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The Chessmaster
aka: Chessmaster

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"They say it's the game of kings. That chess teaches one to think strategically. What a load of rubbish! Both sides have identical pieces, the rules stay invariably the same. How does this mirror real life? ...pawns see only their comrades at their sides and their foes across the field. A king has a different view of the chessboard. His greatest foes surround him. His own chessmen might trap him. And that is check — and death. You see, witcher, chess is the art of sacrificing your own pieces. Now do you see?"
Radovid V the Stern, The Witcher 3: Wild Hunt

The Chessmaster gets their name from their ability to manipulate events (that is, they cause events to develop in the way they want in order to produce a desired result through planning them out) as if they were pieces on a chessboard. Chessmasters tug at their strings of influence, patiently move their pieces into places that often seem harmless or pointless until the trap is closed, and get unaware Unwitting Pawns (who else?) to do all the heavy lifting. The best will also have layers upon layers of misdirection and backup plans in case some unexpected hero appears to gum up the works.

Chessmasters can be on the side of good, but if so they'll almost certainly be a Pragmatic Anti-Hero at best, and a Well-Intentioned Extremist at worst, as it's very hard to plan a Chessmaster scheme that doesn't sacrifice a few pawns along the way. Heroic Chessmasters are very often introduced as a Mysterious Employer. The Svengali, in acting for the (supposed) good of his protégés, will often be this (and if he isn't, he'll pretend).

Chessmasters can occasionally or can always denoted be The Strategist, although given the volatility of war, most Strategists will only ply their schemes one campaign at a time, with an emphasis on short-term goals (and an eye towards all possible future contingencies). The Game Master may be a Chessmaster also, but many of them prefer to give their orders more directly. Many chessmasters are Villains With Good Publicity, but they can also be someone no one has ever heard of. Almost all Ancient Conspiracies are led by a collective of chessmasters, silently working toward their goals over generations. Chessmasters also tend to be overconfident and usually panic when their "perfect" plans fail — unless they just start laughing instead. This is also usually averted when Magnificent Bastard and Chessmaster overlap, since a Magnificent Bastard is quite good at rebounding from defeat. Fond of a Battle of Wits.

Of course, actual chess ability is implied, and some Chessmasters take it literally, mapping their plans out with an actual chessboard, occasionally with pieces shaped like the main characters. Don't ask how this works, or where they get pieces. This is most likely a result of Smart People Play Chess. Compare the Manipulative Bastard who tends to be more personal and controlling in her/his manipulations. Compare/contrast Opportunistic Bastard as well. Contrast Spanner in the Works, though it's possible for a character to be both of these.

Chessmasters are usually (but not always) non-physical and unsuitable for action due to age, infirm, or simply being a thinker, not a fighter.

If the chessmaster is the villain, when the hero defeats them it's usually via the one move they didn't plan for.

Not to be confused with The Chessmaster, a long-running series of chess videogames.

Examples with their own subpages:

Other examples:

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

    Professional Wrestling 
  • Puerto Rican Wrestler Ray Gonzalez's gimmick is that he's a chessmaster (and a good one at that).
  • WWE Wrestler Wade Barrett had this as his gimmick as the leader of the Power Stable called The Nexus, his "endgame" being winning the WWE Championship. He planned situations masterfully, even exploiting Invincible Hero John Cena's Honor Before Reason and Hot-Blooded nature alongside the occasional No-Holds-Barred Beatdown
  • Mick Foley of all people was revealed to be one in TNA. He worked his way silently up into the Network as an executive behind Immortal's back, using his position to make them Screwed by the Network at every turn. When he finally reveals this, they're dumbstruck because he was the last person they'd expect. On May 26th, Hogan believes he's outsmarted Foley and got the Network to give him control again during a meeting the previous week. However, while Hogan is celebrating both that and Eric destroying the X Division, Foley comes out and reveals that after Hogan left, Foley took over the meeting. The end result was the Network furious at Immortal again and giving Foley the authority to revive the X Division. He even found a loophole to give him control of the PPV because the Network funds them.
  • Triple H nicknamed himself "The Cerebral Assassin" for very good reason. He masterminded many different schemes against long-running enemies like The Rock and "Stone Cold" Steve Austin, not to mention Vince McMahon. He could almost be seen as a real life version of this, having maneuvered his way from being a mid-carder during the WWE's Audience-Alienating Era of the New Generation in the mid-1990s to one of the most powerful figures in the company, both as a wrestler and an executive.


