Life is a Game of Chess: The Top Ten “Chessmasters” in Pop Culture & Literature

Posted by Thom Dunn

Life is a game of chess. Somethingsomething Queen takes King. I don’t know.

Chess, that master game of strategy, has always been a popular motif in literature and popular culture, especially in the realms of genre fiction, and the Chessmaster himself is often one of the most popular characters in the story. You know what I’m talking about – he’s smug, clever, full of secrets hid behind a smarmy little smirk. He knows the endgame well before the first pawn is placed, and he spends the entire story manipulating his opponent(s) to reach that one desired outcome, whatever it might be.

Sometimes he’s the most evil guy on the board, playing tricks and screwing over everyone to serve his mysterious purpose. Sometimes, he’s the greatest hero, who just knows what has to happen to ensure that the good guys win. Either way, we’re fascinated by him. Try as the reader or audience might, the Chessmaster always remains 3 to 4,000 steps ahead of them – he always keeps us guessing. And even when we think we’ve got him figured out, suddenly the Pawn becomes a Queen and the game is just beginning.

Here are (in no particular order) 10 of the more notable Chessmasters in the realm of pop culture/fiction. Granted, not all of them won in the end, but certainly all knew how to play the game. Some spoilers to follow, but I’ll try to avoid giving away too many details and ruining the fun.

WINSTON NILES RUMFOORD (The Sirens of Titan by Kurt Vonnegut) – While traveling between Earth and Mars, Winston Niles Rumfoord and his dog Kazak are caught in a chrono-synclastic infundibulum (gezhundheit), which essentially turns them into living waves of quantum probability, aware of the entire past, present, and future all at once. Of course, while omniscient, Rumfoord was hardly required to be honest. At the start of the novel, Rumfoord informs Malachi Constant that he will marry – or at least, be bred with – Rumfoord’s own wife in the future (on Mars, of all places). This statement alone kicks off a series of events that lead to, amongst other things, a Martian invasion of Earth, and a message in an alien language written across human history. And all of it to Rumfoord’s plan. It sounds a little ridiculous, sure, but only in that way that no one but Kurt Vonnegut, Jr. could pull off with such alarming humanity.

BENE GESSERIT (Frank Herbert’s Dune series) – A religious/political Sisterhood in Frank Herbert’s Dune series that have obtained great power and influence in the universe through the intense mental and physical conditioning of their members, as well as through many careful manipulations over thousands of years. The sisters of the Bene Gesserit (or witches, as many people believe them to be) were even able to control the gender of the children bore. This enabled them to carefully guide human progress through selective breeding, positioning their Sisters to reproduce with monarchs and leaders in effort to create the prophesied Kwisatz Haderach, their perfect superhuman savior, and the only male Bene Gesserit. Of course, all of this is in place well before the start of the first Dune novel, and the basic crux of the entire series is what happens when the machinations of the Bene Gesserit finally fail, and the Kwisatz Haderach arrives a generation earlier than expected.

MR. SINISTER (X-Men/Marvel Comics) – Sinister. Mister Sinister. What’s his game plan? As far as anyone can tell, Mr. Sinister sees the entire world and the course of human history as one big laboratory for a wacky science experiment. He receives his abilities from Apocalypse, then uses those same powers to prepare the destruction of Apocalypse – if he deems this necessary. He pulled many strings to ensure that the DNA of Scott Summers and Jean Grey combined to create the ultimate evolutionary weapon (including cloning Jean, just in case something happened, like maybe she became possessed by the Phoenix force and destroyed an entire planet. Or something). His wealth of secrets and knowledge is unrivaled, and he uses this as leverage to get what he wants (like “accidentally” tipping Cyclops off to the existence of his third brother. “Whoops”). But what does he want? That’s the fun part about Mr. Sinister – no one really knows (but we’re all pretty sure that it’s something insidious).

No pictures of John, but his story originally appeared in this issue of Galaxy

JOHN LeCONTE (If There Were No Benny Cemoli by Philip K. Dick) – This is one with which you’re probably less familiar. Themes of master manipulators and paranoia abound in the work of Philip K. Dick, but this short story might be one of the best examples of it. A politician on a post-nuclear war Earth, but his job (and the reconstruction process) are both threatened by the bureaucracy of the larger government, based on Proxima Centauri. When representatives from Centauri visit Earth to observe the status of the reconstruction – and possibly put leaders like LeConte on trial for war crimes – LeConte organizes an elaborate ruse using a deceased pirate radio host named Benny Cemoli. He manipulates the “flawless” computer news systems, as well as individuals, to create a story of Cemoli as a ruthless domestic terrorist threat, sending his political enemies on a manic chase through the country in effort to stop an enemy that doesn’t exist. He basically tricked his opponent into playing chess against an imaginary opponent instead. That’s one way to win, right?

