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The Chessmaster / Fan Works

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Chessmasters in fanfiction.

Examples With Chess Motifs

  • Checker Monarch, the Big Bad of Getting Back on Your Hooves, who uses a chess board (chess itself being described at one point as her favorite game) as a representation of her plans to ruin her sister Trixie's life. Her full first name is actually Checkmate as well.
  • In Kyon: Big Damn Hero, Kyon is most definitely a Chessmaster, often using chess metaphors as he makes strategies.
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  • Herald, Big Bad of The Stars Will Aid Their Escape. He drops a few chess metaphors over the course of the story, as he manipulates everyone to follow his plan.
  • Jewel of Darkness: The mysterious leader of the White Glove qualifies as one of these, and is even seen playing a game with Vandal Savage at one point. Notably, Savage warns him that it's harder to treat people like pieces, as life isn't as simple as a chess game.
    • Midnight also counts, having learned the art of manipulation from Slade.
  • Having a drastically expanded role compared to his original appearance, Dragomon from Zero 2: A Revision has a giant chessboard that he uses to monitor the movements of the Digidestined and the other dark forces that the Digidestined are currently facing, patiently waiting for his next move to absorb the Child of Light.
  • Celestia in Rites of Ascension, who admits that due to working on her own for a millennium, it is hard to counsel with other ponies, even her own sister (who admits to sometimes feeling like just another piece on the board), discussing the matter with Twilight over a chessboard. (Notably, said discussion comes immediately after said tendency has circled back around to bite her in the cutie mark and upend her own plans, with Twilight calling her out on it.) She also notes Council Chairpony Charlemane as being similarly gifted (and that the two of them have had many worthy battles in both chess and the political arena).
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  • In Once More with Feeling Gendo and SEELE are joined (and opposed) by Original character Major General Shigeru Ishiba, the Director of the Japanese Defense Agency (Intelligence).
    The UN, formerly a simple world forum with delusions of power was, in half a decade turned into a powerful body with delusions that it was a world forum as SEELE moved the pieces on its chess board patiently, taking control behind the scenes to divert the resources they needed to GEHIRN and then NERV and the Human Instrumentality Project.
  • Child of the Storm has a truly epic Gambit Pile Up (it is the only work of any kind to have its own Gambit Pile-Up page), meaning that loads of characters are this trope.
    • Loki is Reformed, but Not Tamed. Instead of resenting being in his brother's shadow, he is Thor's shadow. He put together an information network comprising the homeless, cleaners, janitors, taxi drivers, and the like, simultaneously creating an invisible network across the world while gaining a reputation for philanthropy. However, he acknowledges Odin as being even better, the latter able to make Loki do exactly what he wants with just three words.
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    • Lucius Malfoy is a master manipulator whom even Nick Fury (very grudgingly) takes his hat off to. In a number of months, he goes from sitting on his laurels to becoming Master of HYDRA and temporarily basically in charge of the entire world. However, he makes a fatal mistake or two, which leads to...
    • Lucius' somewhat-ally Alexander Pierce is the head of HYDRA within SHIELD, and just as good of a manipulator as that implies, even putting on an Affably Evil act good enough to fool other chessmasters like Albus Dumbledore and Nick Fury. He's even implied to have known about the Shadow Initiative after the Avengers fell, and said nothing so that he could take advantage of the chaos. However, Lucius' desperate phone call to him gets intercepted by Fury, who locks him up. Even then, Pierce stays alive by leaking just a few secrets here and there to his interrogators, making himself more useful alive than dead. However...
    • He gets cracked in minutes by Alison Carter, daughter of Peggy and Steve, though admittedly she does have a trump card. Later, it's revealed that she was able to pull a Batman Gambit on Nick Fury and Phil Coulson, without them even realising they were being manipulated, let along that she was involved. She separately states that while she was only ever Deputy Director of SHIELD prior to her retirement, not only was that because the WSC felt that a Director with the Carter name would be too powerful to control, but that if necessary, she could override the then Director in matters as significant as the discovery of Clark Kent. She's even implied to have mindwiped him.
    • Fury himself is, as per usual, no slouch. As Tony puts it, "his secrets have secrets." He even manages to catch Malfoy red-handed through patience, good timing, and a shrewd assessment of Malfoy's personality, nabbing Pierce at the same time. He and Loki even discuss chess metaphors early on, describing their allies and enemies as chess pieces.
    • And manipulating the heck out of absolutely everyone is Doctor Stephen Strange, seen at one point playing chess with Odin (and winning). He gets everyone from Badass Normals to the freaking Endless to do what he wants, often even when they know they're being manipulated and can't do anything about it, because he's arranged his plans so that whatever people choose to do, it will work out in his favour. As a result, the mere possibility of his involvement is Paranoia Fuel. The one time he hits a blind spot, he's still capable of highly effective Xanatos Speed Chess, and jumps right back on the ball afterwards. When confronting Chthon, who's just pulled a Villain Override and looks like he's going to win, the latter smugly asks if he has any last words. He does, actually. "Check." Cue Strange unfolding the last few steps of his plan, ending it with a soft and triumphant remark of, "Check. Check and Mate."

