Horse racing is something like a religion in Hong Kong, whose citizens bet more than anyone else on Earth. Their cathedral is Happy Valley Racecourse, whose grassy oval track and floodlit stands are ringed at night by one of the sport’s grandest views: neon skyscrapers and neat stacks of high-rises, a constellation of illuminated windows, and beyond them, lush hills silhouetted in darkness.
On the evening of Nov. 6, 2001, all of Hong Kong was talking about the biggest jackpot the city had ever seen: at least HK$100 million (then about $13 million) for the winner of a single bet called the Triple Trio. The wager is a little like a trifecta of trifectas; it requires players to predict the top three horses, in any order, in three different heats. More than 10 million combinations are possible. When no one picks correctly, the prize money rolls over to the next set of races. That balmy November night, the pot had gone unclaimed six times over. About a million people placed a bet—equivalent to 1 in 7 city residents.
At Happy Valley’s ground level, young women in beer tents passed foamy pitchers to laughing expats, while the local Chinese, for whom gambling is a more serious affair, clutched racing newspapers and leaned over the handrails. At the crack of the starter’s pistol, the announcer’s voice rang out over loudspeakers: “Last leg of the Triple Trio,” he shouted in Australian-accented English, “and away they go!”
As the pack thundered around the final bend, two horses muscled ahead. “It’s Mascot Treasure a length in front, but Bobo Duck is gunning him down,” said the announcer, voice rising. “Bobo Duck in front. Mascot fighting back!” The crowd roared as the riders raced across the finish line. Bobo Duck edged Mascot Treasure, and Frat Rat came in third.
Across the road from Happy Valley, 27 floors up, two Americans sat in a plush office, ignoring a live feed of the action that played mutely on a TV screen. The only sound was the hum of a dozen computers. Bill Benter and an associate named Paul Coladonato had their eyes fixed on a bank of three monitors, which displayed a matrix of bets their algorithm had made on the race—51,381 in all.
Benter and Coladonato watched as a software script filtered out the losing bets, one at a time, until there were 36 lines left on the screens. Thirty-five of their bets had correctly called the finishers in two of the races, qualifying for a consolation prize. And one wager had correctly predicted all nine horses.
“F—,” Benter said. “We hit it.”
It wasn’t immediately clear how much they’d made, so the two Americans attempted some back-of-the-envelope math until the official dividend flashed on TV eight minutes later. Benter and Coladonato had won a jackpot of $16 million. Benter counted the zeros to make sure, then turned to his colleague.
“We can’t collect this—can we?” he asked. “It would be unsporting. We’d feel bad about ourselves.” Coladonato agreed they couldn’t. On a nearby table, pink betting slips were arranged in a tidy pile. The two men picked through them, isolating three slips that contained all 36 winning lines. They stared at the pieces of paper for a long time.
Then they posed, laughing, for a photo—two professional gamblers with the biggest prize of their careers, one they would never claim—and locked the tickets in a safe. No big deal, Benter figured. They could make it back, and more, over the rest of the racing season.
Veteran gamblers know you can’t beat the horses. There are too many variables and too many possible outcomes. Front-runners break a leg. Jockeys fall. Champion thoroughbreds decide, for no apparent reason, that they’re simply not in the mood. The American sportswriter Roger Kahn once called the sport “animated roulette.” Play for long enough, and failure isn’t just likely but inevitable—so the wisdom goes. “If you bet on horses, you will lose,” says Warwick Bartlett, who runs Global Betting & Gaming Consultants and has spent years studying the industry.
What if that wasn’t true? What if there was one person who masterminded a system that guaranteed a profit? One person who’d made almost a billion dollars, and who’d never told his story—until now?
In September, after a long campaign to reach him through friends and colleagues, I received an email from Benter. “I have been avoiding you, as you might have surmised,” he wrote. “The reason is mainly that I am uncomfortable in the spotlight by nature.” He added, “None of us want to encourage more people to get into the game!” But in October he agreed to a series of interviews in his office in downtown Pittsburgh. The tasteful space—the top two floors of a Carnegie Steel-era building—is furnished with 4-foot-tall Chinese vases and a marble fireplace, with sweeping views of the Monongahela River and freight trains rumbling past.
Benter, 61, walks with a slight stoop. He looks like a university professor, his wavy hair and beard streaked with gray, and speaks in a soft, slightly Kermit-y voice. He told me he’d been driven only partly by money—and I believed him. With his intelligence, he could have gotten richer faster working in finance. Benter wanted to conquer horse betting not because it was hard, but because it was said to be impossible. When he cracked it, he actively avoided acclaim, outside the secretive band of geeks and outcasts who occupy his chosen field. Some of what follows relies on his recollections, but in every case where it’s been possible to corroborate events and figures, they’ve checked out in interviews with dozens of individuals, as well as in books, court records, and other documents. Only one thing Benter ever told me turned out to be untrue. It was at the outset of our conversations, when he said he didn’t think I’d find anything interesting to write about in his career.
Benter grew up in a Pittsburgh idyll called Pleasant Hills. He was a diligent student and an Eagle Scout, and he began to study physics in college. His parents had always given him freedom—on vacations, he’d hitchhiked across Europe to Egypt and driven through Russia—and in 1979, at age 22, he put their faith to the test. He left school, boarded a Greyhound bus, and went to play cards in Las Vegas.
Benter had been enraptured by Beat the Dealer, a 1962 book by math professor Edward Thorp that describes how to overcome the house’s advantage in blackjack. Thorp is credited with inventing the system known as card counting: Keep track of the number of high cards dealt, then bet big when it’s likely that high cards are about to fall. It takes concentration, and lots of hands, to turn a tiny advantage into a profit, but it works.
Thorp’s book was a beacon for shy young men with a gift for mathematics and a yearning for a more interesting life. When Benter got to Las Vegas, he worked at a 7-Eleven for $3 an hour and took his wages to budget casinos. The Western—with its dollar cocktails and shabby patrons getting drunk at 10 a.m.—and the faded El Cortez were his turf. He didn’t mind the scruff. It thrilled him to see scientific principles play out in real life, and he liked the hedonistic city’s eccentric characters. It was the era of peak disco, with Donna Summer and Chic’s Le Freak all over the radio. On a good day, Benter might win only about $40, but he’d found his métier—and some new friends. Fellow Thorp acolytes were easy to spot on casino floors, tending to be conspicuously focused and sober. Like them, Benter was a complete nerd. He had a small beard, wore tweedy jackets, and talked a lot about probability theory.