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The Chessmaster / Live-Action TV

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Chessmasters in live-action TV.

Examples With Chess Motifs

  • Alcatraz villain Garrett Stillman is an expert at convoluted heists which rely on manipulating others, and was shown discussing chess techniques as a metaphor.
  • The appropriately named villain Chess in The Cape.
  • Gideon from Charmed (1998) relies on the strategy of the Chessmaster, and has forged an alliance with the evil version of himself from the Mirror Universe. There's even a scene in which the two versions of Gideon are talking strategy over a game of chess.
  • Colditz: In the second series, Carter and Mohn begin to taunt each other with chess metaphors once the two establish their enmity. When Carter becomes the new Escape Officer, he makes it clear that he intends to win his game of chess against Mohn, and indeed spars with him across the board literally on multiple occasions, parlaying Mohn's exemplary chess advice into both his game and his schemes. In this role, Carter is also significantly more of a Chessmaster than his predecessor, cooking up deliberately obtuse schemes with limited initial payoff (and even putting lives in danger) with grand long-term plans in mind. As Carter becomes a more proficient escape officer, he also improves at the chessboard.
  • Considering Columbo has been often refered to as a verbal chess match between Columbo and the murderer of the week, it only makes since that he face down an actual Chessmaster at least once in the series run. The second season episode, "The Most Dangerous Match" features a grand master of chess, played by Laurence Harvey, who kills his rival after realizing he has no chance of beating him in an upcoming world championship match.
  • Doctor Who:
    • Sylvester McCoy's Seventh Doctor. The chess metaphor is part of a Story Arc; it first appears in "Silver Nemesis", when he moves the pieces on Lady Peinforte's board; in "The Curse of Fenric", this is revealed to be how he knew fellow Chessmaster Fenric was the force behind it all. Played with in "Battlefield", when Morgan La Fey taunts "I could always beat you at chess, Merlin" and he retorts "Who said anything about chess? I'm playing poker. And I have an Ace up my sleeve!"
    • In "The Wedding of River Song", the Eleventh Doctor plays live chess, in which pieces are electrified, with Gantok to gain information about the Silence.
    • In "Nightmare in Silver", the Cyber Planner is attempting to take control of the Eleventh Doctor, the mental battle is externalized in the form of a chess game while they're also trying to guide the Cybermen and an Imperial Guard unit currently fighting over the planet. Eventually the Doctor claims mate in three moves and the Cyber Planner unintentionally devotes the processing power of all the Cybermen to figuring out how, which disables them long enough for the Doctor to break free and then evacuate all the humans before the planet is blown up.
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  • Literal example in former World Chess Champion Arkady Balagan in Endgame. He uses his talents to solve crimes.
  • Played completely straight with D. Gibbons in Flash Forward, who is mentioned as having become a grandmaster at the age of fifteen. Although he appears to have been out-Chessmastered by an as-yet-unidentified faction of villains, it's worth noting that he knew that he would probably die and likely made plans for the event of his death.
  • In Heroes Sylar manipulates Danko into cooperating with him while toying with the pieces on a chessboard.
  • Malachi of Hex, which should be expected since he is more or less the Antichrist. He gains power over people by tempting them with their deepest desires. This leads some characters to believe they will be fine if they just resist when he tempts him, but unfortunately many people don't even understand what their own desires actually are, nor do they realize when it was Malachi who arranged the opportunities for them to follow them. A couple characters went down because they were actually giving into their desires when they thought they were fighting them.
  • On Law & Order: Criminal Intent Nicole Wallace plays all sides, steals identities and acts as a recurring archenemy of detective Robert Goren. On top of that she manages to escape from justice multiple times.
  • In Leverage, Nate Ford is often referred to as a Black King and in the first episode as a white knight. Hardison comments he often plays online chess and in the episode "Juror #6" he and a opposite Chessmaster both use chess metaphors, an actual chess board and when he wins, he throws her a piece (presumably the king).
    • He also enters a chess tournament as part of a heist and beats two grandmasters in the process.
  • In The Messengers the Devil plays chess with a gambling man to start a chain of events intended to lead to the breaking of a seal.
