Book Review: “Gambler: Secrets from a Life at Risk” by Billy Walters

by Christopher G. Shepard - 9/5/2023

$35. Avid Reader Press. 374 pages.

Legendary sports bettor Billy Walters has wagered more than $1 billion in his lifetime.

Today, riding a 36-year-win streak taking down sportsbooks in this country and off-shore, beating the stock market for hundreds of millions dollars, owning some of the most successful auto dealerships and golf courses in the USA, and doing 31 months in the Federal Pen at Pensacola, Las Vegas’ biggest philanthropist has decided to give back to the sports betting community by revealing the secrets to his success in his book, “Gambler, Secrets from a Life at Risk.”

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From his hardscrabble youth hustling pool, pitching pennies, and mucking stalls at Churchill Downs to winning the Pebble Beach Pro-Am in 2008 with partner, Fredrik Jacobson, Walters was never afraid to bet everything and lose. Indeed, most days his heart wouldn’t get pumping until he had at least a $1 million on the line.

Walters writes he’s wagered $20 million in bets daily. Every day. In his prime, he would bet on 150 games through 1,600 betting accounts worldwide through a sophisticated network of proxies - “Beards”, “Runners”, and “Partners.” Walters’ wagers could range from $8000 on an early-season college basketball game to more than $3 million on an NFL playoff game.

Along the way, Walters said he has learned four important truths: 1.) His bets are based on extensive research. 2.) Betting sports is about one thing and one thing only; value 3.) Sports gamblers need to win 52.38% of their bets just to break even. 4.) Don’t be a GI Joe betting sports; be a Navy Seal.

The first bet nine-year-old Billy Walters ever placed was on a sure thing. Or so he thought.

He wagered his life savings with the Munfordville, Kentucky grocer; $125 on the 1955 New York Yankees to win the World Series against the Brooklyn Dodgers. The fact it had taken Walters several years mowing grass, shining shoes in front of Hart’s Courthouse, and two paper routes before and after school to earn the money, didn’t stop him from putting it all on the line.

And why not? The Yankees had been world champions five of the previous six years, and three of those wins came against the Brooklyn Dodgers. What he hadn’t counted on was southpaw Johnny Podges winning two games and throwing a 2-0 shut-out in Game 7.

And just like that, Walters was broke.

It was a lesson right out of Gambling 101, and he learned it the hard way. He hadn’t done enough research on the game. His sure thing had cost him his entire bankroll. He would learn how important research and bankroll management was, but not until he went broke again and again. Walters writes he went broke more than 100 times in his life. It wasn’t until he quit drinking and betting on casino games for good in his 40’s did his fortunes change for the better.

There are many personal stories in Gambler that Walters uses to highlight the depth and breadth of his research. One chapter titled, “Spinning Wynn’s Wheel” is where he details the lengths he went through to figure out how to beat roulette, long considered a suckers game by casino sharps. In one notable session, he legally won $2 million in roulette winnings off Steve Wynn’s (his friend at the time) casino in Atlantic City.

In another chapter, Walter’s discusses how he founded the Computer Group -- considered one of the country’s first betting syndicates. By the late 1970s, Walters was one of the biggest bookies in Louisville and connected with Mike Kent, a math genius and computer whiz, who Walters said was the inventor of the computer models used for compiling data and statistics that was then in turn used to profit from sports wagers. It became so successful that in 1986 Sports Illustrated featured the computer group’s success.

By 2017, pro golfer Phil Mickelson owed Walters $2.5 million in unsettled bets that Walters had placed for him over their eight-year friendship. In the chapter titled, Lefty and Me, Walters details the extent of Mickelson’s gambling and how Mickelson failed to testify on his behalf in the insider trading indictment that would ultimately send Walters to the Federal Penitentiary in Pensacola for 31 months. Walters did say Mickelson paid him back all the money he owed.

The nuts of Gambler, however, are the two master class chapters on sports betting. In the chapter Master Class, Walters doesn’t break any new ground about sports gambling, but the following chapter Advanced Master Class again shows the depth and breadth of his gambling systems. And, yes, it helps if you are a math major, because it is, as you can imagine, complicated. Hint: parlays and teasers are sucker bets not worth the time it takes to bet them.

Life as the Michael Jordan of sports betting cost Walters a lot in his personal life. He lost a son at a young age, his daughter committed suicide while he was in prison in 2018. He was also addicted to alcohol, and his lifestyle cost him two marriages and countless upheavals.

Gambler’s 8-page index is a veritable who’s who of Las Vegas movers and shakers, famous gamblers, mob figures, media personalities, politicians, musicians, and poker players. Many of whom became good friends or mortal enemies of Billy Walters. Gambler is a must read for anyone who has ever placed a bet or thought about betting on sports.

Today, Walters is considered Las Vegas’ top philanthropists (among other things).

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Book Review: “Gambler: Secrets from a Life at Risk” by Billy Walters

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