Aleister Crowley of A Certain Magical Index is The Man Behind the Man to all of Academy City. He executes several plans at once, some of which are designed to fail in order to further another, and it's not sure whether the failed plan is an actual failure. A character comments that, for Aleister, even the entire planet could just be a resource waiting to be used and discarded.
In Black Lagoon Rock is getting to this point. Depending on your interpretation of the Baille de la meurte arc, he is either a budding chessmaster who set up nearly the entire ending with a few choice words and a really accurate prediction of how people would act, or he was a Manipulative Bastard playing on a Batman Gambit. However, considering that he seems to have deduced that Eda is a CIA agent and used that to his advantage to shape the end-game....
For that matter Kisuke Urahara fits the role well too, though on the non-villainous side. Aside from being opposed to Aizen, it's not really clear what endgame he's playing toward, but that could just be proof of how good a Chessmaster he is.
Amshel Goldsmith from Blood+ is Diva's chevalier, but he is the one who organises most of Diva's plan to replace humanity with Chiropterans. To reach that end, he uses everyone, including Diva's other chevaliers who are on his side. In fact, it is completely plausible to argue that he, instead of Diva, is the main villain as he and the original Joel's experiments on Saya and Diva completely drove Diva insane and made her into a bloodthirsty monster that she is.
There are a couple of people who know Amshel's game. Nathan plays along because he feels like it. Diva just doesn't care, being too insane to focus on anything that takes so much time to develop.
In both the manga and the anime versions, Aion of Chrono Crusade is shown to be a Chessmaster — in the anime, he manages to manipulate Chrono into giving him exactly what he needs for his plans: the Holy Maiden, Rosette. He dies in the end, but manages to come back from the dead (and/or become a symbol of evil—it's hard to tell exactly). In the manga, he manipulates not only Chrono and his True Companions, but the entire demon society to completely obliterate the entire demon race, and nearly the world along with it, so that the world can be rebuilt without the "systems" he despises. The only thing that stops him is that Rosette is the living personification of Chaotic Good, and his biases against humans stopped him from realizing what a pain in the ass she'd turn out to be.
Dietrich, one of the younger warriors from Claymore qualifies. Figuring out Helen and Deneve's identities within seconds was a foretaste of her analytical abilities. Figuring out the only way to defeat the Luciela-Rafaela spawn for good by siccing the Abyssal Feeders on them was a grandmaster move.
Amber/February from Darker Than Black is an example of this trope; however, instead of simply using world class intellect to manipulate outcomes in her desired direction, she uses her ability to rewind time in order to correct failed gambits.
She even pulls off a Gambit Roulette, managing to place Hei at the exact place she needs him to be, at the exact right time, in order to allow him to have an epiphany which leads him to the course of action she needed him to make. And all before she ran out of power (just).
Myotismon from Digimon Adventure 02. All the main things that happened in the series were plotted by him in his own designs, both directly and indirectly, and his plans worked so well that the writers were forced to use some half-assed Deus ex Machina just to make sure he wouldn't win.
Rosalie of the Samura Hiroaki oneshot Emerald plays this astoundingly well. In only sixty odd pages, she saves a young girl from a life of prostitution, orchestrates the death of a legendary criminal, brings an invincible gunfighter out of retirement and brings down the local prostitution ring without once firing a gun. Paying for a tombstone for the aforementioned criminal just might bring her into Magnificent Bastard territory.
In Gundam 00, Alejandro Corner thinks he's the Chessmaster, hijacking Aeolia Schenberg's century-in-the-makingGambit Roulette and arranging to dispose of the late Aeolia's loyal followers so he can take command of the newly-forming Earth Sphere Federation. He's wrong. Alejandro was actually being manipulated himself every step of the way by his apparent lackey, Ribbons Almark. The first hint Alejandro gets of this comes seconds before his death when Ribbons radios him to gloat.
Aeolia Schenberg, managed to accurately predict the events of everything that happened during the first season, and developed effective contingencies for it. What makes him different from all the other different chessmasters? He's been dead for two hundred years.
Nagi Sanzenin's grandfather, Mikado Sanzenin, has proved himself one of these in chapter 249◊ of Hayate the Combat Butler. In past chapters he essentially plays with Nagi, making her a target for people after the inheritance, which is reason enough. In the latest, he forces Hayate, her butler, into deciding her lifestyle, forcing him to choose between protecting a stone which has become the symbol of the Sanzenin inheritance, or breaking it to save his former lover's life. And to make it even worse, he admits to◊ manipulating the boy's life ever since he can remember by posing as innocuous figures. The only good thing about him is the fact that he genuinely loved his daughter, favors his granddaughter's maid, and taught said granddaughter how to invest.. so she's not rendered completely poverty-stricken ''when''◊ the inheritance gets taken away from her.
He also engineered a plot to steal 'the power of the gods' before the story started. Possibly his first, since it failed and got the three who worked together on it cursed.
Naraku of InuYasha manipulates, schemes, lies, cheats and cons every member of the cast, pitting hero against hero and tricking them into doing his dirty work. The only time the heroes get to confront him face-to-face is when he wants them to, or when he think he's gotten strong enough to finally finish them off. The heroes spend a lot of time seeking out Cosmic Keystones that could weaken him, but by the time they get there he either knows and has destroyed or is about to destroy it, or doesn't care because he's too strong for it to work against him anymore. The pinnacle of Naraku's plans comes when he plans for the heroes to kill him as part of a scheme to exist forever. His schemes finally fall apart here: he wanted Kagome to make a selfish wish on the Shikon-no-tama, which would allow him to draw her into the jewel and the two of them would exist inside it in eternal battle. He didn't count on Inuyasha making it to her and convincing her otherwise though, so once Kagome made an unselfish wish, Naraku's plan was broken and he stayed dead at last.
Irresponsible Captain Tylor may or may not be Obfuscating Stupidity, but many both amongst the series characters and the fans believe that he is actually working some master plan of his own, given how he always comes off on top in the end and his opponents invariably find him a Spanner in the Works. A Fanon theory is that Tylor has somehow become enlightened as a boddhistava, and that the beginning and end of the opening trailer showcases both his enlightenment and his plan for the Soyokaze; to lead the Ragtag Bunch of Misfits into enlightenment.
Liar Game is all about games of Xanatos Speed Chess between opposing Chessmasters. Akiyama stands out as the first and the most prominent heroic example, joined later by Fukunaga, though he's not nearly as good. Opposing him is Yokoya, and as of round 4, a cult leader assigned the Code Name "Robes".
Michio Yuki, the main villain of MW plans to use his killings in order to get to the titular chemical warfare and use it to end the world.
Several people from Naruto, such as Shikamaru when he tricked Hidan into injuring Kakuzu by making Hidan drink Kakuzu's blood, then having him perform his Synchronization schtick. However, Black Zetsu is the champion of Chess mastery in the series, having orchestrated the entire History of Shinobi for the purpose of resurrecting Kaguya.
Gendo Ikari from Neon Genesis Evangelion even though he was out gambitted in the end by Rei who also out-gambitted Seele.
Toua Tokuchi from One Outs (an earlier work by the mangaka of Liar Game) is a baseball player version of this; an adept user of gambits. He uses so many in the index, andn so well, that he crosses over into Magnificent Bastard territory. (And no, he's not the catcher!)
One Piece has Sir Crocodile. The country of Arabasta sees him as their greatest protector, while he secretly controls the criminal organization Baroque Works, who likewise do not know his real identity. Anything strange that happens in Arabasta can be traced back to Crocodile's plans: from sandstorms to a countrywide drought to the formation of a rebel army. The final plan of Baroque Works boils down to using the peoples' love for their country to destroy it and allow Crocodile to take over a country that loves him. And that's just the beginning. Arabasta was in no way picked at random. The World Government (which Crocodile also nominally serves as one of the Seven Warlords of the Sea) takes a dim view of any revolutionary activity, so once his betrayal became known Crocodile would need to control a nation that would give him the power to stand up to them. Like one that hides the secret to finding the ancient superbattleship Pluton. Guess what's encoded onto a tablet in the Arabasta royal tomb.
Naturally, Baroque Works' formervice president, Nico Robin, qualifies as well, preferring to manipulate her enemies before resorting to violence. She maintains this trait as a main protagonist and member of the Straw Hat Pirates.
Dolflamingo (another of the 7 warlords) has a lot of this though his imagery is aimed more at being a puppet master and treating everyone like his toy (which seems to be linked to his ability). He's able to out gambit Law and would have perfectly anticipated the Straw Hats had Sabo not shown up and allowed Luffy to resume his role as Spanner in the Works
The only 2 chapters we see Konata from Oto x Maho involve her advancing her exceedingly convoluted 7+ year long Gambit Roulette to force her son Kanata to become a MagicalGirl, which goes off without a hitch. The fact that she can pull off such a plan can only be explained by her being a Chessmaster.
Yukihito Tsuge, the Big Bad of the second Patlabor film nearly drives Tokyo into civil war while operating completely behind the scenes.
Sailor Moon RBig Bad Wiseman/Death Phantom constructs an elaborate plot that will allow him to destroy the universe of both the past and future which involved him playing the role of the Evil Chancellor to the Black Moon Clan, having them attack the earth of the future then in traveling back in time to attack the earth of the past, having the Sailor Senshi foil them, then have the Senshi traveled to the future so he could get his hands on the MacGuffin Girl he needs for his plan, Chibiusa whose power he will feed to his Evil Black Crystal which will then open a gateway of negative energy to to annihilate the universe with.
Ukyo from Samurai 7 constantly manipulates people to serve his own ambitions. Even the shocking news that he is a clone of the Emperor doesn't shock him for long, and he quickly disposes of the Emperor, possibly causes the death of another of the Emperor's as-yet-unborn clones, and takes over the throne himself. The only plan that stops him is a group of samurai who plainly state they have no plan.
The Anti-Spiral collective from Tengen Toppa Gurren Lagann pull this off quite well; they anticipated every move possible the 'spiral beings' could have made, and intentionally let them achieve almost all of their small victories, for "The greatest despair is brought after the failure of the greatest hope". The only reason they failed was due to a not-so-subjugated mind-puppet herald, Princess Nia Tepperin.
Kurama from YuYu Hakusho. A "good guy" example. Unlike the others in the Spirit Detective team, he defeats his enemies by out-thinking them instead of simply overpowering them. You don't ever want to become his enemy or otherwise try to mess with him. Ever.
The Avengers villain Immortus was always a Chessmaster in a big way, but in the Avengers Forever series it turned out he was a Chessmaster on a far greater scale than anyone had imagined, he had manipulated virtually every event in the history of the Avengers simply to prevent the human race from becoming dangerous enough that the malevolent Time Keepers would wipe them out to preserve their own existence.
Batman villain The Riddler is an accomplished chessmaster, notably for smooth sway over the media, especially post-reformation (a quality of Villain with Good Publicity), and for his previous yet strategically subtle maneuverings of other well-known manipulators and dangerous personas.
In Hush: The Riddler discovers Batman's secret identity and manipulates Bat's oldest friend and his old mechanic, Poison Ivy (who in turn uses Catwoman and SUPERMAN), Killer Croc, Harley Quinn, Clayface, Scarecrow, Ra's Al Ghul. Even the Joker was talked in to going along with his scheme. However, Batman ensures his confidentiality when he exploits the Riddler's compulsion: he can't expose Batman because it would be like giving away the answer to a riddle.
