The All-American Confidence Man

The gifted grifter who inspired Damon Runyon’s Sky Masterson was a fake from start to finish

Nearly everythingabout Titanic Thompson was fake. The bottlecap that he would bet you he could toss the length of a city block had a quarter nestled inside, which he’d put there while you weren’t looking. The caddie with whom he reckoned he could beat you and your partner was actually a regular on the PGA tour. Even his name was fake: The “Titanic” moniker earned in a bet, the surname a botch by reporters after he was connected to the murder of the man who fixed the 1919 World Series.

Here are the facts. Alvin Thomas was born in 1892 in the Arkansas backwoods, son of an alcoholic card cheat who abandoned him in the cradle. By the time he died, 82 years later, he had won and lost many millions of dollars as a gambler, bedded Myrna Loy and Jean Harlow, conned Al Capone, killed five men, spent years hustling pool with Minnesota Fats, and become the inspiration for the gambler hero of “Guys and Dolls.”

Master of the proposition bet—an art in which a hustler wagers that he can do something impossible, then does it—Thompson would as soon try you on for a dollar as for a hundred thousand. This was a man who would bet that he could throw a watermelon onto the roof of a building, then take an elevator to the top of a neighboring one and pitch it across, so satisfying his terms. His line—a variant on the classic grifter’s explanation that you can’t work an honest man—was simple: “Nobody ever got hustled who didn’t ask for it one way or another.”

What separated Thompson from his rivals was that he was a pure athlete as well as a pure con. Kevin Cook, a former Sports Illustrated editor, argues that Thompson was the equal of any golfer of his day—the last of the greats for whom tournament pay was just too low to be worth the effort. Thompson was also an expert marksman and world-class in horseshoes, coin-pitching, and card-flipping. He was just a cut below that at pool and poker. Thompson had the athlete’s capacity for learning by repetition, which served him well as he learned odds by dealing himself an untold number of hands of cards in hotel rooms.

Curiously, though—and Mr. Cook’s failure to really account for this is the main flaw in his highly enjoyable biography of the man—Thompson wasn’t a very interesting personality. A sort of elemental force, he seems to have cared about nothing other than rooking marks and keeping the company of teenage girls. This makes it difficult, in the end, to care about Thompson’s life quite the way Mr. Cook would like us to.

Soon after Thompson left home, at 16, he joined a traveling medicine show and began to amass the limitless arsenal of tricks with which he would later bilk suckers. The young grifter’s early travels took him all over the resort towns and bustling cities of the South and Midwest, where he earned his nickname. (“He sinks everybody,” one of his marks explained.) Thompson met his second wife and true love in Pittsburgh; she picked his pocket as he got off the train.

Eventually Thompson made his way to Chicago, where he traded secrets with Harry Houdini and took Al Capone for $500 by tossing a lemon weighted with buckshot onto the roof of a hotel. He then did a brief stint in California, learning the fine points of golf and winning the modern equivalent of millions playing poker. Along the way Thompson learned, several times over, that shooting a man who tried to rob your takings was surprisingly unlikely to rouse the ire of local law enforcement.

The only stage truly worthy of a man willing to make a chump of Scarface was, of course, New York City. Thompson was in his glory there in the 1920s, winning bets on anything you could put a dollar to and losing the takings at the track. A regular at the Times Square hangout Lindy’s, he ingratiated himself into the inner circle of Arnold Rothstein, the gambling kingpin who had bought the Black Sox.

This was the Thompson who inspired Runyon to write the story of Sky Masterson, his great and enduring fraud. And there you have the essential arc of an American life: An act of self-invention carrying an illiterate teenager out of the old, weird Ozarks to become famous on Broadway.

For a hustler, though, obscurity can be a good thing, and Thompson gained unfortunate notoriety after he rigged a card game so that Rothstein lost a half-million dollars he didn’t have. Not long after, Rothstein was shot, apparently by a goon in the employ of the gambler who had hosted the game. Thompson was called as a witness at the trial, and the ensuing newspaper coverage earned him both his new last name and an infamy he was never quite able to shake.

For decades to come, Thompson continued to make and lose stakes, marry teenagers and divorce them as soon as he impregnated them, and refine a dizzying number of scams. As Mr. Cook would have it, these were years in which a great hustler settled into a well-earned status as a legend. He was paid to lend prestige, for instance, to the inaugural World Series of Poker in 1970. As the years passed, though, he was reduced to openly cheating legendary card sharps like Texas Dolly Brunson. They let him get away with it—he was, after all, Titanic Thompson.

Early on, Mr. Cook draws a link between his subject and another fabled American grifter, William Thompson, who inspired Herman Melville’s “The Confidence Man.” More than anything else, Titanic Thompson seems a figure out of that book, a Satanic void in whom a pure love of the grift destroyed any trace of human feeling. In this way, too, he resembles a high-performing athlete—Michael Jordan, say, or Tiger Woods—for whom the need for victory by any means is so consuming that he can fail to enjoy or even notice an extraordinary life happening around him.

Mr. Cook argues that Titanic Thompson’s decline came about because “America changed and there was no more room for such a man.” This isn’t strictly true, as the NBA, Las Vegas and certain brokerage firms remind us. To the extent that it is true, though, it is not necessarily cause for nostalgia. An America that could produce a man like Titanic Thompson had nothing to be proud of.

Tim Marchman, Wall Street Journal


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