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“I could open the case, have a peek, and sneak out again. Just a peek. No one would know…”

Uncle Dougie's Suitcase, Alastair Chisholm

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Somewhere This Way

I don’t usually cover nonfiction here on the site, unless there’s a strong connection to the world of storytelling. Titanic Thompson: the Man Who Bet on Everything both is and isn’t an exception to that rule.

Titanic Thompson, born Alvin Thomas, grew up in the early years of the last century, and became known as one of the greatest confidence tricksters of the era. He made millions of dollars through elaborate cons, and by hustling pool, poker and golf.

The path he cut through twentieth century America also brought him into contact with some of the period’s most famous and notorious characters: he was in on the poker game that led to the death of Arnold Rothstein, and he tricked $500 out of Al Capone over a bet regarding how far he could throw a lemon. He became the basis for the character of Sky Masterson in Guys and Dolls. He also found time to get married five times, and to kill five people.

Titanic’s success seems to have come from a variety of factors: he was naturally talented and dextrous, allowing him to master the sleight-of-hand needed in many of his tricks; he devoted long hours to practice, performing simple actions over and over until he had mastered the most unlikely abilities; he would put great energies into laying the groundwork for his proposition bets, often visiting the planned scene hours or days beforehand, rearranging signposts, planting props, and bribing bystanders. Finally, he had an ability with people, both understanding them and charming them, which allowed him to present his ‘proposition bets’ in just the right way. Here’s a typical story, that takes place during a poker game in a Toledo nightclub:

Ti wad twenty-seven, but the crooks all talked down to him. One night, taking a break to go to the bathroom in the cellar, grumbling to himself, he was startled by a rat. He bumped a crate that fell and pinned the rat to the floor. Watching the animal struggle, he thought there had to be a play in this.

He rejoined the card game, and soon enough another player got up to go to the toilet. “Watch your step down there,” Ti said. “That cellar’s crawling with rats. I swear I could go down there and kill one inside a minute.”

That got a laugh from the loudest gangster. “This kid thinks he’s the Pied Piper!” He asked Ti if he’d like to put his money where his mouth was. Ti bet every dollar he had and headed for the stairs.

“No tricks, kid,” the gangster said. “That rat better be warm. I ain’t paying off on some dead pelt you got in your pocket. And I’m timing you. You got sixty seconds.”

Titanic returned to the cellar. A few seconds later the poker players heard a gunshot. Ti came upstairs and dropped the still-warm rat in the loud man’s lap. They stopped calling him “Kid” after that.

In a story like Thompson’s, it’s never really going to be possible to separate fact from fiction. He was by profession a dissimulator, and always on the move to escape his own increasing fame. His victims, from whom many of these stories must originate, would also not be expected to underplay the ingenuity of the man who conned them. Even Cook’s afterword allows that there may be a little ben trovato in the anecdotes that make up the book. But that hardly matters: Titanic Thompson is about a legend as much as it is about a real man. It reads like a series of adventure stories, and like the best adventure stories it makes you want to believe every word, and induces a kind of nostalgia for an unlikely time when a man could come from nowhere to make his way around America, meeting everybody who was anybody, amassing and losing fortunes through skill, cunning, and marking cards, and encountering a never-ending supply of honourable gangsters who (almost) always paid up on losing a bet.

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