History TheChessmaster / FanWorks

* ''Fanfic/FairyMayCry'': Arkham has managed to manipulate both his enemies and allies to achieve his goals, gathering dark wizards to fulfill the roles of the Seven Sins not only as keys to unlock the tower but powerful enough rival Fairy Tail, having the, fight in order to weaken each other til the moment when Vergil along with Dante, Natsu, Gray, and Erza are too weak to fight, taking advantage of this to beat them down.

* ''Fanfic/CodePrime'': Megatron is shown to be both a powerful warrior as he is a master planner, being capable of pulling the strings of those around him to get them to do what he wants. Accelerating and improvising his plans when gathering new information that could benefit him. His most evil act being the orchestrator of the SAZ Massacre using a Pretender Drone bearing Euphemia's likeness to trigger the event as a distraction, knowing that it will spark an attack from the Black Knights and Autobots in order destroy the Britannian Empire by sacking its capital while everyone is distracted with Japan.

** Lucius' somewhat-ally Alexander Pierce is the head of HYDRA within SHIELD, and [[AuthorityEqualsAsskicking just as good of a manipulator as that implies]], even putting on an AffablyEvil act good enough to fool other chessmasters like Albus Dumbledore and Nick Fury. He's even implied to have known about the Shadow Initiative after the Avengers fell, and said nothing so that he could take advantage of the chaos. However, [[spoiler:Lucius' desperate phone call to him]] gets intercepted by Fury, who locks him up. Even then, Pierce stays alive by leaking just a few secrets here and there to his interrogators, making himself more useful alive than dead. However...

* ''Fanfic/JewelOfDarkness'': The mysterious leader of [[TheConspiracy the White Glove]] qualifies as one of these, and is even seen playing a game with ComicBook/VandalSavage at one point. Notably, Savage warns him that it's harder to treat people like pieces, as life isn't as simple as a chess game.

[[AC:''WesternAnimation/TeenTitans'']]

* ''Fanfic/ChildOfTheStorm'': Has a truly epic GambitPileUp (it is the only work of ''any'' kind to have its own [[GambitPileUp/ChildOfTheStorm Gambit Pile-Up page]]), meaning that ''loads'' of characters are this trope.

* ''Fanfic/OnceMoreWithFeeling'':
** Gendo and SEELE of course, but in this fic they are joined (and opposed) by OriginalCharacter Major General Shigeru Ishiba, the Director of the Japanese Defense Agency (Intelligence).

* ''Fanfic/KyonBigDamnHero'' (''LightNovel/HaruhiSuzumiya'' & Website/TVTropes; author DiedDuringProduction): Kyon is most definitely a Chessmaster, often using chess metaphors as he makes strategies.

