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Chessmaster Sidekick

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Sometimes a Lancer or Psycho Supporter's chief weapons are plans. Sometimes there's a Man Behind the Manipulative Bastard. In those cases, the result is a Chessmaster Sidekick.
The Chessmaster Sidekick is such a master of strategy and tactics that you have to wonder why they aren't The Hero or Big Bad 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 undyingly faithful to them.
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 friendship/romantic bond. Maybe that person did something to forever earn their trust and respect, 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 apathetic about the notion, or actively not wanting the top spot. Maybe it's all four. 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 The Starscream that's simply biding their time, or a case of The Dog Was the Mastermind, where they see it as more convenient to remain in the shadows until the very end.
This trope counts double if the boss of the Chessmaster Sidekick is a badass Strategist in their own right. In this case, the Chessmaster Sidekick is an Infinity +1 Tactician. On the other hand, if the boss is an idiot or otherwise incompetent, this overlaps with Hyper-Competent Sidekick. See also Battle Butler and Guardian Entity.
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Fenrich from Disgaea 4 is an unrepentant, scheming Manipulative Bastard — it's just that all his plots and ambitions are not for himself but for his lord Valvatorez, to whom he is impossibly loyal to.
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The "Puss In Boots"-inspired Maurice of The Amazing Maurice and His Educated Rodents combines this with Jerk with a Heart of Gold.
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 The Amazing Maurice and His Educated Rodents
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The newer Crash Bandicoot games tend to play off Coco as this, given she has all her Idiot Hero 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.
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Dragon Age:
In Dragon Age: Origins, if you want Alistair on the throne you pretty much have to play this. You're up against his resistance every step of the way. However, if you're a Human Noble, you may just 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 accuses Arl Eamon of wanting to put Alistair on the throne as a Puppet King, but mocks him for not realizing that he's being just as "controlled" by the Warden.
In Dragon Age: Inquisition, 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 Big Bad. The Stinger 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.
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The World Ends with You has Sanae Hanekoma, who wins with the Last Plan Standing and is suspected by precisely no one. While the heroes are focused on defeating the Conductor, and, later, the Composer, Hanekoma skips town before the happy ending, only to appear next to the Composer in the last shot. The New Game Plus makes the relationship between the two more obvious, along with going into more detail regarding Hanekoma's decision to turn his skills against the designated chessmaster. It's one of those games.
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X-Men: 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.
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Ronnie Schiatto serves this role for the Martillo Family in 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 being an ungodly powerful Humanoid Abomination and all, and is terrified of the day he decides to turn on them.
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 The Mafia
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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.
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Let the Galaxy Burn: Tyrion Lannister has the name, and logistical genius, but in the scenes they share, it's made clear his subordinate 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 being very good at adapting his plans when outside factors throw off his calculations.
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In 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.
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 Beelzebub (Manga)
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In the Old World of Darkness, 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).
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Noah Bennet, from Heroes, after the reveal that his Magnificent Bastardry is to protect his daughter, Claire.
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Power Rangers Turbo: General Havoc; brother of the series' main antagonist, Divatox; is leagues smarter than his boss and is a legitimately competent and intelligent villain. Yet he displays no interest in overthrowing her and is fully loyal to her cause.
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Fire Emblem:
Fire Emblem: The Blazing Blade has the player represented as a non-combatant tactician who serves as the brains behind the heroes.
Soren from Fire Emblem: Path of Radiance and Fire Emblem: Radiant Dawn is the strategist in Ike's army, and is fiercely loyal to him (and him alone).
The player characters of Fire Emblem: Mystery of the Emblem's remake and Fire Emblem: Awakening serve as the strategists for their respective armies and are fiercely loyal to their Lords.
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Naruto: Joining the Akatsuki and Obfuscating Stupidity as Tobi, Obito Uchiha managed to manipulate events from behind the scenes, though he eventually dropped the act to instead impersonate Madara Uchiha.
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The Mountain's Range: Gregor Clegane positions himself as this to Robert Baratheon and the rest of the Small Council, working hard to use his knowledge of the future to prevent certain tragedies from befalling, or pushing people along certain paths which will prevent the War of the Five Kings and have the Westeroes prepared for the Long Night.
