Playing the High Stakes Game: Meet the Individuals Who Struck Gold in Professional Sports Betting

The world of gambling has its share of legends and myths, but these stories of professional sports bettors who struck it rich are entirely true. Most successful sports gamblers have a strong background in mathematics and spend a significant amount of time calculating odds.

They are far removed from the casual bettor who views gambling as a mere pastime. To make it as a professional bettor, one must start small, learn the trade with lower stakes, take advantage of promotions, and seek guidance from experts.

Matthew "Moneyball" Benham is a shining example of a rags-to-riches story. He left a comfortable job at Bank of America to pursue football betting and even became the owner of his favorite football club, Brentford FC. Matthew Benham, a physics graduate from the University of Oxford, initially worked in finance and held the position of vice president at Bank of America. In 2001, he transitioned to analytics, joining Premier Bet, a sports betting company. There, he developed predictive models using his financial background, and learned the ropes under Tony Bloom, another successful sports bettor. In 2007, Benham, a lifelong Brentford FC fan, provided a $700,000 loan to the club's fans to purchase the team. If they couldn't repay the loan, he would take ownership, which is exactly what happened in 2012.

Tony "Lizard" Bloom, a Brighton native, is one of the most successful professional sports bettors who later ventured into entrepreneurship and ownership of two football clubs, Brighton & Hove Albion and Royale Union Saint-Gilloise. Bloom's journey began when, as a teenager, he used a fake ID to place bets on horse racing events. He held a mathematics degree from the University of Manchester, which he put to good use in the world of sports betting. Nicknamed "The Lizard" for his unflappable demeanor at poker tables, Bloom won £2 million playing for fun.

Bill Benter, a Pennsylvania-born professional sports gambler, made his fortune by betting on horse racing and other sports events. He's known for using mathematical models to gain an edge in betting. After earning a physics degree in 1977, Benter's initial success came from card counting in Las Vegas. However, he switched his focus to sports betting when he met Alan Woods. Together, they moved to Hong Kong in 1984 and developed a statistical model to predict winners in various sports events.

Haralabos Voulgaris, a Greek-Canadian popularly known as Bob Voulgaris, amassed his fortune by betting on sports, particularly the NBA. In the late '90s, Voulgaris began betting on various sports events, particularly NBA games, and became confident enough to place bets worth $1 million in a single day by 2000. He earned the nickname "Bob" for his keen observation of head coaches' game-management tendencies. Voulgaris also found success in poker tournaments, winning over $3 million over 14 years. In 2018, the Dallas Mavericks hired Voulgaris as their quantitative research and development director, but his tenure ended in June 2021 due to front-office conflicts.

William Walters, an American entrepreneur, is one of the most successful professional sports bettors in Las Vegas, maintaining a winning streak for over 30 years. Walters' journey began in Kentucky, where he worked two jobs and engaged in sports betting. He left his jobs in 1981 to pursue betting full-time and eventually moved to Las Vegas, where, he joined the Computer Group, which used computer analysis for sports betting. But later on, Walters also faced legal troubles, including a five-year prison sentence and a $10 million fine for insider trading involving Dean Foods stock.

James "Jeopardy" Holzhauer is famous for his remarkable winning streak on the game show "Jeopardy." In addition to his trivia success, he made a fortune betting on sports events and dabbled in poker. Holzhauer, a moderately proficient poker player, transitioned to professional sports gambling in 2018 after moving to Las Vegas following college graduation. He specialized in baseball, NFL, and college basketball, creating predictive models for his sports betting endeavors.

Zeljko Ranogajec is a businessman and professional sports gambler who used to bet on horse races, and engaged in various forms of advantage gambling. Ranogajec started off with card counting at Wrest Point Casino and later dropped his degree to focus on advantage gambling. His success relied on finding small margins and securing substantial rebates from bookmakers, leading to some controversy. Currently residing in the UK and the Isle of Man, Ranogajec works as a consultant for Newfield Limited and is a co-founder of Colossus Bets.

David Walsh, a successful sports bettor from Australia, won a staggering $17 million on the 2019 Melbourne Cup. He used his winnings to fund the Museum of Old and New Art in Hobart, Tasmania. Walsh initially worked as a car salesman and transitioned to sports betting, founding the Museum of Old and New Art with the proceeds.

Alan Woods, a gambler and mathematician, was known for his successful bets in blackjack and horse racing betting, collaborating with Bill Benter and Zeljko Ranogajec in Australia and Hong Kong. Woods' early success came from card counting in blackjack, but he shifted his focus to professional sports betting after his wife left him in 1979.