5 Celebrities Who Simply Love to Gamble

When most of us gamble, we do it sparingly or with a specific strategy in mind to get the most out of our money. But what if you were a celebrity that could afford to play a little longer, bet a little higher, and join in a little more often? 

Would you allow yourself a couple of high by-in games? Would you allow yourself to play more regularly and become a pro? Or maybe you would still play sparingly but be able to enjoy it a bit more because there’s no financial burden.

The celebrities on this list all share a passion for gambling in some form or another. Most of them play because they love the sport, others because they’re just so good at it! While not all of them are successful every time, some of them have won big and have learned how to get the most from their game.

From the poker table to blackjack, here are 5 celebrities who simply love to gamble:

Ben Affleck

Ben Affleck has gained a bit of a reputation for the time that he spends at the blackjack table–and it hasn’t always been a great one. Ben Affleck was actually accused of counting cards in 2014 and there was concern that he might actually be banned from Las Vegas casinos, but he ended up only being banned from the game.

Card counting is not illegal, but it is frowned upon in casinos because it can give a player an unfair advantage. Affleck doesn’t deny that he counts cards, he says he simply doesn’t see anything wrong with it. In his eyes, he took the time to study the game and get good at it. Once he got too good, casinos didn’t think it was fair to other players. Before the ban, Affleck even took home some pretty impressive jackpots.

Doyle Brunson

Doyle Brunson, or “Texas Dolly,” is a two-time World Series of Poker tournament champion. He is regarded as one of the best poker players to ever live. He even has a poker hand named after him. 

Brunson started out playing hands of poker with friends in town. Once he started to get a reputation, he traveled to different states to play bigger games with more challenging opponents. Fast forward to today, and Brunson has won over 3 million dollars from winning poker games.

Not only is Brunson a great player, but he’s gone on to write several books about his experiences as well. These books teach beginners and other poker lovers how to play the game like a pro. Even away from the table, Brunson shares his passion for poker with fans everywhere.

Jenna Fischer

Jenna Fischer, famous for her role as Pam Beasley in the U.S. version of The Office, recently told a story on the podcast she cohosts with Angela Kinsey called “Office Ladies.” The story she told was of a poker tournament she joined on a whim while in Scotland–and she won!

Though locals were none too happy about being dethroned by a tourist, Fischer was proud of her unexpected win. Both she and her husband are poker enthusiasts and joined the tournament just for fun, expecting to be eliminated in the first few hands. 

Fischer has also appeared in celebrity games for charity. She was one of the players on Celebrity Poker Showdown in 2006 where she came in second place, despite the fact that the hosts of the show thought she was going to win it.

Tobey Maguire

When you talk about celebrities who love to gamble, you have to talk about Tobey Maguire. He is a professional poker player and has won significant amounts of money over the years. Although, the discussion surrounding Maguire’s poker skills is not always positive.

Though he was often successful, he was also sued in 2011. According to Mike Tan at OnlineCasinoGems.com, “The lawsuit was for over $300,000 in winnings he had collected from the illegal games. Maguire eventually settled for $80,000.”

Despite the black eye on his record, he has seen a lot of success in his poker career. It’s estimated that his winnings add up to tens of millions of dollars. In terms of money spent and money won gambling, Maguire is one of the highest rollers in Hollywood. He’s even been known to empty the pockets of world-renowned celebs like Leo Dicaprio, Matt Damon, and Ben Affleck.

Phil Ivey

Phil Ivey has won 10 World Series of Poker tournaments, landing him the title of the youngest record-holder for most WSOP bracelets. Poker is not just his passion, it’s his career. He plays every day for hours on end. This career has earned him over $20 million so far.

Ivey learned to play from his grandpa at a young age and started hitting the casinos as soon as possible. He even made a fake ID so that he could start playing in Atlantic City even before he was legally allowed to.

Ivey has been involved in a lawsuit for years after he was accused of edge-sorting, a strategy where players try to identify cards by markings on the edges and backs of cards. Crawfords Casino accused Ivey and withheld his $10.1 million in winnings. Ivey moved to sue the casino, but the UK Supreme Court turned it down.

Whether playing online or in a casino, gambling can be a fun and exciting way to pass time (and maybe even make some money). These celebrities know that just as well as we do. Luckily for them, they have the freedom to play often and join in high-stakes games. Some of them even become legendary. 

Though they play different games, are at different skill levels, and play to different degrees, these celebrities all have one thing in common: a simple love of the sport. 

Written by Monella