Two-Face can also be a Chess Master, usually having two plans in motion at once, one often entirely different (but also in some way linked) to the other.
You can't say Batman, chessmaster, and villain in the same sentence without talking about Bane. He managed to beat fellow Chessmaster, Ra's Al-Ghul, at a game of Chess even though he's never seen a chessboard before.
Marvel's Grandmaster can come up with some really complicated schemes. Luckily for the heroes he really doesn't care about losing, he just does it for fun. And when he really wants something he's nice enough to let them think they won.
The goddess Athena in the Marvel Universe series The Incredible Hercules is another heroic version of this trope; one of the series' major ongoing threads is a(and, as yet, largely unknown) Batman Gambit she is in the process of executing. Her brother Hercules, a frequent key piece on her chessboard, finds her refusal to be upfront with her plans annoying.
The goddess Athena in DC is possibly an even bigger version. Her scheme to bring down Zeus required the resurrection of Medousa; the death, by Medousa's stone gaze, of a child of one of Wonder Woman's embassy workers (to incense Diana into killing), and then a duel to the death between Medousa and Wonder Woman that culminated in Wonder Woman's blindness and the decapitation of Medousa. This entire chain of events was simply her way of obtaining a fresh gorgon's head (Medousa's previous head having rotted away to uselessness) to use on Zeus's champion, the hecatoncheires Briareos. And that doesn't even count the plot that she undergoes to consolidate her power once Zeus, Poseidon, and Hades try to rebel...
Incredible Hulk: Bruce Banner is this, at least under Greg Pak's pen. As we learn in Fall of The Hulks, Banner's just as dangerous as his savage green alter-ego - if not more so.
Alex Wilder of Runaways. It turns out that, not only did he learn the truth about his parents a full year before the other kids, but he set up virtually every single event in the first volume of the series.
General Wade Eiling definitely fulfills this trope, given the way he manipulates Captain Atom.
Superman enemy Brainiac has often been this, in contrast to Magnificent BastardLex Luthor. Brainiac has frequently set up incredibly complex plans, using every character as a chesspiece in his efforts to steal cities / become a god/absorb the sum total of all knowledge in the universe (his motive keeps on changing), but has trouble changing them once something goes wrong.
The Phantom Blot is (often) at least as close to a Chessmaster as the writers of Disney Mouse And Duck Comics can manage. If there's an unseen mastermind affecting the events and leaving Mickey Mouse baffled for most of the story, it's probably the Blot.
Thanos is a staple Chessmaster in many cosmic crossovers in the Marvel Universe. It's frequently lampshaded how other characters (especially heroes) exist solely to be manipulated by him for whatever agenda he might have at the moment.
V, Anti-Hero of V for Vendetta. In the film, Finch actually figures out part of the plan, but can't do much to stop it by that point.
In the graphic novel, Finch goes as far as to almost stumble upon V's lair, but decides his ordeal is over when he fatally shoots V. This was all part of V's plan....
V also uses a Domino motif for his plan.
Tao from the Wildstorm comics universe, especially as written by Alan Moore or Ed Brubaker.
Deadpool has shown many times that, were it not for his insanity, he would be one of the Marvel Universe's greatest Chessmasters. And even with it, he's shown himself several times to be a cunning and dangerous opponent, such as his tie-in to the Secret Invasion arc, where he joined up with the Skrull and got them to add his regenerative abilities to their Super Skrull. Which resulted in them all basically regenerating so much that they exploded due to not having Deadpool's cancer to keep the regeneration in check, which he knew would happen. And this was all a cover so he could hack into the Skrull's information and find out a way to defeat them for Nick Fury. And the plan was all his.
Jordan179's "The Shadow Wars" My Little Pony: Friendship Is Magic verse depicts both Major Alicorn Princesses of Equestria as this, especially Celestia. In Nightmares Are Tragic, a rewrite of The Elements of Harmony from Nightmare Moon's perspective, Princess Luna is well aware of her sister's cunning and as Nightmare Moon plays (and loses) a very complicated game of Xanatos Speed Chess with Celestia playing by proxy through the Mane Six; the final act of which sees Princess Luna realizing that she's a slave to the NightShadows and fighting and a battle within against the Shadow, paralyzing Nightmare Moon long enough for the Mane Six to destroy the Shadow with the Elements of Harmony. In An Extended Performance, we get to see the same Longest Night from the perspective of Celestia, who not only had the Apples found Ponyville a century ago just to have a place to breed potential Element-Bearers, but has complex contingency plans for the event of the Mane Six failing. Celestia even describes herself in her own thoughts as a "smiling schemer."
In Harry Potter and the Methods of Rationality, we have.. everyone, really. The adult chessmasters are Lucius Malfoy, Dumbledore, and Quirrel, while the kid ones are Draco and Harry, but everyone has at least some elements. The adults also give a good view on different ways this trope can be played: Lawful Lucius prefers the Xanatos Gambit approach, controlling events until the only possible outcomes are one or two he predicted, which will benefit him. The more chaotic Dumbledore and Quirrel, however, prefer to just stack dominoes in their favor, and when everything starts to fall apart, move quickly to take advantage. Draco takes after his father, while Harry is learning from Dumbledore and Quirrel.
Quirrell: In your future career, Mr. Zabini, I do not suggest trying any plots that complicated. They have a tendency to fail.
Blaise: Um, I said that to the Headmaster, actually, and he said that was why it was important to have more than one plot going at a time.
In the Mass Effect fanfic The Council Era, the advisor to the Krogan Overlord, Halak Marr, definitely qualifies as a Chessmaster. In order to bolster his army in preparation for the war with the Citadel, Marr preserved specimens of the dezba (who would naturally have retained a major grudge against the Citadel over their people's genocide) and began a project to resurrect a dezban chieftain, a la Project Lazarus in Mass Effect 2. As mentioned on the Unwitting Pawn page, he usurped his superior in order to enact his dreams of the krogan as a Master Race. He successfully forced Tyrin Lieph to allow his people to take a majority in the Citadel military and give the krogan a Council seat through an excellently-executed plan. He also antagonized the already fragile relationship between the manaba people and the Citadel by faking an attempt on his life by manaban extremists.
Jeft in With Strings Attached. He maneuvered three of the four into getting their major magic, set up the entire Vasyn quest, fooled the other Fans into thinking it was real by having an AI play the Dalns gods, and moved the Vasyn pieces into “entertaining” places for the four to struggle with. He was so overconfident that during the quest for the third piece, he openly forced the four to travel with his best character, the Hunter, which finally clued Varx and Shag into his duplicity.
A number of characters in The Infinite Loops can outwit nonlooping characters easily, but this trope really comes into play when the loopers have some form of competition with each other.
One story-arc in the MLP Loops has a version of Princess Celestia who is a Dumbledore-style "For-the-Greater-Good" manipulator. An Awake Twilight Sparkle throws a monkey wrench in her plans just by acting like her un-Awake self might have.
Camillo and August seem to be this in the Hunger Games fanfic Sink Or Swim. Camillo rather fails at this, though.
Miles Axlerod from Cars 2. In order to turn all the cars in the world away from alternative energy, Axlerod actually invents an explosive chemical called Allinol which he pretends is actually a safe alternative fuel, and he promotes Allinol with the World Grand Prix, a series of races where the world's fastest racecars must compete in three races taking place in different parts of the world. Axlerod then order his Dragon, Professor Z and his army of Lemons to use a powerful radiation cannon to blast away said racecars once the race is in session, then makes everyone think that Z is the one behind the evil plot and not him. After the second race, which takes place in Italy, Axlerod tells everyone that Allinol is actually dangerous and forces the racecars to use ordinary fuel, because since Axlerod secretly owns the largest oil supply in the entire world, he and the Lemons will become unstoppable once alternative energy has been shunned from society, but tricks Lightning McQueen into still using Allinol so that the Lemons can blow him up. Unfortunately for Axlerod, Sarge secretly removed the Allinol from McQueen's body and instead replaces it with Fillmore's, and as a result he has no other choice but to install a detonator onto Mater's body as a last-minute attempt to kill that racecar.
In Death Race, the Warden is clearly the Chessmaster, with the way she manipulates the convicts to play in the Game Show race. In view of the fact that the audience is made not to like her she's also the Anti-Hero, and she's a Manipulative Bastard.
In Little Sweetheart nine year old Thelma (8 and 364 days at the start of the movie) manipulates her new and only friend, her mother, her uncle, the police, the new neighbors who happen to be bank robbers on the run and everyone else she meets throughout the movie. Only one thing goes wrong: her friend doesn't die after going face down in the ocean after an arm shot and what was either a torso or headshot for several minutes. The friend is also nine.
The Oracle is a sentient computer program capable of predicting Neo's reactions so well that she essentially made Neo the One. All of Neo's heroics are all essentially part of her chessmaster plan, even Agent Smith.
The Architect, who managed to manipulate all previous "Ones" into his plan by threatening them with the extinction of the human race.
Tommy from Millers Crossing is a very prolific anti-heroic example. Nearly every character in the movie is deceived by him in some capacity. In fact, he manages to take down Casper's gang simply by sowing seeds of mistrust. Even his closest friends are lied to and manipulated, albeit for their own safety. By the resolution of the movie, even the people he saved are are unaware of the entirety of his schemes.
Senator/Chancellor/Supreme Chancellor/Emperor Palpatine in the Star Wars prequel trilogy. Got a less-than-scrupulous faction to blockade/invade his backwater homeworld just to get the old leader kicked out and himself elected in the process. Then gets his apprentice to start a war to increase his authority under "wartime powers". Then gets his sworn antitheses to attempt to thwart him so he can declare them enemies of the state and use his "severely disfigured in an attempt on my life" sob story to get enough sympathy to be named dictator for life. While playing both sides of the board, so as to have a backup plan if something went wrong (presumably, just sabotage the clones from the Republic side and conquer the galaxy with droids. Not that he ever needed to.)
Wild Things peels back layer after layer of deception until the real Chessmaster is revealed. The studio must have liked this idea, because they did it two more times with direct-to-video sequels.
Ichirō Yashida was behind most of The Wolverine's events, directly or indirectly.
In The Wrong Arm of the Law, Pearly Gates develops into this over the course of the war against the IPO mob. This was played up in advertising.
Edgewood Dirk in A Princess of Landover, by Terry Brooks. After Princess Mistaya gets expelled from school, her father King Benjamin decides to send her to Libiris, a place she is so desperate not to go that she runs away from home instead. Along the way, she meets Edgewood Dirk, who, for reasons of his own, offers to help hide her from her father. He explains to her, the only way to hide her from the King, who, after all, has a magic device that lets him scry on almost any place within the kingdom, is for her to go to the absolutely last place where her father would think to look for her: Libiris—where, it turns out, Dirk wanted her to go for those aforementioned reasons of his own.
Frank Herbert's Dune is filled with them, each with varying levels of skill and subtlety.
The Bene Gesserit tried to execute all their schemes through Chessmaster ploys, many of which spanned generations, to prevent people from realizing how much power their organization really had.
The master of it though would be the God Emperor Leto II, who was so much better than everyone else that even dying was part of his plans, and didn't seem to hinder his continuing influence much at all.
The Bene Tleilax also get a lot of this in Heretics of Dune and Chapterhouse: Dune. They build an intrinsic subversion into their own Chessmastery: it's no fun unless the victim has a possible way out. The thing which fascinates the Tleilaxu is seeing whether said victim can find it.
