Celebrity gambling stories worth reading

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Just like us, many celebrities have a bit of a penchant for the cards, albeit with a little more green to lose. Their outrageous paychecks may seem like stupid money to us, but losing still has that sting to it, no matter how much you’re still left with.

If you don’t have bags of money to throw around like the A-listers, you could get your hands on some online casino bonuses to help you out, just check out Casino Pilot. Or maybe for a few stories of celebs going it tough on the casino floor will lift your spirits? Here’s a few tales of celebrity hits and misses over the years.

Sean Connery

Sir Sean may go down in history as the greatest 007 to have ever filled the shoes, but have you heard of his amazing luck when it comes to roulette? As the story goes, whilst filming From Russia with Love in Italy back in ‘63, Sir Sean tried his luck at a local casino. With 17 being his lucky number and luck on his side, he continuously bet until after 3 successful rounds, he found himself over 15 million Lira up.

Being the dapper gentleman he was, he called it quits and made for an early night. How’s that for class?

Ben Affleck

With a couple of Oscars under his belt, there’s no denying he’s a fine actor. But did you know he is an accomplished poker player too?

Winning a poker championship back in 2004 earned him a seat at the World Poker Tour Final and a hefty 350K pot. He’s a keen Vegas visitor too, although reports are that he was asked to leave the Hard Rock Hotel back in 2014 for reportedly counting cards in blackjack.

Other rumours of $15,000 tips and plenty of donations to charity from his winnings has still kept him in the favour of the public however. Maybe a side career in the poker game?

Robert DeNiro

Although DeNiro played a casino manager in hit film, Casino, he isn’t so well known around the tables as other celebs. However, he could have starred in many more movies if he wanted to. It may come as a shock then that he is the co-owner of the Nobu restaurant chain which has a premise in Caesars Palace in Las Vegas and in the City of Dreams in the Philippines. He has also more recently partnered with famous billionaire James Packer to open a luxury casino resort in Barbuda.

So, it seems that it’s not just at the tables that some high profile celebs can be found, but also around the boardroom table of some great casinos.

Matt Damon

When Damon was cast in 1998’s Rounders, he sought the advice of legendary poker player, Johnny Chan, who proceeded to teach Damon the ins and outs of the game. That knowledge has stayed with him and he since appeared in numerous WSOP charity events to raise money for the less fortunate. Good on you, Matt.

Charlie Sheen

The Two and a Half Men star is no stranger to addiction, eventually losing his role on the hit TV series because of his many demons. But when it came to gambling, Sheen was really in it to win it.

His ex-wife, Denise Richards, has reported that Sheen was commonly losing around $200,000 a week to poor gambling choices, the majority on sports. Rumours have it that he was even placing bets whilst his taking his pregnant wife to the hospital.

Tobey Maguire

Who would have thought that butter-wouldn’t-melt Maguire could have a sinister double life as an underground poker player. Spiderman was big in to the illegal circuit back in the day and also earned himself a steady reputation as not being much of a gentleman when it came to poker games.

In fact, the character “Player X” in the movie Molly’s Game is indeed the real-life actor, whom lured other celebs and billionaires to the star-studded tables to help increase his winning potential. As per the film (and book) Maguire would belittle the host of the events, Molly Bloom, offering large sums of money for degrading acts and eventually cancelling the game due to the amount of tips she was receiving.

Maguire was also caught up in a $40 million illegal poker syndicate that was investigated by the police when the loser of the game wanted his money back. Whom would have thought?

Michael Jordan

The world’s most successful basketball player has had his share of run-ins with gambling over the years too, but when you’re worth over a $1 billion, what else should you do with all that dough?

Reports of many bets on sporting games over the years saw him make a decent profit but also drew the attention of the police who were told that he was betting on his own games. $300,000 a hole golf games between friends were also not too uncommon, just showing what those with countless funds can do to pass the time.

Jordans gambling addiction is no secret, as is his hard work to become free from his demon and kick his habit for good. We wish him well.

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