Billy Walters might just go down in history as the most infamous name in high stakes gambling.
Walters grew up in a small town called Munfordville in Kentucky. His family didn’t have much: the family home didn’t even have indoor plumbing. They were, however, avid gamblers. Walters’ father was a keen poker player and his uncle was actually a professional gambler for a time. These figures in childhood would have a profound effect on Billy Walters. Perhaps inevitably, keen interest in the punt developed early.
At the age of nine, Walters took the money he earned on a paper round and wagered it on the World Series. That bet would be the beginning of one of the great gambling careers.
As he got a little older, Walters raised what money he could by selling second-hand cars, and at the same time set about becoming a bookmaker. This was, of course, illegal in his native Kentucky. He was prosecuted and fined $1,000.
Walters didn’t need any further incentive to move. And he headed straight to the gambling mecca of America: Las Vegas
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Billy Walters: Legendary Sports Bettor
Walters made his name as a sports bettor, but in the early days also played poker and other table games. He was somewhat successful in poker tournaments and won at roulette. The story regarding his roulette success goes that he gained an edge by identifying that older roulette wheels wore in different places, making them predictable and ultimately profitable.
In Vegas, Walters connected with two others to form one of the first computer-based betting syndicates. Walters, Michael Kent and Dr Ivan Mindlin exploited early data techniques to build computer algorithms for sports betting. Walters’ role was largely to get the money on, exploiting the weakest lines the group had identified placing the biggest wagers possible. The size of the bets skyrocketed and ultimately, so did the profits.
Operating in the pre-internet era, Walters and his associates were ahead of their time. One of their famous ploys was dispatching runners to the airport to grab interstate newspapers immediately, getting a jump on any sports news and using it to their advantage. Before long the runners were also placing bets on behalf of Walters, with sportsbooks unwilling to take him on.
As Walters’ wealth grew, so did his search for bigger edges – both in and beyond gambling.
Walters used his wealth to expand into property and the stock market. An avid golfer who plays off scratch, in 1996 he won a contract to develop a Las Vegas golf course. It was Walters’ idea to purchase the land outright, and he negotiated an extremely good price with the city to do so. Real estate values in Vegas would soon take off, with Walters and his partners gaining planning permission to redevelop the land into residential property. This would prove Walters’ biggest payday, pushing his personal wealth well beyond $100 million.
The stock market & coming undone
Walters had long played the stock market successfully, having the same ability to find an edge as he did gambling. But in 2017, Billy Walters’ luck ran out.
Walters was receiving stocks tips from Thomas Davis, chairman of Dean Foods. Davis reportedly had a gambling habit and fed tips to his friend Walters. Investigators would ultimately charge Walters with insider trading. He was convicted and sentenced to five years in prison. In 2020 Walters, 73, was permitted to serve the remainder of his sentence in his California home… where a cable television subscription and phone access will be welcome luxuries!