In the H.I.V.E. Series, the group that the heroes work for is called G.L.O.V.E. In a surprise twist, it's actually being run by Overlord. Rival faction H.O.P.E. takes some of our main characters hostage, and it's revealed that this group is also being run by Overlord. Then, a new group of villains emerges- the Disciples! They seem to be completely different and new- until it's revealed that they are also working for Overlord. Every character who appears for more than three pages and is alive at the beginning of the series works for him at some point.
Hari Seldon actually figures out the "chess rules" of humanity in the form of psychohistory, then uses that knowledge to engineer the recovery of the Empire after an unavoidable social collapse. Seldon is depicted as good; the Ancient Conspiracy that follows in his footsteps... sort of.
R. Daneel Olivaw. Over the course of his twenty-odd thousand year lifespan (he's a robot) he manages to: Engineer humanity's final exodus to the stars, set up the First Galactic Empire, manipulate Hari Seldon into developing his psychohistory in the first place, make sure the plan goes off as it should, and finally set the universe on track to evolve into a single, all-encompassing consciousness. All this whilst being bound by the Three Laws Of Robotics, which he and a fellow robot manage to subvert by realizing that a law even more overriding than the one prohibiting homicide is one "the zeroth law" prohibiting harm to the human race. This is all well and good until the obvious problem arises: judging what's good or bad for humanity. Ultimately, the entire unitary-consciousness push is undertaken in order to subsume the zeroth law into the first and resolve the bind they've created for themselves.
"You are the Beethoven, the Rockefeller, the Michelangelo of deception. The Shakespeare of the gypsy switch, the two-headed nickel, and the rabbit in the hat. What little liver pills are to Carter, lies are to you. You dwell in a world of trapdoors, sliding panels, and Hindu ropetricks. Do I suspect you? Since I met you, I suspect everybody."
Jeeves and Wooster: Jeeves is essentially a Chessmaster who uses his powers for good. His Batman Gambit is always the center of the behind-the-scenes plot, and his philosophy of manipulating people based on the "psychology of the individual" throws a little bit of Clock King in there too.
Zhuge Liang (styled Kongming) is portrayed as a Chessmaster (who skirts into Magnificent Bastard territory quite often) throughout most of the story and probably would have remained one if not for the inevitable weight of history: he dies in the middle of a campaign against his rival Sima Yi, still planning for the future and implementing plans. (Notably however, he has no association whatsoever with chess, since chess is after all not Chinese; his feather fan is far more iconic of him than any board game.)
Cao Cao counts as well (especially in real life), but he's given the Idiot Ball when confronting Zhuge Liang
Chessmasters are common in Korean historical epics. Or at least Strategists. Perhaps it comes of the old Far Eastern tradition of cloak-and-dagger stories that goes back to the likes of Sun Tzu.
In the Sherlock Holmes stories, both Professor Moriarty (Holmes's nemesis) and Sherlock Holmes himself demonstrate considerable Chessmaster talents, most notably in "The Final Problem." Unfortunately, most of the actual plays and counterplays take place offscreen and are merely alluded to by Holmes.
The Continental Op of Dashiell Hammett's Red Harvest. He is hired by a man who is killed before he can give The Op the case, and to deal with this fact, the Op joins every gang in town, convinces each one that the others are playing against them. He almost gets killed, gets everyone else killed, and ends up framed for murder in a way that works out for him. The man was the inspiration for the samurai film Yojimbo which was later adapted into a western, A Fistful of Dollars. Makes you wonder if Dashiell Hammett had this planned from the start...
The Shadow spends most of his stories manipulating both the cops and the criminals until they are brought to a final confrontation where he will finally get involved personally.
Essentially, the murderer in anyAgatha Christie novel. One of her most manipulative murderers would undoubtedly have to be the judge from And Then There Were None, who plays off the psychology of each victim especially Vera Claythorne.
U Po Kyin of Orwell's Burmese Days quickly establishes himself as a chessmaster as well. He states his plan to worm himself a way into the European Club by libelling the town doctor in the first chapter of the book, but it isn't until later that the sheer brilliance of his plan becomes apparent.
Robert Van Gulik's Judge Dee (based on traditional Chinese mysteries) is a subversion of this trope as he is constantly going up against Chessmasters and defeating them because life is NOT predictable - but chessmasters are, at least to Judge Dee! In his final case Dee is trapped by a chessmaster opponent but because he knows how such villains think manages to turn the trap on his rival.
Subverted in "The Twisted Thing" by Mickey Spillane. Private eye Mike Hammer is going crazy trying to sort out who killed a wealthy scientist in the midst of murder and blackmail attempts by all the potential heirs. He eventually realises that there is no money grubbing Evil Plan but a different motive — the killer murdered the victim out of revenge, knowing that the crime would be obscured by everyone else scrabbling for his money.
The Judge and His Executioner by Friedrich Dürrenmatt. Commissar Bärlach knew that his colleague Inspector Tschanz was a murderer, and manipulated Tschanz into pinning his own crime on a master criminal who couldn't be convicted by legal means, ultimately disposing of both of them.
The Talented Mr. Ripley is an interesting variation: he can create elaborate plans on the spur of the moment, then discard then with equal ease and start again. He starts out as a New York City valet and, through fate and quick thinking, turns into a rich-but somewhat crazy-man living in Italy.
In Eleanor Updale's Montmorency, the titular character has some Chessmaster tendencies, but they are completely trumped by the anarchists in the third and fourth books.
John Alpha, the Big Bad of 7th Son, certainly qualifies. It's not until the end of Book One that the Beta clones figure out exactly how long he's been setting up the pieces and just how large and intricate his game is.
A relatively rare female example with Professor Jenna-Jane Mulbridge in Mike Carey's Felix Castor novels: while the series features demons and undead galore, moreover, it is the two human examples, Jenna-Jane and Church Militant leader Father Thomas Gwillam, who draw the most ire from the protagonist.
Steven Brust's Yendi. Members of House Yendi are famed for their machinations that sometimes take centuries to bear fruit (they live for a couple millennia, so they can be patient). It's a saying in the Empire that the only one who can decipher a Yendi's scheme is another Yendi.
Arguably Gentleman John Marcone, from Jim Butcher's The Dresden Files. While neither an antagonist (most of the time) nor a main character, Marcone in eleven books has brought the Chicago criminal underworld under his reasonably organized command, become aware of the supernatural world, hired a Valkyrie, stole the freaking Shroud of Turin, saved Harry's bacon several times and collected a large payment for it, and, in White Knight, talked his way into becoming a freeholding lord in the supernatural world. There are twenty such legal entities; Marcone is the only mortal.
Also Nicodemus, Daddy Raith and Lara, any of the Sidhe by default, the 'Black Council' (assuming it exists), possibly Cowl, Uriel, Harry himself (after Character Development) and many more . . . really, Jim Butcher seems to love these.
He was stage-managing things before that. He's been running rings around Tom Riddle since Riddle was just a weird kid in an orphanage, though he could never prove Riddle did any of the misdeeds he did whilst in school because Riddle was clever and covered it up. Dumbledore had to change his plans when he confirmed that Voldemort had created horcruxes, and this was at the end of the second book. Despite already having theories years in the making prior to that discovery, he only made confirmed active moves to find the horcruxes in the sixth book. While he was uncertain of what Voldemort had done in years prior, he did a lot of research on his history and personality to finally vanquish him. Some state that Dumbledore manipulated Harry, however, other argue that he did not. They believe he gave Harry a choice to live or die, and only put Harry with the Dursleys to protect him with the blood connection, rather than having ulterior motives. Dumbledore also suspected Harry was truly safe from Voldemort at the end of the fourth book when Voldemort took Harry's blood.
Riddle was as smart as Dumbledore (who described him as "probably the most brilliant student Hogwarts has ever seen.") He just let his arrogance and impatience get in the way of his genius. He didn't seem to fully grasp that if he was just as smart as Dumbledore, the reverse by definition was also true, or that Dumbledore's apparently reactionary policy might be masking a plan longer than Riddle's year-by-year plots. However, Riddle DID take over the ministry in a silent coup that slowly took place during both the 6th and 7th books. We do not know of Riddle's actions during the first war, however, we DO know that when the time was right, he would give the order for Lucius Malfoy to slip the Horcrux Diary into Hogwarts, and bring Hogwarts down from the inside. This is Chessmaster worthy thinking on Riddle's part, as he was patiently waiting for the right time to strike, and the plan would have succeeded because there would be no parseltongue-speaking Harry to hear the snake in the walls. This is disregarding the prophecy.
Barty Crouch, Jr in Goblet of Fire. Not only does he plan everything out beforehand, helping Harry and devising ways for Harry to win each Task, but also manages to outplay Dumbledore...until the last minute. However;,it's not him that messes up his carefully-laid plans, but Voldemort.
Makina Seval of The Assassins of Tamurin, whose Gambit Roulette has been years in the making, spanning across an empire but never hitting a snag, and using players in the most obscure and unpredictable roles, who know absolutely nothing about what they're being used for.
The title character of the Artemis Fowl series (being a Teen Genius he is naturally a literal chessmaster as well, though this gets only a passing mention).
Shadows of the Hegemon by Orson Scott Card is a Chessmaster free-for-all, with Achilles betraying everyone, Peter playing his own games behind the mask of Locke, Petra working to screw Achilles from underneath him, and Bean formulating his own tactics and webs. The plot is so complex with betrayals, it's like reading a game of risk.
The opening chapter of Ender in Exile showcases the Wiggins' chessmaster talents, as used on each other, except for Ender, who doesn't appear in that chapter, though when he does show up, he gets to show off his ability to manipulate others as well, albeit to a slightly lesser extent. Also: Hyrum Graff.
And it's not just Younger Wiggins... Mom and Dad have been working the Long Game and subtlety guiding their kids.
Saint Dane from The Pendragon Adventure. Voluntary Shapeshifting abilities and a full knowledge of how to work the Flumes allow him to manipulate everything to work to his whims across Halla. The actual metaphor he uses is dominoes, saying that if one Territory falls, the rest will follow.
The Duke of Wellington, as depicted in the Sharpe novels. To give just one example, he summons Sharpe out of retirement to see him with no explanation, tells him he wants Sharpe to rescue an unnamed missing agent in India, lets Sharpe refuse and walk out... only to find his best friend's wife sitting outside the office. "Oh, didn't I tell you? Mrs. Harper's husband is our missing man." In fairness, that's from the TV adaptation, and it isn't Nosey's idea, but rather the East India Company mandarin's (Wellington is quite uncomfortable the whole idea). A better example from the Sharpe books would be Magnificent Bastard Lord Pumphrey in Sharpe's Prey, Sharpe's Fury and Sharpe's Havoc, who is the only Chessmaster whose schemes can survive Richard Sharpe:
Sharpe's Prey: Sends Sharpe with John Lavisser with tonnes of gold in order to bribe the Danish Crown Prince, as he doesn't trust Lavisser. Blackmails Sharpe into helping him for free, and then uses him to secure Britain's massive spy ring in the Baltic. Goes behind Admiral Gambier's back and sends a team of Navy men into the city to secure the Danish war fleet for Britain. Sends Sharpe into the city to kill Lavisser and recover the gold. Uses the failure of the Lavisser expedition (not his idea) to remove the rivals for his job. Cleans up the whole thing by murdering and replacing his Danish contacts.