    Tabletop Games 
  • 7th Sea has a whole team of them — Novus Ordum Mundi — and the biggest and baddest of them all is none other than Alvara Arciniega.
  • Changeling: The Lost has the Contracts of the Board, which allow the user, by utilising some form of strategic game, whether it's chess or cards or Candyland, to read opponents, send orders, and tweak fate through correspondences and the odd bit of cheating.
  • Dungeons & Dragons:
    • The yugoloths, a race of neutral evil fiends, were typically cast as executing secret, evil schemes across time and the multiverse, particularly in their most fleshed out appearances in the 2nd Edition Planescape campaign setting. In one source book, an illustration (by the impeccable hand of Tony DiTerlizzi), a pair of arcanoloths, the most Affably Evil of these fiends, are shown playing chess with pieces that resemble other races from the setting.
    • The rulebook Fiendish Codex II: Tyrants of the Nine Hells explicitly compares Asmodeus' plans to a game of chess. Supposedly his plan to topple heaven is a few centuries ahead of schedule.
    • Also, the rulebook Lords of Madness: The Book of Aberations describes mind flayers — a.k.a "illithids" — and their leaders the Elder Brains as often being this. They are manipulating politics and slowly working towards reestablishing the illithid empire that was lost long ago.
    • The Illumians, introduced in Races of Destiny, are a species of humanoids organized into cabals where they study and manipulate the world around them, ultimately hoping to accumulate enough power and knowledge to ascend to godhood.
    • Dragons play xorvintaal, the Great Game in which they use mortal servants as chess pieces to compete for each others' hoards. The game itself is far too complex for mortals to understand (a dragon that is killed as a result loses, of course, but seeing as only the most powerful dragons play it, that rarely happens), but in the small term can shape entire lives. In the long term, it shapes continentsWorld War I would have been a particularly complex xorvintaal maneuver, with World War II being a good counter-move. Just as a consequence of powerful creatures to who We Are as Mayflies getting bored.
      • An example: Dragon A uses his magic to cause a volcano to erupt, wiping out a town but forcing Dragon B to evacuate her hoard and leaving her vulnerable to attack by PC mercenaries hired by Dragon A. This would be considered a crude, noobish maneuver. A master of xorvintaal, such as Dragon C, would rush to the volcano, see a family trapped in a burning house, and use just enough magic to save the boy. Over the coming years Dragon C supports the boy as he hones his skills as an adventurer, nurturing his hatred of Dragon A until he's ready to form a party to avenge his parents, afterward continuing as a loyal supporter of Dragon C. That's a character whose entire life was played like a chess piece in a game he may never become fully aware of. And Dragon B? The mercenaries that would have attacked her were instead wiped out by a party sent by Dragon D, a young vassal of Dragon C who is now owed a favor by a powerful rival, who Dragon C only wants around as a buffer against Dragon E...
  • Exalted has the most powerful gods spending their time playing "the Games of Divinity".
    • These games explicitly don't have anything to do with manipulating anyone — that's the job of the Sidereal Exalted, who constantly act as Chessmasters to ensure Fate follows its proper course. Memetic Mutation has cast the Games of Divinity as a cosmic Xbox.
    • Meanwhile, the Deathlords are plotting and scheming against Creation (and each other), dragging the world into Oblivion one Shadowland at a time. And sometimes their grand schemes work, too: just ask the people who died of the Great Contagion.
    • 2e's Ebon Dragon, on the other hand, is playing a speed chess variant of the game, what with his new 50 Infernal pawns and his marriage to a certain prominent woman.
  • Leviathan: The Tempest: A Leviathan's divine nature is hardwired to work through minions and proxies. This is especially pronounced in Ophions, Leviathans whose divine nature has displaced their human and bestial natures. Not to mention that any Leviathan that survives long enough, and indulges the divine nature enough, to become an Ophion is going to have to be a pretty skilled manipulator and strategist.
  • Mage: The Awakening: Archmasters, being superhuman Dimensional Travelers, build cosmos-spanning networks of agents and pawns to enact their will. At a baseline, they multiply the effect of social Merits like "Allies" and "Contacts" up to tenfold, create temporary versions of those Merits on the fly by exploiting Sympathetic Magic, and retroactively prepare for difficult situations. And that's without using magic or their direct access to godlike entities beyond the physical world.
  • In the storyline of Magic: The Gathering, Urza is this. After witnessing the might and horror of Phyrexia as it slowly corrupted his brother Mishra, Urza uses his newfound nigh-godhood to concoct a 4,000 year plan to defeat the Phyrexian invasion of Dominaria. Most notable among his machinations is the creation of the Legacy, a collection of artifacts that, when fully utilized, created a burst of white mana so intense that it vaporized the demonic god of Phyrexia, Yawgmoth, along with the entire northern half of Dominaria itself.