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Eternal Darkness: Pious Augustus becomes one in the timeline where Chattur'gha is the Big Bad. The latter, a millennia-old eldritch being who exists outside of space and time, definitely isn't dumb by human standards, but, being a god of physical strength and matter, isn't the schemer that the other Ancients are and prefers to just use his powers to brute force through any opposition, since, by his belief, that's all he should need to win a battle. Pious, a trained soldier and skilled commander, knows differently, so while Chattur'gha empowers Pious to do his bidding, Pious handles most of the planning and strategy. The only reason Pious is still a minion is because Chattur'gha and the Black Guardian boss him around regardless.
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"Puss in Boots": The miller's son goes from the lowest rung of society to the highest, and he owes just about everything to his cunning, manipulative cat.
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Captain Britain: The Omniversal Guardian was originally the Otherworlder master wizard and former Sorcerer Supreme, Merlyn/Merlin who created the Black Knight's sword Ebony Blade and made Brian Braddock into Captain Britain and later Merlyn's Physical God 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 Captain Britain, she is under no obligation to obey any of them.
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Zigzagged with Zhuge Liang. While Romance of the Three Kingdoms portrays him as equally at home on the battlefield as he is governing, the historical Zhuge Liang wasn't a particularly successful military commander (especially compared to his liege lord Liu Bei)note The novel often took battles led by other people and attributed them to Zhuge instead, two examples being the battle of Bowangpo (his first battle in the novel, which was historically planned and executed by Liu Bei himself) and the battle of Chibi (historically it was led by Zhou Yu and his colleagues from Wu, but the novel instead makes Zhuge the driving force) . He was a genuine genius at statecraft (for example, he almost single-handedly wrote the legal code for Liu Bei's state of Shu and also spearheaded economic reforms that turned the Shu heartland of Yi Province into enough of a powerhouse to fund further campaigns), but he did not command anywhere near as much personal respect as Liu Bei did note  Liu Bei had pulled off multiple Back from the Brink recoveries over the course of his career while somehow maintaining the loyalty of his followers no matter how bleak things became . Played straight with Liu Bei's successor Liu Shan, who was nowhere near as accomplished as his father was.
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Power Rangers:
Power Rangers Turbo: General Havoc; brother of the series' main antagonist, Divatox; is leagues smarter than his boss and is a legitimately competent and intelligent villain. Yet he displays no interest in overthrowing her and is fully loyal to her cause.
Power Rangers Lost Galaxy: Impostra spends her one episode faithfully serving Trakeena, and the plan to trick Destructo into attacking the Rangers, frame Treacheron for treason, and steal the Lights of Orion (all but the last of which goes off perfectly) is entirely hers.
Power Rangers Wild Force: The Duke Org Onikage is the one who allowed Viktor Adler/Master Org to get his revenge on both Mandilok and Toxica and almost Jindrax as well, all while keeping the Rangers in a stalemate they could not win before being defeated by a stroke of luck on Jindrax's part. Even though he ultimately fell, his manipulations nearly led to Master Org's victory in the finale.
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In The Chathrand Voyages, Evil Overlords seem to pick these up:
Magad V, ruler of Arqual, seldom appears on page but is basically characterized as a spoilt, petty, grasping manchild with way too much power. His spymaster and chief assassin (and the real power behind the throne), Sandor Ott, is a Chessmaster par excellence. Fortunately for Magad, Ott's other defining feature is his fanatical Arquali patriotism. Magad is basically content to let Ott do all the work while he gets all the perks.
The Shaggat Ness, ruler of a splinter group of the Mzithrin has a massive god complex and is surprisingly charismatic when it comes to convincing others of his divinity, but is an Ax-Crazy berserker whose reaction to every problem is basically "hit it harder". Luckily, he's got Arunis working his butt off behind the scenes to make sure he comes to Take Over the World. 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.
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Discworld:
The "Puss In Boots"-inspired Maurice of The Amazing Maurice and His Educated Rodents combines this with Jerk with a Heart of Gold.
Appears in Pyramids, in which the Big Bad may or may not be stuck in a Stable Time Loop and has been "advisor" to the entire royal family. As in, since it was founded millennia ago.
Nanny Ogg is this to Granny Weatherwax. While Granny is acknowledged as the smarter and more powerful of the two, Nanny (who may be smarter and stronger still, but doesn't advertise) steers Granny in the right direction, usually by implying she shouldn't because Granny's such a contrarian she'd run over broken glass to go somewhere she was told she can't go.
