Gambling Addicted Celebrities Who Have Won or Lost Huge Amounts

We all have that friend or cousin who has some unbelievable gambling story to share. Some have won huge amounts in the matter of a few hours. On the flip side, some have burnt truckloads of cash in double quick time. But it is wrong to think that such events occur only in the lives of common people. There are many celebrities from different walks of life who can’t resist the lure of a casino. They have much more money to play with, compared to you and me. That is why they can afford this addiction to gambling. We bring you some of these unbelievable gambling stories about gambling.

1. Ben Affleck

There is a reason why this name is right on top of our list. The acclaimed actor has a bittersweet relation with the world of gambling and gaming. He is not the usual celebrity who threw a few thousand dollars around just because he could. Affleck has actually been an accomplished card counter in poker. He has been a winner of the California State Poker Championship, he was that good. So much so, that at some casinos, he has been asked to play a different game. But this is the good side of this story. The penchant for gambling soon turned into an addiction of sorts for Affleck. This began to affect his family life as well. At one point of time it got so bad that he had to seek therapy for his troubles. Some people also say that his separation with his partner in 2015 was also because of this.

2. Tobey Maguire

When it comes to gambling, another name that is often taken along with Ben Affleck is Tobey Maguire. The Spiderman star was also a feted winner of poker championships. But he had another more sinister side to his playing habit as well. The word on the street was that Tobey was part of an illegal betting syndicate that featured mostly celebrities like himself. Affleck also was rumored to be part of this ring. All was going well, and his poker skill helped Maguire win big in this circle. By big, we mean really big. People say he won from $30 to $40 million in this syndicate. But the rule of gambling is that someone wins only when someone else loses. That someone, in this case, was a hedge fund manager from Los Angeles. He squealed to the police, and that brought the curtains down on this syndicate.

3. Michael Phelps

Glamorous casinos and high profile players are things one does associate with casinos. But after two big names from Hollywood, let us move away to a different world – sports. Yes, you read that right. You are wrong to think of all sportsmen as people with very clean private lives. The superman swimming champion is a sportsman who isn’t exactly that. He is insanely addicted to poker and other online gaming options. He has even been spotted at poolside during the 2016 Olympics playing on his phone. But his addiction to poker, it must be argued, is more academic. He picked up the habit around 2011 when he stayed with a professional poker player. And then there was no looking back. There is one difference of Phelps with the other names that came before his in this blog. There are no stories of big amounts of money won or lost by him. The reason is because he plays poker mostly for fun, and not for the big bucks.

4. Michael Jordan

From swimming, we move onto the glamorous world of professional basketball. And the name that shines brightest there is Michael Jordan. We all have heard of his rise from humble beginnings to basketball superstardom. We have also read many quotes from him about how he lost so many times over before he began winning. But his betting and gambling exploits make for equally interesting stories. Stories are legion about how he used to stay up gambling till the wee hours of the morning. And sadly, this often used to happen even when his team had important matches the next day. This happened more than once even when he and his team were at the peak of their prowess and success. Very soon, the regulatory bodies for basketball opened up investigations into his gambling habits. Jordan retired soon after.


Celebrity stories are always interesting. And when it comes to gambling, their big wins make for even bigger headlines. But you can also see the darker side in the above stories. Celebrities might have enough money or contacts to escape from their sticky spots. But the rest of us need to ensure that we gamble only at trustworthy casinos. There are a number of good casinos, both physical as well as online, where one can gamble with complete peace of mind.

About RJ Frometa

Head Honcho, Editor in Chief and writer here on VENTS. I don't like walking on the beach, but I love playing the guitar and geeking out about music. I am also a movie maniac and 6 hours sleeper.

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