  • One of Monk's suspects in Monk, who is an actual chessmaster (a Grand Master, in fact). He uses chess metaphors to taunt Monk about the exact method he used to murder his wife and get away with it. Most notably, he mentions the "Poisoned Pawn" (a name for a particular chess opening) move in which he fooled his second wife into poisoning herself, and Monk's attempt to find the answer buys him enough time to cremate the body in the event that Monk does find out the chess opening. In fact, his actions, and Monk's irritation towards not being to figure out how to nail him, actually caused Monk to nearly cross the line by planting evidence to get him arrested. Monk then gains inspiration from the tactic of swapping the positions of the king and rook to figure out that the suspect had changed the headstone of his first wife in order to prevent the body from being exhumed.
    • After this, Monk then begins to tell off the chessmaster about how it is such poor form to use chess terms when you're talking about people, ending it with "but if you insist... checkmate."
  • Bobby Newport's campaign manager Jennifer Barkley on Parks and Recreation, to the point that she gets bored with the lack of challenge and actually gives her opponent advice to make the "chess game" more challenging for herself.
  • Person of Interest: In one episode, Elias plays a chess game with Finch. In fact in one episode the team needed to Deal with the Devil with him. His wish afterwards? To have Finch come and play chess with him on a regular basis.
    • While training the Machine (in a flashback) in the intricacies of chess, Finch gives a resounding denouncement of the Chessmaster concept, and instructs the Machine to not regard people as unequal, disposable chess pieces.
  • In Power Rangers in Space, Astronema is very much the chessmaster. While she doesn't have an actual chessboard, she does have figurines of the rangers on a mat. She also tends to think her plans through very well.
  • The Queen's Gambit has several literal examples. The heroine Beth is more of an intuitive player, working out her moves as she goes, but she faces the Russian Borgov, who plans methodically and in advance. As Beth plays more difficult opponents, including Borgov, she studies more and plans more, with the help of her chess mentors.
  • In Robin Hood, the Sheriff of Nottingham once gave Guy of Gisborne orders while sitting behind a chess board. And then threw one of the pieces at him.
  • "Absolute Justice" from Smallville features the secret agency Checkmate, with the Chessmaster in question being Amanda Waller, orchestrating a series of murders and news leaks in order to get the older generation of superheroes in the Justice Society of America motivated to get active again, and inspire the new generation of heroes, because the planet will need its heroes in a coming apocalypse.
  • Windom Earle of Twin Peaks is in an ongoing chess game with Coop. Every time Coop loses a piece, Earle kills someone.
  • The Governor from The Walking Dead. Although he's been a Manipulative Bastard since before his first appearance, this goes full chess-metaphor after the fall of Woodbury, when he meets a fatherless family with a little girl and teaches her to play chess. Their conversations reveal how much of a Chessmaster the Governor really is, and the girl paints an eyepatch on the white king to make him look like the Governor. In a later episode, this chess piece is seen falling to the ground and being stepped on as the Governor dies.
  • Warehouse 13 has Artie. There is a chessboard just outside the office: he's been playing the same game for months against himself. Good thing he's using these powers for good instead of evil. Hopefully.
    • When Myka gets trapped in Lewis Carrol's Mirror, she makes reference to Artie's Chessmaster tendencies, calling themselves chesspieces on his chessboard.
  • Joan Ferguson of Wentworth spends whole seasons crafting elaborate plots and most of them being largely successful. In season 5, she is often seen playing chess and eventually comes to carry around one of the pieces with her around the prison.

Examples Without Chess Motifs

  • Molly Hardy, in The Adventures of Shirley Holmes. Many of her plots involve blackmailing, buying and manipulating other people, or using their circumstances to her advantage.
  • The Shadows and the Vorlons in Babylon 5 are two entire races of Chessmasters. Londo Mollari also has some serious game.
  • Genseric, King of the Vandals as portrayed on The History Channel in Barbarians Rising. Rather than being a military commander or guerrilla leader like the other barbarian characters, he excels in statecraft, playing the Western Roman Empire's courtiers off against each other and Attila the Hun against them, then sweeps in for the kill and sacks Rome himself.
  • Number One/Brother Cavil/John in Battlestar Galactica is ultimately revealed to be the mastermind behind "the Plan" that encompassed the near-annihilation of the human race and the subsequent pursuit of the survivors halfway across the galaxy for the next five years. The point of this plan? To prove to Ellen Tigh that humans suck.