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In the James Bond book and later movie From Russia, with Love, Kronsteen plays the role of an organization's master strategist, though his boss is different. In the novel, he's a high-ranking officer of the Soviet counterintelligence agency SMERSH who puts together the details of a plan to sour MI6's image and knock off Bond, making him "sidekick" to General G, or, closer to the main plot, Rosa Klebb. In the movie, he's a member of the criminal organization SPECTRE, and reports to the faceless "Number One".
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The Transformers: 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.
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 The Transformers
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Doc Scratch from 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, Lord English actually gets to his universe in the first place. Of course, he also is Lord English, in a roundabout way.
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Spock fits within the Star Trek (2009) reboot, as Kirk has yet to develop his legendary leadership abilities (or for that matter, much basic competence) while Spock is easily the most competent officer all around aboard the Enterprise.
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In Saints Row: Gat Out of Hell, Dane Vogel states that after getting killed in Saints Row 2 he came to realize that he was better off as a kingmaker who sets up others for success rather than taking power himself (which led to said-mentioned death). As such, he's been preparing for the Saints' inevitable arrival in hell so that he can back them in a war against Satan.
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 Saints Row: Gat Out of Hell (Video Game)
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Chessmaster Sidekick
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The player characters of Fire Emblem: Mystery of the Emblem's remake and Fire Emblem: Awakening serve as the strategists for their respective armies and are fiercely loyal to their Lords.
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 Fire Emblem: Mystery of the Emblem (Video Game)
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Chessmaster Sidekick / int_53446b8
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Chessmaster Sidekick
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An interesting example with Demiurge from Overlord (2012). He is much smarter and much more cruel than his master 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 Running Gag is that, whenever Ainz is asked to explain whatever 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, Ainz ends up taking the credit.
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 Overlord (2012)
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Chessmaster Sidekick / int_55c20cb5
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Chessmaster Sidekick
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Fallout: New Vegas has Yes Man, an A.I who is programmed to follow the orders of anyone who gives him orders and has masterminded a plan involving the usurping of Mr. House and taking over Vegas in his place, free from the influences of the NCR or Caesar's Legion. While he starts off as Benny's henchman, he can be found by the Courier, at which point he'll gladly shift alliances once Benny's out of the picture for good. At no point in the game does Yes Man actively conspires against the player and will even force himself to accept counter-productive actions that he personally thinks is detrimental to his overall plans. Even in the ending when he states that he found an upgrade that allows him to be more "assertive", it's only meant to make sure that he can monitor Vegas by himself without someone else stumbling upon him and pulling the same thing on you.
 Chessmaster Sidekick / int_59da62aa
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1.0
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1.0
 Fallout: New Vegas (Video Game)
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Chessmaster Sidekick / int_59da62aa
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type
Chessmaster Sidekick
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Star Wars: Allegiance: Caaldra has a vast intelligence network whose reports he scrutinizes carefully and forms alliances with mercenaries, Small Town Tyrants, and pirate gangs across the sector to steal weapons and attack Imperial loyalists once the secession plot begins. He's almost singlehandedly responsible for the failed secession being in a position where, if not for several last-minute spanners in the works, it would have probably succeeded despite the active efforts of one of its leaders to sabotage the plot from within.
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 Star Wars: Allegiance
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Chessmaster Sidekick / int_5b31bf
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Chessmaster Sidekick
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Schlock Mercenary: Der Trihs is described by Tagon as one of the best tactical minds he's ever known, whose small adjustments to plans saved lives when both were in the regular military. When Kevyn questions has he can say that of the utter moron he knows, Tagon says part of Trihs' brain was eaten by a torturer.
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1.0
 Chessmaster Sidekick / int_5c897f4a
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1.0
 Schlock Mercenary (Webcomic)
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Chessmaster Sidekick / int_5c897f4a
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Chessmaster Sidekick
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New Gods: 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.
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1.0
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 New Gods (Comic Book)
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Chessmaster Sidekick / int_5cfb879b
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Chessmaster Sidekick
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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 heroic version of this in Neverwhere.
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1.0
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 Neverwhere
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Chessmaster Sidekick / int_5e1213a8
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Vorkosigan Saga:
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. He declined.
