Casinos have the edge in any bet, but people do win real money at the tables and in the sportsbooks. In some cases, we’re talking more than enough for a nice steak dinner. We’re talking millions, even hundreds of millions of dollars.
These gambling legends are proof that it can be done, and it can be done in poker rooms, at a blackjack table, at the track or in sportsbooks. PennStakes.com brings you the breakdown of the wealthiest gamblers in the world. The richest gambler has a net worth of around $1 billion.
Richest Gamblers and Their Estimated Net Worth
|Gambler||Estimated Net Worth|
|1. Bill Benter||$1 billion|
|2. Edward Thorp||$800 million|
|3. Alan Woods||$670 million|
|4. Zeljko Ranogajec||$600 million|
|5. Dan Bilzerian||$150 million|
|6. Billy Walters||$100-200 million|
|7. Phil Ivey||$100 million|
|8. Chris Ferguson||$80 million|
|9. Doyle Brunson||$75 million|
|10. Daniel Negreanu||$50 million|
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The Pittsburgh native with a degree in physics was among the first to use math to his gambling advantage. Benter became an accomplished card counter before eventually being banned from Las Vegas. He shifted his focus to horse racing and moved to Hong Kong, teaming with Alan Woods to develop a formula that, to this day, continues to rake in an estimated $100 million annually.
Benter, born in 1957, has since moved back to Pittsburgh as a noted philanthropist and occasional university lecturer. He is the world’s richest gambler with a $1 billion net worth.
Thorp was a hedge fund manager with a doctorate in mathematics from UCLA. He worked at MIT for two years and was a professor of mathematics at New Mexico State and UC-Irvine. Then he moved to designing probability systems that made him mega-rich.
Before he made billions in the stock market, he invented card counting. The Chicago native used computers to increase odds in blackjack. He wrote the legendary book “Beat the Dealer” about card counting.
Thorp, along with Claude Shannon, invented the first wearable computer in 1961 and crushed casinos in blackjack and roulette while wearing it. He also made a fortune using his card-counting skills in baccarat and backgammon. His backgammon system is lovingly referred to now as the “Thorp count.” In the 1960s, he used what he learned to make his fortune on the stock market. Thorp was born in 1932 and lives in Newport Beach, California.
The Aussie started in card counting at the blackjack tables, but in 1982 retired from that game and moved to Hong Kong to team with Bill Benter to develop a horse racing computer software that would earn him hundreds of millions of dollars.
Benter and Woods dissolved their partnership in 1987 but he continued winning big into the 1990s. Woods died in 2008 as one of the wealthiest gamblers of all-time.
Ranogajec, an Australian of Croatian descent, used his reportedly photographic memory, intense math skills and prolific and massive network to amass huge winnings. After being banned at every major Australian casino, he used his skills to make billions in horse racing. He also won a record $7.5 million on Keno in the 1990s.
Born in 1961, the secretive Ranogajec reportedly worked out of an office in Sydney using an “extensive network of spotters, analysts, bettors and administrators” as the leader of several betting syndicates. Now he spends much of his time in the U.K. and on the Isle of Man as a consultant in the horse racing industry, while reportedly using the name “John Wilson” for other investment and gambling endeavors.
Bilzerian got a head start – a trust fund from his Wall Street corporate raider father. He has since added to it in a big way, both as a poker player and as an investment powerhouse. He claimed to make $50 million on poker in 2014 alone.
Born in 1980, the young Bilzerian is known as a high roller and for living a lavish lifestyle and possessing celebrity rolodex – rapper T-Pain released a song named for Bilzerian in 2016. He splits his time between Bel Air and Las Vegas.
The Kentucky native was the son of a poker players and nephew of a pro gambler, so yo could say professional gambling was in his blood. He got into the family business, running an illegal book before moving to Las Vegas to hone his skills. It wouldn’t be the last time he would get in trouble with the law.
He won $3.8 million on roulette in a 38-hour period in Atlantic City. Since 1987 he focused solely on sports gambling and made an estimated $15 million annually on sports betting. He has claimed to have made $50-60 million in a few good years. He won $3.5 million by backing the Saints in Super Bowl 44.
Walters was found guilty of insider trading in 2017, a scandalous affair that included golfer Phil Mickelson and investor Carl Icahn. He was released from the Federal Prison Camp in Pensacola, Florida, on May 1, 2020 to serve the rest of his five-year sentence in home-confinement in the San Diego area. His scheduled release is Feb. 14, 2022.
Ivey is one of the top poker players of all-time, with 10 World Series of Poker bracelets. He has been crushing casino and online games for years. He had five bracelets before age 30. Unlike many on this list, Ivey doesn’t come from a mathematics background. Instead, he knows the game front to back and is known as a big risk taker – a true gambler.
Born in 1977, the professional poker player is still active on the circuit, residing in Las Vegas while also running the Ivey League, a poker training site.
Another professional poker player, Ferguson has a computer science Ph.D. from UCLA, and he has used it to be a poker monster. He won six WSOP bracelets and was one of the founders of Full Tilt Poker.
Born in 1963, the poker player, nicknamed “Jesus” for his long brown hair, lives in Pacific Palisades, Calif., just miles from his birthplace in Los Angeles.
“Texas Dolly” as he’s affectionately known, retired in 2018 after a 50-year gambling career that earned him a spot among the world’s richest gamblers. He won 10 WSOP bracelets, tied for second-most all-time. He’s such a legend in the game of Texas Hold ‘em, there are two hands named after him: The Brunson is holding a hand of 10 and 2 (he won WSOP events two years in a row with that hand), and the Doyle Brunson is the ace and queen of any suit (because he “tries never to play this hand”).
Brunson, born in 1933, won his first WSOP bracelet in 1976. He lives in Las Vegas.
The Canadian affectionately dubbed “Kid Poker” has won more than $42 million and is the only person to be named WSOP Player of the Year more than once. He refused to give up after early struggles forced him out of the game.
Negreanu started playing illegal poker games in Toronto as a high school dropout, moved to Las Vegas at age 22 but had to go back to Toronto after busting out. He rebuilt his bankroll, went back to Vegas and hit big in a tournament at age 24. Negreanu was a member of Team PokerStars for 12 years before ending the relationship in 2019. He lives in Toronto and is still an active online poker player and one of the world’s most-popular card players.
Bill Benter is considered the richest professional gambler in the world, using his mathematics background to earn an estimated $100 million annually on card games and horse racing.
Floyd “Money” Mayweather is a well-known sports bettor, and the champion boxer is reportedly worth nearly $1 billion. So he can afford to throw a few million on a wager. He did more than that when he put $5.9 million on the Heat to cover the spread against the Pacers in Game 7 of the 2013 Eastern Conference Finals. LeBron James and the Heat won. And so did Mayweather.
Jim McIngvale, known better as Houston furniture store mogul Mattress Mack, has had his share of big sports gambling wins – and big losses. He lost a massive $13 million combined on all his bets backing the Astros to win the 2019 World Series. They lost to the Nationals in seven games.
Among the richest of the rich, blackjack, poker and horse racing have been the most-popular betting platforms to make their fortunes.
In 2008, Terry Watanabe, heir of the Oriental Trading Company fortune, lost more than $200 million in a single year. He played blackjack at $50,000 per hand and lost as much as $5 million on some days at Caesars in Las Vegas.