  • In Old World of Darkness, Kindred in Vampire: The Masquerade makes this about as literal as it gets. Powerful elders are known to play chess against each other; sometimes by themselves, others by Dominating skilled chess masters to play for them. The Jyhad being what it is, few games are actually played for fun. In the more complicated games, each piece has a corresponding real world henchman, location, or valuable resource. When that piece is taken, play is halted so that the attacking player can arrange for the relevant resource to be seized. Should a player advance a pawn, he can promote it to a piece previously taken and the matching objective is restored or released. And according to Camarilla social mores, to quit or forfeit a match should the losses become too severe would result in such a massive loss of status that it becomes less painful for the loser to see it through to the end and lose his stakes rather than quit and become a laughingstock. Such games can become so complex as to be microcosms of the Jyhad and can take years, if not decades, to play out completely, moves being sent to each other through trusted agents, letter drops, burnt into the skin of the ghoul assassin you sent against him whose body is left on your doorstep, etc. Savvy characters can learn much about an elder's political situation and resources just by seeing his chessboard.
  • The rilmani, introduced in the Planescape setting, are like this on a cosmic scale. A True Neutralinvoked race that seeks to preserve what they refer to as The Balance, they make sure no side of a philosophical conflict (such as Good versus Evil, Law versus Chaos, and other minor ones) ever dominates the other. They usually don't act directly in this goal, however; usually throughout history they use disguise, subterfuge, and covert skills to infiltrate governments and empires, posing as advisors or military leaders to either help or sabotage them in order to aid whichever side of the overall conflict is losing until it evens out. They honestly believe that if there was any definite winner in any of these conflicts, the state of the universe would be broken and it wouldn't work.
    • One rilmani of note is Jemorille the Exile, the rilmani assigned to Sigil. He's supposed to be a chessmaster, but if what he says is true, all of his attempts to preserve the Balance have caused Epic Fails, causing disasters and cataclysms. (For example, he claims he taught the halfling Rajaat magic, which if true, means he's indirectly responsible for Athas becoming the place it is today, although he insists it wasn't his fault. He was assigned to Sigil because the other rilmani thought that would be an easy job, but he even managed to mess that up, starting the chain of events that led to the Faction War.
  • Traveller: Cleon Zhunastu, founder of the Third Imperium, manipulated thousands of planets and countless individuals into forming an empire that stood for over a thousand years. The Hivers are arguably an entire race of these, "Manipulator" is a title they all strive to achieve, though many of their manipulations seem benevolent.
  • Warhammer:
    • The Chaos entity Tzeentch is the god of Chessmasters. His followers commonly favour such tactics, but considering that Tzeentch tends to use them as his own pawns in his own schemes, which are both plentiful and occasionally contradicting, it all just comes back to him eventually. It's rumored that Tzeentch is the only force stopping the Immaterium and universe from merging as part of an elaborate plan roughly forty-six thousand years in the making.
    • Warhammer 40,000:
      • Eldar Farseers use their prescient abilities to manipulate galactic events in their favor.
      • Chaos Space Marines of the Alpha Legion are renowned for using sabotage, propaganda, and infiltration when their colleagues would just charge in with weapons blazing.
      • The Emperor is hinted to have anticipated the Heresy, and also to be planning to be reborn when his physical form dies (which may well be soon).
      • Asdrubael Vect is the guy in charge of the largest Dark Eldar kabal in the galaxy, but he actually started out as a lowly slave. How did he manage to do it? He manipulated and backstabbed thousands, including one of his own consorts Aurelia Malys, to climb his way up into a position of power as a lowly Archon of a lowly kabal, the Kabal of the Black Heart, then he set his plan in motion. First, he focused his piracy efforts in one part of space known as the Desaderian Gulf, simultaneously adding to his wealth and power while also provoking the Imperium. Eventually, the Imperium sent a Space Marine cruiser, the Forgehammer to investigate, which he ordered crippled with haywire bombs and transported to Commorragh. Vect then manipulated rival Archon Xelion into trying to claim the contents of the Forgehammer for himself, knowing that his forces would be woefully under-equipped to take on the Space Marines waiting inside. Vect also allowed a Librarian on board to send a psychic beacon, attracting a huge Space Marine force to reclaim the cruiser. During the following battle between Dark Eldar and Space Marine forces which razed most of upper Commorragh and caused ridiculous casualties on both sides, Vect manipulated battlefield communications, battle strategies and reinforcement allocations in such a way that the city would defeat the Space Marine attackers and also leave the leadership of every single noble house and major kabal in Commorragh dead. This created a power vacuum and left Vect's kabal the most powerful in Commorragh, allowing him to easily seize de facto rule over the entire dark city. Just as Planned.
      • In Liber Xenologica, zoats are described as subtle beings who manipulate other societies from behind the scenes, enacting complex schemes and seeding double and secret agents in order to guide worlds towards goals only they understand.

