Top Celebrity Gambling Stories


Gambling is enjoyed by people from all walks of life, but if you want a crazy gambling story you can usually count on celebrities for it. After all, the craziest bet of an average Joe may just be a few thousand bucks while celebrities have so much money that they can turn the betting intensity up a few notches.

Ben Affleck Banned From Hard Rock Casino For Life

Ben Affleck seems to appear in every celebrity gambling story, simply because he’s that notorious. The Batman actor has competed in many poker tournaments and snatched the prize home several times.

ben affleck actor

In 2014, Affleck was playing blackjack at Hard Rock Casino when rumor has it that he was caught for counting cards and received a ban for life from playing blackjack at the casino. However, he came out and said that he simply was a decent blackjack player and the casino was scummy for their behavior.

“I mean, the fact that being good at the game is against the rules at the casinos should tell you something about casinos.”

A few years earlier, Affleck reportedly won $800,000 by playing blackjack in the same casino. However, gambling has had a negative influence on this life and by his own admition, it played a part in his divorce.

50 Cent Bets $750,000 That Floyd Mayweather Can’t Read

Famous for his incredible album Get Rich or Die Trying (which was later made into a movie), 50 Cent also has a peculiar instinct for betting. People started to know about this when he made half a million by betting that the New York Giants would beat the San Francisco 49ers in the NFC Final. He quickly continued the streak by placing a whole million on the Giants to win the Super Bowl. His instincts were right again.

50 cent

Despite being such a phenomenal bettor, 50 Cent doesn’t take himself too seriously. He took the boxing world for a hilarious ride as he bet $750,000 that Floyd Mayweather can’t read one page of a Harry Potter book without stuttering. Unfortunately, there was no definite conclusion to this ordeal as Mayweather just replied by posting pictures of his 8-figure checks.

Tobey Maguire And The Illegal Gambling Ring

Famous for his role in the original Spiderman trilogy, Tobey Maguire apparently is also amazing at poker, yet he doesn’t actually use it for good. In 2005, the actor formed an illegal gambling syndicate with a TV producer named Houston Curtis, where they invite celebrities and millionaires to play high-stakes poker, so high-stakes that up to a few million dollars can be played in one single night.

tobey mecguire

The gambling ring features regular names such as Leonardo DiCaprio, Matt Damon, and Ben Affleck. The whole point of this ordeal was to squeeze as much money out of rich millionaires as possible. These people may lose a bunch of money, but they would keep coming because of the bragging rights of playing with A-list celebs.

Incidentally, this is the event that the movie Molly’s Game is based on. In it, Molly exposes many awful behaviors from Tobey, such as making her bark like a seal to get his tips or taunting people when they lose.

Michael Jordan’s Retirement Conspiracy

Michael Jordan is an NBA legend and a man with a thousand gambling stories, but perhaps none is more significant than the one tied with his retirement in 1993. A very popular conspiracy theory says that it was a fake retirement, and the real reason he stopped playing was that he was suspended due to his gambling addiction.

michael jordan

His father was murdered in that same year by robbers. But many people believed that he was actually killed by gang members for Michael Jordan’s gambling debts. Two investigations had been conducted to find evidence for this yet they all amounted to nothing.

However, that didn’t stop the theory from lingering even to this day, most likely because Michael did have a major problem with gambling. He used to play 36 straight hours of poker with almost every pot being over $20,000. He would bet on everything, from pool, rock-paper-scissor, to the Dunkin’ Donuts scoreboard contest.

Friends Fear For Michael Phelps’ Gambling Problem

Michael Phelps is an American competitive swimmer with the most Olympic gold medals of all time. He said himself that he loves playing poker just for a relaxing time rather than anything competitive. Michael has also made some of his closest friends at the poker table.

‘I could relax, I could be myself, and I could have fun. It’s a place where I can be me.’

michael phelps

However, his friends think Michael is obsessed with the game and fear that he will burn all his millions of winnings away. Apparently, Michael first started to play online with harmless bets of $1 and $2, but now he engages in weekly games with a $25,000 buy-in. The ‘poker friends’ of Michael also provide bad influences on him in different ways, from endorsing his playboy reputation to getting arrested for carrying illegal substances.

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