History Main / ChessmasterSidekick

* ''WesternAnimation/{{Amphibia}}'': [[Characters/AmphibiaKingAndrias King Andrias]] EstablishingCharacterMoment certainly sets him up to be this, plotting from within his palace and having a literal chessboard containing figures carved to resemble Marcy and Anne. The crux of his EvilPlan throughout season 2 involves manipulating the girls into finding out enough information about the Calamity Box to discover the way to recharge it, whilst underplaying his own knowledge of the Box's full capabilities so [[GladIThoughtOfIt they won't suspect that it's a bad idea to do so]], while also simultaneously using the cracks in the girls' relationship to manipulate Marcy into helping return the Box to him fully-charged without using her own knowledge of how it works to open a portal home the second they complete the temples. Finally, once they hand the box to him, he uses Marcy's DarkSecret to try and get the girls to turn on each other, since they need to stand united against him and the Core, according to the prophecy glimpsed briefly in "A Day at the Aquarium". When that fails, he shrugs it off, because he's already tricked the girls into unwittingly de-powering themselves by charging the Calamity Box, and thus there was no way for them to realistically beat a 10-ft tall LightningBruiser like himself armed with {{Magitek}} in direct combat. Really, it's telling that the only reason he doesn't win outright by the end of "True Colors" was due to [[LifeSavingMisfortune a simple accident]] he couldn't have predicted.

* In ''Heretics of Dune'', most people think Patrin is merely Miles Teg's assistant or aide. Later, Teg reveals that Patrin was a "tactical magician" who was "fully capable of taking over command of an entire multi-planet force". His low rank was a personal choice that allowed him to retain an awareness of the feelings and needs of common soldiers and civilians.
* In ''the Iliad'' Odysseus is this to Agamemnon. An important point in character motivations in the work is that Agamemnon's staff is all much more competent than he is.

* Capt. Dudley Smith from James Ellroy's ''L.A. Quartet'', and, of course, the motion picture ''Film/LAConfidential'', is both a MagnificentBastard and a Chessmaster Sidekick. He may not be the Chief of Police but he is both clever and manipulative, making the Los Angeles Police Department serve his ends.

* ''ComicBook/CaptainBritain'': In Creator/MarvelComics, the [[GuardianOfTheMultiverse Omniversal Guardian]] was originally the Otherworlder [[TheArchmage master wizard and former Sorcerer Supreme,]] Merlyn/Merlin who created the ComicBook/{{Black Knight|MarvelComics}}'s sword Ebony Blade and made Brian Braddock into Captain Britain and later Merlyn's PhysicalGod daughter Roma would inherit the Omniversal Guardian position. Acting as the Guardian's lieutenant is the Omniversal Majestrix and this position has always been filled by Opal Luna Saturnyne who commands the Captain Britain Corps. Despite originally being a "mundane human" from an alternate Earth that worships Mitra, Opal got her position through her ruthlessness, cunning, and organizational brilliance. However, as Betsy Braddock ultimately reminds all of them in her time as ComicBook/CaptainBritain, she is under no obligation to obey ''any'' of them.

* Creator/DCComics has Desaad, Darkseid's right-hand man, who is typically the one coming up with most of the schemes and sinister plots on Apokolips. The reason why he never tries to go against his master is that he knows that Darkseid could end him with a thought if he wanted to.
* In Creator/MarvelComics, the [[GuardianOfTheMultiverse Omniversal Guardian]] was originally the Otherworlder [[TheArchmage master wizard and former Sorcerer Supreme,]] Merlyn/Merlin who created the ComicBook/BlackKnight's sword Ebony Blade and made Brian Braddock into ComicBook/CaptainBritain and later Merlyn's PhysicalGod daughter Roma would inherit the Omniversal Guardian position. Acting as the Guardian's lieutenant is the Omniversal Majestrix and this position has always been filled by Opal Luna Saturnyne who commands the Captain Britain Corps. Despite originally being a "mundane human" from an alternate Earth that worships Mitra, Opal got her position through her ruthlessness, cunning, and organizational brilliance. However, as Betsy Braddock ultimately reminds all of them in her time as ComicBook/CaptainBritain, she is under no obligation to obey ''any'' of them.
* In the ''Franchise/XMen'', Mr. Sinister was this to Apocalypse when they used to work together. Apocalypse was stronger, tougher, faster, more skilled, and had far more connections at his beck and call. Mr. Sinister on the other hand was smarter, more cunning, patient, and was much better at manipulating than his boss behind the scenes.

Sometimes a PsychoSupporter's chief weapons are plans. Sometimes there's a [[TheManBehindTheMan Man Behind the]] ManipulativeBastard. In those cases, the result is a Chessmaster Sidekick.

* ''Fanfic/LetTheGalaxyBurn'': Tyrion Lannister has the name, and logistical genius, but in the scenes they share, it's made clear Addam Marbrand is a ''very'' good tactician, who plans out several steps ahead before the first battle is even fought, factoring in some very precise estimates about how the other factions will react (and how to counter this) and [[XanatosSpeedChess being very good at adapting his plans when outside factors throw off his calculations]].

* ''Fanfic/TheVictorsProject'': Beetee is a key member of the rebellion, responsible for strategy as well as inventions, even if he is second to people like Mags. This is best emphasized in Cashmere's chapter he discusses how they need to have "villains" among the other tributes to distract attention and has to address the issue [[ThePawnsGoFirst of which rebels the conspiracy to escape the arena could afford to lose]].