** Lucius Malfoy is a master manipulator whom even Nick Fury (very grudgingly) takes his hat off to. In a number of months, he goes from sitting on his laurels to becoming Master of HYDRA and temporarily [[spoiler: basically in charge of the ''entire world.'']] However, he makes a fatal mistake or two, which leads to...
** Lucius' somewhat-ally Alexander Pierce is the head of HYDRA within SHIELD, and [[AuthorityEqualsAsskicking just as good of a manipulator as that implies]], even putting on an AffablyEvil act good enough to fool other chessmasters like Albus Dumbledore and Nick Fury. He's even implied to have known about the Shadow Initiative after the Avengers fell, and said nothing so that he could take advantage of the chaos. However, [[spoiler: Lucius' desperate phone call to him]] gets intercepted by Fury, who locks him up. Even then, Pierce stays alive by leaking just a few secrets here and there to his interrogators, making himself more useful alive than dead. However...
** He gets cracked in minutes by Alison Carter, [[spoiler: daughter of Peggy and Steve]], though admittedly she does have a trump card. Later, it's revealed that she was able to pull a BatmanGambit on ''Nick Fury and Phil Coulson,'' without them even realising they were being manipulated, let along that she was involved. She separately states that while she was only ever Deputy Director of SHIELD prior to her retirement, not only was that because the WSC felt that a Director with [[HeroicLineage the Carter name]] would be too powerful to control, but that if necessary, she could override the then Director in matters as significant as [[spoiler: the discovery of Clark Kent]]. She's even implied to have mindwiped him.
** Fury himself is, as per usual, no slouch. As Tony puts it, "his secrets have secrets." He even manages to catch Malfoy red-handed through patience, good timing, and a shrewd assessment of Malfoy's personality, nabbing Pierce at the same time. He and Loki even discuss chess metaphors early on, describing their allies and enemies as chess pieces.
** And manipulating the heck out of absolutely ''everyone'' is [[MagnificentBastard Doctor Stephen Strange]], seen at one point playing chess with Odin (and winning). He gets everyone from {{Badass Normal}}s to the freaking Endless to do what he wants, often even when they ''know'' they're being manipulated and can't do anything about it, because he's arranged his plans so that [[BatmanGambit whatever people choose to do]], [[XanatosGambit it will work out in his favour]]. As a result, the mere ''possibility'' of his involvement is ParanoiaFuel. The one time he hits a blind spot, he's still capable of highly effective XanatosSpeedChess, and jumps right back on the ball afterwards. When confronting [[spoiler: Chthon]], who's just pulled a VillainOverride and looks like he's going to win, the latter smugly asks if he has any last words. He does, actually. "Check." Cue Strange unfolding the last few steps of his plan, ending it with a soft and triumphant remark of, "Check. CheckAndMate."
* ''{{Roleplay/Communication}}'': That to prior knowledge that Consensus has of events [[TheOmniscient that had and will occur]], every single [[PlayerCharacter Host]] in every iteration of the quest becomes this quite easily. Thanks to the guidance of their backer, each one them are able to twist, bend, arrange, and/or guide events to their advantage. Every action they take makes sure to obtain and strengthen allies they otherwise wouldn't have gotten in the first place, cripple or outright take out key enemies that could most definitely cause problems in the long run, all the while elevating their powerbase far further than the positions their canon incarnations ended up in.
* ''Fanfic/JWITCHSeries'' (''WesternAnimation/JackieChanAdventures'' & ''WesternAnimation/{{WITCH}}''): Tarakudo proves himself to be an expert manipulator in the chapter "Challenges in Leadership", the author's notes for which make sure to acknowledge it. To wit, [[spoiler: he prods the [[TheStarscream treacherous]] Cedric and Daolon Wong to [[VillainTeamUp team up]] to usurp Phobos, while pretending to be on their side, only to then rat them out to Phobos in order to gain the Prince's confidence and convince him to [[WeCanRuleTogether join Tarakudo in a stronger alliance]]]].

* ''Fanfic/SoulChess'' (''Manga/{{Bleach}}'' & ''Anime/CodeGeass''): Used to focus on Lelouch and Aizen trying to [[UltimateShowdownOfUltimateDestiny fight for control over the Soul Society]]. [[spoiler: Lelouch wins, but Aizen comes back from Hell for Round 2]].
* ''FanFic/TheStarsWillAidTheirEscape'' (Franchise/CthulhuMythos & ''WesternAnimation/MyLittlePonyFriendshipIsMagic''): [[EldritchAbomination Herald]], the BigBad. He drops a few chess metaphors over the course of the story, as he manipulates ''everyone'' to follow his plan.

[[AC:''Franchise/HarryPotter'']]
* ''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.

* ''FanFic/BreakYourHeart'': Scootaloo, of all ponies. She carefully attempts to manipulate everything around her to better her chances of getting Rainbow.
* The WesternAnimation/MyLittlePonyFriendshipIsMagic crossover story ''FanFic/AHollowInEquestria'' portrays Princess Celestia as attempting to be this, and failing miserably at every turn.

