History Main / ChessmasterSidekick

* In ''WesternAnimation/WanderOverYonder,'' Commander Peepers as TheDragon to Lord Hater. Due to his [[TheNapoleon unimposing]] [[AdorableEvilMinions appearance]], his [[TakeOverTheWorld galaxy-conquering ambitions]] depend on Hater's power to intimidate, but he [[EvenEvilHasLovedOnes cares about Hater]] to IgnoredEnamoredUnderling levels and [[VillainousFriendship considers him his best friend]].

* In ''WesternAnimation/WanderOverYonder,'' Commander Peepers as TheDragon to Lord Hater. Although he depends on Hater's power to intimidate due to his [[TheNapoleon unimposing]] [[AdorableEvilMinions appearance]], he also [[EvenEvilHasLovedOnes cares deeply about Hater and considers him his best friend]].

* In ''Anime/LegendOfGalacticHeroes'', Kircheis, [[spoiler:and later, Hilda]] serve as Reinhart's Chessmaster Sidekick: both have Reinhart's trust, and both save his life [[spoiler:Hilda manage to OutGambit Yang, who just managed to OutGambit Reinhart: [[SugarWiki/MomentOfAwesome Demonstrating]] that she is the smartest Chessmaster in a series [[GambitPileup full of them]], way to go, Fraulein]]

* Askeladd to Canute in ''Manga/VinlandSaga''.
* ''Manga/FullmetalAlchemist'' features Maes Hughes filling this role to Roy Mustang's badass [[TheStrategist Strategist]]. Roy Mustang even lampshades this in the aftermath of [[spoiler:Hughes's funeral]].
* In ''Manga/YuYuHakusho'', [[TheChessmaster Kurama]] is much more cunning and ruthless than the other members of the Tantei (even [[TokenEvilTeammate Hiei]] balks at the idea of facing off against him), but remains fiercely loyal to the team.

* In ''Manga/AttackOnTitan'', Armin grows into this role as a result of his CharacterDevelopment. He's easily one of the most ruthless and brilliant characters, but fiercely loyal to his friends and respectful of his equally ruthless commanders.

* 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.]]

* ''Franchise/FinalFantasy'':
** In ''VideoGame/FinalFantasyXII'', [[spoiler:Cid is the sidekick of Vayne, while Venat is the sidekick of Cid]]. On the other side, we have an aversion in [[spoiler:Vossler, who wants to be Ashe's sidekick, but end up betraying her and loses his life for it]] and a subversion in [[spoiler:Larsa, who does not ''serve'' Ashe, but helps her regain her throne because he feels that an independent Dalmasca serves the interests of Archadia]].
** In ''VideoGame/FinalFantasyVI'', Kefka reveals himself to be this to Emperor Gestahl. [[TheStarscream Or so it would seem.]]

There are a number of reasons why the Chessmaster Sidekick is fiercely loyal to the person they should probably be barking orders at. Maybe they place a higher value on their [[ThePowerOfFriendship friendship]]/[[ThePowerOfLove romantic bond]]. Maybe that person did something to forever earn their trust and respect, [[BecauseYouWereNiceToMe and this is their way of returning the favor]]. Maybe their boss has so much more raw power than them that they could never overthrow them if they tried. Maybe it's as simple as them being [[BrilliantButLazy apathetic about the notion]], or [[TheCreon actively not wanting the top spot]]. Maybe it's all three. Whatever the reasoning, the Chessmaster Sidekick is more than content with manipulating events from the sidelines without desiring to gain any power for themselves.

There are a number of reasons why the Chessmaster Sidekick is fiercely loyal to the person they should probably be barking orders at. Maybe they place a higher value on their [[ThePowerOfFriendship friendship]]/[[ThePowerOfLove romantic bond]]. Maybe that person did something to forever earn their trust and respect, [[BecauseYouWereNiceToMe and this is their way of returning the favor]]. Maybe it's as simple as them being [[BrilliantButLazy apathetic about the notion]], or [[TheCreon actively not wanting the top spot]]. Maybe it's all three. Whatever the reasoning, the Chessmaster Sidekick is more than content with manipulating events from the sidelines without desiring to gain any power for themselves.

