Billy Walters has always been good at keeping score. During childhood, this lent him a killer instinct in the bedraggled pool halls and bars of Munfordville, Kentucky. “I learned who craved competition and who crapped their pants in crunch time,” he says. “That knowledge made me dangerous from a young age.”
In his career as a gambler, meanwhile, it meant becoming one of the most successful sports bettors of all time, with a winning streak that lasted three decades (along with the rollicking, high-flying lifestyle this encouraged, of course). In a good year, Walters has said he’d pocket around $60 million in profits: a bounty that led rival gamblers to raid his trash and hack his phones in an attempt to deduce the source of his betting genius. (Amateur gamblers may decide simply to read his excellent new book, Gambler, instead.) Raised by his grandmother in a home with no running water, Walters set up a lawn-mowing business at seven and took on a paper route at nine — before becoming a teenage prodigy on the used-car scene, selling more than a vehicle a day and breaking all sorts of state records.
In the pages of Gambler, however, Walters keeps score in a different way — by chronicling the highs and lows of a quite remarkable life and career, one punctuated by bankruptcies and addiction and betrayal as much as colossal successes. “At my peak I was making a billion dollars a year in gross wagers,” he says. “I had 1,600 accounts around the world and a very sophisticated system in place to conceal who was behind those bets.” There is something genuinely Scorsesean about the swirling, swaggering melodrama of the entire tale — not least in its heady courtroom denouement, where Walters finds himself convicted for insider trading in 2017 at the age of 71. The case, which Walters describes, with some understatement, as “tangled and complicated,” notably sucked in golfer Phil Mickelson, a close associate of Walters, who the bettor feels let him down when he needed him the most, leading to a five-year sentence in a Pensacola prison camp. Mickelson’s personal testimony, Walters believes, would have plainly exonerated him. “Phil just had to publicly tell the truth and he wouldn’t do it,” Walters says. “He’s no longer a friend.”
Mickelson, a giant of the sport with a much-discussed gambling addiction, at one point allegedly approached Walters to help him put a $400,000 punt on a Ryder Cup tournament he was playing in. Walters advised his friend against the bet — but it would not be the first or last time that punters have leaned on him for counsel, in search of some magic formula or revelatory incantation.
His most-repeated advice, however, is more pragmatic and prosaic. “Do your homework. Be disciplined. Success has a lot to do with information,” he says. On the “big betting companies” that have recently exploded in the wake of legalized, app-based sports gambling, he is characteristically sanguine, too. “None of these companies, the DraftKings and FanDuels of the world, are your friends — they want your money and assume you are a sucker.” Oh, and “put a strict money management plan in place so you don’t go broke,” he advises us, along with the deflating reminder that “it’s next to impossible to be a winning gambler” — one of those truisms, one feels, that will only encourage thrill-seeking bettors further.
ESPN minted Walters “the world’s most successful sports bettor” of all time in 2015, and he is often seen as a savant-like Warren Buffett of betting. Walters laughs at this characterization now. “Every success I had I pretty much threw away drinking and gambling,” he says. “I went from rags to riches back to rags and riches about a hundred different times.” But, he says, “while I’ve been broke more times than I can count, I also was driven by this fierce desire to succeed, to win.”
One of Walters’s lowest moments came with his high-profile conviction, in which U.S. federal prosecutors claimed he conspired to obtain information about a company called Dean Foods — which would have netted him up to $32 million in profits. “Phil [Mickelson] is a great golf talent,” Walters says of the case, damning with praise. “But he didn’t live up to his promise to tell the truth when I needed it most. I lost so much more than my freedom and I will never forgive him for that. I lost my daughter Tonia to suicide when I was inside Pensacola.” Walters explains how he feels he would have been able to do more for Tonia, who had a history of addiction, had he not been incarcerated. Her death stretches like a deep, raw wound across the pages of the book.
Even under these circumstances, Walters did not stew or fester. His relentless work ethic rumbled on inside the walls of FPC Pensacola — a place that “was anything but a ‘Club Fed,’ ” he says. “Frankly, it’s dehumanizing.” Walters was released to house arrest in 2020, having served 31 months of his sentence, but while inside he “met a lot of men who had no hope — they simply don’t have the necessary skills to survive on the outside.” And so, “over time, I became something of a mentor to about two dozen men. I understood from these men, my friends, that I am the exception, not the rule, for prisoners re-entering society,” he explains.
It’s for this reason that Walters is now working closely with Hope for Prisoners: “a Las Vegas non-profit that provides long-term support and services to formerly incarcerated men and women,” he says. “This year, close to 500 ex-offenders will graduate the program, setting them on a path to lifelong success.” For the rest of us, there is wise counsel in the pages of this book, which hums with anecdotes and feeling throughout. The one thing Walters hopes readers take away from it, he says, is simply to “work hard and don’t give up” — or, ironically enough, to leave as little to chance as possible.
Featured illustration by Claudine Derksen.