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* Professor Vee in ''FanFic/AnonymoosesMonsterGirlSaga''. Joining Count Aaron's forces against Yaleria? A distraction allowing him to uncover the Tower of Babel; essentially a doomsday device for all of Yaleria. Equipping The Count with nigh invulnerable PoweredArmor? Just a test subject for his latest golem model, which glitches out at the worst possible moment for Aaron. Killing Nerick, another nigh invulnerable character right before he kills Laven? He only did just to steal the void crystal, the key for the Tower of Babel. Well done, Vee.
* ''[[https://www.fanfiction.net/s/14158315/1/Breaking-Providence Breaking Providence]]'': Volupa, a Dark General who worked for the previous Dark Lord, spends a decade working as the Pope's loyal Shadow. In that time, she assassinates several troublesome nobles and clergymen (on the Pope's orders no less), ensures a specific letter reaches another Dark General, arranges for the current Destined Hero (who's also the Dark Lord) to overhear the Dark General has been sentenced to be raped to death, and aids the crown princess in obtaining her independence while also cementing herself as the girl's one true ally. In the end, she helps the princess force her mother to AscendToAHigherPlaneOfExistence and dispose of the Pope so the princess can become queen. All of it done so that the Dark Lord could easily take control of the Empire now that the only person in power left is a girl madly in love with him.
* Fan novelization of ''Videogame/TheLegendOfZeldaBreathOfTheWild'' titled ''Fanfic/BreathOfTheWild'' turns the Golden Goddesses and Goddess Hylia into these, and very patient ones in that [[spoiler: they all set up a 10,000-year LongGame dedicated to finally ending Demise's ancient evil curse on the land. Apparently, every event seen and unseen in the time between Calamity Ganon's initial encounter 10,000 years prior to the Great Calamity was part of the Goddess's LongGame.]]
* 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/ErasedPotential'' [[{{Deconstruction}} deconstructs the concept]] with Nedzu. Upon becoming aware of Izuku's existence, he immediately starts weaving plans around him, such as pointing Toshinori in his direction while hinting that he could be a potential candidate for One For All... despite being well aware that Izuku intends to become a Quirkless superhero. His various manipulations make Izuku increasingly paranoid, and seriously undermine others' ability to ''trust'' the principal. Even his own staff start regarding him with suspicion and disgust.
* [[ManipulativeBastard Checker]] [[TheSociopath Monarch]], the BigBad of ''FanFic/GettingBackOnYourHooves'', who uses a chess board (chess itself being described at one point as her favorite game) as a representation of her plans to ruin [[spoiler: her sister]] Trixie's life. Her full first name is actually Checkmate as well.

** Gendo and SEELE of course, but in this fic they are joined (and opposed) by Original character Major General Shigeru Ishiba, the Director of the Japanese Defense Agency (Intelligence).

* A number of characters in ''FanFic/TheInfiniteLoops'' can outwit non-looping characters easily, but this trope really comes into play when the loopers have some form of competition with each other.
** One story-arc in the MLP Loops has a version of Princess Celestia who is a Dumbledore-style "For-the-Greater-Good" manipulator. An Awake Twilight Sparkle throws a monkey wrench in her plans just by acting like her un-Awake self might have.
** For a non-looping example, we have [[spoiler:YHVH from the SMT loops, who managed to convince everyone from the local loopers to the Admins that he's capable of interfering with Yggdrasil code, which in turn would eventually give him the power to actually do it due to that part of Yggdrasil running on ClapYourHandsIfYouBelieve. Fortunately, that's stopped; eventually]].
* ''FanFic/JewelOfDarkness'': The mysterious leader of [[TheConspiracy the White Glove]] qualifies as one of these, and is even seen playing a game with ComicBook/VandalSavage at one point. Notably, Savage warns him that it's harder to treat people like pieces, as life isn't as simple as a chess game.