Sharpe's Havoc: Turns up at the end. Sent by the Foreign Office to defeat fellow Chessmaster Colonel Christopher. Sends Sharpe to kill Christopher and his knowledge with him. Again uses Sharpe to murder threats to his job. As a side project, secures communication and financial links with Spanish and Portugese partisans.
Sharpe's Fury:' Directing the transfer of money to Spanish partisan operations from Cadiz. Recovers important Foreign Office documents using Sharpe, fights personally for once (he's okay at it). Kills all threats to the Crown. Discredits hostile Spanish politicians. Mocks Sharpe to his face when the latter finds out about his murder of his Danish friends.
Pierre Ducos is a sublime Chessmaster. His problem is that Sharpe has a cockroach-like refusal to die at the right time, which means he inevitably survives to muck everything up.
Kelsier, the main character from the first book of Brandon Sanderson's Mistborn series, is a nice inversion as a heroic Chessmaster. He demonstrates his talent through a multi-layered Batman Gambit.
It's not just him. The Lord Ruler, Straff, Preservation, Ruin, and others all have more than a little Chessmaster in them (of varying degrees of skill), and indeed the whole trilogy can best be described as a bunch of peoples' (and gods') plans running roughshod over each other, with the ending arguably amounting to a Gambit Pileup.
Human/alien merger Mademoiselle in Alastair Reynolds' Revelation Space and Redemption Ark "saw information flows with the clarity most people lack". Ironically, she was destroyed by H, a formidable but ordinarily inferior Chessmaster, because she got so wrapped up in what was essentially a science project, she stopped paying attention to her webs.
H: "she was a very powerful influence in Chasm City for many years, without anyone realising it. She was the perfect dictator. He control was so pervasive that no one noticed they were in her thrall. Her wealth, as estimated by usual indices, was practically zero. She did not 'own' anything in the usual sense. Yet she had webs of coercion that enabled her to achieve whatever she wanted silently, invisibly. When people acted out on what they imagined was pure self-interest, they were often following Mademoiselle's hidden script."
Emperor Ezar in Lois McMaster Bujold's Shards of Honor. He starts a war that he knows he's going to lose, in order to: 1) Kill off his psychopathic son, 2) Discredit his political opponents, 3) Set up Aral Vorkosigan to become regent for his grandson. (Vorkosigan is only man he trusts to a) hold power for 13 years, and b) turn that power over to an 18 year old emperor who will no doubt be an idiot (since everyone is an idiot at 18.))
Several characters in Megan Whalen Turner's Queen's Thief series have Chessmaster attributes, if they aren't full Chessmasters - most notably, the title queen in The Queen of Attolia. Nahuseresh in the same book tries to be one. Eugenides is the best at it, successfully pulling off a Batman Gambit in every book. Interestingly enough, most do it for the purposes of good.
Ardneh, from Fred Saberhagen's Empire of the East. In the first volume, he actually quotes an ancient (especially by that time) real-world Hindu myth to the villain in order to tell him exactly how he's going to kill him. He then lets said villain get control of the invincible super-weapon in order to kill him in exactly the manner he said he would (with foam). In the process, he liberates the entire west coast from The Empire. In the second volume, he manipulates two of the villains from the first volume into Heel Face Turns in order to defeat the demon, using the very fact that the main villain of that volume has moved his one vulnerability to a more secure location. And then, in the third volume, he wipes out The Empire, and most of the world's most powerful demons, in a single stroke.
Paladine, in the Dragonlance Chronicles, but especially in the Legends. In the former, he recruits and manipulates the Ragtag Bunch of Misfits into saving the world, while disguised as the senile pyromaniac Fizban. In the latter, he actually lets Raistlin kill him and destroy the world in an alternate future, so that when Caramon travels back in time and shows Raistlin said future, Raist finally repents.
Both The Ellimist and Crayak in Animorphs are Chessmasters by necessity (though The Ellimist has been one since his space bird gamer days), because a direct fight between them could destroy the fabric of reality and themselves along with it
The Ellimist is a classic one, though. At one point he reveals the location of the Kandrona (a strategically important target, since it generates the rays Yeerks need to periodically absorb to survive) via a vision of a future where the Yeerks won...
The Obsidian Trilogy presents us with Queen Savilla of Shadow Mountain. She saw her father make certain that all the Races of the Light lived in fear of the demonic creatures called the Endarkened, and was forced to retreat alongside him after all who feared the Endarkened forged an alliance that nearly destroyed them. After... inheriting... the leadership of demonkind, Savilla spent centuries insuring that most of the surface world more-or-less dismissed Demons as something from the distant past, kept the various races distracted with their own issues, and most importantly keeping the High Mages of Armethalieh and the Wild Mages scattered elsewhere from making common cause for any reason. All the while using agents, catspaws, and breeding programs to set up the next war to her advantage.
Chired Anigrel only seems an understudy compared to the Demon Queen he worshipped since childhood. Managing to both attain effective control of Armethalieh and come within moments of handing the whole thing over to Savilla.
Gaius Sextus in Codex Alera is one of these, though the limitations of trying to do this without inexplicable perfect knowledge of all events is clear. A lot of people became extremely angry at these tendencies, and many people considered him less "masterful" than "feeble" and blamed him for the situation of Alera.
Lord Kalarus tries to be one of these, but while he has a few tricks, he's not nearly in control as he thinks he is. A good example of this is when he conspires with the Cane to raid Alera to distract attention from his rebellion. He expects them to bring a few hundred raiders. They bring thousands and have no intention of leaving.
Admiral Sun Ji Guoming from the Dale Brown novel Fatal Terrain carries out an unconventional warfare plan that succeeds in getting the rest of the world to see China as a Villain with Good Publicity even as it nukes Taiwan. This plan also makes Taiwan and the US look like aggressors, at least twice fooling them into misusing their military might. He comes quite close to his goal of retaking Taiwan.
National Security Adviser Robert Chamberlain from Act of War plays everyone in his quest to kill Harold Kingman.
Lisbeth Salander of Stieg Larsson's Millennium Trilogy, if she doesn't start as a chessmaster, certainly becomes one by the end of the third book. As an example, she encounters her half-brother Roland Niedemann, who has repeatedly tried to kill her. Now, she could just kill him, and thereby give the authorities cause to start pursuing her again. So, she doesn't do this. She makes an anonymous tip to the gangster scum who previously employed him, and now want to kill him. Then she makes an anonymous tip to the police that said gangster scum have likely murdered Niedemann. In doing so, she manages to wipe out three of her enemies without any of them knowing she is responsible for doing so.
"Mister X" in the third Empire from the Ashes book, whose elaborate plans stretch back ten years or more and involve minions buried everywhere in the government, military, and largest terrorist organization (until they serve their function, at which point they inevitably die).
Merlin from The Warlord Chronicles makes sure that plenty of powerful people on all sides he has influence on owe him favours, and that everybody fears his questionable magical powers, simply to ensure that he can always recruit people for his personal quest for the Treasures of Britain. If his goals were less abstract and religious, he could have probably controlled the entire island from behind the various thrones.
From Peter F. Hamilton's Humanx Commonwealth novels, we have The Starflyer. The action starts with this Chessmaster funding an astronomical observation that indirectly kicks off a genocidal war, has minions working at the highest levels of the military (helping humanity just enough so that the two sides can destroy each other), has another minion hosting one of the highest rated news shows, with more minions everywhere you look. It takes most of two books for all of the good guys to become convinced that the Starflyer even exists. It doesn't appear on stage until near the end of the second book... the only clues to its existence are the behavior of its agents.
The Hostage Prince by Jane Yolen and Adam Stemple features the Chessmaster Jack Daw, who is the only one kind to the hostage prince, Aspen, for many years, and then convinces him that he's about to be assassinated. Aspen runs back to his home kingdom, only to discover that he was actually safe, Jack Daw had lied, and now the two realms of Seelie and Unseelie must go to war because he ran away.
Discussed in Lord Chesterfield's Letters to His Son. "A man who hath studied the world knows when to time, and where to place them; he hath analyzed the characters he applies to, and adapted his address and his arguments to them" (letter 163)
Viviane in The Mists of Avalon. Ultimately to little avail and the general detriment of everyone involved.
The Power of Five: The Chairman of the Nightrise Corporation is a pretty impressive example of this - he rigs a US presidential election, manages to capture two of the Five, takes over Hong Kong and already has a business empire that controls most of South East Asia.
Matt Freeman is perhaps the best example in the series, outwitting both the King of the Old Ones and the aforementioned Chairman.
The Master of the Mountain is another heroic example.
Sisterhood Series by Fern Michaels: Charles Martin, former agent of MI6 and James BondExpy, is definitely this. He works for the Vigilantes and it could be argued that he uses this trope for good, but he is an Anti-Hero. He tries his hardest to come up with foolproof plans for the Vigilantes to use in order to succeed in their missions. However, there have been times when those plans go awry, and he really hates it when that happens. Under The Radar reveals that he has a large network of contacts and agents who are well-funded and good at their job, which helps to explain how his plans are effective. By Vanishing Act, however, the Vigilantes make it clear to Charles that they call the shots and not him, and that he had best stop lording over them or he will get the boot.
Song at Dawn: Moving pieces and outgambitting are required skills for anyone in this setting: nobles, merchants, bishops, bodyguards, etc. The greatest of them is al-Hisba who plays everyone to accomplish his own objective while placating his enemies and helping a friend.
"According to his circumstances and his intimacy with people, he constantly formed various plans and schemes which he himself was not quite aware of, but which constituted all the interest of his life. He would have not one or two or these plans and schemes going, but dozens, of which some were only beginning to take shape for him, while others were coming to completion, and still others were abolished."
Inquisitor Ramius Stele from the Warhammer 40,000Blood Angels novels rather masterfully steers the titular Space Marine Chapter towards Chaos, though as we are reminded several times, he's still a pawn to a greater power.
Jonathan Stonagal is made to be this in the Left Behind series, particularly in the prequel books where he funds the Designer Babies project that creates Nicolae Carpathia, with the intention that he would be Jonathan's puppet to rule the world with. Unfortunately, Jonathan gets an Et Tu, Brute? moment when Nicolae murders both him and Joshua Todd-Cothran in a secret meeting where he appoints the ten subpotentates for the coming Global Community.
In S.A. Swann's Terran Confederacy, elements of the composite AI called Random Walk/Tjaele Mosasa/Mike Kelly/Ambrose/Adam have been manipulating human society to its own ends and that of its alien creators for centuries.
Aly, the protagonist of Daughter of the Lioness, naturally takes this role because she's the spymaster for the raka rebellion. She's very good at manipulating people and setting up event to weaken the Rittevons and strengthen the raka, like fake evidence of a royal affair and converting enemy spies with carrot-and-stick.
Please Don't Tell My Parents I'm a Supervillain gives us Spider, a supervillain who uses spider imagery. She's the lord of Chinatown, controlling the entire area to such an extent that heroes are not allowed to patrol there—which they allow since they know they don't need to, with her in charge. She also wrote the treaty that governs hero/villain interactions, and is a spider the size of a car.
A Mage's Power: Everything went as Tasio directed. He arranged for Eric to meet Annala and join the Dragon's Lair. He worked with Basilard to engineer a Darkest Hour that would force Eric into action. He removed the sound-proof runes from Tahart's apartment so Eric would hear Annala's cry. Even Selen's Evil Plan only unfolded as it did becuse Tasio incorporated it into his own.
