The Richest Gamblers in the World and Their Biggest Wins

Gambling has made many people millionaires, but only a few have turned it into long-term success. Some built their wealth through skill, others through strategy, and a few simply got lucky. From professional poker players to betting masterminds, here’s a look at the richest gamblers in the world, ranked by their biggest wins and net worth.

Bill Benter is known as one of the most successful gamblers in history. A brilliant mathematician, he developed an advanced algorithm for betting on horse racing in Hong Kong, allowing him to consistently beat the odds. His betting system has reportedly earned him over $1 billion, making him the highest-earning gambler of all time.

Biggest Win: Estimated $30 million in a single day

Edward Thorp wasn’t just a gambler—he was a game changer. As a mathematics professor, he pioneered the card counting strategy in blackjack, allowing him to win millions before casinos altered their rules. Thorp later applied his statistical knowledge to hedge funds, where he made even more money.

Estimated Net Worth: $800 million

Dan Bilzerian is famous for his extravagant lifestyle and high-stakes poker games. While he claims to have won over $50 million in private poker matches, many question the legitimacy of his gambling career. Regardless, he has built a massive fortune through investments and social media.

Estimated Net Worth: $200 million

With 10 World Series of Poker (WSOP) bracelets, Phil Ivey is widely considered one of the greatest poker players ever. His biggest tournament win came in 2014, when he took home AU$4 million at the Aussie Millions Poker Championship. However, his most controversial win was $10 million at Crockfords Casino in London, which the casino refused to pay after accusing him of using an “edge sorting” technique.

Total Poker Winnings: Over $100 million

Antonio Esfandiari, a former magician turned poker pro, holds one of the biggest single tournament wins in poker history. In 2012, he won $18 million at the Big One for One Drop, a tournament with a record-breaking buy-in.

Biggest Win: $18 million

Chris Moneymaker’s story is legendary. He turned a $39 online poker tournament into a $2.5 million win at the 2003 WSOP Main Event, proving that anyone could make it big. His victory sparked the Poker Boom, inspiring thousands to take up the game professionally.

Biggest Win: $2.5 million

Archie Karas started with just $50 in 1992 and turned it into an unbelievable $40 million within three years. His streak remains one of the most incredible gambling runs ever recorded. However, just as fast as he won, he lost it all by 1995.

Biggest Win: $40 million, but ended up with nothing

Not all massive gambling wins come from skill—sometimes, luck plays a huge role. Here are a few of the most famous casino jackpots:

• $18.1 million in Arabian Nights (2011) – A Norwegian player struck gold on this progressive jackpot slot.
• $39.7 million at Excalibur Casino (2003) – A software engineer won this massive jackpot playing the Megabucks slot in Las Vegas.
• $17.2 million in Mega Moolah (2015) – A British soldier hit one of the biggest online slot jackpots ever with a 25-cent bet.

Most of the richest gamblers made their fortunes in poker, sports betting, or brick-and-mortar casinos rather than online casinos. However, some major progressive jackpot wins have been recorded in online slots like Mega Moolah and Arabian Nights, proving that huge wins can happen in digital gaming as well.

Looking to test your luck? Check out our Best Online Casinos for exciting games and jackpot opportunities!

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Last updated: March 28, 2025

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Reviewed by Felipe Morgante

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