Examples Without Chess Motifs

  • The My Little Pony: Friendship Is Magic crossover story A Hollow in Equestria portrays Princess Celestia as attempting to be this, and failing miserably at every turn.
  • Ancient Sins: Despite never comparing his actions to a game of chess, Dante creates numerous variables that come into play much later. He later uses this to aid the heroes after his Heel–Face Turn, but with less powerful results.
    • Possibly the only one who can rival Dante's chessmasterness is The Nothing/Tadmir, who has set events in motion that cause hundreds of different things to happens, all of which she predicted.
  • 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 Night Shadows 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."
  • Higher Learning:
    • Kaoru is trying to save humankind from Gendo and SEELE's plans. But in order to achieve that goal he works in the shade, manipulates and deceives people. He feels guilty about it, even though he is trying to save everybody.
    • Gendo proves to be better at it, though, when he realizes the pilot's teacher is up to something, so he has Kaoru abducted and puts a bullet in his knee.
  • Once More with Feeling:
    • Gendo and SEELE of course, but in this fic they are joined (and opposed) by Original character Major General Shigeru Ishiba, the Director of the Japanese Defense Agency (Intelligence).
    • Shinji is trying to become one, too. He is trying to outmaneuvering Gendo and SEELE using knowledge what they do not know he has. Time will tell if he is successful.
    • Early impressions don't bode well; Shinji helping to bond the Children together gives Gendo more levers to pull on, and mere moments after first meeting Shinji Keel discovered that the pilot knew far more than he should.
    • After the aforementioned meeting, Kaji outright tells Shinji to leave Gendo and SEELE to him and his colleagues, as attempting to deal with them himself is likely to end up in disaster for him, and to focus on his most important duty: piloting the EVA and defeating the Angels to prevent them from causing the Third Impact.
  • Calvin slowly develops into this over the course of Calvin and Hobbes: The Series.
  • 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.
  • Soul Chess used to focus on Lelouch and Aizen trying to fight for control over the Soul Society. Lelouch wins, but Aizen comes back from Hell for Round 2.
  • 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.
  • In Vinyl and Octavia Duel Destiny, Winter Snow reveals at the end that they were behind the events of the last two stories, with nopony realising so.
  • Soul Eater: Troubled Souls has Medusa Gorgon. Her plan is to destroy and ruin the DWMA, but she is very thorough in making that possible. Prior to the beginning of the story, Medusa retrieves her minions and brainwashes Krysa as well as turn Atlas, a giant Kishin Egg, into a mindless slave via Reanimation Magic and teams up with her younger sister, Shaula. In addition, she engineers a curse named Ouroboros. When she kicks off her plan, she has Eruka plant a fake VIP mission on the mission board that requests the presence of the Academy’s strongest students (Maka and the others, of course) to weaken the military overall. Aware of Lord Death’s and Stein’s keen eyes, she also wrote down the names of random students to eliminate suspicion. A disguised Free and Mizune ships them to Cobra Island, far away from home and cut off from communication. With Ouroboros, she removes a personality or ability from each and every person as they venture deeper into the island, and they don’t realize that until she’s forced to reveal her hand. Meanwhile, Shaula’s role is to promote infighting with her poison back at Death City, but when she fails, Medusa isn’t even fazed. She keeps things on Cobra Island going without a hitch and simply plots to take care of the rest when she’s done. As Chapter 33 shows, her master plan worked.
  • The Second Try: Subverted. Shinji and Asuka try to use their knowledge of the future and of NERV and SEELE's goals to outwit them and avert The End of the World as We Know It, but they're not Gendo Ikari and he eventually figures their secret out. Though they do have some small successes here and there, such as playing matchmaker for Toji and Hikari.
  • Shinji from Thousand Shinji trained for ten years to become one, learning the ways of plotting and scheming, and coming up with schemes within schemes within schemes to outwit his enemies.
  • Break Your Heart: Scootaloo, of all ponies. She carefully attempts to manipulate everything around her to better her chances of getting Rainbow.
  • Subverted in Advice and Trust. Gendo thinks he knows what's going on and that everyone can easily be manipulated to forward his goals, while being entirely unaware that he pretty much lost the second that Rei was ordered to hang out with Shinji and Asukua. Even if he could recover from that, every other major character is actively working against him, and he's none the wiser.