A similar state of affairs can be said of Aral's son Miles to Gregor (although Miles would have far greater trouble holding the throne, considering his... deformities), Miles to Illyan, Illyan to Gregor, Illyan to Aral, Tung to Miles and Negri to Ezar.
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1.0
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Chessmaster Sidekick
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In Pokémon Adventures, 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 Kalos Elite 4. This ultimately culminates her in capturing and commanding Yveltal into battle. However, it's clear that she follows Lysandre because she wants to be in an Unholy Matrimony with him, and that she honestly believes in his ideals.
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1.0
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1.0
 Pokémon Adventures (Manga)
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Chessmaster Sidekick / int_610a694a
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Chessmaster Sidekick
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The Lord Master Tactician Narsus from The Heroic Legend of Arslan has destroyed an alliance without sending a single soldier by spreading rumors, forced a group of soldiers led by 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.
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1.0
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 The Heroic Legend of Arslan
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Chessmaster Sidekick / int_625f8f3
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Chessmaster Sidekick
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In Dragon Age: Origins, if you want Alistair on the throne you pretty much have to play this. You're up against his resistance every step of the way. However, if you're a Human Noble, you may just 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 accuses Arl Eamon of wanting to put Alistair on the throne as a Puppet King, but mocks him for not realizing that he's being just as "controlled" by the Warden.
 Chessmaster Sidekick / int_629cd094
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1.0
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1.0
 Dragon Age: Origins (Video Game)
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Chessmaster Sidekick / int_629cd094
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Chessmaster Sidekick
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The Lost Stars: Artur Drakon is The Hero (or one of them anyway) and military genius, but Colonel Bran Malin is arguably the real brain behind his faction. Malin is The Spymaster 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 that makes Drakon and President Iceni more trusting of each other, all for the goal of making a stable, lasting and benevolent government.
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1.0
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 The Lost Stars
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Chessmaster Sidekick / int_63655cb9
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Chessmaster Sidekick
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The Dragon That Will Pierce the Heavens has Hikari, who while co-vice captain of the Straw Hats, is openly their chief tactitian and saboteur. She's smart and knowledgeable enough to plan around Luffy's chaos, strong enough to be considered part of the Monster Trio, and is usually one good push away from wanting to punch Luffy in the head. But she loves him, and has no interest in being captain.
 Chessmaster Sidekick / int_6bff737b
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1.0
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1.0
 The Dragon That Will Pierce the Heavens (Fanfic)
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Chessmaster Sidekick
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The Victors Project: 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 reluctantly address the issue of which rebels the conspiracy to escape the arena could afford to lose.
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 The Victors Project / Fan Fic
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Chessmaster Sidekick / int_6e73440d
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Chessmaster Sidekick
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Porky Pig when he's the second-in-command to Daffy Duck.
 Chessmaster Sidekick / int_6ef684b9
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1.0
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 Porky Pig
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Chessmaster Sidekick / int_6ef684b9
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Chessmaster Sidekick
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Soren from Fire Emblem: Path of Radiance and Fire Emblem: Radiant Dawn is the strategist in Ike's army, and is fiercely loyal to him (and him alone).
 Chessmaster Sidekick / int_6f1bcb62
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1.0
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1.0
 Fire Emblem: Path of Radiance (Video Game)
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Chessmaster Sidekick / int_6f1bcb62
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Chessmaster Sidekick
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TRON: Alan Bradley in the Expanded Universe material. He doesn't have Flynn's raw talent or charisma, and he withered when forced into the spotlight as CEO after Flynn vanished, but he is very sneaky, good with planning, and aware of contingencies. He spends much of the Betrayal comic being the one who actually puts Flynn's brilliant ideas into practical use, running interference between Flynn and the corporate board, running Flynn Lives as "ISOlated Thinker" under everyone's nose, and "The Next Day" shows that he's going to be the real power behind Encom's revival with Sam as a figurehead.
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 TRON (Franchise)
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Chessmaster Sidekick / int_7560e8e0
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Chessmaster Sidekick
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Somos Familia: De La Cruz Records employee Vincente shows signs of this. He's deeply loyal to Ernesto and the Rivieras, effortlessly figures out a Loophole Abuse 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 Long Game to get Hector to ease up on his destructive music ban, although it gets derailed pretty quickly due to external factors.