  • Gotham: Penguin is a definitely this; in the very first season he is able to rise from being a nobody umbrella carrier, to overthrowing 3 crime families and becoming the defacto leader Gotham's underworld purely by using his ability to manipulate people.
    • In later seasons, several of the other villains qualify, including the Riddler, Jerome Valeska and Jeremiah Valeska:
      • The Riddler/Ed Nygma successfully plans a complicated series of events in order to set Jim Gordon up for murder, and although this eventually backfires on him, the plan succeeds for long enough that Jim has to spend some time in prison, where he barely escapes with his life.
      • Jerome Valeska, though he starts out as someone who likes to cause chaos just because he can, is even more terrifying when he uses the full extent of his planning abilities. He spends his entire second stay in Arkham Asylum planning both his escape, and an elaborate scheme that involves driving the citizens of Gotham just as mad as he is and getting revenge on his family for years of mistreatment. Only the latter half of his plan succeeds; specifically, he kills his abusive uncle, and drives his brother Jeremiah mad with Joker toxin, turning him into the show's true version of the Joker. He orchestrated nearly all of the significant events in those episodes, including his own death.
      • Jeremiah Valeska is even more of a chessmaster than his brother. He is such an intricate planner that the fact that more people don't die due to his plans is usually due to sheer luck. Even lampshaded by him in the last episode of season four, when he is trying to convince Gordon that he has additional bombs hidden throughout the city:
    Jeremiah: As an engineer, you expect systems to fail, so you build in redundancies. I am a very good engineer.
  • Blake's 7. This is the job of the 'psychostrategist', a Federation officer whose role is to predict and manipulate people. Unfortunately he's informed too late about a random element and, realising his plan will therefore collapse, smartly decides to vanish before Servalan finds out. Servalan, a bit of a Manipulative Bastard herself, seems amused rather than incensed over his cunning.
    • And the Puppeteer in question, Carnell, is also very good at chess.
      Carnell: I'm very good, Supreme Commander, believe me. I've taken everyone and everything into consideration. It's all as predictable as... that very expensive chess machine.
  • In later seasons of Breaking Bad Walter White becomes a Chessmaster, manipulating Jesse into killing Gustavo Fring by poisoning Brock, the 9 year old son of Jesse's girlfriend, and making him believe that it was Gus who poisoned him.
  • Day Break (2006): Barry Colburn has been running a city-wide conspiracy along with other corrupt officials for decades, had Hopper framed through his front-men for Garza's murder and then acted as his attorney, and even the dismantlement of his organization just results in him choosing to cut his losses, while remaining a free man protected from any and all prosecution and never even having been a suspect.
  • Doctor Who:
    • The Doctor themself is a Chessmaster, though some incarnations more than others and they often Obfuscate Stupidity.
    • The High Council of Time Lords would often function as this. They openly forbid interference in the affairs of other planets, but secretly use people like the Doctor or the Master as pawns to further their own interests.
  • Adelle DeWitt of Dollhouse, especially if you believe the Wild Mass Guessing that "speaks-through-Echo" was a deliberate false mole to manipulate Ballard into leaving the FBI and "letting the Dollhouse win" to get him off their backs and feed him whatever information they wanted to.
  • The Flash:
    • Eobard Thawne in season 1 —- pretending to be another person and the ally of your enemy for over a decade takes some real chessmaster dedication
    • Also Leonard Snart/Captain Cold. In his first appearance, "Going Rogue", we see that he methodically plans his heists down to the second. He's only thrown off by the intervention of the Flash, who existence is only an Urban Legend at this point, so something Snart couldn't have planned for. Snart then adapts his game plan, obtaining a Cold Gun to negate the Flash's Super Speed.
  • Game of Thrones:
    • Varys, the enigmatic Master of Whisperers.
    • Littlefinger, who has engineered the entire War of the Five Kings for his own ends.
  • Linderman of Heroes seems to have his hooks in everything, especially DL and Niki. His apparent omniscience is helped along by being a collector of art... particularly art made by a guy who paints the future.
