Chess is the King of Games. It just is. It’s not Buckaroo. It’s not Kerplunk. You don’t see political strategists huddled in a bunker in the Pentagon trying to model geopolitical implications by extracting a plastic stick from a tube so that the marbles don’t fall. No. They play chess.
Chess is the King of Games because it is a map.
If we look at the brief history of chess we see a game that evolved out of chaturanga in 6th century India. It spread to the Persians. T...
Chess is the King of Games. It just is. It’s not Buckaroo. It’s not Kerplunk. You don’t see political strategists huddled in a bunker in the Pentagon trying to model geopolitical implications by extracting a plastic stick from a tube so that the marbles don’t fall. No. They play chess.
Chess is the King of Games because it is a map.
If we look at the brief history of chess we see a game that evolved out of chaturanga in 6th century India. It spread to the Persians. Then the Arabs got a hold of it. Then it made its way to Europe, where the Europeans, in their infinite wisdom, decided what the game really needed was a phenomenally powerful, hyper-mobile Queen, presumably because medieval European men desperately needed a strong maternal figure to tell them where to go and who to kill.
But through all of these iterations, from the dust of India to the pristine digital boards of chess.com, chess has remained fundamentally the same thing. It is a map.
A map… of POWER.
Become a member to watch the video essay here
Members get access to all my videos, essays and posts
Just let that sit there for a minute. A map of power. If you’ve come here for a whimsical romp, you’re in the wrong place. We’re doing structural analysis of power dynamics using board games. We’re doing the coolest scifi novel ever written about gameplayers. And we’re doing a brutally honest look at Why Leftists Always Lose.
But first we need to talk about Contrapoints.
Buckle-up.
Contrapoints: The Online Left’s Token Liberal
The Liberal centrist is a dying breed. They stay on their reserves in the mainstream media, CNN, MSNBC, The New York Times. Channels nobody watches. Newspapers nobody reads.
Meanwhile the Left, the actual Left, is online. And the online Left is very VERY Left wing. If you’re outraged by Hasan Piker you need to know he is the LEAST Left the online Left gets.
And with good reason. Gen Z and the rest of us have been living through the “slow cancellation of the future” named by the much missed Mark Fisher.
A future imagined in the 60s and 70s built on widespread redistribution of wealth has been replaced with an 80s cyberpunk future where a tiny oligarchy uses all the money to build the torment nexus.
It’s no surprise the most googled subject among unemployed young people is how to build a guillotine. The online Left has formed from ideologies of utopian socialism, Marxism and anti-Imperialist Leninism that were made for such unequal times.
And that, to be perfectly blunt, do not have the best track record of success.
Which brings us to Natalie Wynn, AKA Contrapoints.
The Left’s answer to the shrieking hysterical vitriol of Right wing streamers is…the gentle understated irony of the video essayist.
Contrapoints is, or was until more recent entrants like FD Signifier, the biggest YouTube video essayist on the Left. Kind of.
In her own words Contrapoints costumed, trans identity videos are “communist coded” attracting a much more Left audience than her actual politics. Wynn describes herself the social democratic end of liberal, but to her detractors she is just plain vanilla liberal.
A shitlib, as they say on the Left, that uses such terms for anyone right of Lenin.
Which makes Natalie Wynn the online Left’s token liberal, trapped in an endless, agonizing cycle of “audience capture” as her incredibly well-lit, feature-length theatrical video essays are ever more centrist, while the audience goes ever further Left.
If we summarize the “Contrapoints controversy” – and frankly, pick your era, pick your specific cancellation, it’s a repeating fractal of minor grievances – it usually boils down to Natalie suggesting that perhaps, occasionally, engaging with electoral politics or dealing with the world as it actually exists, rather than how it exists in a 90-page zine about anarcho-syndicalist polycule farming, might be a good idea? For this, she is routinely ritually humiliated.
But the anger directed at Contrapoints isn’t actually about Contrapoints. It’s about the fundamental, irreconcilable and quite valid animosity the Left holds towards a liberal centre that cannot admit its own part in creating the fascist revival of MAGA and Trump, cannot say the letters g e n o c i d e and Gaza in the same sentence, still believes the answer to everything is to go back to the 90s and still, basically, loves capitalism.
Contrapoints carries the can for all liberals, who are still the vast majority of the not so online public. Because she says the things that the majority actually thinks about today’s online Left.
That you’re unrealistic. That you just don’t understand the position on the Chess board. If we let you play, you will lose.
Because liberals, you see, want to win at Chess.
Leftists want Chess to fuck off and die.
How Chess Models Power
Let’s look at the map. Let’s look at how chess actually models power. It does so through four fundamental concepts. Position, Materiel, Initiative, and Checkmate.