Rahze el'Dax in Dark Heart, despite his impassive, detached manner, is disturbingly good at manipulating people into doing his bidding. He nudges Shial and Kail into falling in love to fulfill a prophecy, although Kail is certain it would have happened even without his interference.
Live Action TV
The Shadows and the Vorlons in Babylon 5 are two entire races of Chessmasters.
Londo Mollari also has some serious game.
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.
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.
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.
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.
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.
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.
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.
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.)
John Connor of 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.
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!
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.
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.
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.
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.
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.
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.
In Justified, Limehouse is constantly manipulating the various criminals and other violent elements in Harlan County to keep his own community safe.
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.
Once Upon a Time: Mr. Gold/Rumplestiltskin. It seems that everything in the show was done by him.
Regina (The Evil Queen): I assume this was all your doing.
"The Impossible Astronaut/The Day of the Moon" has the Eleventh Doctor trick the Silents into brainwashing the human race to kill them on sight.
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.
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.
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 others), dragging the world into Oblivion one Shadowland at a time. And sometimes their grand scheme works, too: just ask the people who died of Great Contagion.
The Ebon Dragon on the other hand, are playing a speed chess variant of the game, what's with his new 50 Infernal pawns and his marriage to a certain prominent woman.
In Warhammer and Warhammer 40,000, 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.
Possibly also the Emperor - it is hinted that not only did he anticipate the Heresy but also plans to be reborn when his phsycial form dies (which may well be soon)
Cypher. But with a name like that...
Asdrubael Vect? No mention of him? He's 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.
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.
The Dungeons & Dragons 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 continents - World 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...
The rilmani, introduced in the Planescape setting, are like this on a cosmic scale. A True Neutral race who 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.
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.
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.
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.
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.
Prince Hal in Henry IV part one 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.
In Pokémon Live!, Giovanni orchestrates the entire plot and manipulates just about everyone.
Fable II has Theresa whose also a Manipulative Bitch the DLC reveals That she was the one who gave the music box to murgo, then convinced Sparrow to buy it while manipulating Lucien to become obsessed with the spire and possibly convincing him to kill Rose and try to kill Sparrow. So she could guide Sparrow to become a hero and gather the heroes of legends to claim the spire for her own. May also constitute as a Gambit Roulette
Final Fantasy Tactics was completely filled with Chessmaster-on-Chessmaster action. The Galbados Church was trying to manipulate commoner legends to set themselves up as faux-saviors in the Lion War. The church's new "Zodiac Braves" were actually the demonic Lucavi, playing the church for fools and using the bloodshed of the Lion War to revive their leader. Both Prince Larg and Goltana were using the recent death of the King to try and place their preferred puppet candidates on the throne, setting themselves up as Regent. Dycedarg was using Larg, hoping to kill him and take his place in the whole plot. And Delita was outmaneuvering them all, using the church and Goltana to set himself as the new king by marrying Ovelia (The fact that he seemed to genuinely like her was almost problematic for him), and using the protagonist to stop the Lucavi, as he couldn't deal with them personally without screwing up the rest of his plans. Delita succeeded, and every other contender was dead when the dust settled. About the only people not trying to screw everyone else like a two-dicked billygoat was the protagonist and his crew, but his actions definitely were manipulated for other peoples' gain.
Rufus Shinra, of Final Fantasy VII: Advent Children, was a very sneaky, wheelchair-bound chessmaster who, with only four hired goons and his wits about him, manages to fool Kadaj for the entire movie. While suffering from a fatal disease, no less.
Not as though this is his first act of such. He's been doing this for years as revealed in Before Crisis wherein he was shown to be the financial backer and chessmaster behind the second incarnation of the ecoterrorist group AVALANCHE, simply because he wanted his father out of the way. Though, the whole thing does come back to bite him on the ass with the third incarnation of the group in Final Fantasy VII proper.
Though, this trait runs in the family as we see in Crisis Core with Rufus' all-bastard half-brother Lazard is revealed to be effectively using both SOLDIER and the Genesis Army to play chess with himself in his efforts to topple the company. But again, it all comes back to bite him in the ass when people start investigating him too closely and he ends up a victim of the very same Send in the Clones style plot he had been orchestrating. It proves though that only by having his DNA rewritten will he ever stop being a Shinra. Which he absolutely hates being, but in trying to destroy his family, he proves how much of a Shinra he really is.
Frozen Synapse's Charon's Palm can be seen as a chessmaster with a perhaps unique twist; it splintered itself in two to create Tactics and assist Graham Nix with his coup, creating more destruction and death of innocent and guilty lives than was necessary. Why? Because it was bored
However, the undisputed king of this in Kingdom Hearts has to be Xehanort. Everything that has happened in the Kingdom Hearts saga from Birth by Sleep onwards can be traced back to Master Xehanort, although his future incarnations kind of drifted away from his original plan. Sheer Power Of Friendship is the only reason his plan to restart the Keyblade War didn't succeed at the Keyblade Graveyard, and after losing all his memories, he's able to continue his plans in some form thanks to Braig.
The Administrator from Team Fortress 2 could certainly qualify: though it's never specified why, it's clear that she's been deliberately prolonging and encouraging the conflict between RED and BLU for years.
Gray Mann also qualifies as one. He patiently waited over a century to solidify his power and weaken both his brothers enough, and when they are both old (to the point of dying mid - conversation occasionally)he tricks them into negotiating a truce, and then he kills them both, taking their assets. Then in order to take over Mann Co.'s Saxton Hale, he steps down from his position, makes his little daughter the CEO, then takes over Mann Co. by playing off Hale's refusal to fight a child. The most recent comics are hinting at a chess match between the Administrator and Gray Mann.
Xenogears could feature a football team full of chessmasters. Just to name a few who were playing (and they were each manipulating each other): Miang, Krelian, Grahf.
Wilhelm in the Xenosaga series manipulates most, if not all, the protagonists and antagonists in the story in some way as well as the overarching flow of events, often by assuming leadership of companies and organizations (where all positions appear to be held by different individuals).
In Super Robot Wars (in various timelines), Shu Shirakawa and Ingram Prisken often act as chessmasters, manipulating the protagonists into doing their bidding unwittingly, and with unparalleled amounts of panache (Shu has even garnered an unwanted harem in the past). Interestingly, they take to the field of battle quite often, but this is perhaps solely to show off their (incredibly cool) Humongous Mecha. Due to the crossover nature of the series, Shu and Ingram have butted heads with each other, Gendo Ikari, The Titans, Big Fire, and various other factions and have generally come out on top. They could also be considered a subversion of this trope,because they themselves are being forced to do the bidding of higher powers, and actually fall under direct control of them on several occasions. The protagonists generally end up killing them, or being unable to prevent their deaths. Ironically, after noting just before dying that he was now free of all the chains that bound him, Shu is actually brought back from the dead to resume his previous role. Perhaps proving what a magnificent bastard he is, Shu is actually -released- from his bonds upon his resurrection. Whether or not this was intentional is up in the air, but if it was, it most definitely counts as a Gambit Roulette.
Mortal Kombat has Quan Chi, who has manipulated virtually everyone in the series, such as taking in the form of Sub-Zero/Bi-Han and subsequently slaughtering the Shirai Ryu, leading to Hanzo Hasashi's resurrection as the hellspawned revenant Scorpion, who ultimately kills Bi-Han out of revenge, leading to that person's resurrection as Noob Saibot, to manipulating both Raiden's and Shao Kahn's sides in 9 so he could make conquest by Shinnok easier by having the latter disposed of by the Elder Gods as a consequence for violating the Mortal Kombat laws.
Grand Master of the Order, Jacques de Aldersberg in The Witcher computer game, who used crime group Salamandra along with mad wizard under his power, sparked full-scale racial war and manipulated the whole bunch of people to solidify the power of his Order - and all this just to save humanity from his vision of terrible future, which makes him into Well-Intentioned Extremist as well.
The prosecutors of the original trilogy, (excluding Winston Payne) also seem to have Chessmaster-ish qualities, Edgeworth even has a chess set in his office with a suspiciously spiky blue pawn.
In Ace Attorney Investigations 2, the chess motif becomes literal, with Edgeworth engaging in "Logic Chess" to get people to talk. There's also a witness who is obsessed with chess, and another who plays long-distance chess with the former. The real Chessmaster of the game is the former's best friend and the latter's protege, and the one acting as courier for their games. Amusingly, he himself doesn't particularly like chess. He does, however, take the grandmaster title for the role, masterminding every murder in the game save one and manipulating most of the cast to do his bidding.
Hikawa from Shin Megami Tensei III: Nocturne manipulates people and events from the shadows, never taking any unnecessary actions and always moving towards his goal.
Lucifer arguably counts as well, attempting to maneuver the player into unmaking reality and spearheading Armageddon. Granted, he more or less admits this upfront and gives the player a choice in the matter. However, failing to follow his plan means the player will miss out on most of the game's backstory and some nice rewards...
A non-villain example is Sereph Lamington from Disgaea. His Batman Gambit was so well executed that he qualifies for this trope. Sending his most loyal angel on a false assassination mission (knowing that she'll take the change in mission he was expecting), turning the ambitions of his 2nd in command to his advantage (humans, angels, and demons had to share in it) which causes said traitor to be exposed to him (and punished). Even his battle with Laharl was part of the plan. There's a reason why he's the Seraph, and this is it. Far more intelligent than he looks.
Kil'jaeden the Deceiver from the Warcraft Universe. His motto is "There are more ways to destroy one's enemy than with an army. Sometimes those ways are better." He corrupts the race of orcs by posing as the spirits of their ancestors and makes them think the Draenei are evil and should be destroyed, because if he used his personal demon army to raid the planet the Draenei are living on, they would simply run away (or so he thought, they were actually stranded).
One interpretation of the events of Warcraft III is that Kil'jaeden created the Lich King knowing that it would betray Archimonde (his counterpart and co-leader of the Burning Legion), leading in Archimonde's death and Kil'jaeden becoming the absolute ruler of the demons.
He also managed to enslave a race of demons known for their clever trickery.
The Old Gods take the cake, though. First they infest the Titans' newly-created world with "the curse of flesh", causing their mechanical creations to become organic. Then they rig it so that the Titans can't actually destroy them without destroying the world alongside them, forcing them to just seal the Old Gods away. Even that doesn't do the job so well for C'thun and Yogg-Saron...which is where the players step in. In fact, the latter could be counted a Chessmaster among Chessmasters - even after being sealed away he manages to corrupt the wardens of his prison into loyal, if batshit insane, servants. When you do fight him, he takes you on a brief guided tour of the events throughout Warcraft's history he has been responsible for, including the assassination of a king and the creation of an important MacGuffin.
Lich King Ner'zhul deserves special mention. He was the mastermind behind the Scourge Invasion and plotted successfully against his masters. He even succeded to deceive his guardians, the Dreadlords... who are considered to be chessmasters themselves.
The player in this game of Galactic Civilizations 2, who ended the existence of his galaxy's then greatest military power in a single turn. When his race specialized in cultural influence and entertainment programming, and had zero military power whatsoever. Via a combo of diplomatic, financial, and cultural maneuvering that... seriously, just read it. * g* (The relevant parts are at Day 9 and 10.)
Player: I don't care that my foreign intel reports rate you as the most powerful race in the galaxy. I don't care that I come dead last on that same list. I don't care that I couldn't even fight back if I had any gunships because of a pledge to spread peace throughout the galaxy. In fact, you know what? That's it. Your race ends this week. When I next click that 'Turn' button, you're out of the game.