    • Rebel/Micah is showing signs of this. He certainly prefers to operate by proxy given that he's a 12-year-old kid with no combat powers. He's a Technopath, which enables him to covertly communicate with his "pieces" and listen in on government communications. However, he hasn't done much in the way of manipulation - he prefers to give direct instructions, and his plans tend to be short term. Then again, you don't need to be much of a chessmaster to outsmart the federal government.
  • Silas Blisset from Hollyoaks of all shows. "You'd better raise your game or I may grow weary of such a dull opponent."
  • On the subject of Chessmasters using their powers for good... sorta... Mickey from Hustle is a pretty good example. For example, he (at the time of writing) stole from a corrupt banker turned financial consultant and, when arrested, bluffed his way out of it by pretending he'd actually been consulting him on pension schemes - vindicated when the briefcase full of money was opened to show... pension plan leaflets. He does similarly every episode.
  • Clayton Webb in JAG. A cold blooded CIA officer who is skilled and subtle in manipulating operations all over the world.
  • Joy of Life is a show filled with chessmasters (special mention to the main character, Fan Xian, Chen Pingping, and the emperor, leading to lots of Gambit Pileups.
    • Li Yunrui and Li Chengze from the royal family, and Shen Zhong from Northern Qi aren't shabby at this either.
  • In Justified, Limehouse is constantly manipulating the various criminals and other violent elements in Harlan County to keep his own community safe.
  • Kamen Rider
    • Kamen Rider Ryuki has Shiro Kanzaki, who orchestrated the Rider War and rigged it to ensure his chosen candidate of Kamen Rider Odin would win so he could use the wish to save his sister from dying. He's aided by the fact that, whenever the war reaches an unfavorable outcome, he can just rewind time and try again. Unfortunately for him, no matter how carefully he plans and no matter how many times he resets, he soon finds that there are some things he can't change, leading him to accept that his sister's death is inevitable and put an end to the Rider War.
    • Kamen Rider Gaim has several contributing to its Gambit Pileup.
      • Ryoma Sengoku controls the flow of information to his boss Takatora Kureshima to effectively usurp his place as head of Yggdrasill and manipulates everyone, including both the heroes and his own allies, towards his goal of achieving the Golden Fruit and using it to become a god.
      • Redyue of the Overlord Inves is another example and is effectively Ryoma's counterpart among the Overlords, as she was responsible for instigating the Overlords' invasion of Zawame City and plans behind her superior Rosyuo's back to steal her species' Golden Fruit from him.
      • Mitsuzane Kureshima tries his best at being this, but while he certainly isn't stupid, he ends up finding himself being used by either one of the former two.
      • Ultimately, the series' biggest Chessmaster would have to be DJ Sagara, a radio host in charge of Yggdrasil's Propaganda Machine who is actually the living embodiment of Helheim Forest. Nearly everyone, including the aforementioned three, were all pawns in his master plan to select an inheritor of the Golden Fruit to become Helheim's new Man of the Beginning.
    • Kamen Rider Drive has the Freeze Roidmude, who works behind the scenes in his guise as Japan's Secretary of Defense to cover up the Roidmudes' existence.
    • Kamen Rider Ex-Aid has several, but on top of all of them is Masamune Dan, who orchestrated a pretty impressive Gambit Roulette that involved getting himself sent to prison for a crime he didn't do all to absolve himself of the future crimes his son and Parado would commit and make himself seem like the innocent victim of a Frame-Up. Once he's let Kuroto and Parado finish Kamen Rider Chronicle for him, he waltzes in, reclaims his company and takes control of the game.
    • Kamen Rider Build definitely has one of the franchise's most devious manipulators in Evolt/Blood Stalk, who orchestrated a gambit spanning over a decade that involved using pretty much everyone in the show as his Unwitting Pawns to reopen Pandora's Box. Every small thing that happens is part of his carefully crafted Evil Plan to raise the Hazard Levels of the Kamen Riders so he can possess them and use them to level up to the point where can activate the Hazard Trigger and regain his full power. On the other side, Sento Kiryu can be seen as a heroic version of this, which given who he's going up against is kind of a necessity as, if not for his quick thinking, the villains would have achieved their goals a lot sooner. In fact, by the end, he manages to turn Evolt into his pawn by using him in his plan to undo all the damage Evolt caused.