  • Lucy is this in 13. She tells Kendra she shouldn't kiss Brett because she's a good girl. Then all she has to do is turn Brett's head for an Accidental Kiss between Brett and Archie then when Evan reunites Brett and Kendra Lucy starts a rumor about Kendra and Evan.
  • Molokov and Walter are tag-team Chessmasters who play the protagonists against each other for political purposes in the musical Chess. Ironically, they are the only prominent characters who don't play chess in the show, and the ones they manipulate, are international chess grandmasters.
  • Prince Hal in Henry IV, Part 1 monologues about how he's using his time drinking, whoring and stealing with the lowest of ruffians as part of a public image long game. He's manipulating perceptions and expectations of him so that when he becomes the glorious, reformed king he knows he will be, it will appear that he has risen even higher by starting so very low. He plays everyone, from the Eastcheap rascals to his father the king. It's up to interpretation whether this makes him super cool or a total bastard.
  • Edmund, Regan, and Goneril from Shakespeare's King Lear. They all fully take advantage of their fathers' weaknesses.
  • Oberon from A Midsummer Night's Dream. He had only planned on a few simple maneuvers, but things get complicated when you let Puck handle the Applied Phlebotinum.
  • Iago from Othello plays off of Barbantio's racism, Othello's jealousy and distrust in Desdemona, and Roderigo's love for Desdemona all to destroy a man he hates — but for whom he has no good reason to hate.
    • In the Oliver Parker film adaptation, Iago (played by Kenneth Branagh) illustrates his plan with an actual chessboard.
    • Interestingly enough, Iago is actually a failed Chessmaster — he allows his own personal hatred (and thus contempt) for Othello and women to screw up his plans — for instance, getting Emillia to steal the handkerchief but then thinking he can keep her quiet simply by ordering her to. An example of a chessmaster who really does win is Caesar from Antony and Cleopatra.
  • The Phantom of the Opera is initially the Chessmaster until the part where Christine rips his mask off and the theatre burns down. He even has a model of Il Muto where the characters have interchangeable heads to help him in his plans.
  • In Pokémon Live!, Giovanni orchestrates the entire plot and manipulates just about everyone.
  • In the musical Rudolf — Affaire Mayerling, the Classic Villain Graf Taaffe is playing chess throughout the story, sets The Hero Rudolf Checkmate during a song with Rudolf's lover Mary Vetsera and is actually revealed to be the one behind everything by having everyone including Rudolf's father Franz Joseph be his pawns.