At the end of that same game, He exploited his own cultural influence technologies and a law he passed at the beginning of the game to override the normal limitations on ship movement in order to place the final starbase he needed in order to wipe out his remaining rivals and end the game. Day 30. I cried at the beauty of the move:
Player: I'd catapulted the slowest unit in the galaxy 600 trillion kilometers in an instant: right to the sun it was built to destroy.
He's come a long way since his last GalCiv II game, then. In that attempt, it took him the entire game to realize that all of his strategies and tactics were merely a sideshow to some byzantine maneuvering between the AI opponents, and the only reason he hadn't been exterminated by one faction long ago was because they knew it would allow another faction to win.
Chrono Cross has a rare example of the Chessmaster actually being a good guy. Belthasar manipulated 10,000 years of history across multiple parallel dimensions to make sure the protagonist would acquire the (eponymous) ultimate item needed to completely destroy the Big Bad.
Final Fantasy X has a heroic Chessmaster tag-team of Jecht and Auron, who spend the game (and the 10 years prior to it) preparing Tidus so he'll someday kill Sin, instead of letting it get sealed back into its can.
One of Auron's moves in the game was getting Tidus and Yuna alone together in one of the most romantic spots in Spira long enough for the inevitable to happen, ensuring that Tidus would not allow the Grand Summoning to happen as scheduled. Bonus points for sending Kimahri along as chaperone, the only member of the party who wouldn't have stopped them.
On the villain's side, there is Yu Yevon and Yunalesca. The former sacrifices an entire city so that the latter can build a cycle of Senseless Sacrifice in his name.
Not quite as bad as the former entry, but The Maesters have a bit of this going too. The whole of Operation Mi'hen was to make the Crusaders look like they were ignoring scriptures and doctrine to strike off on their own, while in fact, the Church of Yevon was the driving force behind it all along. Hell, even if the Operation worked the group could claim credit, which turns the Operation into a Xanatos Gambit.
Halo's Gravemind displays the traits of a chessmaster throughout parts two and three in the series. Gravemind, as the collection of Flood intelligence, managed to turn an AI that had been specifically designed to destroy the Flood over to his side milennia ago, manages to in five seconds convince the Arbiter to prevent the rings from firing, takes over the flood's ruling ship, and uses the Chief and Arby to stop Truth from activating the Ark and destroying all life in the galaxy, just so that he could infest all life in the galaxy. When the Halo was about to fire and destroy the flood yet again, Gravemind says that all it'll do is delay the inevitable.
On the subject of Halo, there's also the Prophet of Truth. In Halo 2 he is the epitome of the Chessmaster, going as far as to eliminate the Sangheili without them even knowing it, kills off his two co-leaders with no mercy or regret (hahaha...), and having the Arbiter run a wild goose chase, culminating in the latter's "demise" at the hands of Tartarus.
Tsukihime has, of all people, Kohaku - the cheerful and seemingly carefree maid who ends up single-handedly killing off the entire Tohno family in Hisui's True Ending (and comes close in the other paths too). She gives Akiha her blood to awaken the Tohno blood in her, as well as being responsible for the resultant insanity of the real SHIKI. On top of that, she leads Shiki into believing HE'S the one responsible for all the murders and that it won't stop until SHIKI dies. Oh, and during the final battle, she deliberately gets herself attacked knowing there's a good chance that Akiha will jump in the way and sacrifice herself to save her. All this while never letting go of that cheerful smile, even up to her eventual suicide after her revenge is complete.
If you are in a Suikoden game and your last name is Silverberg, chances are you're a Chessmaster. If your name is Lucretia Merces, you are a crazy, crazy chessmaster.
The World Ends with You, has around three - Joshua, who initiated the whole thing, and kept it moving whilst on the sidelines for a good portion of the game, Megumi Kitaniji, who carefully made sure that everyone was kept in the dark about his game with Joshua, whilst slowly infiltrating Shibuya with the Red-Skull pins, and finally, (possibly) Sanae Hanekoma, who popped up here and there, never letting on too much, and in the end turned out to be an Angel. This is hardly surprising, coming from a game with a Gambit Pileup.
A somewhat odd version occurs in Sanitarium. It initially appears that the Big Bad has an incredibly elaborate plan to stop The Hero. However, it later turns out that there are two versions of the villain: one in the real world and one in a parallel world. Each was attacking the hero independently of the other, meaning that the elaborate plan was actually two simpler plans. Although both versions still fit this trope, the fact that the plan wasn't as elaborate as initially thought makes them somewhat diminished variations.
In Modern Warfare 2 General Shepherd sends a CIA agent, Joseph Allen, to infiltrate the terrorist cell of Vladimir Makarov. Makarov reveals he knew Allen was CIA, and kills him after a terrorist attack in a Russian airport; this leads Moscow to declare war on the US and invade the East Coast; which the US manages to repel by the skin of their teeth (and with a little help from Taskforce-141). Anyways, Shepherd is revealed to have planned this all along; after the events of the first Modern Warfare, he felt that the US public hadn't appreciated the sacrifices his men made. So by starting a war with Russia, he's a hero, and the public has rallied behind him.
Half-Life has the G-Man, the mysterious suited man who has been shadowing Gordon Freeman since the beginning of the series. He speaks of his "employers," but it's obvious that the G-Man has been subtly influencing events since the first game and that Gordon is really just his pawn, at least until the Vortigaunts intervene in Half-Life 2: Episode 1. The real question is which side the G-Man is on.
The Kimono Girls take on a role that could be described as this in Pokémon HeartGold and SoulSilver. I'm as surprised as you. Their actual plan is horribly vague; apparently it involves finding a kindhearted Trainer to summon Ho-oh or Lugia (depending on the game). What purpose this serves is not made clear, and the whole plan seems to be rendered a bit useless by the fact that said kindhearted Trainer proceeds to beat the crap out of the aforementioned Pokémon and, if they're feeling merciful, capture it in a tiny ball and make it their slave.
Darkai from Pokémon Mystery Dungeon: Explorers of Time/Darkness/Sky, who actually came up with different plans to kill the heroes over the course of the game. During the post game story, he has no less than five backup plans in place!
Lenora from Pokemon Black And White has this as her battle style, in the game, Anime, and Manga. In the game, defeating her first Pokemon is a no win situation, as both of her Pokemon know Retaliate, which with the STAB granted by it being a normal type move, which makes it one of the most powerful moves you'll see early in the game. In both the Anime and Manga, her battle style resolves around forcing her opponents to play into her hand. There's a reason she's considered That One Boss.
Mass Effect 2 has the leader of Cerberus, the Illusive Man, who pulls string after string to get things to go as he wants them to throughout the game. He does, however, make one flaw- he under-estimates Commander Shepard. Depending on the player's actions, Shepard can disobey the Illusive Man by blowing up a "potential resource", after which possibly telling him to "fall in line or step aside- but don't get in my way", and potentially getting Cerberus' most loyal and intelligent operative to disobey a direct order and quit in the same moment.
The cake must go to the Shadow Broker. He killed his master and took control of his information network. He uses that network to keep himself in power, playing rivals off against each other and controlling galactic espionage in order to prevent anyone gaining the upper hand, and thus making sure his service are no longer.
...Who is subsequently Out-Gambitted by the Illusive Man. He knew that Liara had no hope of finding the Shadow Broker alone, so he sent her data tipping her off to the Broker's location and plans. After she dispatched and replaced the Shadow Broker, the Illusive Man recognized that the new Shadow Broker's organization was at an all time low in power from the recent coup. So he sent a small army of Cerberus soldiers to destroy her main base and splinter her organization. Liara just barely managed to escape.
However, Liara DID escape, with the hardware needed to maintain the network while using her base as a convenient way to take out a chunk of Cerberus troops by blowing it up.
The Reapers as a whole are this on a galactic scale stretching over a billion years. Using an incredibly clever Batman Gambit (mixed with unbelievable firepower and technology), they have successfully waged completely one-sided wars and harvested thousands of advanced and intelligent civilizations over the course of their existence.
Sarah Kerrigan, full stop. Brood Wars was Kerrigan playing her own constant Chessmaster, to the point where she was more playing a game of Gambit.
Both Starcraft and Brood Wars actually have several of them. The Overmind definitely counts, maybe also Dugall. Alan Shezar and Ulrezaj also count, if you take Blizzard's bonus campaigns as canon. Oh, and Duran (who also qualifies as a Magnificent Bastard).
In Sonic Adventure 2, Shadow the Hedgehog allows Eggman to believe that he is gathering Emeralds as a favor for waking him from a 50 year sleep that his only friend put him in before she is killed, then tells Eggman he can hold the world ransom with the Eclipse Cannon on the Space Colony ARK, when really Shadow has been doing all this just so the Cannon could destroy Earth. Why? Because in SA2, Shadow the Hedgehog really, REALLY hates human beings and just wants them to suffer. So much that even when his plan fails, he is content to watch the Earth be destroyed anyways even if it's by a way that wasn't in his plan.
Until Amy shows up and talks him out of it.
Malefor from The Legend of Spyro trilogy is a shining example. He's such a good example, it's hard to tell what WASN'T a part of his plan did he really intend to kill Spyro in the raid or did he want him alive to set him free? Did Spyro really free Cynder or did Malefor let her free so he could use her to lure Spyro to the Well of Souls to free him? And to top it all off, the Hannibal Lecture he gives the two when they finally confront them even has them wondering whether they'd done anything but play right into his claws.
In BlazBlue, we have Hazama / Yuuki Terumi. While one of the most powerful people in the world, Hazama has manipulated dozens if no hundreds of people into furthering his evil deeds. He even ends up outwitting an omniscient supercomputer that has three minds and runs reality. Just don't mention a certainsquirrel girl to him.
There are two real chessmasters in Eien no Aselia, and in general they don't really show up until the last 15% of the game. Temuorin is the big bad and set up the whole plot and Tokimi interfered so that the game doesn't get a downer ending.
Lord Alden in Vanguard Bandits is a literal chessmaster, being the best player on the continent and rumored to be undefeated. Then Milea beats him in her second time playing the game at all. Meanwhile big bad Faulkner, is more of the moving and controlling of wars type of Chessmaster. And he's very, very good at it.
The Sith Emperor of Star Wars: The Old Republic managed to be the Man Behind the Man for nearly all of the major events of the galaxy since the Exar Kun War, including all of the events in the Knights of the Old Republic series. He manipulated theMandalorians into attacking Republic space leading them into the Mandalorian Wars, a devastating war which he orchestrated entirely to lead Revan to him, who he took as his apprentice and sent off to find the Star Forge. When this failed due to Malak's betrayal and Revan's subsequent redemption, he set up puppet leaders on Republic worlds on the Outer Rim, infiltrated the Jedi Order, and rigged the Mandalorian gladiator tournament to place a Sith agent as the new Mandalore. All of this was in preparation for their strike on the Republic border worlds, in which he struck while the Mandalorians (under the leadership of aforementioned Sith agent) blockaded Coruscant and disrupted Core World trade routes. At the time of the first cease-fire, his Sith Empire controlled nearly half of of the known galaxy—the closest any Sith Lord has gotten to conquering the galaxy until Emperor Palpatine himself, nearly four millenia later.
Whether played on the Light Side or the Dark Side, the Sith Inquisitor is not too far behind in this department; having risen from a Slave to Dark Councillor over the course of their storyline and even leading the entire Empire along with Darth Marr as of the end of Rise of the Hutt Cartel expansion. Only fitting, since the class was inspired by Emperor Palpatine.