* ''Fanfic/TheEndOfTheWorld'' series by [[https://www.fanfiction.net/u/5615/FernWithy Fern Withy]] put Haymitch Abernathy in this role. He's not the senior member of the rebellion, or the most respected, but he's good at thinking out long-term strategies that play on the actions and reactions of people, such as the idea of using emotional attachment to the tributes to force the Capitol to change the rules. The fact that he often plays chess adds to this.

* Ronnie Schiatto serves this role for [[TheMafia the Martillo Family]] in ''LightNovel/{{Baccano}}''. Everyone is completely baffled as to ''why'' he bothers to stay with such a small camorra organization when he could probably take over the entire criminal underworld single-handedly [[spoiler:being an ungodly powerful HumanoidAbomination and all]], and is terrified of the day he decides to turn on them.

* During the TournamentArc, the protagonist Tatsuya Shiba from ''LightNovel/TheIrregularAtMagicHighSchool'' is this trope to those who were participating, specifically the women's division as he is the CAD engineer assigned. Let's just say a lot of his strategies, plus him being AlwaysSomeoneBetter than any engineer in that building gave the women's division a winning landslide.
%%* In ''LightNovel/KyoKaraMaoh'', [[spoiler:Ken Murata]] winds up being this for Yuuri. [[spoiler:And his [[PastLifeMemories first incarnation]] was the Great Sage, who played this role for Shinou.]] (Zero-Context: Entry is just names)

* Head Maid (yes, [[EveryoneCallsHimBarkeep that's her name]]) in ''LightNovel/{{Maoyu}}'' is the right hand of the super-economist Demon Queen. Besides tending the house, being [[NinjaMaid her bodyguard]] and ''commanding her armies'' in her absence, she also makes sure she dresses like a [[MsFanservice proper]] EvilOverlord and gives her advice on her love life.

* An interesting example with Demiurge from ''LightNovel/Overlord2012''. He is much smarter and ''much'' more cruel than his master [[VillainProtagonist Ainz Ooal Gown]] in almost every conceivable way. He comes up with most of the plans that advance Ainz's eventual goal of world domination, and it is extremely rare that something happens outside of his predictions. Yet due to his earnest belief that Ainz is an infallible mastermind operating on a level of thought beyond comprehension he's completely in the dark about this fact. This in turn leaves Demiurge under the delusion that even Ainz's most innocuous actions have some hidden meaning behind them when in reality his motivations and reasonings were ''far'' less complex than what Demiurge is imagining. A RunningGag is that, whenever Ainz is asked to explain whatever [[ThePlan plan]] the Floor Guardians think he has hatched, he "allows" Demiurge to explain it in his place; once Demiurge has explained what he believes to be Ainz's plan, [[SureLetsGoWithThat Ainz ends up taking the credit.]]

* In Creator/MarvelComics, the [[GuardianOfTheMultiverse Omniversal Guardian]] was originally the Otherworlder [[TheArchmage master wizard and former Sorcer Supreme,]] Merlyn/Merlin who created the ComicBook/BlackKnight's sword Ebony Blade and made Brian Braddock into ComicBook/CaptainBritain and later Merlyn's PhysicalGod daughter Roma would inherit the Omniversal Guardian position. Acting as the Guardian's lieutenant is the Omniversal Majestrix and this position has always been filled by Opal Luna Saturnyne who commands the Captain Britain Corps. Despite originally being a "mundane human" from an alternate Earth that worships Mitra, Opal got her position through her ruthlessness, cunning, and organizational brilliance.

** Doctor Strange functions as this for the heroes. He's not the most powerful hero, or even the most powerful mage (Merlin takes that, with Wanda next in line), but he's easily the smartest and most experienced. Along with being a time-traveller, an extremely powerful {{Seer|s}} and [[spoiler:nigh-immortal]] thanks to [[spoiler:the Time Stone]] means that he could probably take over the world in a day if he ever felt like it. His unparalleled skills as a manipulator and utter ruthlessness means that he justly terrifies many of his allies, let alone his enemies. However, he was chosen not to be TheChosenOne, but TheChooserOfTheOne, and spends his entire vastly extended life machinating to prepare the universe, the Nine Realms, Earth, the heroes, and most specifically, Harry, to face down Thanos.

** ''WesternAnimation/TransformersPrime'' gives us Soundwave, who was essentially TheDragon to Megatron (until [[ProudWarriorRaceGuy Dreadwing]] showed up). Soundwave not only keeps an eye on ''[[SinisterSurveillance everything]]'', he's also feared by almost everyone (with Airachnid learning '' why'' [[CurbStompBattle you shouldn't pick a fight with him]]), to the point where [[TheStarscream Starscream]] kept trying to tiptoe around him/gain his approval whilst attempting to usurp Megatron. Also, according to one of the background novels, Soundwave ''almost'' bested '''[[AuthorityEqualsAsskicking Megatron]]''' in gladiatorial combat, and would have outright ''won'' if not for the fact that their duel was [[VictoryByFirstBlood to first wound]] and not to the death.

* Surprisingly, Josef Stalin was this in the Soviet Government. While no one would ever dare question his authority, he never officially assumed the role of head of state. The reason was quite pragmatic: it let him get away with whatever crimes and/or mistakes he might commit.