Will Billy Walters Bet on Sports Now That He’s out of Prison?

Image of Gambler Billy Walters  and a Sportsbook

Billy Walters is the most-successful sports bettor of all time. He’s won bets as large as $3.5 million and experienced a 30-year winning streak.

However, Walters committed insider trading and went to prison for a few years. But he’s now in home confinement and eligible to wager on sports.

Will Walters resume his legendary betting career now that he’s back at home? I’ll discuss more on this gambling icon along with if he’ll continue dominating sportsbooks.

Who Is Billy Walters?

Billy Walters made his name in the gambling world by crushing Las Vegas. However, the grew up far from the bright lights of Sin City.

Walters was born in the small town of Munfordville, Kentucky. His father, an auto mechanic, died when he was just 18 months old.

Walters’ mother was an alcoholic who left the family shortly after the death of her husband. Billy and his two sisters were raised by their grandmother.

His grandma couldn’t provide indoor plumbing or running water. However, she did show Billy how to work hard through her multiple cleaning jobs.

Walters began hustling like his grandma at age seven. He received a $40 bank loan (via his grandmother) and began mowing people’s lawns for money.

By age nine, he was working a paper route. At 13, he held a morning job at a bakery and an evening gig at a gas station.

Profile Picture of Gambler Billy Walters

Walters began selling cars in Louisville in his early adult years. He worked harder than any local salesman, sending out mailers and cold calling customers.

This hard work paid off as Walters sold over 30 cars per month and made more $50,000 each year (approx. $400,000 today).

By 1967, Billy became the sales manager of a dealership. He used this experience to launch his own dealership in 1972.

Around the same time, he also became enamored with sports betting. Walters gambled with local Kentuckians and even ran his own bookmaking service.

The latter business earned him a misdemeanor charge, which was later expunged. However, the arrest convinced Walters that he needed to move to Las Vegas and in 1981 and take up sports gambling full time.

Why Is Billy Walters Such a Big Deal in Sports Betting?

Walters wasted little time becoming a success in the gambling world. Shortly after moving to Vegas, he joined the “Computer Group.”

The Computer Group was the first betting syndicate to rely on computer analysis to beat the bookies. They compiled numerous statistics and crunched data using the latest PCs.

With the help of his colleagues, Walters went on to win betting profits in 38 out of 39 years. He booked a profit for 30 straight years before the insider-trader conviction.

This feat is quite impressive when considering that Billy was once a terrible sports gambler. He lost over $50,000 wagering on sports by the time he was 22 years old.

Besides his consistency, Walters has collected some of the biggest wins in sports betting history. Here are some of his most-notable feats:

  • Won $3.5 million betting on Super Bowl XLIV (picked the underdog New Orleans Saints)
  • Won $2.2 million wagering on the USC football team beating the University of Michigan (Jan. 2007).
  • Earned as much as $60 million in a single year of betting.

Walters’ gambling acumen goes beyond just sports. He and the Computer Team also hit Atlantic City for nearly $4 million while playing roulette.

The group observed and recorded roulette spins at the Atlantic Club casino. They discovered that one of the wheels was biased and favored certain pockets.

Walters and his teammates proceeded to win over $3.8 million from the Atlantic Club. This mark beat Richard Jarecki’s $1.28 million win at Italy’s Remo Casino for the biggest roulette win ever.

Billy is also an astute poker player. He won the 1986 Super Bowl of Poker (Lake Tahoe) and a $175,000 prize.

Insider Trading Conviction & Prison Time

Billy Walters has not only experienced lots of success with gambling but also through business as well. Sports Illustrated estimates that he has somewhere in the neighborhood of a $500 million net worth.

Unfortunately, Walters got a little too greedy. He engaged in insider trading by getting exclusive information from Dean Foods Chairman Thomas C. Davis.

Walters relied on a prepaid cell phone for conversations with Davis and used the code words “Dallas Cowboys” to discuss Dean Foods shares.

Thanks to Davis’ advice, he made $32 million in profits from 2008 to 2014. Billy also avoided an $11 million loss at one point when Dean Foods stock took a nosedive.

Famed golfer Phil Mickelson also became part of the case. Mickelson “traded in Dean Foods shares and once owed $2 million in gambling debts [to Walters].”

He made around $1 million in profits through Dean Foods trades. Mickelson later forfeited these profits through a civil suit and avoided jail time.

Walters, however, wasn’t so lucky after fighting insider-trading charges and losing his case. In April 2017, he received a five-year prison sentence and a $10 million fine.

Billy served three out of the five years at Federal Prison Camp in Pensacola, Florida. His legal team tried to appeal the charges and lost the appeal in December 2018.

Billy Walters Is Now Serving a Home Confinement Sentence

Walters was scheduled to serve his entire five-year sentence in Pensacola. In April 2020, a judge agreed and allowed Billy to serve the remainder of his sentence at his home in Carlsbad, California.

Walters is still technically in incarceration until January 10, 2022. However, he now enjoys more freedoms from home, including the ability to gamble on sports and engage in other business activities.

Will Walters Resume Betting on Sports?

As covered before, Billy Walters is the most-successful sports bettor ever. He’s won millions of dollars by wagering on everything from the NFL to NBA.

He didn’t have an opportunity to gamble on sports while in Federal Prison Camp. However, Walters now has more luxuries in home confinement.

Billy has the option to continue building his legacy in sports gambling. The only question is if he sees any need to continue placing sports bets.

Walters built his initial fortune by wagering on sports. He claims to have won as much as $60 million in a “good year.”

Image of a Busy Sportsbook

Of course, he’s also one of the most-infamous bettors in Vegas history. Walters had to use “runners” to place his bets because sportsbooks wouldn’t take his action.

He also had trouble placing online wagers as well. Online sportsbooks grew wise to Billy’s accounts and also refused to accept his bets.

Therefore, Walters would need to continue resorting to incredible lengths when placing the six- and seven-figure wagers that he’s accustomed too.

The other thing worth nothing here is that he doesn’t exactly need the money either. Walters owns several car dealerships, a golf course on the Vegas Strip, and various real-estate holdings.

He could never place another sports bet and be just fine. Furthermore, he’s 73 years old and may no longer have the passion for gambling on sports.

As time goes by, more legendary stories involving Walters’ betting heroics may come out. But I wouldn’t be surprised if he’s ultimately done with sports wagering—at least the big bets anyways.


Billy Walters is already etched in history as the best sports bettor ever. Although no exact information exists, he’s likely won over nine figures through gambling.

Walters had to stop betting, though, when he went to prison in April 2017. He’s in home confinement now and has the opportunity to bet again if he so chooses.

Billy may not be in any rush to bet back to gambling, though. He’s already a highly successful businessman thanks to his car dealerships and real estate. Therefore, he may just retire from sports betting and focus on his business endeavors.