Titanic Thompson was a brilliant con man, a world class engineer of stunts and easily the most outrageous character you’re likely to encounter in a book of non-fiction.
This was previously published on Head Butler.
Titanic Thompson: The Man Who Bet on Everything By Kevin Cook
Sometimes what you want most from a book is to be able to sit back in a comfortable chair, smokes and drinks and snacks near at hand, and have someone tell you an evening’s worth of outlandish, improbable, impossible yet mostly true stories.
That’s what “Titanic Thompson: The Man Who Bet on Everything” is, for Alvin “Titanic” Thompson (1892-1974) was the greatest “proposition gambler” in American history—a brilliant con man, a world class engineer of stunts and easily the most outrageous character you’re likely to encounter in a book of non-fiction.
Each incident dazzles. Collectively, the stories make you sit back in a kind of dumb awe. And although Thompson’s immorality offends everything you believe in—first and foremost: the level playing field and respect for others—you kinda admire the guy. Because he was, at the very least, the Mozart of his trade.
Like: Thompson conned Al Capone out of $500.
Like: Arnold Rothstein, who fixed the 1919 World Series—Thompson double-crossed him.
Like: Thompson hired Lee Elder—who’d become the first black golfer to play in the Masters—to pretend to be his chauffeur. At a golf course, Thompson would make his pitch: “Heck, my chauffeur and I could beat your country club’s two best players.” And then they’d clean everybody out.
Like: Thompson bet that he could drive a ball 500 yards. Of course he didn’t say when. He waited until December, when Chicago freezes and Lake Michigan ices over. Then he drove the ball—onto the icy lake.
Like:Thompson could bring a quail down with a rock. At 50 yards, he could shoot a crow between the eyes.
Like: He married five times, and every bride was a teenager.
Like: He killed five men, and got off every time: “They’d all tell you they had it coming.” How did it feel to shoot five men? “It felt like good shooting.”
Kevin Cook, a former Sports Illustrated writer who had considerable experience with golfers and gamblers, is still shaking his head over all he learned about this legendary character. [To buy the paperback from Amazon, click here. For the Kindle edition, click here.]
Happily, Cook wrote his book in a style worthy of his subject. Here’s how it starts:
He blew into town like a rogue wind that lifted girls’ skirts and turned gamblers’ pockets inside-out. Tall and thin with a bland mask of a face, he had close-set eyes that looked a little dead, at least until he offered you a bet. Then those dark eyes sparked and he smiled like he had good news.
“Are you a gambling man?” he’d ask. “Because I am.”
Who was he? I mean, under the slickness. That’s the second level of the book, and it’s a mystery. Thompson’s father, a poker hustler, left his family the night his son was born. Alvin grew up poor, resourceful—and talented. “A deck of cards was an extended family to him, the only friends he ever had,” Kevin Cook notes. Though illiterate, he mastered percentages. He marked cards in a way that couldn’t be detected. He could deal from the bottom of the deck.
“Tall and thin with a bland mask of a face, he had close-set eyes that looked a little dead, or at least until he offered you a bet,” Cook writes. “Then those dark eyes sparkled and he smiled like he had good news.”
Thompson quickly moved beyond cards to “proposition gambling.” That is, you say you can do something impossible, something no one has ever done before—and then you do it. One of my favorites: Playing right-handed, he’d beat a golfer, then offer double or nothing to play the course again left-handed. His opponent went for it—too late he learned that Thompson was really left-handed Was he really that great a golfer? Indeed he was. As he told Ben Hogan, “Pro golf’s not for me. I couldn’t afford the pay cut.”
I’ll leave you with a bet that can make you a small fortune. You tell the sucker: “I can throw a watermelon to the roof of a 20-story building.” Then you take an elevator to the 21st floor of a building, walk over to a window and toss the melon to the roof of the 20-story building that’s conveniently right next to it.
Damon Runyon wanted to write his life story. Thompson declined: “Mine ain’t the kind of business publicity helps.” So Runyon made him the model for Sky Masterson, the high-roller in “Guys and Dolls.”
Over the decades, Thompson made at least $10 million. Of course he died broke.
Image of Titanic Thompson book cover presented under fair use agreement