Position. Where are your pieces? Do you control the center of the board? In warfare position is geography. Do you hold the high ground on the battlefield? But in politics, position is Institutional Capture. Are you in control of the House, Senate and Presidency? Or is your total influence some underfunded NGOs and academic departments in Gender Studies?
Materiel. How many pieces do you have on the board? Have you got your rooks? Your bishops? Or are you down to a single, traumatized pawn shivering behind a king who has completely lost control of the situation? Materiel in politics is people and capital. How many senators and judges do you have? Who are your billionaire backers?
Initiative. Who is doing the doing? Are you dictating the pace of the game, forcing your opponent to react to your threats? Or are you constantly on the back foot, defending, scrambling, apologizing? Initiative in politics is the news cycle. It is the narrative. Donald Trump is incompetent and most things, but his political brilliance is in winning the narrative, and holding the initiative.
Checkmate. The end. The absolute cessation of the opponent’s ability to resist. The realization that there are no legal moves left. In Chess the king is never destroyed. He is trapped. The aim of politics is not to destroy but to entrap your opponents and make them pieces in your in future battles.
Now, imagine politics in the year 2026 as a massive game of chess. Played on a board of near infinite size, with a vast number of players and pieces that all have their own agendas. Keep that in mind, we’re going to think about a game like that very soon.
With a few exceptions, like New York mayor Zoran Mamdani, the Left seems determined to lose at chess, by adopting strategies that cannot win.
The Right-wing Advantage and the Liberal Game
Here is the brutal political reality. The Right have a massive, almost insurmountable advantage in this game. Why? Because all they do is play to win.
The Right don’t care if the knight is supposed to move in an L-shape. If the referee isn’t looking, they will pick up the knight, smash it into the side of your head, and declare a glorious victory for traditional family values. They understand materiel. They understand initiative. They will sacrifice the pawns. My god, will they sacrifice the pawns. They will sacrifice all the pawns in their stupid red hats if it means the King gets a slight tax break. They play the map of power exactly as it is designed to be played and the win.
Liberals have it much harder. Liberals play to win ethically.
A liberal sits at the chess board and says, “Well, I could take that bishop, but has the bishop been offered a negotiated settlement? Have we done an environmental impact study on moving this rook to D4? Is it fair that the Queen has so much mobility while the pawns are downwardly mobile professionals? We should probably form a committee.”
The great triumph of liberalism – the reason we are not all currently living in a Mad Max dystopia paying tithes to a local warlord – is that liberalism triumphed by LIMITING the game. They introduced rules. They introduced HR departments, and human rights tribunals, and the concept of “democracy.” The launched a four hundred year offensive to make the game survivable and they won.
What a pragmatic liberal like Contrapoints is worried about, deep down beneath the corsets and the neon lighting, is that this hard-won advantage, this delicate, limited game of liberal democracy, will be entirely lost if we succumb to playing “Leftist Chess.”
Because she knows, as anyone who has spent more than fifteen minutes in a left-wing organizing meeting knows, that Leftist Chess is an unremitting fucking disaster.
How Leftist Factions Play Chess
If you want to know why Leftists always lose, you just have to watch them play the game. Let us break down the factions. It’s a very rich tapestry of failure.
And because I know how chill and open to critique Leftists factions are, I’m sure you’ll all take this with good humour.
The Utopian Socialists
They refuse to start the game. They look at the mass-produced, factory-molded board and declare it a symptom of profound spiritual alienation. They demand the board be remade as a circle, and the squares must be abolished, because alternating black and white squares enforces the brutalist, soul-crushing logic of the industrial loom. They sit there, cross-legged, weaving a new, non-competitive game out of locally sourced hemp, while the Right-wing player silently reaches across the board and takes their King.
The Orthodox Marxists
The Orthodox Marxist sits at the board, folds their arms, and does absolutely nothing. They have read the theory. They understand the dialectic. They know, with absolute scientific certainty, that the contradictions inherent in the opponent’s opening strategy will inevitably lead to the collapse of their position. Moving a piece would be adventurism. It would delay the inevitable historical process. The Conservative player checkmates them in four moves. They claim this checkmate proves they were right all along.
The Leninists
The Leninist arrives at the table and immediately establishes a “vanguard party” consisting entirely of their own Rooks. They execute the opponent’s pawns. Then, just to be safe, they execute half of their own pawns for exhibiting counter-revolutionary tendencies. They declare victory. Five years later, the Rooks realize they are now just playing capitalism, but with worse food and more concrete. The Right wing player wins by default.
The Stalinists
The Stalinist plays exactly like the Leninist, but after executing their own pawns, they meticulously airbrush those pawns out of all the official tournament photographs, and if you point out that the pawns used to be there, you are sent to a gulag located on square H8.