If the Chessmaster Sidekick ''isn't'' a loyal lackey through-and-through, then you have an example of TheStarscream that's simply biding their time, or a case of TheDogWasTheMastermind, where they see it as more convenient to remain in the shadows until the very end.

* [[AlternateCharacterInterpretation One interpretation]] of ''Anime/NeonGenesisEvangelion''[='s=] Yui Ikari is that she was one of these, since a flashback at the end of the series hints that she knew far more about what was going to happen than she let on.
* General Blue of ''Manga/DragonBall'' is shown to be this to the Red Ribbon Army and Commander Red. Blue possessed superhuman endurance, superhuman strength, possibly superhuman speed, and PsychicPowers. Because of this, he could easily take over the Red Ribbon Army and dispose of Commander Red and Staff Officer Black if he so desired. Instead he follows their orders to the letter.[[note]]Of course, had he lived long enough to learn about Commander Red planning to use the dragon balls to make himself taller, he probably wouldn't mind partaking in a big TheDogBitesBack moment.[[/note]]

* In ''Manga/{{Beelzebub}}'' Natsume is ''clearly'' much tougher and smarter than his boss Kanzaki. However Natusme claims that he really follows Kanzaki because it always leads to interesting and fun situations, and so he's happy.

* Ibushi Arima in ''Anime/CuteHighEarthDefenseClubLove'', for Kinshiro. While he doesn't do much in the anime, in the manga and the game he's the one who comes up with all the plans that don't suck.
* In ''Manga/PokemonAdventures'', Malva is this for Lysandre. She is much more hands on than he is in Team Flare matters, giving out instructions and dealing punishments to the Grunts and Scientists, and even going out on missions herself. Not to mention that she is an extremely powerful Trainer in her own right, given that she's an official member of the the Kalos Elite 4. This ultimately culminates her in [[spoiler:capturing and commanding ''Yveltal'' into battle]]. However, it's clear that she follows Lysandre because she wants to be in an UnholyMatrimony with him, and that she honestly believes in his ideals.
* The Lord Master Tactician Narsus from ''Literature/TheHeroicLegendOfArslan'' has destroyed an alliance without sending a single soldier by spreading rumors, forced a group of soldier led by [[BigBad Silver Mask]] to flee while he was alone and forced a 1000 men army to flee while he and his companions were only six in total (the enemy thought they were surrounded by at least a few hundred men). He is also very loyal to Prince Arslan.
* An interesting example with Demiurge from ''Anime/Overlord2012''. He is much smarter and ''much'' more cruel than his master [[VillainProtagonist Momonga]] in almost every conceivable way. He comes up with most of the plans that advance Momonga'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 Momonga 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 Momonga's most innocuous actions have some hidden meaning behind them, when in reality Momonga's motivations and reasonings were ''far'' less complex than what he's imagining.

* 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 by her ruthlessness, cunning and organizational brilliance.
* 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 because he knows that Darkseid could end him with a thought if he wanted to.

** Sinister, to anyone he works with, from Weapon X to the Red Room, since he's generally NotInThisForYourRevolution. Instead, as a MadScientist brilliant enough to give Zola lessons and behind-the-scenes manipulator immune to Strange's foresight, he arranges to get exactly what he wants: time, lab-space, funding, and as many test subjects as he wants. However, [[spoiler:Strange figures out a way around that immunity and tracks him down...]]

* ''Fanfic/SomosFamilia:'' De La Cruz Records employee Vincente shows signs of this. He's deeply loyal to Ernesto and the Rivieras, effortlessly figures out a LoopholeAbuse way to get Coco out of an unwanted contract, and runs the company almost single-handedly by the 1950s. He also puts a lot of thought into a LongGame to get Hector to ease up on [[spoiler:his destructive music ban, although it gets derailed pretty quickly due to external factors.]]

* Before the ''Franchise/StarWars'' prequels revealed the utter depth and breadth of Palpatine's EvilPlan, [[Literature/TheThrawnTrilogy Grand Admiral Thrawn]] was often seen this way by fans. Thrawn was loyal to the Emperor, and seemed to be a much better plotter.

** Admiral Count Aral Vorkosigan is this to Emperor Gregor Vorbarra, having served variously as His Regent, Prime Minister and Viceroy of one third of the Empire of Barrayar since Gregor was six years old. Indeed, the case could be made that Aral had just as strong (if not a stronger) claim to the throne than the Vorbarras, and many urged him to declare himself Emperor and murder/execute young Gregor while he was Regent. [[{{Cincinnatus}} He declined]].

