9 Great Celebrity Gaming Stories

It is no secret that all famous stars earn loads of money and love to expend their money with both hands, maybe some more wildly than others. It is also common fact that these celebrities buy everything from luxury watches, jewellery, and fancy cars to real estate. Though, they try very hard to keep secret any liking to gamble, and there are an increasing number of celebrities who share an addiction to gamble away what they earn at casinos, poker games and other tournaments. The list includes some of the biggest names, many of them may blow you while some may seem like less of an exposure, men and women alike. There are plenty of female celebrities who are evenly addicted to gambling.

Actually celebrities love to gamble. They are used to the lifestyles of the rich and famous. Winning is the only choice and being competitive is something that big time gambling athletes live for. Whether its $100,000 hands of blackjacks or $500,000 riding on a college football game Saturday morning athletes and celebrities have bets that are not for the faint of heart. Celebrities live a special lifestyle and are on a higher pay score than the rest of us.

For that reason, they can have the funds to bet much higher stakes than the normal person.

This has led to some hard to believe stories linking multimillion-dollar wagers, exclusive underground poker rings, and scandals. Some of these stories have surfaced in the news and become legends.

A number of celebrities are even considered “pros” at wagering and are recognized to do well, almost making it a second career. However, for most celebrity players, the losses are great on all levels including economically, professionally and socially. Who is truly addicted to gambling and who seems to have a hold on it? Which celebrities are the winners and who are the losers? The bottom line is, we all know the odds in gambling are never really in support of the player. Have a look at this top 8 list and decide for yourself who wins, and who is really just lost.

Below are some great stories we have put together about casino gambling from famous people that you know. Celebrities who’ve been involved in the biggest gambling news stories of all time

  • The Queen of Poker

You may be familiar with Academy Award Nominee, Jennifer Tilly, from movies like The Fabulous Baker Boys and Bride of Chucky or more recently, as Shorty’s girlfriend on Modern Family. This sexy screen lady could be recognized as a skilled gambler in her own right. She won the World Series of Poker Ladies bracelet in 2005 and took home $158,625 in a Ladies’ No-Limit Texas Hold’em event against 600 other players. This renowned celebrity gambler also appeared in the cover page of Card Player Magazine. She is known as the queen of the poker.


  • Ray Romano

In his most recent television series, the comedy-drama, Men of a Certain Age Ray Romano plays Joe Tranelli a genial, middle-aged man who is an addicted gambler. The actor drew from real life experiences to play his part. Romano’s gambling habit reportedly spiraled out of control, and he required help from Gambler’s Anonymous. It would appear that Romano was doing well in overcoming his bad habit, or at least get it under control. The artist continues to gamble, but generally ‘virtual bets’ when playing golf. He also competes in the World Series of Poker and says he continues to dream about winning big time at the main occasion. The comedian-actor though, is practical and be familiar with the fact that he doesn’t stand a chance against the players who make a living playing the game.

  • Tobey Maguire

In 2011, the Spiderman star was one of some celebrities charged for participating in a multi-million dollar unlawful gambling ring. He won more than $300,000.00 illegal money, stolen from hedge finance investor Bradley Ruderman, who is currently in lockup for a ponzi plan. Maguire is apparently a very skilled Texas Hold’Em player, and won the $300,000 at secret poker games in New York and Los Angeles, whilst Ruderman lost 5 million in all of them. The actor was unaware that Ruderman didn’t have the funds to cover his debts.

  • Michael Phelps

It would seem that Olympic swimmer, Michael Phelps has another much loved pastime besides collecting medals around the pool. His close friends and those close to him admitted that they are concerned about his addiction to gambling. It appears as even if the young Olympic diver is awfully preoccupied with poker and could easily waste millions of dollars without even noticing. Phelps, who is one of the most admired Olympians of all time, winning a total of 22 medals, has been playing poker for years. Friends say that Michael is very competitive, part of what made him to be so unbeaten in the pool, could be extremely damaging to his bank balance at the poker table.