The Social Democrats
Ah, the Social Democrats. Bless them. They start the game by apologizing for being there. They try to implement a welfare state for the pawns, funded by a tax on the King’s diagonal movements. They are then brutally crushed by a nakedly aggressive Conservative Queen who has offshored all her wealth to a different board altogether.
The Democratic Socialists
The Democratic Socialists spend three and a half hours agonizing over whether moving a pawn is a betrayal of the working class. They hold a plenary session and after intense factional infighting, they reach a historic compromise where they agree to move a pawn one square forward only with a unanimous vote of other pawns, before realising all their pawns have now been taken by the Right wing knights. They write an academic paper about it.
The Anarchists
The Anarchists insist that the game can have no rules. They immediately declare the center of the board a temporary autonomous zone. Knights attempting to move in an L are beaten with sticks and anyone asking what the rules are is targeted with a bombing campaign to preserve the “principles of non-violence”. After declaring them terrorists the Right wing player has them rendered to a black site and rewrites the rules to his own advantage.
The Trotskyists declare their own side ideologically impure and form a splinter group before the game can begin.
The Internet Tankies lose every game specifically so they can accuse it of being a CIA backed colour revolution.
Hasan Piker chess is played on a pearl inlaid board with solid gold and silver pieces made by Cartier.
And the liberals. The dull, stolid liberals pop in their ear buds to listen to Ezra Klein and make one cautious, boring move after another, slowly, surely accruing material advantage, trading initiative for position, and close in on Checkmate…
…only to be removed from the players seat by a populist Left who want cheaper bus fares.
Contrapoints looks at this absolute circus of self-sabotage, ideological purity spirals, and historical LARPing, and she is right to doubt it. She is right to say, “Maybe, just maybe, we should try to actually win the game of chess we are currently forced to play, rather than pretending we are playing a different game entirely.”
But she, and other pragmatic somewhat dull liberals, miss something essential.
The Player of Games
If you want to understand the solution to all of this, you shouldn’t be reading political theory. You should be reading Scottish science fiction. Specifically, you should be reading Iain M. Banks.
In Banks’ 1988 novel The Player of Games, we are introduced to a society called the Empire of Azad. The Empire of Azad is held together entirely by a staggeringly complex board game, also called Azad. The game is the system, and the system is the game. Your social standing, your political power, your entire life is determined by how well you play Azad.
And that system is as brutal as they come. Late in the story we are shown the “secret channels” the Azadian Epstein class watch livestream torture and murder.
The protagonist, a man named Jernau Morat Gurgeh, comes from a post-scarcity, fully automated luxury space communist society called the Culture. Morat means “gameplayer”. Jernau Morat Gurgeh, the greatest gameplayer in the Culture, is sent to the Empire of Azad to play them at their own game.
He doesn’t go there and complain that the game is unfair. He doesn’t go there and write a blog about how the board is structurally oppressive. He doesn’t try to organize the game pieces into a syndicalist commune.
He sits down. He learns the rules. He plays. And he wins.
And in winning, destroys the game entirely.
There is a lesson here. Two lessons, actually. One for the Leftists, and one for the Liberals.
The lesson for Leftists is this: The only way to change the game is to win.
You cannot ignore the map of power. You cannot wish it away with purity tests and theoretically flawless critiques published in obscure journals. If you want chess to fuck off and die, you cannot achieve that by refusing to play. You have to sit down at the board, look the bastard across from you in the eye, and systematically, relentlessly dismantle their position. You have to master position, materiel, and initiative. You have to learn to corner your opponent, reduce their possible moves to zero and force checkmate. You have to beat them at their own game before you can flip the table, burn the board and shred all the pieces.
The lesson for Liberals, however, is this: The only way to really win is to transcend the system.
In The Player of Games, Gurgeh doesn’t just beat the Emperor of Azad by playing the Emperor’s style of game better than the Emperor. He beats him by playing his own style. He plays a style of game that reflects the values of his own, utopian, egalitarian society. He plays so fluidly, so beautifully, and so completely outside the narrow, brutal, fascistic paradigm of his opponent, that the game itself, and the Empire based on the game, are destroyed forever.
Liberals like Contrapoints want to protect the limited rules of the game because those hard won rules keep us safe. And they are right, in the short term. But in the long term, Chess always ends with carnage. You must play not to preserve a slightly better version of the game, but to transcend Chess entirely.
You have to play to win, yes. But you have to play in a way that proves a better world is possible. You have to master the board not to become the King, but to demonstrate that the very concept of the King is obsolete.
And you did this once. Liberals deposed the kings, established democracy, won human rights. Then you just fucking gave up. You decided your expensive cities and more expensive college degrees were enough.
You stopped playing to change the the game and started just…playing the game.
Chess is the King of Games. It is a map of power.
But maps can be redrawn. And Kings, historically speaking, can be removed from the board entirely. You just have to be willing to make the move.
Listen to the podcast audio here