* 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.

* ''Literature/TheLostStars'': Artur Drakon is TheHero (or one of them anyway) and military genius, but Colonel Bran Malin is the arguably the real brain behind his faction. Malin is TheSpymaster for Drakon, works out the long term-details of military and political strategies and is good at asking seemingly innocuous questions and doting out information which make Drakon and President Iceni more trusting of each other, all for the goal of making a stable, lasting and benevolent government.

*** Fits even better in the MirrorUniverse. Mirror Spock could easily take over Mirror Kirk's role as captain, but is content to stay as first officer as it means he's a lesser target for [[KlingonPromotion assassination]].

--> [[RunningGag "Haaave you met Ted?"]]

* In the ''TabletopGame/OldWorldOfDarkness'', the Ceilican (faerie were-cats) have a gift called ''Small Cousin'' that allows them to assume the shape and size of an ordinary housecat, while retaining their social and mental attributes in the tradition of Puss in Boots. They sometimes call this gift ''Blofeld's Cat'', after James Bond's nemesis (who they insist was the cat, and not the man).

** In ''Videogame/DragonAgeInquisition'', Solas plays this role to the Inquisitor. He is the one who reveals the location of Skyhold, but makes it look like the Inquisitor is the one who found it to make them look like a more inspiring leader. He also provides surprisingly accurate insight into the actions and plans of the BigBad. [[spoiler:TheStinger reveals that he basically manipulated the Inquisition into helping him save the world from his own mistake.]] The ''Trespasser'' DLC spells out the full extent of this, but also reveals that Qunari intelligence thought it was so obvious that it didn't even occur to them that the Inquisitor didn't realize it.

* The newer ''VideoGame/CrashBandicoot'' games tend to play off Coco as this, given she has all her IdiotHero brother's abilities, but with the benefit of a much bigger IQ and sense of lucidity, plus the ability to talk allowing her to strategise and negotiate with teammates. ''Crash on the Run's'' bio for her even states she could take over from Crash at any time if she wanted to. This was downplayed in earlier titles. While Coco was certainly still more intellectual than Crash, she wasn't as physically apt and role reversals where she only ''thought'' she was the sensible one were more common.

* ''WesternAnimation/TheTransformers'': In the 80s "post Movie 2005 era cartoon" Cyclonus was easily this to Galvatron. Galvatron at least could lead by example as he had the unrestrained gung ho and toughness needed in a fighter. And he certainly wasn't afraid of rushing headfirst into the thick of battle with no regard for his own safety. Cyclonus, however, was more intelligent, careful, calmer, saner, less violent, and wasn't prone to beating his subordinates around. Cyclonus also knew how to plan strategically and act in purely diplomatic situations. In most of the situations where the Autobots and Decepticons were required to join forces and work together, the involved Decepticons were under the command of Cyclonus. However, throughout the entire cartoon, Cyclonus remained devotedly loyal to "Mighty Galvatron", refusing to usurp him even when pressured by the other Decepticons losing patience with their current insane leader.

** Cao Cao could be considered this to Emperor Xian of Han, if not TheManBehindTheMan. His highest rank was Imperial Chancellor, and while miles more accomplished than his nominal liege (partially because Emperor Xian spent most of his life [[DistressedDude being held prisoner by various warlords claiming to protect him]]), he was very careful to make sure he was at least ''seen'' to defer to the Emperor. Some of his subordinates actually suggested he take the imperial throne himself, but his response can be summed up as, "I already have power, what need to I have for the imperial title? But if someone wanted to make me an emperor posthumously... well, that's out of my hands." Sure enough, after Cao's passing his son Cao Pi forced Emperor Xian to abdicate and took the imperial throne for himself, formally declaring the Wei Empire as successor to the Han Empire.