 Chessmaster Sidekick / int_766e8369
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1.0
 Chessmaster Sidekick / int_766e8369
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 Somos Familia (Fanfic)
hasFeature
Chessmaster Sidekick / int_766e8369
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Chessmaster Sidekick
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Fire Emblem: The Blazing Blade has the player represented as a non-combatant tactician who serves as the brains behind the heroes.
 Chessmaster Sidekick / int_78e27fa7
featureApplicability
1.0
 Chessmaster Sidekick / int_78e27fa7
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1.0
 Fire Emblem: The Blazing Blade (Video Game)
hasFeature
Chessmaster Sidekick / int_78e27fa7
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type
Chessmaster Sidekick
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Star Trek:
Star Trek: The Original Series:
This is the role Spock plays. While Kirk is shown to be a competent leader, Spock is physically stronger, more technically knowledgeable, and has telepathic abilities.
Fits even better in the Mirror Universe. 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 assassination.
In Star Trek: The Next Generation, Riker is deemed more than capable of captaining a vessel (having turned down command of other starships on multiple occasions), but prefers to work under Picard on the Enterprise. Data follows Riker's example, remaining third-in-command on the Enterprise throughout the series.
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 Star Trek (Franchise)
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Chessmaster Sidekick / int_81692f99
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Chessmaster Sidekick
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Gargoyles:
Even Xanatos himself has one. Towards the end of the series, it is revealed that 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 "Xanatos is many things, but never boring."
Also Preston Vogel, who succeeded in a plan with Fox to steal Renard's company but backed out at the last minute because of personal loyalty.
To a lesser extent, Glasses is this to Dracon.
 Chessmaster Sidekick / int_83d41855
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 Gargoyles
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Chessmaster Sidekick / int_83d41855
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Chessmaster Sidekick
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Transformers: Prime gives us Soundwave, who was essentially The Dragon to Megatron (until Dreadwing showed up). Soundwave not only keeps an eye on everything, he's also feared by almost everyone (with Airachnid learning why you shouldn't pick a fight with him), to the point where 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 Megatron in gladiatorial combat, and would have outright won if not for the fact that their duel was to first wound and not to the death.
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 Transformers: Prime
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Chessmaster Sidekick / int_85a5a3b9
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Chessmaster Sidekick
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Power Rangers Lost Galaxy: Impostra spends her one episode faithfully serving Trakeena, and the plan to trick Destructo into attacking the Rangers, frame Treacheron for treason, and steal the Lights of Orion (all but the last of which goes off perfectly) is entirely hers.
 Chessmaster Sidekick / int_86aff994
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1.0
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 Power Rangers Lost Galaxy
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Chessmaster Sidekick / int_86aff994
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Chessmaster Sidekick
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In the Sam & Max games, Max is perfectly content to let Sam be in charge of their duo, despite Max gradually gaining more and more power, both political and supernatural.
 Chessmaster Sidekick / int_8a6d4a19
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1.0
 Chessmaster Sidekick / int_8a6d4a19
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 SamAndMax
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Chessmaster Sidekick / int_8a6d4a19
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Chessmaster Sidekick
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The Wheel of Time character Faile mostly serves as an adviser to her husband, because- although very knowledgeable about governance- she isn't sociable or patient enough to inspire the common people like he does. In fact, she met him because she escaped her hereditary responsibilities in Saldaea to go off adventuring. Also, her parents really want her to marry a man who is powerful in his own right, so they won't have to deal with any mooching.
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 Chessmaster Sidekick / int_90f42a9b
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 The Wheel of Time
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Chessmaster Sidekick
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When the elf-emperor's fourth son unexpectedly ascends the throne in The Goblin Emperor, his secretary acts as this. He excels in Bothering by the Book methods and gets the most acceptable empress approved by the court due to presenting her name along with two others who will siphon support from each other and make Csethiro get the majority of the votes.
 Chessmaster Sidekick / int_9264f35d
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 The Goblin Emperor
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Chessmaster Sidekick / int_9264f35d
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Chessmaster Sidekick
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Manhattan Murder Mystery: It is only late in the film that the Lipton's recruit Marcia to help with their investigation, but as soon as they do, she quickly pieces together all of their hard-gathered clues to understand how and why the murder must have happened and also comes up with the plan about how to expose Mr. House.
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1.0
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 Manhattan Murder Mystery
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Chessmaster Sidekick
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Ouran High School Host Club: Kyouya is this for Idiot Hero Tamaki. Kyouya originally wanted nothing to do with Tamaki and his Host 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".