    Web Animation 
  • Dreamscape: Melinda's plan in breaking her seal involves parallel universes and using another Sealed Evil in a Can to manipulate her former apprentice into nearly breaking that evil out! It only went awry because of an "I Know You're in There Somewhere" Fight. In "Confronting the Dark", Melissa even lists cunning, manipulation, and trickery as Melinda's biggest qualities.
  • Andross qualifies as this in Gaming All-Stars: The Ultimate Crossover and Remastered. While the remainder of the villains capture other characters as trophies and attempt to establish themselves at the top of the barrel, this character waits in outer space, planning for one of those worthless baddies to force the moon to plummet toward the Earth and allow him to unleash titans that had been contained inside of it. While doing so, he makes arrangements with Polygon Man to lure the main antagonist/s (Eggman, G-Man, and Cortex in The Ultimate Crossover, Radec in Remastered) by having PM claim that he’ll provide them a boost of power to help them kill the heroes if they meet within inside the moon. Once Polygon Man takes care of them/him, Andross finally reveals himself and manages to kill nearly every hero standing against him. However, his plan comes undone when Master and Crazy Hand break free from Polygon Man's hypnosis, summoning a subspace bomb to destroy the moon and undo the chaos Andross had orchestrated.
  • Inanimate Insanity has Steve Cobs, who has managed to control Me Phone 4’s every action in some way.
  • The Most Popular Girls in School:
    • Mackenzie Zales, as shown in Episode 57 when she reveals her plan on how she got Jenna Darabond arrested.
    • Jenna Darabond herself was pretty manipulative, as the start of Season 3 reveals she was behind everything of the last two seasons.
  • Malcom Hargrove from Red vs. Blue has been manipulating the Chorus Civil War from the start knowing that nuking Chorus from orbit would attract attention, so he makes sure all the inhabitants kill each other in order to prevent any suspicion. Hiring mercenaries Felix and Locus' infiltrate both sides, and plans to exterminate the whole planet for profit. He is also the reason the Reds and Blues crashed on Chorus in the first place and why they haven't found rescue in Season 11.
  • RWBY:
    • The Big Bad Salem's entire methodology revolves around careful manipulation, using pawns to covertly act and cause destruction and chaos, while leaving her motives and even existence nearly impossible to determine. As a result, humans tend to blame each other for her manipulations, and Salem herself outright says that she divides and breaks apart humanity to weaken them.
    • Her subordinate Cinder Fall is carrying out her long-running plan, which endangers Remnant. Her mission is to obtain the Fall Maiden's powers and bring down Beacon. She predicts most of the cast's moves and adapts with great flexibility when something occurs that hasn't been accounted for. She recruits Mercury and Emerald, saps half the Fall Maiden's powers, recruits Torchwick and the White Fang, then commands Dust robberies and infiltrates Beacon. From there, she takes control of almost every defense available through the CCT Tower, including the Vytal Tournament match-ups and Penny. At the end of Volume 3, she succeeds in her mission, although she is badly injured in the process. Four volumes later, she deliberately presses Ironwood's Trauma Button by leaving a glass chess piece in his office; attempting to secure the Winter Maiden's powers inadvertently leads him to reveal her secret location to her.


    Web Videos 


With Chess Motifs

  • Roodaka of BIONICLE describes how she has "spun a web" in one issue where she speaks to a Visorak underling, complete with a board of miniature figurines of the heroes and villains. While it's not actually a chess board but an alt-universe equivalent, the chess motifs are still there.

Without Chess Motifs

  • Makuta (Teridax, specifically) in BIONICLE: As he tells one of the heroes in one of the novels: "Even my...setbacks have been planned for." Turns out he's right....
  • A list of tongue-in-cheek predictions for 2010 included the revelation that Taylor Swift has been moonlighting as a Chessmaster-for-hire, having orchestrated not only Kanye West's outburst at the 2009 MTV Video Music Awards, but other celebrity scandals.

Alternative Title(s): Chessmaster


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