* This is often TruthInTelevision in monarchies, when the king sits on his throne and the [[EvilChancellor Chancellor]], Steward, Prime Minister, or other top servant of the Crown actually runs things, as seen in the quote above. This is sometimes even an official arrangement, like the Japanese Shogunate.
* This is a good summary of how the government of the United Kingdom is run. While the reigning monarch is technically the head of state and the church in name, the elected ministers are the ones who have all the power. In theory the monarch still has some significant powers, but would never even consider using them. (Or in the case of dissolving Parliament, the power has become a mere formality to be carried out a few weeks ahead of a scheduled election.) And despite the prevailing wisdom that the U.S. President is basically King of America, what makes a great U.S. President more often than not boils down who they choose for their cabinet.

* William I of UsefulNotes/ImperialGermany had this relationship with both Bismarck and Von Moltke. They were more competent then he, being {{Consummate Professional}}s at the crafts of scheming and slaying respectively. However William was reasonably competent himself, sensible enough to use their talents effectively and a skillful enough leader to keep them working together instead of at cross-purposes. William II's failure to listen to Bismarck - or at least keep his alliance with Russia - would have disastrous consequences for Germany in the decades to come.
* [[http://en.wikipedia.org/wiki/Belisarius Flavius Belisarius]] was a Byzantine general of immense skill: he reconquered North Africa, destroying the Vandalic Kingdom in ''weeks'', part of Southern Spain, almost all of Italy and some of modern France. Since generals of such legendary skill usually had designs on the throne, this left the Empress Theodora in constant fear that he would stage a coup, resulting in Emperor Justinian frequently recalling him right in the middle of a campaign. Ironically, Belisarius was loyal to a fault, despite being given more than adequate reason to rebel.

* [[http://en.wikipedia.org/wiki/Lin_Biao Lin Biao]] was this to UsefulNotes/MaoZedong, and for a time was considered the heir apparent to the leadership of the Chinese Communist Party. Unfortunately he sealed his own fate when he leveraged his popular support and respect within the party to became TheStarscream. Or so the official Chinese version says; in the West it's widely believed that at least parts of the official story are lies.

* William I of UsefulNotes/ImperialGermany had this relationship with both Bismarck and Von Moltke. They were more competent then he, being {{Consummate Professional}}s at the crafts of scheming and slaying respectively. However William was reasonably competent himself, sensible enough to use their talents effectively and a skillful enough leader to keep them working together instead of at cross-purposes.

** Then, Yang is a subversion of this trope: [[spoiler: He never wanted to be more than the Chessmaster Sidekick of the Alliance, but its inept and corrupted politicians, fearing his popularity, and unable to see the man's selflessness, never believed he was content with his role and kept trying to constrain him, causing their own doom]].

* ''Manga/OuranHighSchoolHostClub'': Kyouya is this for IdiotHero Tamaki. Kyouya originally wanted nothing to do with Tamaki and his Hose Club idea, but eventually Tamaki's charisma and genuine friendliness won him over. While the club is Tamaki's vision and is the public face of the club, Kyouya runs the nuts and bolts as the "shadow king".

* In ''Manga/PokemonAdventures'', Malva is this for Lysandre. She is much more hands on than he is in Team Flare matters, giving out instructions and dealing punishments to the Grunts and Scientists, and even going out on missions herself. Not to mention that she is an extremely powerful Trainer in her own right, given that she's an official member of the the Kalos Elite 4. This ultimately culminates her in [[spoiler: capturing and commanding ''Yveltal'' into battle]]. However, it's clear that she follows Lysandre because she wants to be in an UnholyMatrimony with him, and that she honestly believes in his ideals.

** Sinister, to anyone he works with, from Weapon X to the Red Room, since he's generally NotInThisForYourRevolution. Instead, as a MadScientist brilliant enough to give Zola lessons and behind-the-scenes manipulator immune to Strange's foresight, he arranges to get exactly what he wants: time, lab-space, funding, and as many test subjects as he wants. However, [[spoiler: Strange figures out a way around that immunity and tracks him down...]]

** With the complete story of Palpatine's rise on the table, it was more like they were equals, but in different areas- Palpatine was the master of political and personal manipulations, while Thrawn was the master of military strategy.

* In the ''Literature/HarryPotter'' series, Snape is this for Dumbledore - and he'd be the HypercompetentSidekick, if not for the fact that Dumbledore is the most ridiculously powerful and cunning wizard alive. Of course, Dumbledore {{manipulat|iveBastard}}es Snape rather shamelessly, and Snape has his [[TheLostLenore own]] [[TheAtoner reasons]] for working for him, but they nonetheless seem to be friends.

