10 of the Top Celebrity Gambling Wins

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10 of the Top Celebrity Gambling Wins
Photo by Melissa Walker Horn on Unsplash

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Australia has one of the world’s top gambling industries based on the revenue generated by bettors. Sports betting is one of the most popular markets, and it also has the highest per capita spend on online betting. Its love of online casinos and slot machines, or “pokies” has helped these statistics.

With a population of just over 27 million, Australia has just 0.3% of the world’s population, but the country has 18% of the world’s slot machines.

Gambling expert Vlad Grindu looked at a variety of factors when compiling Techopedia’s real money pokies recommendations and rates the RTP (return to player) percentage, free spins, and bonus rounds as some of the most important.

Australian gamblers find the lure of multi-million dollar wins on progressive pokies almost too tempting to resist, and they offer some of the best opportunities to win big for small stakes.

While stories of ordinary people winning big can occasionally make the news, it is the gambling activity of celebrities that often takes the headlines. Here are some of the top celebrity gambling wins to happen.

Ben Affleck

While Ben Affleck is more likely to be found in the gossip columns for his failed romance with Jeniffer Lopez, his ability as a Blackjack player has seen him making news by winning almost $1 million.

While this might be a life-changing sum for many, it isn’t for a movie star like Affleck, and this could work in his favour as there is less pressure.

However, there is some controversy surrounding his Blackjack wins with the Hard Rock Las Vegas banning him from their blackjack table for life after he was caught counting cards.

Drake

Drake is best known for his award-winning music career, but his gambling success could give him an alternative career if he ever chose to hang up his microphone.

Two of his biggest wins come from playing roulette, winning $17.9 million in May of 2022, and a further $25 million just two months later. He has also been known to bet on UFC fights and American Football, with multi-million dollar wins in both.

50 Cent

50 Cent is another popular American musician who is not afraid to put his money where his mouth is. Gambling with your heart over your head is never a good thing, but he has backed his hometown team the New York Giants twice, winning big by betting a million on Super Bowl XLVI.

Dana White

As the UFC president, it would be unethical for Dana White to back any of his fighters, it would also call into question the validity of results if he was seen to be winning big.

Instead, White used his blackjack skills to win more than $2 million at the Palms in Las Vegas. Betting limits and a ban followed this, causing White to retaliate by using other venues for UFC events. The two parties have since resolved their differences.

Charlie Sheen

Charlie Sheen’s well-documented wild lifestyle would lead many to believe he would be just as frivolous with his bets. However, a dream that Manny Pacquiao would beat Oscar De La Hoya turned out to be true and saw him walk away with a cool $1 million.

He has since given up on gambling, but he has been the subject of betting markets with operators offering odds on him being arrested or institutionalised.

Ashton Kutcher

From one ‘Two and a Half Men’ star to another, Ashton Kutcher is another star of film and TV that has enjoyed big winnings. In his case, it was from betting on college football as part of a syndicate.

He put his $750,000 winnings over the course of half a season down to the ability of other syndicate members to identify numerical anomalies and understand the different factors that would affect results and performances.

Connor McGregor

Connor McGregor’s fighting and film careers have given him a lot of money over the years, and he has enjoyed gambling some of it successfully.

July 2024 proved to be a great month for the controversial Irishman, backing Spain in the Euro, Argentina in the Copa America, and Carlos Alcaraz to win Wimbledon. It was reported that he earned $8.2 million in winnings in that month alone.

Tobey Maguire

Tobey Maguire is best known for his role as Spiderman, but his poker skills have surprised a lot of people. It is estimated that Maguire won from $30 to $40 million by taking part in an underground poker ring.

This might sound more like a story from one of his movies, and it did actually go on to inspire the 2017 movie ‘Molly’s Game’. In the movie, Michael Cera plays ‘Player X’ who is rumoured to be Tobey Maguire, and the depiction sees him cast as the movie’s villain.

In reality, the games involved a lot of other celebrity high-rollers like Matt Damon, Benn Affleck, and Leonardo Di Caprio.

Phil Mickelson

Golf legend Phil Mickelson knows what it takes to be a world-class athlete, and his instincts helped him win almost half a million by nacking the Baltimore Ravens to win the Super Bowl in the 2000 season.

He created a betting syndicate that backed the Ravens successfully, but over his career, he lost a lot more. In his recent book, he estimates that he has gambled over $1 billion, and suffered losses of around $100 million.

Victoria Coren Mitchell

Fans of British TV might know Victoria Coren Mitchell as a successful TV presenter, and she is also a columnist for The Daily Telegraph. Some may also recognise her as the wife of Peep Show star David Mitchell.

What many don’t realise is that Coren is an accomplished poker player who has amassed career winnings of over $2 million, and also became the first female winner in the European Poker Tour.

Her 2006 European Poker Tour London main event victory netted her a prize worth half a million. She is well-placed among the top female poker earners, and in 2016 this was recognized as she became an inductee into the Women’s Poker Hall of Fame. 

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