Gambling Legend Billy Walters on Phil Mickelson, Legalized Betting, and How to Win

Billy Walters has long had sports gambling advice to give. For decades, the bettor and entrepreneur worked in Las Vegas with the Computer Group, a celebrated network of algorithmically minded sports gamblers, and ESPN described him in 2015 as “the world’s most successful sports bettor.” Several times, Walters’s feats attracted the attention of state and federal authorities, but it was ultimately his investing that sent him to prison after he was convicted on insider trading charges in 2017. Federal prosecutors said he conspired with a member of the board of Dean Foods to obtain information about the company that would have allowed him to make as much as $32 million in profits from trades. At 70 years old, he was sentenced to five years.

Walters’s imprisonment happened to coincide, more or less, with a broad move toward legalized, app-based sports gambling throughout much of the United States. He was granted home confinement amid the COVID pandemic in 2020, and Donald Trump commuted his sentence the following year. By the time he was released, a new, emboldened audience for his life’s work had emerged. Sports betting, for so long conducted in the shadows, has become a fixture of the major leagues over the past few years, with advertisements for mobile gambling apps now a constant of live television presentations.

That was part of the reason, Walters recently said at the publisher Simon & Schuster’s Manhattan headquarters, that he decided to write a memoir. Gambler: Secrets From a Life at Risk will be published on Tuesday; two of its 28 chapters are presented as masterclasses specifically aimed at both FanDuel dilettantes and longtime enthusiasts.

Walters also had a more personal motivation for the book. While imprisoned, his daughter died by suicide following a long struggle with addiction. In his view, laid out in his book, the sequence of events that led to the tragedy can be traced to professional golfer Phil Mickelson, who didn’t testify in Walter’s insider trading trial. (Walters is also an avid golfer, and he and Mickelson were friends for years.) Walters believes that Mickelson’s testimony would have exonerated him, and that had he not gone to prison, he could have cared for his daughter and helped her through persistent setbacks. (A representative for Mickelson didn’t return requests for comment.)

Gambler’s focus on Mickelson, an all-time great with a well-publicized gambling addiction, made headlines in the golf press earlier this month with the release of an excerpt focused on Walters’s claim that Mickelson sought his help in attempting to bet $400,000 on a Ryder Cup he was playing in. (Walters says he discouraged Mickelson from making the bet, and after the excerpt was published, Mickelson issued a statement saying that he never bet on the tournament.) Mickelson has been one of the foremost proponents of LIV Golf, the lucrative and controversial Saudi-backed professional tour founded in 2021. Gambler added fuel to one of the lingering questions about Mickelson’s involvement. “A new book alleges massive gambling losses for the Hall of Famer,” Sports Illustrated wrote. “Did those losses drive him to LIV Golf and the sport’s upheaval that continues now?” (Mickelson told the magazine last year that his gambling “isn’t a threat to me or my financial security.”)

Walters is a generous talker but not particularly sunny. In an interview last week, he was happy to examine the psychology of gambling but less inclined to explore his own. He’s a gruff competitor and a lifelong practitioner of numbers games. As he recalls in Gambler, he first started betting while growing up in poverty in Munfordville, a roughly 1,700-person farming town in Kentucky, and visiting pool halls beginning at six years old. “I learned who craved competition and who crapped their pants in crunch time,” he writes. “That knowledge made me dangerous from a young age.”

During our conversation, Walters discussed the development of his career, the evolution of sports gambling over his lifetime, and his competitive streak across his hobbies and occupations—golf, car dealerships, investing. These excerpts have been edited and condensed.

Vanity Fair: You have a lot of stories. A lot has happened to you. At what point did you think, I need to write a book?

Billy Walters: When I was in prison, and my daughter committed suicide, I knew I had to write a book. And I had several things I wanted to accomplish in the book. I wanted to help people who have issues in their life, whether it be addiction, or whether they have other issues in their life. When sports [betting] got legalized, it was like a dream come true to me. I’ve been hoping sports will be legalized my entire life, all the years I bet sports. Now it was legalized. I wouldn’t have sold this information for $20 million a year ago. I wouldn't even have thought about it. But sports is legalized now, I can see a lot of people have gotten involved with sports, and so I put everything in this book that I know about sports betting, everything I’ve learned in all the years I’ve been doing this.

Now the millions of new sports bettors that we’ve got, I almost couldn’t believe it when I decided to write the book. There’s no information out there whatsoever telling any sports bettor, Okay, what is the fair price to pay for half a point?