* The Marquis de Carabas - aptly named for the alias Puss In Boots comes up with for his master in the fairy tale - serves as a [[spoiler: heroic]] version of this in ''Literature/{{Neverwhere}}''.

** [[GodEmperor The Shaggat Ness]], ruler of a splinter group of [[ProudWarriorRace the Mzithrin]] has [[AGodAmI a massive god complex]] and is surprisingly charismatic when it comes to convincing others of his divinity, but is an AxCrazy berserker whose reaction to every problem is basically "hit it harder". Luckily, he's got [[EvilSorcerer Arunis]] working his butt off behind the scenes to make sure he comes to TakeOverTheWorld. [[spoiler: Subverted in that Arunis actually cares not one whit for the Shaggat, despite what the Shaggat believes. Arunis is using him to kickstart the apocalypse]].

** In ''VideoGame/DragonAgeOrigins'', if you want [[spoiler:Alistair]] on the throne you pretty much have to play this. You're up against his resistance every step of the way. [[spoiler:However, if you're a Human Noble, you may just [[ManipulativeBastard take it yourself]] - or if you're the Human Female Noble, you can do ''both'' by marrying him.]] Lampshaded by Loghain during the Landsmeet. He [[AlternateCharacterInterpretation accuses]] Arl Eamon of wanting to put Alistair on the throne as a PuppetKing, but mocks him for not realizing that he's being just as "controlled" by the Warden.

* Fenrich from ''VideoGame/{{Disgaea 4|A Promise Unforgotten}}'' is an unrepentant, scheming ManipulativeBastard - it's just that all his plots and ambitions are not for himself but for his lord Valvatorez, to whom he is [[UndyingLoyalty impossibly loyal to]].

* Doc Scratch from ''Webcomic/{{Homestuck}}'' is literally omniscient, and has manipulated every single character in the comic, from the lowliest carapace to the most powerful player, to do his bidding. However, his bidding consists pretty much solely of making sure his boss, [[BigBad Lord English]] actually gets to his universe in the first place. Of course, he also [[spoiler: ''is'' Lord English, [[ItMakesSenseInContext in a roundabout way]]]].

* ''WesternAnimation/{{Gargoyles}}'': Even Xanatos himself has one. Towards the end of the series, it is revealed that [[spoiler: his assistant Owen Burnett is actually the powerful fairy Puck.]] Oddly enough, he remains a loyal servant and even friend all the way. His official explanation is that [[ItAmusedMe "Xanatos is many things, but never boring."]]

* In ''Manga/PokemonAdventures'', Malva is this for Lysandre. She is much more hands on than he is in Team Flare matters, giving out instructions and dealing punishments to the Grunts and Scientists, and even going out on missions herself. Not to mention that she is an extremely powerful Trainer in her own right, given that she's an official member of the the Kalos Elite 4. This ultimately culminates her in [[spoiler: capturing and commanding ''Yveltal'' into battle]]. However, it's clear that she follows Lysander because she wants to be in an UnholyMatrimony with him, and that she honestly believes in his ideals.

* Head Maid (yes, [[EveryoneCallsHimBarkeep that's her name]]) in ''LightNovel/{{Maoyu}}'' is the right hand of the super-economist [[HollywoodNerd 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.

The Chessmaster Sidekick is such a [[TheChessmaster master]] of strategy and tactics that you have to wonder why ''they'' aren't TheHero or BigBad of the story. After all, they seem to surpass their superior in almost every category required for the role. Most characters who qualify for this label are fully aware that they could easily take control of the operation and establish their own dominance if they so wished. But that's the thing: they don't want to. Maybe the thought will cross their mind once or twice, but they'd never seriously consider stepping up and overthrowing their boss or "master" for the simple fact that they are [[UndyingLoyalty undying faithful to them]].

* ''Literature/TheLostStars'': Artur Drakon is TheHero (or one of them anyway) and military genius, but Colonel Bran Malin is the arguably the real brain behind his faction. Malin is TheSpymaster for Drakon, works out the long term-details of military and political strategies and is could at asking seemingly innocuous questions and doting out information which make Drakon and President Iceni more trusting of each other, all for the goal of making a stable, lasting and benevolent government.

