron was sitting in his throne all impressed with how brilliant he was because he managed to a way to spy on Blackarachnia... and then we cut to Tarantulas spying on 'him.'
** Tankor, [[DumbMuscle of all characters]], became one in ''WesternAnimation/BeastMachines'' after his spark was reawoken.
* Azula of ''WesternAnimation/AvatarTheLastAirbender'' -- TheVamp, MagnificentBastard, 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 [[DangerouslyGenreSavvy 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 ''WesternAnimation/TheLegendOfKorra'', has claimed himself to be a chessmaster. [[DangerouslyGenreSavvy 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/AvengersEarthsMightiestHeroes''.
* 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]].
* Cartman from ''WesternAnimation/SouthPark'' 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.
** 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.
* Anti-Cosmo and HP on ''TheFairlyOddparents'' could both qualify, usually tricking Timmy or some other third party into helping with their plans.
* Xanatos isn't the only one ''WesternAnimation/{{Gargoyles}}'' has to offer. 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]]. Also, [[AncientConspiracy the Illuminati]] are implied to be a whole ''organization'' of these (at least, the ones at the top are).
* James [=McCullen=] makes a good ''attempt'' at being this in the ''GIJoeRenegades'' episodes, playing the Joes and Cobra against each-other [[spoiler: but gravely underestimates who it is he's really up against in Adam [=DeCobray=]]].
* ''WesternAnimation/MyLittlePonyFriendshipIsMagic'':
** The BigGood, [[EverythingsBetterWithPrincesses 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.
* The supercomputer from ''WesternAnimation/PhineasAndFerb'' is a rare benevolent example.
[[/folder]]

[[folder:Other]]
* Makuta (Teridax, specifically) in ''{{Bionicle}}'': As he tells one of the heroes in one of the novels: "Even my...setbacks have been planned for." [[spoiler:Turns out [[GambitRoulette he's right...]]]].
* A list of tongue-in-cheek predictions for 2010 included the revelation that TaylorSwift has been moonlighting as a {{Chessmaster}}-for-hire, having orchestrated not only KanyeWest's outburst at the 2009 MTV Video Music Awards, but other celebrity scandals.
[[/folder]]

[[folder:Real Life]]
* The Athenian politician Themistocles.
* RichardNixon was quite the chessmaster; he just forgot what happens when you let a minor pawn get up the board.
* BillClinton fits this trope in his handling of the Monica Lewinsky scandal and his subsequent impeachment. What was intended to be Clinton's downfall instead lead to the downfall of his main political rival, NewtGingrich.
* William Pitt the Elder can be credited for founding TheBritishEmpire with [[{{Plunder}} conquests]] in the Seven Years War. He was Britain's and maybe the world's greatest Chessmaster of the eighteenth century and at least verges on being a MagnificentBastard. Although that was more a case of exploiting a situation created by other politicians and rulers, a simple matter of shoring up one continental ally (Prussia) and concentrating Britain's own military efforts against France and her overseas empire. As a chessmaster, Pitt actually was outshone by Count Kaunitz, Maria Theresia's chief minister, who with a little help from the ineptitude of FrederickTheGreat (who managed to alienate France by an somewhat rash alliance with Britain) brought about the "Reversal of Alliances" before the SevenYearsWar and managed to preserve the anti-Prussian alliance of several powers with greatly divergent interests (for starters, France had continually been at war with the Habsburgs for centuries) throughout most of the duration.