 Chessmaster Sidekick / int_9688ee61
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1.0
 Chessmaster Sidekick / int_9688ee61
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1.0
 Ouran High School Host Club (Manga)
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Chessmaster Sidekick / int_9688ee61
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Chessmaster Sidekick
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Star Trek: The Original Series:
This is the role Spock plays. While Kirk is shown to be a competent leader, Spock is physically stronger, more technically knowledgeable, and has telepathic abilities.
Fits even better in the Mirror Universe. 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 assassination.
 Chessmaster Sidekick / int_9a7088bc
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1.0
 Chessmaster Sidekick / int_9a7088bc
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1.0
 Star Trek: The Original Series
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Chessmaster Sidekick / int_9a7088bc
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Chessmaster Sidekick
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Appears in Pyramids, in which the Big Bad may or may not be stuck in a Stable Time Loop and has been "advisor" to the entire royal family. As in, since it was founded millennia ago.
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 Pyramids
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Chessmaster Sidekick / int_a0ff9e30
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Chessmaster Sidekick
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Interestingly, Moses serves as this in The Bible. When God first manifests in the burning bush, Moses protests that he cannot speak before Pharaoh because he is "slow of speech, and slow of tongue"—most scholars believe this is a reference to some kind of speech impediment. As such, it is actually Aaron, Moses's brother, who does all of the talking and bargaining with Pharaoh, while Moses serves as something of a sidekick (albeit one who is infused with God's power). As the story of the Golden Calf proves, Aaron was a terrible leader to the Israelites once they were free (largely because he was something of an Extreme Doormat who repeatedly bent to their will), and Moses ended up having to clean up a good deal of his messes. Most adaptations of the Exodus story ignore the "slow of speech" element, though, and simply have Moses do all of the talking as well.
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 The Bible
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Chessmaster Sidekick / int_a5549ed0
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Chessmaster Sidekick
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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.
 Chessmaster Sidekick / int_a5b8b965
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 The Iliad
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Chessmaster Sidekick
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Capt. Dudley Smith from The L.A. Quartet, and, of course, the motion picture L.A. Confidential, is both a Magnificent Bastard 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.
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 Chessmaster Sidekick / int_b4d4ecb5
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 LA Quartet
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Chessmaster Sidekick / int_b4d4ecb5
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Chessmaster Sidekick
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Troll Mountain: Ko accompanies Raf for most of his adventure. While Raf is quite clever in his own right, Ko is the one to educate him on troll customs and how to look past generalizations, and comes up with a Trojan Prisoner ploy to bring a bunch of explosives into the mountain and rescue Raf after his young friend is captured.
 Chessmaster Sidekick / int_b9534bb1
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 Chessmaster Sidekick / int_b9534bb1
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 Troll Mountain
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Chessmaster Sidekick / int_b9534bb1
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Chessmaster Sidekick
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Cornfed is this to Duckman.
 Chessmaster Sidekick / int_bb7d6a95
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 Duckman
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Chessmaster Sidekick
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In Warhammer 40,000, the High Lords of Terra are supposed to be the leaders of the Imperium of Man (since, you know, the Emperor himself is permanently enshrined on the Golden Throne). However, upon the revival of Roboute Guillemane, one of the Primarchs and a son of the Emperor, he assumes the role of commander of the Imperium's military and nominally leaves the High Lords in power rather than assume regency and take full political as well as military power.
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 Warhammer 40,000 (Tabletop Game)
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Chessmaster Sidekick / int_bcadd7cb
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Chessmaster Sidekick
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In Dragon Age: Inquisition, 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 Big Bad. The Stinger 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.
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Power Rangers Wild Force: The Duke Org Onikage is the one who allowed Viktor Adler/Master Org to get his revenge on both Mandilok and Toxica and almost Jindrax as well, all while keeping the Rangers in a stalemate they could not win before being defeated by a stroke of luck on Jindrax's part. Even though he ultimately fell, his manipulations nearly led to Master Org's victory in the finale.
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This Bites!: Jeremiah Cross, being a Self-Insert, has knowledge of the past, present, and future of the world of One Piece. And while that's his biggest asset, he's quite cunning in his own right, which leads Luffy to appoint him as the crew's tactician. Yet amidst all the plans and connections he makes, he remains as loyal to Luffy as any of the Straw Hats, with everything he does being to help his captain reach the throne.