** 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}} 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.

* Since they were inherently anarchic with "the situation is in charge" as a mantra, everyone in the Music/GratefulDead was this TO THE BAND ITSELF, extending into the crew and fanbase since they "kept the lights on" and were all seen as the same entity by anyone involved at that level. Slightly subverted when most people just started assuming Jerry Garcia was the leader, this mass cognitive dissonance eventually lead to his death.

* Since they were inherently anarchic with "the situation is in charge" as a mantra, everyone in the Music/GratefulDead was this, extending into the crew and fanbase since they were all seen as the same entity by anyone involved. Slightly subverted when most people just started viewing Jerry Garcia as the leader, this mass cognitive dissonance lead to his death.

Since they were inherently anarchic with "the situation is in charge" as a mantra, everyone in the Music/GratefulDead was this, extending into the crew and fanbase since they were all seen as the same entity by anyone involved. Slightly subverted when most people just started viewing Jerry Garcia as the leader, this mass cognitive dissonance lead to his death.
UsefulNotes/ReinhardHeydrich, the head of the infamous Wannsee Conference planning UsefulNotes/TheHolocaust, was the right hand of Reichsfuehrer-SS Heinrich Himmler who would've been barely able to survive inter-Nazi rivalry without his loyal Reinhard. There was even a joke in Nazi Germany exemplifying this: ''"Himmlers Hirn heisst Heydrich"'' (''"Himmler's brain is called Heydrich"''). [[JustifiedTrope Justified]] as Heydrich was a very poor public speaker, had no talent to win sympathy from the common people and was feared and hated by everyone, Himmler included. Even if he gained political power, he was not going to survive long enough to enjoy it.

* Since they were inherently anarchic and with"the situation is in charge"as a mantra, everyone in the Music/GratefulDead was this, extending into the crew and fanbase since they were all seen as the same entity by anyone involved. Slightly subverted when most people just started viewing Jerry Garcia as the leader, and this mass cognitive dissonance lead to his death.

* UsefulNotes/ReinhardHeydrich, the head of the infamous Wannsee Conference planning UsefulNotes/TheHolocaust, was the right hand of Reichsfuehrer-SS Heinrich Himmler who would've been barely able to survive inter-Nazi rivalry without his loyal Reinhard. There was even a joke in Nazi Germany exemplifying this: ''"Himmlers Hirn heisst Heydrich"'' (''"Himmler's brain is called Heydrich"''). [[JustifiedTrope Justified]] as Heydrich was a very poor public speaker, had no talent to win sympathy from the common people and was feared and hated by everyone, Himmler included. Even if he gained political power, he was not going to survive long enough to enjoy it.

* In Creator/MarvelComics, the [[GuardianOfTheMultiverse Omniversal Guardian]] was originally the Otherworlder [[TheArchmage master wizard and former Sorcer Supreme,]] Merlyn/Merlin who created the ComicBook/BlackKnightMarvelComics'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 by her ruthlessness, cunning and organizational brilliance.

* ''Literature/TheLostStars'': Artur Drakon is TheHero (or one of them anyway) and military genius, but Colonel Bran Malin is the arguably the real brain behind his faction. Malin is TheSpymaster for Drakon, works out the long term-details of military and political strategies and is could at asking seemingly innocuous questions and doting out information which make Drakon and President Iceni more trusting of each other, al for the goal of making a stable, lasting and benevolent government.

This trope counts double if the boss of the Chessmaster Sidekick is a badass [[TheStrategist Strategist]] in their own right. In this case, the Chessmaster Sidekick is an [[InfinityPlusOneSword Infinity +1 Tactician]]. On the other hand, if the boss is an [[ConservationOfCompetence idiot or otherwise incompetent]], this overlaps with HyperCompetentSidekick. See also BattleButler, SidekickExMachina and GuardianEntity.

* ''Literature/TheLostStars'': Artur Drakon is TheHero (or one of them anyway) and military genius, but Colonel Bran Malin is the arguably the real brain behind his faction. Malin TheSpymaster for him, works out the long term-details of military and political strategies and is could at asking seemingly innocuous questions and doting out information which make Drakon and President Iceni more trusting of each other, al for the goal of making a stable, lasting and benevolent government.