* In ''Fanfic/OnceMoreWithFeeling'' Gendo and SEELE are joined (and opposed) by Original character Major General Shigeru Ishiba, the Director of the Japanese Defense Agency (Intelligence).
-->The UN, formerly a simple world forum with delusions of power was, in half a decade turned into a powerful body with delusions that it was a world forum as SEELE moved the pieces on its chess board patiently, taking control behind the scenes to divert the resources they needed to GEHIRN and then NERV and the Human Instrumentality Project.
* ''FanFic/ThePiecesLieWhereTheyFell'': [[spoiler: Balance, who's been manipulating the situation for years - among other things, he guided events to make sure all six of the new Bearers would be in Canterlot at the right time, even if it meant disrupting their relationships with their families or other loved ones, and ensured Sharp Point and his gang would find the Bearers to give Night Blade his final chance at earning his Element.]]
* Celestia in ''Fanfic/RitesOfAscension'', who admits that due to working on her own for a millennium, it is hard to counsel with other ponies, even her own sister (who admits to sometimes feeling like just another piece on the board), discussing the matter with Twilight over a chessboard. (Notably, said discussion comes immediately after said tendency has circled back around to bite her in the cutie mark and upend her own plans, with Twilight calling her out on it.) She also notes Council Chairpony Charlemane as being similarly gifted (and that the two of them have had many worthy battles in both chess and the political arena).
* [[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."
* ''Fanfic/SoulEaterTroubledSouls'' has Medusa Gorgon. Her plan is to destroy and ruin the DWMA, but she is very thorough in making that possible. Prior to the beginning of the story, Medusa retrieves her minions [[spoiler: and brainwashes Krysa as well as turn Atlas, a giant Kishin Egg, into a mindless slave via Reanimation Magic]] and teams up with her younger sister, Shaula. In addition, she engineers a curse named Ouroboros. When she kicks off her plan, she has Eruka plant a fake VIP mission on the mission board that requests the presence of the Academy’s strongest students (Maka and the others, of course) to weaken the military overall. Aware of Lord Death’s and Stein’s keen eyes, she also wrote down the names of random students to eliminate suspicion. A disguised Free and Mizune ships them to Cobra Island, far away from home and cut off from communication. With Ouroboros, she removes a personality or ability from each and every person as they venture deeper into the island, and they don’t realize that until she’s forced to reveal her hand. Meanwhile, Shaula’s role is to promote infighting with her poison back at Death City, but when she fails, Medusa isn’t even fazed. She keeps things on Cobra Island going without a hitch and simply plots to take care of the rest when she’s done. [[spoiler: As Chapter 33 shows, her master plan worked.]]
* Shinji from ''Fanfic/ThousandShinji'' trained for ten years to become one, learning the ways of plotting and scheming, and coming up with schemes within schemes within schemes to outwit his enemies.
* [[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]].
* Having a drastically expanded role compared to his [[Recap/DigimonAdventure02E13HisMastersVoice original appearance]], Dragomon from ''FanFic/Zero2ARevision'' has a giant chessboard that he uses to monitor the movements of the Digidestined and the other dark forces that the Digidestined are currently facing, patiently waiting for his next move to absorb the ''Child of Light''.

[[AC:''ComicStrip/CalvinAndHobbes'']]
* ''Fanfic/CalvinAndHobbesTheSeries'': Calvin slowly develops into this.

** Lucius' somewhat-ally Alexander Pierce is the head of HYDRA within SHIELD, and [[AsskickingEqualsAuthority just as good of a manipulator as that implies]], even putting on an AffablyEvil act good enough to fool other chessmasters like Albus Dumbledore and Nick Fury. He's even implied to have known about the Shadow Initiative after the Avengers fell, and said nothing so that he could take advantage of the chaos. However, [[spoiler: Lucius' desperate phone call to him]] gets intercepted by Fury, who locks him up. Even then, Pierce stays alive by leaking just a few secrets here and there to his interrogators, making himself more useful alive than dead. However...

* Having a drastically expanded role compared to his [[Recap/DigimonAdventure02E13TheCallOfDagomon original appearance]], Dragomon from ''FanFic/Zero2ARevision'' has a giant chessboard that he uses to monitor the movements of the Digidestined and the other dark forces that the Digidestined are currently facing, patiently waiting for his next move to absorb the ''Child of Light''.

* ''Fanfic/JWITCHSeason1'' (''WesternAnimation/JackieChanAdventures'' & ''WesternAnimation/{{WITCH}}''): Tarakudo proves himself to be an expert manipulator in the chapter "Challenges in Leadership", the author's notes for which make sure to acknowledge it. To wit, [[spoiler: he prods the [[TheStarscream treacherous]] Cedric and Daolon Wong to [[VillainTeamUp team up]] to usurp Phobos, while pretending to be on their side, only to then rat them out to Phobos in order to gain the Prince's confidence and convince him to [[WeCanRuleTogether join Tarakudo in a stronger alliance]]]].

