Billy Walters is one of the most talented and richest sports gamblers, with over 30 years of experience and an astonishing win rate of 50–60%. Like many of the world's best gamblers, he used a keen eye for analysis and probability to accumulate a growing net worth.

Aided by computer software, Walters was able to gain more accurate odds than those provided by sportsbooks. Basketball, NFL and college football were his go-to betting options. Sadly, he was found guilty of insider trading in 2017 and has stayed under the radar since his early release.

Zeljko Ranogajec: $435 Million

Nicknamed ‘The Joker,' Zeljko Ranogajec made his millions playing casino blackjack. In fact, he was so adept at counting cards and making money against the house that major casinos in Las Vegas and Australia had no choice but to ban him from playing. 

Ranogajec runs his own betting syndicate nowadays, mainly focused on horse racing. The syndicate places bets worth over $3 billion annually, essentially operating one of Australia's biggest sports-betting networks.

Alan Woods: $500 million

Card counting is a running theme that's beginning to develop and the pattern continues with Alan Woods. Another blackjack player who eventually crossed the line with casinos, Woods went from blackjack to horse racing to keep his gambling options open.

Shortly after setting up a betting syndicate in the Philippines, Woods was forced to flee the country when the legitimacy of his operation came into question. He now places bets and wins wagers from the comfort of home, playing online casino real money games with his substantial fortune.

Andrew Black: $670 million

Born in Belfast, North Ireland, Andrew Black is a professional poker player with an illustrious career spanning decades. He has competed in several major tournaments including the main event of the 2005 World Series of Poker, where his fifth-place finish earned him prize money of $1.75 million.

Black boasts career earnings of $5,139,690 altogether, making him one of the best gamblers in the world and demonstrating his ability to wield poker hands with extreme efficiency. Now a London-based entrepreneur and successful casino owner, Black co-founded the largest bet exchange in the world, which was listed on the London Stock Exchange with an estimated value of £1.4 billion ($1.8 billion) back in 2010.

Edward Thorp: $800 million

Edward Thorp is a renowned author, mathematics professor and professional blackjack player. Credited as the founder of modern card-counting strategies, Thorp has inspired countless gamblers with his proven skill in games of blackjack and baccarat. 

His book on how to beat the house edge, “Beat the Dealer,” has sold over one million copies since it was published in the ‘60s. Thorp has also turned his attention to the stock market, with a book titled “Beat the Market” that has achieved similar success.

Bill Benter: $1 billion

With a degree in physics and a fierce passion for betting, Bill Benter used his intelligence to make a fortune off of blackjack and horse racing. It took seven years for Las Vegas casinos to ban him, but by then he had made millions and switched to horse racing in Hong Kong instead.

Together with Alan Woods, Benter created an algorithm that could predict the results of horse races with astonishing accuracy. With tens of millions in profit per year, Benter appears to live a comfortable life giving lectures at universities and donating to charitable causes.

Tony Bloom: $1.5 billion