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Big Losses For Big Stars: 5 Celebs That Gambled Their Way to Debt

Luck was not on their side

While it can often seem like celebrities have enough money to last forever, this isn’t always the case. Bad financial decisions and reckless spending habits can lead to a lifetime of financial problems. Here are 5 celebrities that gambled their way into serious debt.  

Charlie Sheen

While Sheen is known more for his huge public breakdown a few years ago, he has also had some major gambling issues. According to documents from his divorce from Denise Richards in 2006, Sheen was spending $200,000 a week on sports betting.

David Milch


Milch is a 4-time Emmy award winning producer and has worked on several popular shows. He made a ton of money throughout his career, but sadly gambled most of it away. From 2000 to 2011, it’s reported that he lost about $25 million to his gambling problem.

Charles Barkley


While Barkley has rebounded to become a successful TV analyst, the former NBA star has a noted history of gambling problems. He says himself he has lost over $10 million to casinos in his life, including losing over $2 million in one single night of blackjack.

Gladys Knight

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Knight was once known as the “Empress of Soul” and recorded hit songs back in the 1960s and 70s. However, she was hiding a massive gambling addiction throughout her career and after her retirement. She was reportedly spending about $40,000 a night on table games.

Ben Affleck


Ben Affleck loves to play both poker and blackjack religiously. He has had some big wins, but also some huge losses. He once lost $400,000 on a single hand and in 2001 decided to check himself into rehab for his gambling issues. On top of that Affleck has also been banned from several casinos.

Debt of any kind is difficult and stressful to deal with. if you’re currently dealing with debt problems, Rebound Finance, your one stop shop for all your second chance credit needs, can help. We offer a wide variety of debt relief options for Americans. Visit for more information.