Ever wondered who the biggest high-rollers are and how they made their colossal fortunes? It’s not just about luck, for these individuals, it’s a thrilling blend of sharp minds, strategic risks, and sometimes, a bit of controversy! Let’s peek into the fascinating stories of some of the wealthiest gamblers who turned their passion into billions.
1. Kerry Packer: The Billion-Dollar Roller Coaster
Imagine being worth $6.5 billion through a family business, yet being remembered for your audacious gambling! That was Kerry Packer, Australia’s media mogul who certainly played as hard as he worked. Packer was known for his “go big or go home” approach, which meant both staggering wins and eye-watering losses. In one infamous 10-month stretch from 1999 to 2000, he reportedly lost around $40 million across London’s Crockford’s and Las Vegas’s Bellagio.
But fear not for Packer, because his wins were just as legendary. In May 1995, he famously scooped up $20 million in just 40 minutes by playing multiple $250,000-stake blackjack hands simultaneously. Talk about a hot streak!
2. Tony Bloom: The Lizard’s Strategic Empire
Tony Bloom, often nicknamed “The Lizard” for his cool and calculated poker style, has an estimated net worth of $1.5 billion. A mathematics graduate from The University of Manchester, Bloom started his journey with poker, winning about $2.5 million and even snagging a second-place finish in the Poker Million IX.
However, poker isn’t the main source of his immense wealth. Bloom is a major player in the sports betting world, particularly through his highly successful betting consultancy firm, Starlizard. This firm is rumored to be one of the top betting operations globally, wagering millions on soccer leagues worldwide. It seems his mathematical prowess truly pays off!
3. Bill Benter: The Horse Whisperer of Hong Kong
Meet Bill Benter, another math wizard with an estimated net worth of around $1 billion. Benter began his career by counting cards in Las Vegas, a skill that quickly made him a “casino nightmare.” But his real game-changer came when he shifted his focus to Hong Kong horse racing.
Partnering with fellow gambler Alan Woods, Benter developed a sophisticated algorithm that could predict race outcomes with incredible accuracy. After some initial hurdles and fine-tuning, his model started raking in tens of millions annually. His most famous win involved correctly predicting the “Triple Trio,” a challenging bet requiring you to pick the first three horses in three separate races. Today, Benter dedicates his time to lecturing and philanthropy, sharing his unique journey with the world.
4. Edward Thorp: The Godfather of Card Counting
If Bill Benter was inspired to gamble, it was by the man who invented card counting: Edward Thorp. With an estimated net worth of $800 million, Thorp used his mathematical genius to devise a system to overcome the house advantage in blackjack.
His very first weekend trying the technique, he won a cool $11,000. Convinced of its effectiveness, he published his groundbreaking book, “Beat the Dealer,” in 1962, selling over a million copies! Thorp didn’t stop there; he also invented the first wearable computer to gain an edge in roulette. He eventually applied his analytical skills to the stock market, where his wealth truly skyrocketed.
5. Alan Woods: From Las Vegas to Philippine Fortunes
Alan Woods, a former partner of Bill Benter, also amassed a fortune of around $500 million through similar methods. Both started as card counters and even worked on the same team before being blacklisted from Las Vegas casinos. This led them to the lucrative world of Hong Kong horse racing.
After their partnership dissolved, Woods developed his own highly successful betting model. Faced with investigations into his syndicate, he relocated to the Philippines, continuing his operations from private property. He even formed a close partnership with former rival Zeljko Ranogajec, further solidifying his massive wealth.
6. Zeljko Ranogajec: The Joker of Syndicates
Known as “The Joker,” Zeljko Ranogajec is another incredibly wealthy “advantage gambler” with an estimated net worth of $420 million. After turning a few hundred dollars into millions at the blackjack table, Ranogajec worked with Alan Woods before establishing his own powerhouse betting syndicate, “The Bankroll.”
His syndicate primarily focuses on horse racing and is reported to place bets worth over $3 billion annually! Even with non-winning bets, Ranogajec profits from special discounts and rebates offered by bookmakers due to the sheer volume of his wagers. While he prefers to keep a low profile, his immense fortune is evident, including owning an apartment in the world’s most expensive building, One Hyde Park. Astoundingly, bets placed by his syndicate reportedly account for a third of Betfair Australia’s entire operations!
7. Billy Walters: The Sports Betting Maestro
Billy Walters stands as one of the most successful sports bettors in history, with an estimated net worth of $200 million. He famously claims to have had only one losing season in 39 years of sports gambling! Walters achieved his success by using in-depth analysis to create more accurate odds than bookmakers, allowing him to win a remarkable 56-60% of all bets.
He found particular success in collegiate sports, where bookmakers invested fewer resources in calculating odds. Walters was known for placing enormous wagers on smaller teams, with one employee recalling a $250,000 bet on an NCAA Division I basketball team. Unfortunately, his winning streak was interrupted when he was found guilty of insider trading, though he was later pardoned by President Donald Trump.
8. Dan Bilzerian: The Instagram High Roller
While most on this list made their money through sports betting, Dan Bilzerian (estimated net worth $200 million) prefers the poker table – and flaunting a lavish lifestyle on social media! Bilzerian claims his extravagant life is funded by private, high-stakes poker games, where he alleges to win up to $50 million in a single night.
While there’s no public proof of these epic wins (his only recorded public result was 180th in a 2009 World Series of Poker Event), some professional gamblers believe it’s plausible, given his reputation for playing only against extremely wealthy individuals he believes he can beat.
9. David Walsh: Art, Algorithms, and a Lottery Bet
David Walsh, with an estimated net worth of $200 million, began his gambling journey by counting cards at the University of Tasmania, where he met future syndicate leader Zeljko Ranogajec. He later developed his own software to predict horse race outcomes, which became a crucial tool for Ranogajec’s “Bankroll” syndicate.
Walsh combined his intellectual gifts with audacious bravery, once buying $11 million worth of lottery tickets to win a $60 million jackpot! Today, Walsh is primarily known for his extraordinary underground art museum in Tasmania, a project rumored to have cost over $200 million.
10. Phil Ivey: The Poker Legend
There’s no debating the poker prowess of Phil Ivey, widely considered one of the best players in the world, with an estimated net worth of $100 million. He’s got the trophies to prove it, including a World Poker Tour title and 10 World Series of Poker bracelets, which come with millions in prize money.
Ivey has also made huge sums playing high-stakes games against billionaires, such as banker Andy Beal. Stories circulate that Ivey once bested Beal out of a staggering $16.6 million in a single game!
Do any of these gambling stories surprise you, or are there other legendary gamblers you’d like to know about?