  • The Pieces Lie Where They Fell: Balance, who's been manipulating the situation for years - among other things, he guided events to make sure all six of the new Bearers would be in Canterlot at the right time, even if it meant disrupting their relationships with their families or other loved ones, and ensured Sharp Point and his gang would find the Bearers to give Night Blade his final chance at earning his Element.
  • Professor Vee in Anonymoose's Monster Girl Saga. Joining Count Aaron's forces against Yaleria? A distraction allowing him to uncover the Tower of Babel; essentially a doomsday device for all of Yaleria. Equipping The Count with nigh invulnerable Powered Armor? Just a test subject for his latest golem model, which glitches out at the worst possible moment for Aaron. Killing Nerick, another nigh invulnerable character right before he kills Laven? He only did just to steal the void crystal, the key for the Tower of Babel. Well done, Vee.
  • That to prior knowledge that Consensus has of events that had and will occur, every single Host in every iteration of the Communication quest becomes this quite easily. Thanks to the guidance of their backer, each one them are able to twist, bend, arrange, and/or guide events to their advantage. Every action they take makes sure to obtain and strengthen allies they otherwise wouldn't have gotten in the first place, cripple or outright take out key enemies that could most definitely cause problems in the long run, all the while elevating their powerbase far further than the positions their canon incarnations ended up in.
  • A Knight's Tale as Inquisitor features a Chessmaster operating in plain sight vs a Chessmaster controlling things behind the scenes: Arturia is constantly making moves and decisions with far more layers than at first glance in order to rally more and more allies to her cause and spread the overall influence of the Inquisition in the long run. At the same time, she knows that she's facing off against some unknown force - so far only named as the Elder One by its followers - that's manipulating multiple and major factions from the shadows, with its machinations resulting in the death of Divine Justinia V and countless others at the Mage-Templar Conclave explosion. Currently, the Elder One is playing a mean game of Xanatos Speed Chess thanks to the giant wrench in the Evil Plan due to Arturia's interference.
  • Prince Jewelius in Loved and Lost. In order to usurp his aunt Princess Celestia as Equestria's ruler, he sets the events of "A Canterlot Wedding" in motion by allying with Queen Chrysalis and helping her steal Princess Cadance's identity. However, as he becomes acquainted with Twilight Sparkle and witnesses the canon Plot-Mandated Friendship Failure, he devices a new plan and betrays the Changelings by helping Twilight and Cadance out of the crystal caves right before the invasion begins. He makes Twilight use the shrinking spell he showed her earlier to stop the Changelings, and he immediately afterwards tricks the shaken ponies to blame all the other heroes for the invasion, successfully turning the public against them and making himself "Holy King Jewelius I". However, Jewelius soon trips up by unnecessarily scheming a set of events that includes luring the banished heroes back to Canterlot and telling them everything about his evil actions because he wants to kill Cadance and Celestia.
    • The canonical Queen Chrysalis escapes from Canterlot's dungeons with her army and leaves one disguised Changeling behind to help Twilight (after she has come to her senses) escape to Ponyville with her parents and the Elements of Harmony. After Jewelius is cornered by the heroes, Chrysalis appears and has her Changelings kill the traitor, attempting then to subdue the heroes who are exhausted from fighting his minions. Unfortunately for her, Shining Armor and Cadance blast the entire Changeling army out of Equestria by Twilight's suggestion.
  • Turning Tables: In Chapter 57, it is revealed that Doctor Strange made Thanos see Tony as a threat so that Tony would be dusted in the Blip instead of Peter, having deliberately changed the variables when none of the many, many timelines where Tony lived through the Blip seemed to go well and made it so that Peter would be the one to discover time-travel and prevent the AT!Thanos from wreaking havoc in the main timeline. He admits that it was a gamble, but it still paid off in the end.
  • Erased Potential deconstructs the concept with Nedzu. Upon becoming aware of Izuku's existence, he immediately starts weaving plans around him, such as pointing Toshinori in his direction while hinting that he could be a potential candidate for One For All... despite being well aware that Izuku intends to become a Quirkless superhero. His various manipulations make Izuku increasingly paranoid, and seriously undermine others' ability to trust the principal. Even his own staff start regarding him with suspicion and disgust.


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