* Mayor Cory Booker, depending on your Alternate Character Interpretation, and invoked indirectly by Ice-T ("Who is playing whom?"). After Conan O'Brian made a joke about Newark, New Jersey, Mayor Booker banned Conan from Newark Airport as a joke (which, required the TSA to clarify the counter-joke that no, a mayor cannot actually do that due to some people believing it to be true and being outraged). This resulted in a back and forth exchange between the two and ended up involving various other mayors of New Jersey (who sided with Conan... probably a trope) as well as Secretary of State Hillary Clinton (acting as TheHighQueen and telling the two to works things out as Conan had, she claimed, been acting differently due to a RealLife head injury). It resulted in the two airing out their 'grievances' on air... which involved Mayor Booker and six of his family as well as a few other New Jersey residents getting flown out to California for Conan's show, Conan and Universal giving a 100K donation (half Conan's personal money and half he got Universal to match... cause he's Awesome that way) to his charity, and a Newark joke box in which 500 dollars will be put in whenever Conan makes a Newark joke (which may or may not remain in continuity). To quote Conan, "Boy, that was a really expensive joke!"
* Sun Tzu wrote a good guide on how to be the Chessmaster called ''TheArtOfWar''. Although the primary focus groups are generals and monarchs, nearly all of it can be generalized to any chessmaster activity.
** Ironically, Sun Tzu's theories were almost all entirely influenced by {{go}}, which emphasizes misdirection and maneuvering, while de-emphasizing direct contact.
* Niccolo Machiavelli's book ''ThePrince'' is another guide to this trope (or else a parody of such politicians). While Sun Tzu focused more on military strategy, Machiavelli focused more on political strategy and how to use them in order to gain power and how to keep it for a long time.
* The I Ching is a great book for Chessmasters.
* Louis XI, [[UsefulNotes/LEtatCestMoi King of France]]. Began his reign with a weak and small kingdom and a really powerful neighborhood (''Charles le Téméraire'', duke of Burgundy). He '''never''' fought Charles directly, hiring other countries (Switzerland, Flanders...) to finally kill him. When he died, Burgundy was a part of ''his'' kingdom. To be fair his kingdom was a bit stronger and more powerful than it had been under his predecessors (it was only his father who saw the English presence in France reduced to just Calais) and that Louis was helped to a large degree by Charles of Burgundy being his own worst enemy ("téméraire" means "reckless, rash" as well as "bold"). Also, the larger half of the duchy of Burgundy ended up in the possession of the another powerful neighbor, the Habsburgs.
* OttoVonBismarck, who orchestrated several ''wars'' among Europe to manipulate the populace and political power to unite the German states into the nation that exists today.
* Ruben Amaro Jr., general manager of the Philadelphia Phillies, just might be one of these- now that a one-year process of trades and signings has left him with four of the best pitchers in baseball on his squad.
** But [[http://sanfrancisco.giants.mlb.com/index.jsp?c_id=sf it's not like there isn't a team that hasn't beaten all of them in the playoffs]].
*** You could say that Sabean was a chessmaster during 2010. He made all the right moves during 2010 to win the World Series.
* Red Auerbach, legendary coach and general manager of the Boston Celtics, was notorious for his Chessmaster tendencies (particularly in the form of elaborate trades with other teams). So much so that the process by which he acquired Larry Bird for the team was later banned by the NBA.
** Many good basketball coaches fit the profile, but while legendary Phil Jackson is more famous to be an OldMaster figure, it fits San Antonio's Gregg Popovich to the T. To the point that he got ''fined'' by the NBA because his management strategy (forcing some of his players to take a break) was supposed to be bad for business.
* Stalin, at least in the way he orchestrated his rise to absolute power within the party apparat against rivals considered a great deal more brilliant or popular than himself, by forming various alliances against one rival, and then turning on his erstwhile ally after that rival had been eliminated.
** Before his rise to power, Stalin was viewed as a [[CorruptCorporateExecutive petty clerk]] attending to [[PunchClockVillain meaningless paperwork]], but nobody stopped to think of the extreme command he was developing of obscure laws. In some ways, his most potent ability was actually to ''RulesLawyer'' his opponents.
* Cardinal Richelieu of France was a startling example of this trope. The man was the world's first Prime Minister, and raised up alliance after alliance during the UsefulNotes/ThirtyYearsWar. He's the main reason that France became as powerful as it did.
