Famous Gamblers and Where They Are Today

Gambling has always been a mix of fortune, fearlessness, and strategic calculation. While most players walk into a casino with a budget for the night, a few have made the tables and racetracks their life’s work.

These gamblers didn’t just play for fun; they rewrote the rules of risk and reward, turning bets into billions. Let’s take a closer look at some of the most famous names in gambling history and where life has taken them.

Kerry Packer is perhaps the most legendary of them all. The Australian media tycoon was as comfortable at the blackjack table as he was running a business empire. His reputation for high stakes is unmatched, with stories of him winning $20 million in under an hour.

Of course, it wasn’t all wins; he also lost staggering sums, including $22 million in one year alone. Packer passed away in 2005, but his mix of wealth, bravado, and love for the game keeps his name alive in gambling circles.

Across the globe, Tony Bloom earned the nickname “The Lizard” for his calm and calculated approach to poker. While his poker achievements are significant, his real success lies in his betting consultancy, Starlizard, which places massive wagers on football leagues worldwide. Bloom has since expanded into sports ownership, becoming chairman of Brighton & Hove Albion, where his betting background and business acumen intersect.

Then there’s Bill Benter, a mathematician who went from card counting in Las Vegas to cracking the code of Hong Kong horse racing. By designing one of the most successful betting algorithms ever, he turned himself into a billionaire.

Today, Benter spends much of his time lecturing at universities and donating to philanthropic causes, showing that the mind behind the system values giving back as much as winning.

Edward Thorp, another genius with numbers, famously invented card counting—a technique used to track the ratio of high to low cards in a deck—and proved it worked by consistently winning at blackjack.

His book, Beat the Dealer, remains one of the most influential texts in the history of gambling. Thorp later applied his probability skills to Wall Street, further growing his fortune. Now in his nineties, he enjoys recognition not just as a gambler but as a pioneer in quantitative investing.

Alan Woods and Zeljko Ranogajec, once collaborators, became giants in the horse racing world through syndicates that placed billions of dollars in bets annually. Ranogajec, known as “The Joker,” has kept a low profile in recent years but remains linked to massive wagering operations.

David Walsh, another member of this elite circle, shifted his focus from betting to art, creating the Museum of Old and New Art (MONA) in Tasmania, one of Australia’s most remarkable cultural landmarks.

Poker has also produced its fair share of gambling icons. Phil Ivey is widely regarded as one of the best players in the world, with ten World Series of Poker bracelets and a reputation for taking on billionaires in private games, where buy-ins can reach millions of dollars.

Dan Bilzerian, by contrast, has built more of a persona than a proven record, flaunting his supposed poker winnings across social media. Love him or doubt him, his name remains synonymous with the wild side of gambling culture.

What these stories prove is that gambling at the highest level requires more than luck. It’s about strategy, resilience, and the nerve to push limits.

They all had a passion for the world of sports and casino games, which inevitably made them a nightmare for betting operators at the time and no doubt would be a handful for the most technical and highly innovative brand, such as the recently launched Swiper Ontario, a cutting-edge gambling platform that is pushing the boundaries of the industry.

From boardrooms to poker rooms, racetracks to art museums, the legacies of these gamblers show that their influence stretches far beyond chips and cards. Some remain in the spotlight, others have stepped back, but all of them have left their mark on an industry where fortune always favours the bold.