Stuff You Should Know: Hustling


Fascination with the art of hustling is at an all-time high these days. You can’t turn on the television or radio (if you still listen to the radio, anyway) without hearing some rapper or singer boasting about how tight their hustle is. The problem is, with so much talk about hustling, the term has become far too diluted.

Let’s get this out of the way right now, if you have a paper route or work at Target, you’re not a hustler. You just have a job. It’s not the same thing. You know who was a real hustler? Titanic Thompson was a real hustler.


Titanic Thompson (1892-1974) was the greatest gambler and con man in American history—the inspiration for the Broadway musical “Guys and Dolls.” If you want to learn about the art of hustling, reading up on Titanic Thompson is the way to do it.

Here are eight things you should know about hustling, straight from the play book of Titanic Thompson…



The way to hustle suckers is to bet you can do what seems impossible. So you set up a foolproof bet. Thompson would point to a highway sign that read CHICAGO 20 and say, “It’s not twenty miles from here to Chicago.” Other gamblers bet it was. Titanic won because he’d paid a road crew to move the sign five miles closer to Chicago the night before.

He also once bet he could throw a peanut across Times Square—he’d filled the peanut with buckshot.

Lose First


Titanic often lost bets. On the golf course he’d lose a $1000 wager, then say, “You were lucky! Let’s play for ten times as much—I’ll even play left-handed!” A natural left-hander, he finished $9000 ahead.

Charm ’em


His cons were so colorful and memorable that many of his marks felt they’d been touched by a sort of genius. Even after losing to him they’d tell Titanic stories for years, building his legend.

Sound Humble


Newspapers called him “the man who never loses,” but Ti told his marks he was luckless. He once fixed a horse race only to watch his horse break her leg on the homestretch. He lost $10,000 to a golfer who made a lucky putt with his eyes shut. (Of course, that golfer lost ten times as much to Titanic the next day.)

Live the Life

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He dressed the part of the prosperous gambler, sporting tailored three-piece suits, cool camel-hair coats and diamond rings. The diamonds weren’t just for show—if he went bust he could always sell or hock them to raise another bankroll. But like the pretty girls on his elbow, the diamonds signaled that he was no two-bit player. If you wanted to gamble with Ti, it had to be worth his while. He once won a restaurant on one throw of the dice. And when poker players asked, “What’s the limit in this game?” he said, “The sky.”

Hook the Big Fish


Titanic conned Al Capone and New York crime boss Arnold “the Brain” Rothstein. First he dared their underlings to play him, and cleaned them out. Then he said, “Isn’t there anyone in this town who bets big?” By the time he sat down at a card table with Capone and Rothstein, they couldn’t wait to take him on.

Know When to Move On


After he double-crossed Rothstein in the poker game that cost the Brain his life, Titanic testified in the Rothstein murder trial. Suddenly his picture was in the papers over the caption Unbeatable Gambler. “I famoused myself out of a good situation,” he said. But there were still places where nobody knew him. Rolling into a dusty town in his two-ton Pierce-Arrow, with his golf clubs, a shotgun and a suitcase full of cash in the trunk, he’d fill his pockets and hit the road before the police knew he’d been there.

Die Happy


They say every real gambler dies broke. Titanic, who rolled into New York in 1928 with a suitcase full of C-notes—almost a million dollars in $100 bills—died in a Texas nursing home 46 years later with $400 to his name. But he wasn’t complaining. He’d spent most of his last bankroll playing poker with other patients, and paying young nurses $100 at a time to take their clothes off and stand where he could see them.

Read more about Titanic Thompson at Special thanks to Kevin Cook, author of “Titanic Thompson: The Man Who Bet Everything” for his contributions to this article.