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Tom Murphy, the Chess Hustler Who Will Stare Down Anyone

One of the best chess players in the world didn’t cut his teeth at stuffy tournaments—he worked his way up by playing in parks, in jail, and against anyone with a few dollars to bet

Getty Images/Ringer illustration

Gamblers is a podcast about men and women who live by their wits and wagers. People who bet big on themselves, and won. From golf and chess hustlers to a Super Bowl handicapper, Season 2 focuses on the fascinating lives of professional underground gamblers and how they make their money.

I’m at a Starbucks in the Old Town section of Chicago, on a rainy night. And I’m playing chess. For money.

The man I’m playing is a large and gregarious 65-year-old, wearing a heavy coat, a Chicago Bears beanie, and a surgical mask.

We’re playing for $10, but we aren’t playing straight up. I mean, I’m no patzer. I know my way around a chessboard. But the man I’m playing is no simple woodpusher. Hell, he’s famous. He’s been on magazine covers and featured in television commercials. And all the other players who have gathered at this all-night Starbucks to play chess on this rainy Friday night have taken a break from their own money games to sweat ours.

Because in order to make this game a tad bit more fair—since this guy is light-years better than me at chess—he not only has to checkmate me, but at some point in the game he also has to sacrifice his queen. For those of you who don’t know chess: The queen is the most powerful piece on the board. It’s as valuable as three of the other pieces combined. And in this game, he can’t just trade his queen for my queen. He’s gotta let me get her basically free and for nothin’. Giving up your queen is a huge handicap. And one that I, foolishly, thought might even the score between me and my opponent.

But even I, your humble host and chronicler of all manner of gamblers and hustlers, am capable of succumbing to wishful thinking from time to time. Even I, believe it or not, can get hustled.

The man who just hustled me out of 10 bucks has been doing this for the past 40 years. He’s not just a great chess player. He’s made some portion of his livelihood, and at times lived only on money he’s won, by gambling with people on chess.

Now I know what you’re probably thinking: People gamble on chess? And if your idea of chess is that it’s a game for geniuses and eggheads who play silently in coffee houses while smoking and reading Russian novels or some shit like that—well you’re only half right. Plenty of geniuses and eggheads play this game, but they don’t all come in the same shape and size.

There are really two worlds of chess: The world of professional tournament chess, marked by silent tournament halls and stressed-out, nail-biting players, and the world of park chess, marked by loud and boisterous kibitzing across the board by players who are moving their pieces furiously fast and always with money on the line. And though these two worlds often overlap, they are very, very different.

And the guy I just lost this game to? He lives in both of these worlds. He’s known in parks and all-night Starbucks in urban areas across America and international tournament playing halls alike. Over the past 40-plus years of playing chess, he’s befriended millionaires, dignitaries, political leaders, gang members, drug dealers, and he’s been a teacher and a role model for future champions and stars of the game.

This is the story of Tom Murphy, the philosopher king of chess hustlers.

To hear the full Tom Murphy episode, click here. Be sure to follow on Spotify and check back every Wednesday for new Gamblers episodes. This excerpt has been lightly edited for clarity and length.