* Hitler started out as one, getting the people of Germany to give him the power, and the nations of Europe to just give him several nations before the war even started, but his ability to control the board quickly vanished after making one horrible choice after another. The British actually stopped their plans to kill Hitler because they figured out somebody who was competent would take his place.
** Hitler was a brilliant politician and diplomat who became convinced that he was also a brilliant military leader; he wasn't. He was able to take Austria and Czechoslovakia without firing a shot, and then cut a deal with Stalin to isolate France (France was allied with Britain, but the British lacked significant land power), allowing Hitler to take Poland and France quickly and easily. The problem was that after the success of his military campaigns against Poland and France, and the early successes against Russia after Hitler broke his deal with Stalin, Hitler became convinced that he was also a brilliant military leader, and so ''abandoned'' diplomacy. All he had to do to win the war was either make peace with Britain before attacking Russia, or persuade the Japanese to also attack Russia, or both. If he had continued his diplomatic campaign, he would have won.
* Creator/BenjaminFranklin spearheaded the early American response to British surveillance during the American Revolution by devising a system of counter-surveillance, securing aid, playing a role in privateering expeditions against the British, and waging a public relations campaign on behalf of the patriots. He also played the role of TheChessmaster during his and UsefulNotes/JohnAdams's diplomatic tour of duty in France, where Franklin's political savvy and understanding of how to play the game of court politics allowed him to secure French support for America during the Revolution.
* Magic Johnson and the other owners of the Los Angeles Dodgers pulled off a series of well-timed waiver claims to land a trade in August the Red Sox best players
* The ByzantineEmpire in legend has this as a hat. Even the real ByzantineEmpire was ''very'' good at it.
* Sultan Abdulhamid, nicknamed "The Crimson Sultan" by the French, is an entirely forgotten member of Ottoman Monarchy. In his age, the Empire was little more than a wreck, its economy ruined and battered, yet he re-furnished it to survive another 2 decades. His extensive efforts to reduce debt and corruption, launching the first submarine and torpedo test shot in history, setting up thousands of schools and charities in an Anatolia untouched by previous sultans, a series of "firsts" in history, was overlooked by its resistance of Zionism (he kicked Theodor Herzl out when he heard the offer to buy Israel out of Ottoman land) and brutal suppression of every uprising due to nationalism. He organized a colossal spy network reaching into Europe, and thwarted countless attempts at assassination and manipulation. Had he an Empire with perfect economy, heavy military and solid demography, world conquest might not have been a distant possibility.
* [[HornyVikings Ivar Boneless]], if the Icelandic chronicles are correct. Having the handicap og missing his legs (or suffering from brittle bone-disease) he was not exactly the warrior type having to be carried around. Instead he embraced the wisedom aspect of Odin (and certainly the "''Father of Treachery''" aspect) and executed a RoaringRampageOf Revenge by turing King Ćlla's people against him and [[YouKilledMyFather carved a blood eagle]] on the king.
* A common saying is that the best-laid plans never survive contact with the enemy. [[BernardLawMontgomery Bernard Montgomery]], British Field Marshal, scoffed at that. At the Second Battle of El Alamein his meticulous plan, which depended on [[BatmanGambit anticipating Rommel's notoriously impulsive maneuvers]], was carried out to near-perfection. He also correctly predicted the length of the battle ''and'' how many casualties the allies would take, ensuring that his forces had sufficient logistic and medical support, [[FatalFlaw something that Rommel always struggled with]].
* Brazilian history had the figure of the UsefulNotes/DukeOfCaxias. A man who fought in no less than ''seven'' wars, and never lost any of them. A tactical genius both in the battlefield (being always two steps ahead of his enemies, able to conquer any type of field, pulling outflanking moves out of his sleeve) and out of it (perfecting espionage tactics ahead of his time, acquiring allies by charisma and sowing disorder among his foes). It can be said the reason the Empire of Brazil lasted a century was, in great deal, due his influence.
[[/folder]]