Lord Fain of Lusternia. Ostracised by his fellows Gods eons ago for his questionablemethods, upon his return to the First World he adopts the guise of a shadowy manipulator, using mortals and other Gods as tools to carry out his complex plans. Though progress through his service is characterized by chess motifs, it's just flattery designed to ingratiate him to his more competent followers - to Fain, everyone is a pawn.
Master Li from Jade Empire. They don't call him the Glorious Strategist for nothing.
In Diablo II, most of the plot and background involving apparently fluctuating fortunes for all sides in the conflict between the Burning Hells, the High Heavens, and the humans in between, including significant losses for the Three Prime Evils Diablo, Mephisto and Baal along the way, turns out to have been all part of the long-term plan of the Prime Evils themselves. This trend continues in Diablo III.
The ending of Ghost Trick reveals that the course of the entire game is orchestrated by Ray, who is actually Missile from an Alternate Timeline where he did not have the necessary ghost tricks to save anyone, so he goes back in time and waits for ten years for the right moment to come around again, so he could manipulate Sissel's self-interest into saving Lynne and everyone else that could be a lead in Sissel's Quest for Identity.
Ganondorf from The Legend of Zelda series tends to stay two steps ahead of Zelda and Link, even though he eventually gets defeated in the end. Some of his grand schemes include the following:
The Legend of Zelda: Ocarina of Time: Ganondorf seeks entry into the Sacred Realm so he can claim the Triforce. The entrance is barred by a lock requiring 3 Spiritual Stones and the Ocarina of Time. He allows Link to collect the stones and knew that Zelda would entrust the ocarina to him. Using this to his advantage, he simply waits for Link to bring all of items to the Temple of Time, waits for Link to lift the Master Sword, and then waltz in to steal the Triforce right in front of him after the sword puts Link in a deep sleep. Ganondorf only obtains the Triforce of Power and he knew Zelda held the Triforce of Wisdom while Link held the Triforce of Courage. Rather than taking Link head on or endlessly search for Zelda, Ganondorf lets Link undo the corruption in the temples so that Zelda could be lured out of hiding, making her believe that Link was making progress. He is proven right and he snatches Zelda away to lure Link to him, having all 3 Triforce pieces in one place.
The Legend of Zelda: The Wind Waker: Ganondorf's powers are sealed by the Master Sword and the sword needs to be removed from its shinre to restore his powers. Already knowing firsthand at what the sword can do to him, Ganondorf kills the two sages that are praying for the Master Sword, which is the source of its power. By doing so, the Master Sword would be nothing more than a normal sword. He knows Link would go and obtain the sword to strike him down with, so he lets Link go through his trials to reach the sunken Hyrule and unsheathe the sword. Ganondorf gets his power back and Link can't stop him due to the sword having no power left. Knowing that Zelda has the Triforce of Wisdom and Link has the Triforce of Courage, he lets Link go around the Great Sea obtaining the Triforce fragments and waits for him to return to Hyrule to see Zelda. Once Link does so, Ganondorf snatches Zelda away and then he successfully extracts Zelda and Link's triforce pieces to form the complete Triforce. If the King of Hyrule hadn't stepped in to make his wish to the Triforce first, Ganondorf would have succeeded in his plans.
Super Smash Bros Brawl had a single-player mode named the Subspace Emissary that actually had a plot, and a good one too, about the various heroes banding together to stop the world being destroyed. In this mode it turned out that King Dedede, of all people was the one with the best plan: he protected himself by appearing to be a bad guy, created a backup reserve so that if the rest of the heroes were wiped out then there could still be some left who were ignored before but could now take up the quest and incapacitated some of the other villains as he did this. He did this with badges on a timer that could restore the defeated fighters he had collected for safekeeping in his castle back to life, so that they would be safe until the time was right and they were needed. No-one saw this coming - not even smart characters like Ganondorf. Read the above entry on legend of Zelda, and know that Ganondorf was Out-Gambitted by this guy.
Mannimarco. In Online, he successfully plays Varen and the other four companions into getting the Amulet of Kings for him, allowing his Worm Cult to rise to power and kicking off the game's plot. In the same game, Meridia uses you (her own words) to build up an army and end the Planesmeld that Mannimarco is attempting.
The Daedric Prince Mephala, also known as the Webspinner and the Lady of Whispers, is known for her complex, long-reaching plans that are likened to spider webs.
MAG ISA — We have an unnamed reptoid (or demon) villain who seems to be calm even though the mind-control experiment has seemingly failed. Is it because... he's got another plan and its all a diversion?
In The Order of the Stick, Lord Shojo provides an interesting example of the non-villainous chessmaster, ruling Azure City and the Sapphire Guard with the aid of a series of deceptions.
And Nale, especially at the Cliffport arc, gives us the more traditional villainous one.
In the SNAFU hosted webcomic Grim Tales from Down Below, Grimm's journal reveals that Mandy, had planned a series of events to convince Grimm to give Billy his powers for a day. Then when done, she convinces him to give his powers to her to make it fair. Later, while snooping through her room, Grimm finds plans for initiating the 9/11 attacks on the World Trade Centers and Pentagon. Her plans also included the United State's response: Operation Iraqi Freedom BEFORE it happened.
Yukizane Masamune from No Need for Bushido, is also one of the few 'good' Chessmasters. He starts out in the series as being questioned on his leadership capacity due to his silliness and focus on playing Go (the Japanese answer to chess) as opposed to grunting manly and flexing. He, however manages to shine several times and manages to deceive a ninja.
The nigh-omnipotent AI Petey from Schlock Mercenary doesn't have a chessboard (although one strip features him playing checkers). One of his most complicated capers involved:
convincing all AIs to join him and mutiny against their captains, forming an instant galactic power for the purposes of combating an enormous threat to said galaxy.
Refused to pay the main characters for their ship, which blew up while carrying out his orders, then bribed a few councilmen to get them a new one anyway (at the expense of most of their savings). While keeping it all under the table in an attempt to force the company's AI to act as his spy.
Manipulated the government into hiring the (now short-on-cash) main characters to destroy a reality-TV network.
When the main characters got in trouble carrying out his gig, bailed them out with blackmail (after playing with their heads) and turned it into his own form of leverage on them.
The new ship AI 'Tag" finished to discover his true plan but only revealed the Social Ingenering from the government to let Petey know that he know he is the one the manipulated them into it. (ironicly the only clue that permit to the AI "Tag" to come to this conclusion was the analysis that the UNS government leadership is too short-sighted to plan that much.
In Erfworld, Charlie manages to manipulate circumstances - WARS - so that he will * always* end up on top. And he gets paid to do it.
"When you're working for Charlescomm, you'll learn. We prefer to play games that don't even contain a losing outcome. You see?"
"Yeah, yeah... you turned it into a no-lose situation by rejoining him."
"Oh no! No, I got paid to turn it into a no-lose situation. :)"
Biggs from Dan and Mab's Furry Adventures appears to be leaning in this direction. Even his sister, who is well-aware of his deviousness, falls for his tricks.
In spite of her misleading middle name, Pandora Chaos Raven of El Goonish Shive is the epitome of this trope. As an Immortal who has lived for millenia, her joy comes from notknowing what will happen next. Despite this, her actions are cold and calculated, and she pulls the strings of everyone she meets. Her tendency to stay behind the scenes is not due to any sort of weakness (Immortals possess near god-like power when on the Spirit Plane, and can use magic without being detected), but rather because the other Immortals get seriously pissed off if one does anything more than empower or guide people on the Physical Plane. That, and doing everything herself would just be boring to her.
Sonorous Aria, from Keychain of Creation, is stated to be one. Most of her chessmastery is offscreen, so far.
Marena: Everything she does is layer on layer of sheer deviousness.
Aria: Now, a feast! Lavish meals and fine drinks for everyone! Then: Party games!
Marena: She's up to nine layers already.
Aria: Extra drinks for the handsome bearded fellow in the corner!
Sluggy Freelance has Dr. Schlock, who seems like a harmless coward and Chew Toy with some minor Manipulative Bastard tendencies for a long time until Hereti-Corp finally pushes him too far by becoming a never-ending threat to the one thing he cares the most about (his own well-being). At this point, pushed into a corner, he feels forced to execute a plot to take over H-C and become the new Diabolical Mastermind behind its schemes, taking everyone by surprise and becoming the closest active character to a Big Bad in the comic.
Mojo Nixon from Princess Pi relies entirely on such plans committing evil deeds.
Skerry from Fite!, who uses a more generic gameboard rather than a chessboard. And really, he's just a doctor trying to wake Lucco from his coma.
In The Gamers Alliance, quite a few villains such as the Master and Iblis end up being quite good at manipulating events into their liking.
Bavandersloth in Angel Of Death pulled a pretty impressive gambit when he set fire to a police station to free Cody and kill detective Williams.
He's since been revealed to be planning something much bigger, though little is known about his new plan, save that it's objective is to turn the partial breaking of The Masquerade to the community of liches' advantage.
The Snake in Above Ground is a prime example, particularly because he can use magic to enslave others into doing his will.
The Emperor, leader of TAROT, has his fingers in nearly every criminal enterprise on Earth in The Global Guardians PBEM Universe. He's also got his fingers in nearly every major legitimate business enterprise on Earth as well. But then, what do you expect of a villain who is secretly an immortal Niccolo Machiavelli?
Nick Fury, Charles Xavier Sr., Forge, Tzigone, Vengeance and many others from Marvels RPG.
Regine in Addergoole - the school, and the students, exist to fulfill her plans.
The Architect (no, not that one) is hinted at being this in Shadowhunter Peril. However, he tends to go against the grain of the usual Chessmaster, as he is a genuine hero...he's just hiding a lot. He's actually a dimension hopper who has visited multiple universes and seen how events will play out depending on the choices made, so he's just really knowledgeable because of his experience.
A downplayed version gets subverted in Noob Season 2 finale. Two of the protagonists arrive at the only place where they can destroy an item that can put them in big trouble with the game authorities if discovered in their possession. Their former Guild Master, who wants them kicked out of the game, suddenly shows up, claims to have requested one of the MMORPG's Game Masters and plans to fight them while waiting for its arrival. When asked if he had been planning this all along, the former Guild Master replies that had just been spying on them and had come up with the plan on the spot.
Megatron of Beast Wars (and later Beast Machines), nearly ended the Beast Wars several times without leaving his hot tub. His ultimate weapon in the Grand Finale was, in fact, unwittingly furnished by an especially treacherous minion.
This role almost equally describes Tarantulas - who was a third party in and of himself, only pretending to work with the Predacons. He frequently even pulled one over on Megatron. At one point Megatron was sitting in his throne all impressed with how brilliant he was because he managed to a way to spy on Blackarachnia... and then we cut to Tarantulas spying on 'him.'
Her father, Evil Overlord Ozai, prefers the 'set the chessboard on fire and stand back laughing maniacally' approach, rather than messing about with all those fiddly little pieces. Until her Villainous Breakdown, Azula was a genuine (and, fortunately for Ozai, genuinely loyal) Chessmaster, so she got to do all the thinking.
Oh, Ozai can scheme fine (note the flashback in "Zuko Alone", where he very clearly exploits the weak spots of everyone around him to get exactly what he wants, and he managed to keep Azula under control for years- no mean feat!). Problem is, he's usually far too Drunk with Power to put that cunning to effective use.