    • Kamen Rider Zi-O has Swartz, leader of the Time Jackers, who secretly manipulated Sougo Tokiwa into becoming Oma Zi-O. While his comrades believe they are creating the Another Riders to find a candidate to replace Sougo as Oma Zi-O, they're really being used by Swartz to keep Sougo on the path to become the Demon King. By the end of the show, Swartz is able to arrange a scenario where all of the outcomes are favorable to him - either he claims the power of Oma Zi-O for himself or Oma Zi-O ascends as his Puppet King, allowing him to repeat the events of the series by having Tsukuyomi and Geiz go back in time until he achieves his desired outcome. It's only when the power of Oma Zi-O proves too powerful that Swartz is finally defeated, but even then the post-series V-Cinema shows that Swartz was able to evade punishment in the new timeline created following his defeat.
  • Benjamin Linus from Lost has pulled off at least one Gambit Roulette, as well as quite a few plans that are so roundabout and convoluted one has to wonder if he's actually omniscient. Case in point, in the season 3 finale, he gave advance orders to some of his men to pretend to shoot their captives over an intercom so that he could manipulate Jack, knowing that Jack would assume Ben was bluffing, and having to survive with the guilt of killing three people by not giving into Ben's demands.
    • Ben Linus also fits in the Manipulative Bastard trope, seeing as most of his schemes have to do with toying with people's emotions.
    • Ben always has a plan, but his plan pales in comparison to that of Jacob's Enemy, The Man In Black. As of the Season 5 finale, we know that The Man In Black is the true Chessmaster of Lost. The guy's scheme includes everything in Ben's plans, plus some extra behind-the-scenes manipulation of both Locke and Ben to get them in position to execute The Man In Black's master plan.
      • The Man In Black may be the show's master in terms of raw skill and speed. In The Candidate, we see him discover one of his enemies's plots to kill him, subvert it and then with only minutes to spare rebuild a bomb that was intended for him into a device that appears active but will only actually activate when someone tries to disarm it, get the main characters he needs to kill to go where he wants them to, slips the bomb into one of their backpacks, and then relies on the fact he knows they will double cross him to keep him clear of the trap he's just set up. The end result: three main characters die at the hands of a master Xanatos Speed Chess player.
    • According to Jacob's enemy, Jacob has manipulated the main characters' lives so that they would get on Ocean 815 and crash on the island. He proves this by showing several familiar names written on on a wall in a cliffside cave.
  • Million Yen Women: The person who sent the invitations for the women to come live with Shin, once revealed, turns out to be behind quite a few of the story's major events.
  • Once Upon a Time: Mr. Gold/Rumpelstiltskin. It seems that everything in the show was done by him.
    Regina (The Evil Queen): I assume this was all your doing.
    Gold: Most things are.
    • Pretty much every arc villain is a chessmaster in their own right. Pan and Season 1 Regina especially come to mind. Mayor Regina had the entire town under her thumb, and consistently played Emma into her hands over and over to get her to be run out of town, even managing to make an iron-clad frame job against Mary-Margret.
  • The Outer Limits (1995): In "Better Luck Next Time", the Energy Beings in the bodies of Gerard and Kimble set up the events of several previous episodes ("Living Hell", "A Stitch in Time", "Heart's Desire" and "Ripper") for no reason other than their own amusement.
  • Michael Scofield from Prison Break is a chessmaster on par with people like Light Yagami. You can be sure that, no matter how short the time is or how hard the creation of a plan is, he will come up with something. And if his plan fails he will have a backup-plan or it was supposed to fail all along. Adding to that, he's sometimes Crazy-Prepared.
  • In Resurrection Ertugrul, this is the schtick of some of the major antagonists, such as:
    • Kurdoglu Bey, the envious younger brother of Suleyman Shah. First, he forges a secret alliance with Karatoygar to receive some weapons that he needs in order to stage a rebellion against his brother. Then, just after his lackey Baybora stages a protest against Ertugrul, he offs him so as to scrub any connection that the men had with one another. Then, once the Kayis settle into a patch of land given to them by Emir Al-Aziz, he orders an alp to attack his brother, then shoots him with an arrow so as to make himself appear heroic to the clan. Then, he sends his other goon Alpargu to attack Gokce (Thinking that the man approaching her is Kurdoglu), then have Ertugrul kill him in order for them to not realize that the mastermind himself is still well and alive. He also agrees to help the Knights Templar by using the now-drugged Turgut as his top soldier in his path to taking over the tribe, only becoming blatant to the others after he takes the marquee by force.
