Celebrity Gambling and Dating Stories

Celebrity Gambling and Dating Stories
Reading time: 4 minutes

Celebrities may already have a lot of money from their various jobs, but it doesn’t stop them from enjoying life as much as the next person. Like many of us, living life on the edge is all part of the fun, with celebrities often enjoying a bit of a gamble as well.

The only difference between their gambling and ours? The amount of money they’re willing to spend on it! Surprisingly though, some of these celebs are actually good at gambling, which means they are able to boost their already considerable wages while having fun too.

But it appears that some celebs gamble with more than just their money, often taking a gamble with love as well. With that in mind, here are some of the biggest celeb gamblers out there alongside some of their most notable dates.

Interestingly enough it’s very rare to see celebrities play games like pokies. Most seem to either go with sports betting or table games like live blackjack or roulette deep in the private rooms of land based casinos.

Ben Affleck

Topping the list is Good Will Hunting’s Ben Affleck. This star is well-known for playing poker. In fact, he’s very good at it. Affleck is also superb at live blackjack. He’s so good he has been asked to leave casinos. That’s right, the man can actually count cards!

However, this affinity for gambling wasn’t necessarily the best as it did begin to affect his family life. His longest-running relationship with Jennifer Garner took a turn for the worse. The couple split a few years later. Since then, Affleck has been linked to a number of co-stars, most recently Ana de Armas.

Tobey Maguire

Maguire is rather infamous on this list, being the villain of the piece in Molly’s Game. Maguire might seem to be the personification of Peter Parker, but it seems he’s more similar to the bad boy version than we all thought. In fact, Maguire’s involvement in one of the biggest underground poker rings hit the headlines in 2011.

This ring actually involved a number of other notable Hollywood names too, including Ben Affleck. However, Maguire was one of the biggest winners. He raked in prizes in excess of $30 million in real money gambling prizes! However, his treatment of the other players has cast him in a more negative light recently.

None of this has set him back in the dating world though, with Maguire linked to Kirsten Dunst, Rashida Jones and Sara Gilbert over the years.

Michael Phelps

Everyone knows Michael Phelps as a swimmer. ut maybe you didn’t know that he’s also great at poker too. However, unlike his swimming, Phelps is unlikely to be winning any golds in his poker game!

Despite hopes from the poker world that Phelps would be the perfect way to get some endorsements going, he prefers to play for fun. This doesn’t mean that his competitive side doesn’t show through though — he still likes to win! Famously, at the 2016 Olympics, Phelps spent time relaxing poolside playing Crazy Pineapple while his competitors got themselves fired up for the race ahead.

Paris Hilton

The only woman on this list, Hilton may not be a professional player, but she’s still got her hands on some big wins. Some of those wins are in excess of $50,000! However, this hasn’t stopped her from getting run out of casinos, although these were for drug-related incidents rather than gambling.

Her dating life has had a little more success. However, the men in her life do change rapidly. Some of her notable relationships include Rick Salomon, Benji Madden and Fred Durst.

Charlie Sheen

Another well-known and unsurprising celeb on this list is Charlie Sheen. Known for his meltdowns and propensity for addictions, it comes as no surprise he’s here. In fact, his ex-wife, Denise Richards, announced that at one time Sheen was losing $200,000 a week while gambling.

Unlike some others on this list, Sheen preferred to bet on sports rather than play games. Sadly for him, he wasn’t very good at it. He also prioritised his gambling, even placing bets while taking his pregnant wife to the hospital.

He’s not had much luck in the dating world either. While having a number of ladies attached to him, none have lasted. Some of his most notable relationships include Robin Wright, Winona Ryder, Kelly Preston, Bree Olson and Brooke Mueller.

Michael Jordan

Last on our list is another sports legend, Michael Jordan. Similar to Sheen, he preferred to bet on sports and, as a sportsman himself, turned out to be quite good at it. In fact, he would place bets on almost anything. He famously bet a friend $300,000 on a single golf swing.

However, his gambling came under scrutiny when he bet on basketball events right before the Bulls won their third straight NBA championship. Needless to say, his activities came under scrutiny before he chose to quit basketball four months later.


And there you have it. Here are some of the most prolific celebrity gamblers out there. Some of them are quite good at what they do, others are not. There are also a number of other top gamblers we didn’t even mention here, including Charles Barkley, 50 Cent, Matt Damon and Floyd Mayweather. Each having varying levels of success when it comes to gambling.

It’s also likely that we will see a lot more celebs join this list in future.

If you’re looking to gamble online for money, our recommendation would be real money online pokies. These offer a great return to player percentages and can be played for very low stakes if that’s what you are after.

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Olivia Hughes
Olivia Hughes
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Olivia is an experienced journalist passionate about keeping our readers up to date with the latest in casino and iGaming news.

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