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Regardless of whether you are just an average person, a well-heeled millionaire or a celebrity, gambling can still be an entertaining and very engaging way of spending time. The activity is not just reserved for people who want to get rich since there are several famous people and flush celebrities that are engaging in it. While you may wonder why these moneyed people choose to risk their hard-earned – but not always – money at the gaming tables, it is quite obvious that many of them like spending money extravagantly and gambling is one of the most popular ways of doing so. Here are some famous people that you may not have known are into gambling.

Ray Romano

Ray Ramano featuring in a Netflix Stand up show
Ray Ramano has his own proclivities for gambling. Photo credit: Netflix

Best-known for his appearance as Raymond in the hit TV Show “Everybody Loves Raymond”, Ray Romano is one of the famous people that has seen a lot of what he world of gambling has to offer – both good and bad. Ray got is so deep that he eventually decided to voluntarily admit himself into a rehabilitation program that was run by the famous Gamblers Anonymous. This saved him from losing everything and helped him to manage his gambling habits. The actor still gambles but these activities are limited to virtual bets only. He also occasionally tries his luck at the World Series of Poker.

Michael Jordan

Michael Jordan during a game for the Chicago Bulls
A triumphant Michael Jordan during an official game for the Chicago Bulls.

Michael is considered by many to be the greatest basketball player of all time. However, the same could not be said about his attempts at sports betting and blackjack, his two favorite gambling activities. The pro basketball player first admitted that he indeed had a gambling problem when he lost $165,000 after betting in Atlantic City. He would go on to lose a whopping $1.25 million when he and San Diego businessman Richard Esquinas gambled on a golf game. It is even speculated that his gambling problem was so bad that it contributed to his retirement from the NBA.

Tiger Woods

Tiger Woods during an official golf game.
Always a smile for the crowds.

It goes without saying that Mr. Woods‘ golf-playing prowess is nearly unmatchable but this is not the only thing that he is good at – no, we are not talking about his womanizing habits either. As it turns out, Tiger Woods is an avid gambler who has reportedly spent up to $25,000 on every hand when playing blackjack. He is also not afraid to splash money into the activity – a Las Vegas casino has even gone as far as limiting his betting to a maximum of $1 million. To make it even worse his circle of friends consists of people like Michael Jordan and Charles Barkley, both of whom are also into gambling. Interestingly, Mr. Woods helped a gambler who bet on him winning the Masters in 2019 win $1.2 million.

Charlie Sheen

Charlie Sheen during a speech.
A controversial Charlie Sheen and his love for the occasional costly flutter.

If you have ever watched “Two and a Half Men”, then you might be able to tell if Charlie Sheen was playing a fictional character as the actor went to adapt the role he played in real life. Just like Uncle Charlie, his character, Mr. Sheen loves to live largely and he did this through gambling. According to his ex-wife, the actor spent over $200,000 every week on his favorite gambling activities which included poker and sports betting.

Ben Affleck

Ben Affleck at an official press panel.
A Dare Devil of gambling.

Ben Affleck has not only played gambling roles in movies but he is also a regular visitor of the gambling tables in real life. Known for the love he has for poker and blackjack, Ben has actually had a bit of success when it comes to gambling – he won the California State Poker Championship back in 2004. He was apparently also so good at winning hands when playing blackjack that in 2014, he was banned from playing the game at one of the casinos in Las Vegas. Still, he has had his fair share of bad runs and has previously been admitted to rehab for alcohol and gambling addiction.

Dana White

Dana White during an official UFC press conference.
Dana White bets staggering sums, but he also wins huge amounts.

Dana White who is the president of the Ultimate Fighting Championship (UFC) is one of the few famous people that have been very lucky when it comes to gambling. Even so, he is still as extravagant as all of the other rich and famous people who spend up to $50,000 on each hand. The only difference is that in his case, the odds are usually on his side – on some nights he would walk away with up to $5 million in earnings.

Charles Barkley

Charles Barkley is speaking to an NBA reporter discussing the current meta.
Mr. Barkley is a fury in gambling and basketball both.

Barkley, another famous figure in the sporting fraternity, is also a well-known gambler. As mentioned earlier, he is friends with Michael Jordan and Tiger Woods and this is perhaps one of the things that fueled his activities. Unsurprisingly, his gambling career was nowhere close to being as good as his sporting career with reports emerging that he had lost millions of dollars gambling at casinos. He would later vow to stop gambling in 2008 when a casino he owed a whopping $400,000 acted against him.

Pamela Anderson

Pamela Anderson's posing for a photo in a new outfit.
Pamela Anderson has costly appetites.

The former Baywatch star reportedly got in too deep after she developed an interest in gambling. Her games of choice were casino slots and poker but the gambling world was not too kind to her as she not only lost huge sums of money but also accumulated a huge amount of debts along the way.

Tobey Maguire

Tobey Maguire's at an official Spiderman event
Tobey Maguire’s Spidey Sense has been helpful in poker at WSOP.

No one would have imagined that the guy from some of the best Spider-Man movies would be a gambling addict. Well, the actor took his spidey-sense to the gaming tables and he has seen quite a number of losses and bagged some cash as well. Tobey Maguire is so good at poker that he has won a total of $10 million playing poker games. In addition to that, he is also an active player in the World Series of Poker where he has also been quite successful. It was not always rosy though – he has had issues with a gambling addiction in the past

Floyd Mayweather Jr.

Floyd Mayweather
Mr. Mayweather is a regular gambler, but his ability to win outside the ring is diminished.

Floyd Mayweather may be an undefeated professional boxer but his prowess when it comes to picking the most profitable sports to bet on has only proven that he has a gambling problem. While he occasionally wins huge sums of money from the bets that he places, the amounts of money he spends on these bets are staggering. He usually never speaks about his losses but is it pretty easy to tell that he is very confident about himself and has therefore lost a few hundred thousands of dollars while gambling.