    • Ural Bey, whose jealousy toward Ertugrul kickstarts much of his villainy and initially makes his guilt appear obvious in the eyes of his kin. However, he manages to turn the tables against Ertugrul, first by hiring Francisco to kill the women and children of his tribe, then killing Francisco himself to hide the relationship between the two men, then gains the favor of his father and sister after the latter have a falling out with Ertugrul and Aliyar. Only until the last few episodes of season 3 does Ertugrul finally defeat Ural and his followers.
    • Commander Dragos in season 5. He passes himself off as a bell ringer and assigns his disciples to pose as merchants in Sogut (And in Lais’ case, as a right-hand man for Tekfur Yannis) so no one would easily identify them before they become powerful enough to make an meaningful impact. He also murders Umur Bey as part of an attempt to frame Gunduz not because he holds a personal grudge against Gunduz, but merely so that it would benefit Dragos’ cause. Even after the Kayis finally expose him, he resorts to escaping from the city as an upper-class merchant, then gathering his men and slaughter its whole population so no one would remember how they might have risen to power.
    • Emir Sadettin Kopek should not be forgotten. First, in season 2, he sends Gumustekin to falsely accuse Ertugrul of a crime. Then, he personally stops by to release Noyan from his execution, knowing full well the extent of the casualties that would result from his freedom. The following two seasons, he arranges legal deals with Ural, Simon, Vasilius, and Ares, poisons the Sultan, and prompts Alaeddin to frame Emir Nizamettin and try cutting ties between him and Ertugrul as a result of the latter suspecting Sadettin of being the guilty party. When that comes to pass, he injects another poison into a roast pheasant, this time proving fatal, and succeeds in convincing Giyaseddin (The to-be sultan) to incarcerate Ertugrul since he was the only other person present at the sultan’s final meal.

  • The Shadow Line has several:
    • Gatehouse, who's very skilled at planning events in his favour, to the point where the BBC website actually calls him a puppetmaster. Indeed, it's his skill at this that ensures his ultimate victory.
    • Glickman, who actually manages to out-plan Gatehouse in his first appearance and ultimately proves at least as good at planning as Gatehouse.
    • Joseph Bede, who, while not as good at it as the two above, successfully manages to dupe Customs into looking the other way while he carries out his deal.
  • Sherlock: Moriarty and Mycroft both. Possibly Irene.
    • Moriarty exploits what matters most to people to get whatever he wants - which, often, is just to prove that he can do whatever he wants. He even drives Sherlock to suicide by framing him for kidnapping and threatening to kill John. He manages to ruin Sherlock's reputation by convincing everyone that Sherlock's a fraud, which they want to believe anyway because of Sherlock's annoying personality.
    • Mycroft even admits to having more-or-less-intentionally driven Sherlock into harm's way as a result of a failed attempt to win his (metaphorical) chess game with Moriarty.
    • Irene fakes her death twice, in part to mess with Sherlock's head. Her fatal flaw is that she lets her heart rule her head, and actually is in love with Sherlock.
  • On Smallville, Lex has used the quote at least once to describe the comparison of his scheming to that of his Magnificent Bastard father. Then there's Brainiac who usually sets his plans in motion months in advance, and Waller of the appropriately named Checkmate.
  • In Sneaky Pete, Marius makes a living by manipulating people into furthering his goals through subtlety and deception. It doesn't always work, though.
  • Zora, from Sonny with a Chance does this once in the episode where she makes Chad believe he's the host of a TV program that plays pranks on celebrity stars. After she has all the characters together, she herself explained that she was manipulating everyone around the whole time, as she is the true host of the program and their true victim was Chad himself from the beginning. Then they stick Chad's feet on the floor, his face on the window and they spill manure over his new car. Chad was not happy. Played for Laughs.