  • Michael Jordan

Michael Jordan has some of the most well-known stories when it comes to gambling. There are various reports of him gambling on the golf course to gambling right before playing in a oppose game. He is the true example of a celebrity gambling addict. One of the best stories about Jordan was in the 1993 NBA Playoffs. The Bulls were playing the New York Knicks and this was Jordan’s final season before his first retirement. He headed down to Atlantic City to do some gambling before the start of his playoff game against the New York Knicks. In a double header that only MJ could pull-off, he ended up playing that game the same day and winning the NBA Championship weeks later. After that season he retired and some wonder it is because he bet on the NBA so he was suspended, but we may never know the truth.

  • Charlie Sheen

That was interesting, but, for Charlie Sheen, gambling has been anything but the matter of fun. During his divorce with Denise Richards, it came out that he was blowing $200,000 a week playing games of luck. En route to the hospital, for the birth of their child, Richards claimed, Sheen placed a call to his bookie to bet on a sporting event. Apparently, he’s since given up on gambling for good. Maybe, though, he was just approaching it the wrong way. Sheen’s brother Emilio Estevez earned the most of his gambling by helping as the big player for the blackjack team direct by Rob Reitzen, one of the most triumphant gamblers in times past.

Of course, though, few things would be more excellent than sitting at a blackjack table with Sheen and hearing him shout his oft voiced “Winning!” every time an ace and picture card came his way. Surely that’d earn the star a steak dinner and cement his status as a Sin City legend.

  • Ben Affleck

The breathtaking accusations report that, Academy Award winner, Ben Affleck was involved in one of Tinseltown’s top secret poker games and lost a $400,000 hand of poker to Ron Meyer, President of Universal Studios. This actor and significantly highly praised filmmaker reportedly checked into rehab in 2001 for his gambling problems and alcohol addictions. This year, Affleck co-stars with Justin Timberlake in the gambling themed thriller “Runner, Runner.” Perhaps this was not the wisest alternative of roles for this actor.

  • Floyd Mayweather

Retired boxer Floyd Mayweather has never been against creating a spectacle. And his showmanship, joint with his 50-0 boxing record, has helped him collect a $400-million net worth. Mayweather likes using his wealth to make some of the biggest wagers in the sports betting world. He apparently won $5.9 million by betting on a 2013 NBA playoffs game between the Miami Heat and Indiana Pacers. He chosen the Heat to cover the spread, and they won by a comfortable 23-point margin.

Another story claims that Mayweather wagered $10 million on the Denver Broncos in the 2014 Super Bowl. His wager reportedly revolved around Denver both covering the spread and leading at the half. The Broncos lost 43-8 to the Seattle Seahawks, meaning he would’ve dropped a lot of money. Mayweather denied the rumors; but then again, he doesn’t talk about or tweet his losing bets.

While “Money” has never confirmed the Heat and Broncos bets, it’s well known that he’s placed other huge wagers. In fact, he bets so much on sports that Las Vegas casinos regularly offer him superior VIP service.

Mayweather also attempted to wager on himself in a 2017 boxing match with Conor McGregor. He’d tried wagering $400,000 on himself at -200 odds, and the fight ending in fewer than 9.5 rounds.

The M Resort had concerns over the validity of Mayweather betting on his own fight. Money eventually grew tired of waiting for a decision and left without placing the wager.

  • Allen Iverson

In reading these stories, Allen Iverson’s fall from grace simply tops my list for losing everything to his addictions. He earned over $200 million dollars in his NBA profession and due to his gambling addiction and drinking problems, Iverson is now both ruined and in debt. He has lost his lucrative endorsements one of which was for his lifetime collaboration with Reebok which was valued at $50 million. And his wife divorced him and has full guardianship of their five kids. According to NY Daily News, Iverson was blamed by his ex-wife of kidnapping his children, although, the charges were dropped. It seems that the life of a once very successful athlete has been distressed by his bad gambling addictions.

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