OZYMANDIAS (Watchmen by Alan Moore) – In a world at the brink of nuclear war where superheroes still exist despite their outlaw status, how is the Smartest Man in the World going to stop us from destroying ourselves? Systematically wipe out all of the other players on the board that could possibly put a stop to your plans (for example, framing the only “man” more powerful than you as a walking cancer and tricking him into self-imposed exile offplanet) and then fake an attack an earth by a giant Cthulhu-esque psychic alien squid and unite the warring nations against this (fictionalized) extraterrestrial threat, and then kill anyone and everyone who was involved in any aspect of your scheme to make that no one ever finds out the truth. I mean, obviously. They don’t call him “The Smartest Man in the World” for nothing.

THE CIGARETTE SMOKING MAN (The X-Files) – Throughout the course of The X-Files, the Cigarette Smoking Man was almost always the man behind the curtain in some sense. Was there any significant event of the 20th century that the Cigarette Smoking Man didn’t have a hand in? As revealed over the course of the series, CSM/Cancer Man/CGB Spender was working for or with countless other shadowy masters, but he was always manipulating several sides of at the same time for some alternative agenda. He would feed Mulder information when it was convenient for him to do so – or he would destroy evidence and sabotage the case (or have someone else do it), if someone got too close to the truth. He was never outright evil – but he always had some kind of plan, and he knew how to make it happen.

Samuel L. Jackson makes one awesome Nick Fury

NICK FURY (Marvel Comics) – Simply put, Nick Fury is the ultimate badass. The top spy of the Marvel universe, every one of Nick Fury’s plans has eighteen other contingency plans, each accompanied by a dozen more back-up plans, just in case. Sometimes he might seem a bit insidious; other times he might be straight up lying. But all of Fury’s closest confidantes know that sometimes, you just have to trust the guy, because whatever he’s doing, he’s doing it for the greater good, and he’s been around the block enough times to make it work. Just check out the recently completed series SECRET WARRIORS, written by Jonathan Hickman, which depicts the ultimate battle between Nick Fury and his sworn enemy in HYDRA. There are wheels within wheels within wheels within wheels – and Nick Fury spins them all.

BEN LINUS (Lost) – Oh, Ben Linus. Every time someone trusts you, you somehow manage to screw them over. And yet, no one ever learns. The first thing he does is go undercover as another crash survivor to infiltrate the “Losties,” while having his cronies kidnap Walt to blackmail Michael into letting Ben Linus escape if his deceit didn’t work. Ben’s entire modus operandi for the show is to promise one thing to someone in exchange for a favor, only to somehow screw that person over on their end of the bargain. Granted, this came back to haunt him when Alex was shot and killed, but, you know, minor details. What makes Ben a great character is that everybody – even the viewer, to an extent – keeps falling for it, because somewhere deep, deep inside, there is a good intentioned person. Well, maybe. While ultimately (depending on your interpretation) Ben might lose the match, he knows how to prolong it by constantly moving himself in and out of Check.

Bonus Irony: the Fifth Season reveal that the entire cast had been manipulated by the Man In Black all along, who (amongst other things) tricked Ben into doing his dirty work for him by bringing Locke’s body back to the Island and killing Jacob.

EMPEROR PALPATINE (Star Wars series, created by George Lucas) – I’ve said it before and I’ll say it again: the best way to win a war (and, consequently, control of the entire galaxy) is to start the war yourself and then secretly control both sides. Okay, so I never said that before, but still. Despite what you might think about the Prequel Trilogy, Palpatine’s plan was ingenious. He manipulated events to cause the Clone War, secretly ran two opposing armies, which he used to wipe out his enemies on either side, and then used his public position as a Senator to elevate himself into a position of power, which he exploited to become Emperor once the war (that he himself single handedly started and ran!) was complete. Also, Force Lightning.

DUMBLEDORE (Harry Potter series, by JK Rowling) – The seemingly benign head master of Hogwarts, Dumbledore always knew what was going on. He knew that Voldemort was still alive, and that his power and influence wouldn’t fade away so easily, and spent the intervening years preparing for every possibility. From the mysterious gifts and information that he would provide for Harry as he (supposedly) turned a blind eye to the boy’s behavioral indiscretions at school, to his undercover allegiance with Snape, to, well, everything, Dumbledore was able to predict the events of Voldemort’s return in almost frightening detail. Dumbledore knew that some sacrifices would have to be made, but that there was only one way to defeat Voldemort for good. So next time a geriatric gay man in a silly wizard’s hat challenges you to a game of chess, you might want to pass.

Bonus Chessmaster: THE DEVIL – Isn’t this pretty much his original MO? Manipulating people into doing the dirty work for him, in order to get back at the big G-man? Both in the Bible, as well as over the course of popular literature, the Devil has been constantly playing a game of Chess against God, a sort of revenge for casting him out of Heaven (and other variations on the story). Whether or not God is actually is actually paying attention to/actively playing the game, that’s a whole other story. But the Devil just loves to use man’s inherent flaws against to get what he wants – whatever that might be.

Thom Dunn is a writer, musician and comic book fan. Follow him on Twitter (@thomdunn) and visit his blog at