  • Captain Benjamin Sisko manages to be one on Star Trek: Deep Space Nine, episode "In the Pale Moonlight". In truth, he asks for Garak's help, who, in the end, proves to be the real chessmaster.
  • Seska on Star Trek: Voyager. (Especially when she showed up to torment the crew three years after her death.)
  • Ruby in Supernatural. Though there is always suspicion amongst the rest of the characters that she is playing Sam, the enormous scale of her plans aren't revealed until Sam kills Lilith and it is revealed that Lilith was the last seal all along, and Ruby has been working towards Lucifer's release since the very beginning.
  • John Connor of Terminator: The Sarah Connor Chronicles. Specifically, John Connor from the future, where one of the resistance fighters even comments on "his chess game with Skynet." Current John Connor seems to be headed that way, too.
  • Katherine Pierce in The Vampire Diaries. If everyone just accepted that she is always playing them no matter how vulnerable or uncertain she seems, then it probably wouldn't change the actual outcome, but they wouldn't waste time and energy trying to beat her at her own game.
  • Veronica Mars:
    • Veronica pulls off several of these to catch criminals. The plan she uses to allow Duncan to escape the USA with his child crosses into roulette territory.
    • There's also the epic scheming of Cassidy Casablancas. Not only did he kill a dozen people, keep any attention off him for months, manipulate and blackmail his way through the stock market, he's also the only person I can ever remember lying to Veronica's face and not having her suspect at all. And he's just 16. He's good dammit.
  • In Watchmen (2019), Lady Trieu has been manipulating the Seventh Kavalry the whole time, allowing them to do the dirty work of building the materials necessary to capture Doctor Manhattan and steal his powers.
  • CJ Cregg, press secretary on The West Wing, manages to manipulate both the press and the House of Representatives into making the HR be the one handling the investigation of the president, instead of the Special Prosecutor, because she feels they'll bungle it. And she does it entirely by complimenting the Special Prosecutor and talking up his credentials too!
  • Stringer Bell of The Wire is a cunning and ruthless player in Baltimore's drug game who manipulates and betrays those around him to advance his own goals. That said, he's not quite as good at it as he thinks, and is eventually conned out of a lot of money by the even more shrewd Clay Davis. His plan to set Omar Little and Brother Mouzone against each other backfires on him fatally.
    • Stringer has more flash, but he can't hold a candle to Prop Joe who is the actually the one who came up with the idea of putting Omar on Mouzone, but was smart enough to route the plan through Stringer, and thus avoided all of the blowback. When we first meet Joe, plays Avon and Stringer by getting them to double-down on their basketball bet (by holding back a ringer on his team). Later, runs a fairly brilliant gambit to bring Marlo into the co-op (earning himself a nice little payday in the process). Ultimately, he was too slow in getting out of Marlo's way, but unlike Stringer, he saw his doom coming and managed to die with some dignity.
    • Lester Freamon also deserves a mention. Lester, like any good chessmaster, understands that "all of the pieces matter" (as he tells Prez). Though he's obviously a part of a team effort, Freamon plays a huge role in bringing in the victories for his side; like Jimmy and Kima, he contributes good detective work, but beyond that his big picture view, political savvy, and capacity for deception and subtle manipulation (sometimes of his allies and coworkers) are what really allow his investigations to (sometimes) break through the wall; there's a reason why Daniels says to Lester, "as far as I'm concerned, you ARE the Major Crimes Unit."
    • Interestingly, when the trope is made explicit by D'Angelo, he, unlike many others who talk about chess metaphors, does not believe he is a Chessmaster. He is fully aware that he is only a pawn, and his growing bitterness with this role, and the callous actions of the "kings" and "queens," fuels much of his growth as a character.
  • Sir Humphrey Appleby in Yes, Minister and Yes, Prime Minister pulls off several devious yet intricately devised gambits designed to flummox the far-less intellectually cunning (Prime) Minister Jim Hacker, in order to thwart Hacker's agenda, cement his power and influence over the department and government, and to feather his own nest. However, Hacker - whilst nowhere near Humphrey's level of ability - is not without some low cunning himself, and is occasionally able to pull a fast one on Humphrey, and events occasionally conspire to leave Humphrey spluttering in astonishment as his plan collapses around him.


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