Top Hollywood Celebrity Gamblers

Celebrity Gamblers Michael Phelps Gambling Addiction

Gambling is the wagering of money or something of material value (referred to as “the stakes”) on an event with an uncertain outcome with the primary intent of winning additional money and/or material goods. Gambling thus requires three elements be present: consideration, chance and prize. The outcome of the wager is often immediate, such as a single roll of dice or a spin of a roulette wheel, but longer time frames are also common, allowing wagers on the outcome of a future sports contest or even an entire sports season.

Gamblers Anonymous

Celebrity Gamblers Who Have Gambling Problems


Tiger Woods

Tiger Woods became good friends with Charles Barkley and Michael Jordan, both of whom are high rollers who enjoy their gambling and perhaps, that is when Woods’ own gambling addiction issues surfaced. However, he is responsible for his own actions, as we already know of this golfer. Woods became a regular at the Mansion, a club for high rollers at the MGM Grand in Las Vegas, where he was given a $1 million dollar betting limit and routinely played blackjack at $25,000 a hand. In fact, abc news has stated that, according to an unknown Vegas nightclub source, Woods would always request that his table always be filled with, “hot party” girls.


Ray Romano

In his most recent television series, the comedy-drama, Men of a Certain Age Ray Romano plays Joe Tranelli an affable, middle-aged man who is an addicted gambler. The actor drew from real life experiences to play his part. Romano’s gambling addiction reportedly spiraled out of control, and he sought help from Gambler’s Anonymous. It would appear that Romano was successful in overcoming his bad habit, or at least get it under control. The actor continues to gamble, but mostly ‘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 event. The actor-comedian however, is realistic and knows he doesn’t stand a chance against the players who make a living playing the game.


Tobey Maguire

In 2011,  Spiderman star, Tobey  Maguire was one of several celebrities sued for participating in a multi-million dollar illegal gambling ring. According to the suit, Maguire won more than $300,000.00 worth of illegal funds, allegedly stolen from hedge fund investor Bradley Ruderman, who is currently in jail for a ponzi scheme. 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, while Ruderman lost five million in all of them. The actor was apparently unaware that Ruderman didn’t have the funds to cover his debts.

Interestingly enough, 36-year-old Maguire has done much of his gambling in public. After learning the game from professional player, Daniel Negreanu the actor competed in and won the World Series of Poker. Professional poker player Phil Hellmuth once said on Poker After Dark, that Maguire has won as much as $10 million through playing the game. Friends close to the actor are concerned about, what they fear is a new place for Maguire to channel what, he himself calls his, “addictive nature” since the actor has struggled with an alcohol addiction and joined AA when he was only 19.


Gladys Knight

She is known as the ‘Empress of Soul’. In her autobiography, “Between Each Line of Pain and Glory: My Life Story” singer Gladys Knight wrote about her ten year gambling addiction with baccarat and sports betting. Though, throughout her career she sidestepped and avoided getting hooked into the world of drugs and alcohol, she didn’t manage to avoid the gambling pitfall. She loved sports betting, but her addiction to Baccarat would cost her tens of thousands of dollars at just one table sitting. In the late 1980’s, after a high-stakes binge that cost her no less than $45,000, she finally bottomed out. At that point, Knight turned to Gamblers Anonymous and got the help she needed to put an end to her addiction.


Charlie Sheen

Charlie Sheen‘s gambling habit has been rumored for years and it became public knowledge in 2006 when his second wife, Denise Richards, said in divorce papers filed in court that he was spending about $200,000 a week on gambling. Most of Sheen’s gambling losses came from sports betting, according to Richards. According to People magazine, Richards said that in 2005, Sheen would have called his bookie to place a bet, while in the car on the way to the hospital for the birth of their daughter, Lola. Sheen has recently claimed in an interview that he no longer gambles. He did admit to spending large amounts of money on cocaine in a national television interview. “That’s how I roll,” Sheen declared. Either way, the man seems to have an addictive personality.


Michael Phelps

It would seem that Olympic swimmer, Michael Phelps has another favorite pastime besides collecting medals around the pool. His friends, and those close to him reportedly admitted that they are worried about his addiction to gambling. It appears as though the young Olympic diver is extremely preoccupied with poker and could easily fritter away millions of dollars without even noticing. Phelps, who is one of the most popular 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 enabled him to be so successful in the pool, could be extremely damaging to his bank balance at the poker table.

Michael Phelps Apologizes

The sensational 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 critically acclaimed 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 choice of roles for this actor.

Charles Barkley

Former NBA player and current TNT NBA sports analyst, Charles Barkley revealed his personal struggles with gambling during an interview with ESPN, admitting that his problem has cost him over $10 million. Barkley said, “It is a problem for me” and added, “My agent has really worked with me to try to get it where I can go and gamble and have fun,” he said.”That’s easier said than done.” Do I have a gambling problem? Yeah, I do have a gambling problem but I don’t consider it a problem because I can afford to gamble. It’s just a stupid habit that I’ve got to get under control, because it’s just not a good thing to be broke after all of these years,” he added. Barkley told ESPN that he’s working to solve the problem.


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 career and due to his gambling and drinking issues, Iverson is now both broke 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. More importantly, his wife divorced him and has full custody of their five children. According to NY Daily News, Iverson was accused 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 devastated by his addictions.

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