* ''Fanfic/KyonBigDamnHero'' (''LightNovel/HaruhiSuzumiya'' & Wiki/TVTropes; author DiedDuringProduction): Kyon is most definitely a Chessmaster, often using chess metaphors as he makes strategies.

* ''fanfic/AbraxasHrodvitnon'': [[Characters/AbraxasHrodvitnonHumans The Executive]] [[spoiler:[[AdaptationalIntelligence Maia Simmons]]]] is skilled at using [[FemmeFatale looks]] and subtle body language to help her get what she wants out of people. She also uses fairly subtle means of communication when manipulating the grieving [[spoiler:Bernie Hayes]] to get him on the track of investigating her father's company.

* ''Fanfic/SoulChess'' (''Manga/{{Bleach'' & ''Anime/CodeGeass''): Used to focus on Lelouch and Aizen trying to [[UltimateShowdownOfUltimateDestiny fight for control over the Soul Society]]. [[spoiler: Lelouch wins, but Aizen comes back from Hell for Round 2]].

* ''FanFic/BreakYourHeart'': Scootaloo, of all ponies. She carefully attempts to manipulate everything around her to better her chances of getting Rainbow.

* That to prior knowledge that Consensus has of events [[TheOmniscient that had and will occur]], every single [[PlayerCharacter Host]] in every iteration of the ''{{Roleplay/Communication}}'' quest becomes this quite easily. Thanks to the guidance of their backer, each one them are able to twist, bend, arrange, and/or guide events to their advantage. Every action they take makes sure to obtain and strengthen allies they otherwise wouldn't have gotten in the first place, cripple or outright take out key enemies that could most definitely cause problems in the long run, all the while elevating their powerbase far further than the positions their canon incarnations ended up in.

* The WesternAnimation/MyLittlePonyFriendshipIsMagic crossover story ''FanFic/AHollowInEquestria'' portrays Princess Celestia as attempting to be this, and failing miserably at every turn.

* ''Fanfic/AKnightsTaleAsInquisitor'' features a Chessmaster operating in plain sight vs a Chessmaster controlling things behind the scenes: [[GuileHero Arturia]] is constantly making moves and decisions with far more layers than at first glance in order to rally more and more allies to her cause and spread the overall influence of the Inquisition in the long run. At the same time, she knows that she's facing off against some [[HiddenVillain unknown force]] - so far only named as the Elder One by [[CultOfPersonality its followers]] - that's [[TheManBehindTheMan manipulating multiple and major factions from the shadows]], with its machinations resulting in the death of [[BigGood Divine Justinia V]] and countless others at the Mage-Templar Conclave explosion. Currently, the Elder One is playing a mean game of XanatosSpeedChess thanks to the ''giant'' wrench in the EvilPlan due to [[SpannerInTheWorks Arturia's interference]].

* Camillo and August seem to be this in the Hunger Games fanfic ''FanFic/SinkOrSwim''. Camillo rather fails at this, though.

* ''Fanfic/SoulChess'' used to focus on Lelouch and Aizen trying to [[UltimateShowdownOfUltimateDestiny fight for control over the Soul Society]]. [[spoiler: Lelouch wins, but Aizen comes back from Hell for Round 2]].
* [[EldritchAbomination Herald]], BigBad of ''FanFic/TheStarsWillAidTheirEscape''. He drops a few chess metaphors over the course of the story, as he manipulates ''everyone'' to follow his plan.

* ''Fanfic/TurningTables'': In Chapter 57, it is revealed that [[spoiler:Doctor Strange [[BatmanGambit made Thanos see Tony as a threat so that Tony would be dusted in the Blip instead of Peter]], having deliberately changed the variables when none of [[MultipleChoiceFuture the many, many timelines]] where Tony lived through the Blip seemed to go well and made it so that Peter would be the one to discover time-travel and prevent the [[AlternateTimeline AT]]!Thanos from wreaking havoc in the main timeline. He admits that it was a gamble, but it still paid off in the end.]]
* 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.