Who Are the Most Famous Gamblers?
Many gambling enthusiasts dream of making a living from their winnings, but only a handful of highly successful professional gamblers manage to turn that dream into reality. An even smaller percentage achieve such incredible results that their profits reach tens or even hundreds of millions of dollars. Here, we look at the best and wealthiest gamblers in the world, featuring individuals from all walks of life.
10. Chris Moneymaker
Chris Moneymaker is a legend in the gambling world, primarily for his incredible victory at the 2003 World Series of Poker (WSOP). As a relative unknown, he won the main event and took home $2.5 million. What made his win so historic was that he was the first person to become a WSOP champion after qualifying through an online poker site. This phenomenal success story created what the media dubbed the “Moneymaker effect,” inspiring a generation of online players. He was inducted into the Poker Hall of Fame in 2019 and remains an inspiring example of how poker provides an equal playing field for anyone to achieve greatness.
9. Archie Karas
Archie Karas is the man behind one of the most incredible stories in gambling history, known simply as “The Run.” This is the longest and most successful documented winning streak ever recorded. It started in December 1992 when Karas arrived in Las Vegas with just $50. After securing a $10,000 loan, he turned it into $17 million within six months by playing poker and pool. By 1995, his bankroll had swelled to over $40 million. Unfortunately, his luck ran out. Karas lost his entire fortune in just three weeks by making increasingly risky bets. Though he had smaller streaks later, he never replicated the magic of his historic two-and-a-half-year run.
8. Phil Ivey
Often regarded as the best all-around poker player, Phil Ivey has earned over $32 million from poker competitions alone. His career is decorated with 10 WSOP bracelets and a World Poker Tour title, securing his place in the Poker Hall of Fame. Beyond poker, Ivey is a skilled baccarat player, though his passion for the game led to controversy. He was involved in an edge-sorting incident where he won over $11 million, but the casino refused to pay, accusing him of cheating. Despite this, Phil Ivey remains one of the most respected and famous gamblers in the world.
7. Alan Woods
Alan Woods was a brilliant mathematician who became a professional gambler. He collaborated with Bill Benter and Zeljko Ranogajec to develop pioneering horse betting software that made him hundreds of millions. Initially, Woods mastered blackjack card counting but later shifted his focus to horse racing. He and his partners created software that analyzed numerous variables to predict race winners with remarkable accuracy. Though his partnerships were brief, the system he helped create made him one of the richest gamblers on record.
6. Bill Kaplan
While not a household name, Bill Kaplan is one of the most effective gamblers ever. A Harvard graduate, Kaplan formed and trained the famous MIT Blackjack Team. He taught students sophisticated card-counting techniques to gain an edge over casinos worldwide. His system gave his team up to a 4% advantage, allowing them to earn massive profits. In the first nine months alone, his team generated a return 35 times their initial investment. The story of Kaplan and the MIT team was so compelling it inspired the 2008 movie "21.".
5. Daniel Negreanu
With a net worth estimated at over $50 million, Daniel Negreanu is one of the wealthiest and most famous gamblers today. He has won over $42 million in poker prize money, with his single largest cash prize exceeding $8 million. A 2014 Poker Hall of Fame inductee, Negreanu holds six WSOP bracelets and two World Poker Tour titles. He is also a two-time WSOP Player of the Year. Beyond his winnings, Negreanu is a major personality in the poker world, appearing in TV shows, movies, and even teaching his strategies through a MasterClass.
4. Billy Walters
Billy Walters is a legendary sports bettor with a career spanning decades. He started gambling at age nine but was a losing player until his thirties. Everything changed when he applied his analytical skills to sports betting and roulette. On one occasion, he and a partner won nearly $4 million at a roulette table over 38 hours. However, his greatest success came from sports betting, where he maintained a winning streak for over 30 years. With a fortune estimated at over $100 million, Walters claims he can still make tens of millions in a good year.
3. Zeljko Ranogajec
Zeljko Ranogajec, born in Australia, is one of the richest gamblers in history, with estimated winnings of over $1 billion. His success comes from mastering multiple games, including blackjack, keno, and horse racing. Ranogajec was an innovative advantage player, particularly in blackjack, which earned him a spot in the Blackjack Hall of Fame in 2011. He was also skilled at negotiating rebates and discounts with casinos and sportsbooks, which further amplified his massive profits.
2. Bill Benter
Bill Benter is a professional gambler who earned nearly a billion dollars by developing one of the most successful computer software programs for horse race betting. After reading Edward Thorp's book "Beat the Dealer," Benter mastered card counting and was eventually banned from all Las Vegas casinos. He then moved to Hong Kong with Alan Woods, where they used a starting bankroll of $150,000 to build a horse betting empire. Benter is also a notable philanthropist, donating millions to charities.
1. Edward Thorp
Topping our list is Edward Thorp, a mathematics professor and blackjack legend widely known as the father of modern card counting. Thorp used his mathematical genius to develop a system to beat the house, which he detailed in his groundbreaking 1962 book, "Beat the Dealer." He successfully put his theories into practice in Las Vegas, winning consistently. Thorp later applied his mathematical skills to the stock market, developing quantitative investment strategies that earned him a fortune estimated close to $1 billion. His analytical approach reshaped both gambling and finance, cementing his status as one of the best gamblers in the world.
