Alvin Clarence Thomas might have been one of the great American golfers of the 1920s, but it’s hard to tell; he refused to turn pro, he always said, because he didn’t want to take the cut in pay. Thomas, better known as "Titanic Thompson" ("Titanic" not, as some stories have it, thanks to an escape in drag from the doomed ocean liner, but from the way he kept sinking ‘em at pool; "Thompson" from a reporter’s error that he was fond of), could play golf right- as well left-handed. He was a poker shark, a pool hustler, a crack shot. The basis for Sky Masterson in Guys and Dolls, he never found a gimmick he didn’t like. Somewhere between the big con and the short con lies the proposition bet: a bet that you can do something or that something will happen. Titanic’s most famous proposition bet was that he could hit a golf ball five-hundred yards. The men who took the bet were a step ahead of the average sucker: they insisted he drive the ball at sea level, preventing him from winning the bet by simply hitting at the lip of the Grand Canyon. Titanic got the rules in writing, went to a lakeshore golf course in February, and hit a shot that skidded along the icy surface of Lake Erie for the required distance.

Titanic didn’t usually need to cheat (although he was apparently capable of stacking a deck of cards like nobody’s business). Mostly he seemed to rely on hanging around with a crowd willing to bet on anything and thinking through all the angles before anyone else realized that there were angles to think through. The essence of a proposition bet to a bookie is finding something unusual that can be bet on — how many field goals will be kicked, how long the longest drive of a golf tournament will be, how long the longest speech of Oscar night will last — and pricing it in such a way as to encourage people to lay down their money while ensuring that the bookmaker retains an edge. In a way, it’s like pricing insurance. When Lloyd’s of London agents priced insurance for sea voyages (a storm could destroy a huge investment in minutes; the modern insurance industry and the modern limited-liability corporation both grew out of responses to this sort of risky but potentially hugely profitable venture) or for something more unusual (the world’s largest cigar, sea-going bathtubs, Betty Grable’s legs), they were attempting to find a level at which they’d attract business and make enough money when their luck was good to counteract huge losses when their luck was bad. It’s the same process Ajit Jain‘s team of number-crunchers use when they offer insurance covering hole-in-one contest prizes, terrorist damages to World Cup games, or billion-dollar earthquakes; in a way, it’s what Thompson’s cronies did when they bet that he couldn’t guess how many watermelon were on a truck. Thompson, of course, had slipped the farmer $200 to have him count the melons in advance.

Titanic was a strong poker player, although the way Byron "Cowbody" Wolford tells it, it’s not clear how much he played poker to win and how much he played it to find takers for his proposition bets, although in a millieu where people would bet on which sugarcube a fly would land on, it’s hard to imagine he had a hard time finding takers. Among the high rollers he associated with, gambling seems to have been a mania akin to that of eighteenth-century England. Thompson made a living winning proposition bets involving pool, horseshoes, and golf, but older bettors sought more outlandish things; Ricky Jay writers in Jay’s Journal of Anomalies that

[p]erhaps the rage for proposition wagers paved the way for the peculiar profession of performance fasting. In 1771 a man from Helpston, near Stamford, was sad to have lived on drink alone for seven weeks and two days in order to win ten pounds (and to lose a great many more).

A hundred years later, fasting for money was in full flower. In 1880, the leading exponent of such performance was the English-born, American-schooled, and self-described "eclectic physician," Dr. Henry Tanner. Dr. William Hammond, debunker of the famous fasting girl, Mollie Fancher of Brooklyn, offered a stipend of one thousand dollars to anyone able to abstain from food and water for thirty days, but negotiations with Tanner grew contentious. Instead, Tanner undertook a fast of forty days, with small amounts of water…[h]eld before a paying audience at New York’s Clarendon Hall….

Titanic Thompson never had to starve himself for money, but his pickings grew slimmer after he became famous. In 1928, he had been playing poker with Arnold Rothstein, the gambler and organized crime pioneer best known for fixing the 1919 World Series. Rothstein had lost over $300,000 (a tenth of it to Thompson), and refused to make good, suspecting that the game had been rigged. Two months later, Rothstein was shot; two days later, on Election Day, he died. (Rothstein had gambled heavily on the outcome of the 1928 election; his death voided over a half-million dollars in winning proposition bets.) The trial made Thompson’s name and face famous, forever ruining his chances of convincing big New York money that his propositions were on the up-and-up. On the other hand, well into his seventies, Thompson could apparently find people to gamble against him on the golf course for ten or twenty dollars. The marks weren’t gambling with him any more; they were investing a few dollars for a story, the story of how they lost to perhaps the greatest gambler that ever lived.