How did we get to this moment of legalization?

First and foremost, the US had been living in the Dark Ages in regards to sports betting. Let’s face it. This has been going on in this country for years and years, over a century. Everybody knew it. But there’s no jobs being created. There’s no taxes being collected. It’s been controlled in large part by people that, you know, aren’t necessarily the greatest people. And all at once the lawmakers finally realized, Okay, we can legalize this, Okay, we can create jobs, we can collect taxes. And by the way, we can let the American citizens do something they’ve been doing all this time. And they can do it with someone that is going to pay them if they win. And it’s a win-win for everyone because this is going on already.

How does it feel for you on a personal level?

I was in Nevada in 1982 and I had an organized group of people that were working with me, we were doing nothing but betting. And in 1985, our homes got raided, all of our records got seized under the pretense that we were organized group bookmakers and we were affiliated with organized crime. We were indicted in 1991. We were indicted in our home in the gaming capital of the world. The FBI came, they took my wife, Susan, out in leg irons and handcuffs. They took me out in handcuffs. We finally went to trial in 1992. Not that long ago. We were charged with being part of a criminal conspiracy conspiring to bet on ball games. Now stop and think about that for a moment. And then after that, we went to trial, we were exonerated. After that I was indicted three more times for basically the same thing, because I was betting on ball games. I never went to prison for it, because we weren’t doing anything to violate the law. We were paying our taxes, we did everything we were supposed to do. But it still didn’t stop us from being indicted. It still didn’t stop me from spending millions and millions of dollars, my family going through this, my employees going through this. Finally, we’re here today. And you can do it. And you don’t have to worry about somebody kicking your door down and dragging you out in handcuffs.

You’ve pursued gambling, golf, dealing cars, and investing with equal amounts of vigor. Is there any unifying appeal?

Oh, it’s the victory, really. There was a point of time of my life, it was obvious that money was extremely important. Fortunately, now the money is secondary. I mean, clearly whatever I’m doing, I’m looking to be successful at it. And if I’m betting money, I’m looking to win. But that’s not the driving force behind what I do now.

You have an excerpt from the book out now. What’s your experience of the reaction been?

That’s a very small part of my book. I had to put that in there, because I believe that if Phil had testified in the Southern District in New York, in my trial, I would have never gone to prison. We would have never suffered the family tragedy that we did. I can’t tell the story about Phil and that point unless I explain to the reader what our relationship was, how did we get there to start with? I put the basics in there to explain how he and I met, what our relationship was, and I didn’t put anything in about his personal life. I left that out.

I put the quote in there when he called me and he wanted to bet on the Ryder Cup. I was shocked. I said, Have you lost your mind? You’re viewed to be a modern-day Arnold Palmer. You’ll risk your entire career. I said I don’t want any part of it. He never made the bet. Up until then he never attempted to bet on golf. After that, he never attempted to bet on golf. We never even had a discussion about betting on golf. Now he’s issued a statement. I read the statement. Bottom line is, the statement’s real clear. He never bet on golf. There’s no denial in there whatsoever about the phone call. So he’s essentially just confirming what I said. Nothing more, nothing less.

What do you make of the idea that Mickelson’s gambling is responsible for LIV?

I really don’t know. All I know is, let’s say he lost 100 million bucks. He’s made way in excess of a billion. He got to live, he got to pay taxes. So let’s say he ended up with $600 million out of whatever he made. He lost a hundred. He’s still got $500 million. Being forced to do this deal with LIV, I kind of doubt it. I mean, I’d be surprised if he was, but I don’t know anything about his personal concerns. I couldn’t say whether he did or whether he didn’t.

One thing that is pretty clear about his career is he’s very aggressive when it comes to making money. So he’s worked with a lot of sponsors, things like that. He came out, I don’t know, a couple months ago, and said he was worth almost a billion dollars now. So he must have made a lot of money with LIV. If you come out and make a statement that I’m almost worth a billion dollars, it must be pretty important to him.

When I think of a professional athlete, I think of someone who’s so organized, focused. It’s hard for me to square that perception with someone who’s losing lots of money gambling.

I don’t think you’re wrong about that. I think there’s a lot of people that are exceptions to the rule. He possibly may be one of them.

You’re a basketball fan?

Sure. I’m any kind of sports fan.

In The Last Dance, Jordan’s gambling with the security guard. You just think, how does he do it?

When I was doing sports, I was doing a lot of other things besides that also. Some people can multitask.