Skip to main content

5 Top Celebrity Gambling Losses

Recently updated on November 10th, 2023

Some top celebrities have a tendency of spending their money on a few questionable things. That’s hardly unusual, so unanticipated spending won’t even scratch the surface of their wealth. Besides, being a top celebrity means not only fame and glory but also unfathomable sums of money. This accumulated wealth can be used to fund a variety of unusual hobbies and opulent pursuits such as gambling.

Money defies all the conventions of a mundane daily routine and while some top celebrities make money from gambling not all of them are that lucky. So, which top celebrities have a soft spot for gambling, especially table games, and why does online blackjack continue to captivate players? We take a look at the top 5 celebrities that have lost hundreds of dollars while gambling.

Celebrity Gambling Losses

Biggest Celebrity Gambling Losses

Gambling is a combination of a risky environment, large stakes, and thrill. Not all players can afford a seat at top tables where the bets are high, and winnings are life-changing. Well, some celebrities have the cash to bet thousands or even millions of dollars and not worry about winning or losing. Gambling is, without a question, always associated with dangers and obstacles. There is never a certain guarantee that your wager will be successful. When it comes to celebrity gamblers, though, the losses can sometimes appear to be catastrophic. Five celebrity gamblers have been chosen.

1. Charlie Sheen

The popular and much-loved actor from Two and a Half Men was quite a fan of placing large bets. Sheen was a regular bettor who had absolutely no problem with spending lots of money on bets. He is notorious for spending about $200,000 a week at casinos. But it doesn’t end well, Sheen reportedly lost $2.5 million in only three months while gambling.

2. Allen Iverson

The former American professional basketball player who was nicknamed “the Answer” definitely didn’t have all the answers when it came to placing bets. He gambled away his entire $200 million fortune throughout his professional career. Due to his gambling issues, the 11-time NBA All-Star has been barred from casinos in both Detroit and Atlantic City. Besides gambling the pro player also got into some other trouble that saw him be kicked out of the NBA. We guess luck isn’t really a thing he is familiar with.

3. Gladys Knight

The incredible American singer and songwriter who is also known as “The Empress of Soul” was an avid blackjack and baccarat gambler. Gladys tried to hide her vice even after her retirement in 2000 when she was busy creating many R&B singles. Later, in her memoirs, she detailed her battle with a gambling addiction. Gladys’ actual losses were never revealed, but she is said to have spent up to $40,000 per night playing table games. So, you can imagine how much was spent in a year.

4. Leonard Toe

Toe ended up with a $25 million debt and had to sell his ownership of the Philadelphia Eagles NFL franchise in 1985 to pay it off. In casinos, Leonard Toe lost about $50 million of his trucking industry profit. Furthermore, Toe was unable to resolve his staking issues, which resulted in the seizure of two of his homes for unpaid taxes. Talk about some bad gambling habits.

5. David Milch

Well-known for losing $25 million in a casino once, this famous producer had a risky tendency of gambling. David Milch engages in a variety of staking activities and ended up being in debt.  Milch attempted to repay his debt and was successful in repaying around $17 million. However, he was unable to pay the complete loan, and as a result, they were able to seize the $100 million that he had acquired through his efforts.

Gamble Responsibly

As you can tell, gambling has nothing to do with who you are. Sure, these celebrities may have won a few games, but they ended up spending more than what they should have. Some of them went into debt and developed a gambling problem. We don’t want that for you. That is why we emphasize the importance of responsible gambling, keeping and sticking to a budget and playing at casinos that allow self-exclusion. In fact, we highly recommend playing at top casinos as they make it a bit difficult to spend more than what you should with depositing limits. But also make sure that you are playing within your limits!


Related Posts