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Child of the Storm:
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, he's an extremely powerful Seer and nigh-immortal thanks to the Time Stone. Put all that together with a genius intellect and 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 The Chosen One, but The Chooser of the One, 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.
Sinister, to anyone he works with, from Weapon X to the Red Room, since he's generally Not in This for Your Revolution. Instead, as a Mad Scientist brilliant enough to give Zola lessons and a 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, Strange figures out a way around that immunity and tracks him down...
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Legend of the Galactic Heroes:
Kircheis, and later, Hilda serve as Reinhart's Chessmaster Sidekick: both have Reinhart's trust, and both save his life Hilda manage to Out Gambit Yang, who just managed to Out Gambit Reinhart: Demonstrating that she is the smartest Chessmaster in a series full of them, way to go, Fraulein
Then, Yang is a subversion of this trope: 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.
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General Blue of Dragon Ball is shown to be this to the Red Ribbon Army and Commander Red. Blue possessed superhuman endurance, superhuman strength, possibly superhuman speed, and Psychic Powers. 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 The Dog Bites Back moment.
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Haunted Mansion (2023): Father Kent often takes a backseat to Ben and Gabbie, but he is the one who researches and recruits new members of the ghost-busting crew, plans out how to use their skills, and lures them to the mansion so that they will be cursed if they try to leave instead of help.
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In every Suikoden game, the tactician is the Chessmaster Sidekick of the Tenkai Star. In all games except the third, the hero leads the field operations while the Strategist devises the plans. In Suikoden V, if the player gives the good answers in some discussions, the Tactician will even claim that she is impressed by the intelligence and insight of the hero, which puts more emphasis on the fact that the Prince is not merely a figurehead.
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Mega Man X: The main protagonists of the franchise are this. X and Zero are more than capable of taking down some of the most ungodly-powerful foes on earth alone, and because of it are very well established in the chain of command. However, they still answer and take orders from the Maverick Hunters' supreme commander, Signas, who is said to be as good in combat as his predecessor, Sigma.
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The End of the World series by 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.
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Ibushi Arima in Cute High Earth Defense Club LOVE!, 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.
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Amphibia: King Andrias Establishing Character Moment 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 Evil Plan 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 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 Dark Secret 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 Lightning Bruiser 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 a simple accident he couldn't have predicted.
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The Mountain and the Wolf: The Wolf's sorcerer is a Tzeentchian, meaning he's always planning something that may not be in his master's best interest. The Wolf, however, is perfectly aware that he has a likely traitor work for him and freely abuses him (claiming that if he's going to be betrayed, he wants to be sure he's earned it), having some experience with backstabbing wizards.
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Barney from How I Met Your Mother, though his schemes mainly involve getting Ted (and himself) laid. It's explained as Barney already having everything he wants; he's wealthy, good-looking, and has to expend little-to-no effort in everyday life. Helping a little guy like Ted gives Barney a challenge and makes him feel like he's doing something charitable.
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In Wander over Yonder, Commander Peepers as The Dragon to Lord Hater. Due to his unimposing appearance, his galaxy-sized ambitions depend on Hater's power to intimidate, but he cares about Hater to Ignored Enamored Underling levels and considers him his best friend.
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From the Belisarius Series:
Rana Sanga is this to Damodara.
Aide is this to Belisarius.
Irene is not only Kungas' Chessmaster Sidekick she is his wife.
Belisarius himself is this to Justinian and Theodara.
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Transformers:
The Transformers: 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.
Transformers: Prime gives us Soundwave, who was essentially The Dragon to Megatron (until Dreadwing showed up). Soundwave not only keeps an eye on everything, he's also feared by almost everyone (with Airachnid learning why you shouldn't pick a fight with him), to the point where 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 Megatron in gladiatorial combat, and would have outright won if not for the fact that their duel was to first wound and not to the death.
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In Star Trek: The Next Generation, Riker is deemed more than capable of captaining a vessel (having turned down command of other starships on multiple occasions), but prefers to work under Picard on the Enterprise. Data follows Riker's example, remaining third-in-command on the Enterprise throughout the series.
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The following is a list of statements referring to the current page from other pages.

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Characters as Device
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Gambit Index
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Older Than Steam
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