Long Feng is very good at this too, keeping a city under his control for years with no one but his immediate henchmen the wiser. Really the only things keeping him from being a full fledged Magnificent Bastard are underestimating his opponents and not dealing well with sudden reversals- both of which Azula exploits....
Nerissa from W.I.T.C.H.'s second season is excellent at this. Her opposition is so thoroughly manipulated and played that despite the heroines' best efforts, they can only score the smallest of victories in comparison to her Magnificent Bastardry until the absolute end of the season... and were only then able to overcome it because Phobos is also good at chess and moved Nerissa into being absorb into her own Seal.
And then we find out that Will was manipulating Phobos like a fiddle, expecting him to betray them as soon as he had the Seal of Nerissa and easily putting him in a situation in which he would be defeated.
Cartman from South Park is the chessmaster in quite a few episodes.
Kyle's also shown to be quite capable of this, usually as direct opposition to Cartman. This is best seen in Le Petit Tourettes where he orchestrates a series of events to stop Cartman's faking of the disorder.
Anti-Cosmo and HP on The Fairly Oddparents could both qualify, usually tricking Timmy or some other third party into helping with their plans.
Xanatos isn't the only one Gargoyles has to offer. Fox, Thailog, and the Weird Sisters all play close to Xanatos's own level (Thailog and Fox have even bested him once each). Demona does some of this, though she's often so hot blooded and/or generally screwed up that she'll inadvertently sabotage herself. The Archmage doesn't have the same skill as the above, but he makes up for it with the sheer grandiose nature of his ambitions. Also, the Illuminati are implied to be a whole organization of these (at least, the ones at the top are).
James McCullen makes a good attempt at being this in the G.I. Joe: Renegades episodes, playing the Joes and Cobra against each-other but gravely underestimates who it is he's really up against in Adam DeCobray.
The Big Good, Princess Celestia, seems to be able to play this part when necessary, and is a rare benevolent example, working for the good of her subjects. She remains somewhat enigmatic, but seems to have wisdom fitting her millennial experience of ruling. She generally seems on top of everything that's going on, but has twice been shown doing some serious plotting: At the beginning of the first season, she pulled off a Gambit Roulette with the twin goals to a) make her student Twilight Sparkle get out more and make some friends and b) save the world. In the beginning of the second season, she performs a much simpler and more elegant single-step Batman Gambit with somewhat similar goals.
Celestia's old Arch-Enemy Discord — a being so dangerous and chaotically ingenious that he's actually able to catch her off balance and unnerve her — plays a round against her in "The Return of Harmony", with the main characters as pawns. (Although, if we're doing Chess Motifs, there's more than one reason why it might be fitting to call them Celestia's knights.note If you want to know... "pawns" is a metaphor for ones regarded as mere tools and not valued, and knights are also more powerful; Celestia actually does a "knighting" gesture to Twilight Sparkle before sending them out; and, of course, the characters in question are miniature horses.) Discord's plan aims at making sure that the ponies will be psychologicallybroken and unable to use the only thing that can stop him even after they do find it, although given his power, it looks like he's also doing things the hard way just For the Evulz.
Changeling Queen Chrysalis apparently planned an invasion of Canterlot (the pony capital) by deliberately scaring them to set up their defences, which only worked to her advantage when no-one knew she was already inside and working on something that would both give her great power and make sure the magical shields would fall at the right moment anyway.
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.
The Athenian politician Themistocles.
Richard Nixon was quite the chessmaster; he just forgot what happens when you let a minor pawn get up the board.
Bill Clinton fits this trope in his handling of the Monica Lewinsky scandal and his subsequent impeachment. What was intended to be Clinton's downfall instead lead to the downfall of his main political rival, Newt Gingrich.
William Pitt the Elder can be credited for founding The British Empire with conquests in the Seven Years War. He was Britain's and maybe the world's greatest Chessmaster of the eighteenth century and at least verges on being a Magnificent Bastard. Although that was more a case of exploiting a situation created by other politicians and rulers, a simple matter of shoring up one continental ally (Prussia) and concentrating Britain's own military efforts against France and her overseas empire. As a chessmaster, Pitt actually was outshone by Count Kaunitz, Maria Theresia's chief minister, who with a little help from the ineptitude of Frederick The Great (who managed to alienate France by an somewhat rash alliance with Britain) brought about the "Reversal of Alliances" before the Seven Years' War and managed to preserve the anti-Prussian alliance of several powers with greatly divergent interests (for starters, France had continually been at war with the Habsburgs for centuries) throughout most of the duration.
Mayor Cory Booker, depending on your Alternate Character Interpretation, and invoked indirectly by Ice-T ("Who is playing whom?"). After Conan O'Brian made a joke about Newark, New Jersey, Mayor Booker banned Conan from Newark Airport as a joke (which, required the TSA to clarify the counter-joke that no, a mayor cannot actually do that due to some people believing it to be true and being outraged). This resulted in a back and forth exchange between the two and ended up involving various other mayors of New Jersey (who sided with Conan... probably a trope) as well as Secretary of State Hillary Clinton (acting as The High Queen and telling the two to works things out as Conan had, she claimed, been acting differently due to a Real Life head injury). It resulted in the two airing out their 'grievances' on air... which involved Mayor Booker and six of his family as well as a few other New Jersey residents getting flown out to California for Conan's show, Conan and Universal giving a 100K donation (half Conan's personal money and half he got Universal to match... cause he's Awesome that way) to his charity, and a Newark joke box in which 500 dollars will be put in whenever Conan makes a Newark joke (which may or may not remain in continuity). To quote Conan, "Boy, that was a really expensive joke!"
Sun Tzu wrote a good guide on how to be the Chessmaster called The Art of War. Although the primary focus groups are generals and monarchs, nearly all of it can be generalized to any chessmaster activity.
Ironically, Sun Tzu's theories were almost all entirely influenced by go, which emphasizes misdirection and maneuvering, while de-emphasizing direct contact.
Niccolo Machiavelli's book The Prince is another guide to this trope (or else a parody of such politicians). While Sun Tzu focused more on military strategy, Machiavelli focused more on political strategy and how to use them in order to gain power and how to keep it for a long time.
The I Ching is a great book for Chessmasters.
Louis XI, King of France. Began his reign with a weak and small kingdom and a really powerful neighborhood (Charles le Téméraire, duke of Burgundy). He never fought Charles directly, hiring other countries (Switzerland, Flanders...) to finally kill him. When he died, Burgundy was a part of his kingdom. To be fair his kingdom was a bit stronger and more powerful than it had been under his predecessors (it was only his father who saw the English presence in France reduced to just Calais) and that Louis was helped to a large degree by Charles of Burgundy being his own worst enemy ("téméraire" means "reckless, rash" as well as "bold"). Also, the larger half of the duchy of Burgundy ended up in the possession of the another powerful neighbor, the Habsburgs.
Otto Von Bismarck, who orchestrated several wars among Europe to manipulate the populace and political power to unite the German states into the nation that exists today.
Ruben Amaro Jr., general manager of the Philadelphia Phillies, just might be one of these- now that a one-year process of trades and signings has left him with four of the best pitchers in baseball on his squad.
You could say that Sabean was a chessmaster during 2010. He made all the right moves during 2010 to win the World Series.
Red Auerbach, legendary coach and general manager of the Boston Celtics, was notorious for his Chessmaster tendencies (particularly in the form of elaborate trades with other teams). So much so that the process by which he acquired Larry Bird for the team was later banned by the NBA.
Many good basketball coaches fit the profile, but while legendary Phil Jackson is more famous to be an Old Master figure, it fits San Antonio's Gregg Popovich to the T. To the point that he got fined by the NBA because his management strategy (forcing some of his players to take a break) was supposed to be bad for business.
Stalin, at least in the way he orchestrated his rise to absolute power within the party apparat against rivals considered a great deal more brilliant or popular than himself, by forming various alliances against one rival, and then turning on his erstwhile ally after that rival had been eliminated.
Before his rise to power, Stalin was viewed as a petty clerk attending to meaningless paperwork, but nobody stopped to think of the extreme command he was developing of obscure laws. In some ways, his most potent ability was actually to Rules Lawyer his opponents.
Cardinal Richelieu of France was a startling example of this trope. The man was the world's first Prime Minister, and raised up alliance after alliance during the Thirty Years' War. He's the main reason that France became as powerful as it did.
Hitler started out as one, getting the people of Germany to give him the power, and the nations of Europe to just give him several nations before the war even started, but his ability to control the board quickly vanished after making one horrible choice after another. The British actually stopped their plans to kill Hitler because they figured out somebody who was competent would take his place.
Hitler was a brilliant politician and diplomat who became convinced that he was also a brilliant military leader; he wasn't. He was able to take Austria and Czechoslovakia without firing a shot, and then cut a deal with Stalin to isolate France (France was allied with Britain, but the British lacked significant land power), allowing Hitler to take Poland and France quickly and easily. The problem was that after the success of his military campaigns against Poland and France, and the early successes against Russia after Hitler broke his deal with Stalin, Hitler became convinced that he was also a brilliant military leader, and so abandoned diplomacy. All he had to do to win the war was either make peace with Britain before attacking Russia, or persuade the Japanese to also attack Russia, or both. If he had continued his diplomatic campaign, he would have won.
Benjamin Franklin spearheaded the early American response to British surveillance during the American Revolution by devising a system of counter-surveillance, securing aid, playing a role in privateering expeditions against the British, and waging a public relations campaign on behalf of the patriots. He also played the role of The Chessmaster during his and John Adams's diplomatic tour of duty in France, where Franklin's political savvy and understanding of how to play the game of court politics allowed him to secure French support for America during the Revolution.
Magic Johnson and the other owners of the Los Angeles Dodgers pulled off a series of well-timed waiver claims to land a trade in August the Red Sox best players
Sultan Abdulhamid, nicknamed "The Crimson Sultan" by the French, is an entirely forgotten member of Ottoman Monarchy. In his age, the Empire was little more than a wreck, its economy ruined and battered, yet he re-furnished it to survive another 2 decades. His extensive efforts to reduce debt and corruption, launching the first submarine and torpedo test shot in history, setting up thousands of schools and charities in an Anatolia untouched by previous sultans, a series of "firsts" in history, was overlooked by its resistance of Zionism (he kicked Theodor Herzl out when he heard the offer to buy Israel out of Ottoman land) and brutal suppression of every uprising due to nationalism. He organized a colossal spy network reaching into Europe, and thwarted countless attempts at assassination and manipulation. Had he an Empire with perfect economy, heavy military and solid demography, world conquest might not have been a distant possibility.
Ivar Boneless, if the Icelandic chronicles are correct. Having the handicap og missing his legs (or suffering from brittle bone-disease) he was not exactly the warrior type having to be carried around. Instead he embraced the wisedom aspect of Odin (and certainly the "Father of Treachery" aspect) and executed a Roaring Rampage Of Revenge by turing King Ćlla's people against him and carved a blood eagle on the king.
Brazilian history had the figure of the Duke Of Caxias. A man who fought in no less than seven wars, and never lost any of them. A tactical genius both in the battlefield (being always two steps ahead of his enemies, able to conquer any type of field, pulling outflanking moves out of his sleeve) and out of it (perfecting espionage tactics ahead of his time, acquiring allies by charisma and sowing disorder among his foes). It can be said the reason the Empire of Brazil lasted a century was, in great deal, due his influence.