The Celebrity Casino Curse: Examining the Most Noteworthy Losses

Celebrity Casino Curse

Winning and losing is part and parcel of gambling. But what if your action becomes history? Yes, you read it right. The gambling industry is packed with various examples where the winning and losing amount has made people a celebrity overnight. These losses are so massive that some losers hadn’t even survived them. 

In our discussion at, we’ll outline some of the most noteworthy losses that have made history. Scroll down the page and learn from their fates. 

The Biggest Gambling Losses in History

Gambling is addictive, and people cannot control themselves to place continuous bets until they win or lose everything. And believe me, the history is full of such examples. If you play properly, you can win big and transform your life in a couple of hours. However, if you are inclined to impulsive playing, you can lose everything in seconds, leaving you frustrated and disappointed. 

Ahead, we have outlined a few such stories that will surely drop your jaw in surprise and make you believe in real-time losses and misfortunes. So, without further ado, let’s get into it. 

1. Drake


The famous Canadian rapper is not only known for his stunning sound and vibrant albums but also for losing over $1 billion in 2 months, and the credit goes to gambling. Drake began his casino journey in December 2021 under the username DeepPockets6, and he lost around $1 Billion in just two months by placing bets on various sports and casino games. 

One of the surprising factors about Drake’s loss is that the Canadian Rapper has never hesitated to post his casino losses or journey on his social media account. And how could we forget about the Drake curse? 

Any gambler who keeps up with Drake’s high-profile sports wagers must have heard about this celebrity curse. Most people believe that everything this rapper touches turns to loss. Although we don’t believe the facts, people do, and the majority wins. From Serena Williams to Anthony Joshua, whoever has been endorsed by Drake has suffered great losses. The Drake Curse has now become a legendary norm, and even analysts are trying to see if that’s true. 

In November, the rapper lost a whopping $2 million on a $ 287,000 bet, and the story continues. He also crashed out $235,000 by betting on Charles Leclerc, a Formula 1 racer to win the Spain Grand Prix. All in all, Drake has a very odd history in terms of gambling, be it casino games or sports. 

2. Terrance Watanabe

Terrance Watanabe

Let’s proceed further with yet another name, Terrance Watanabe. His gambling journey started in 1977 when his father passed away, and he inherited the Oriental Trading Company. Watanabe instantly indulged himself in a year-long gambling binge in LA. He once placed a stunning $835 million in bets and lost $127 of it. 

Studies also suggest that Watanabe was often seen drunk during his gambling sessions, leading to further losses and frustration. All this happened in Caeser’s Palace, Las Vegas. The owner of the casino has fined him $225,000 for his drunken behavior. 

It is said that Terrance Watanabe still owes $15 million and risks going to jail if he doesn’t pay this amount. 

3. Harry Kakavas

Harry Kakavas

The next celebrity curse is Harry Kakavas. A former Australian millionaire, Harry once lost $20.5 million in his gambling session. This real estate magnet has sued Crown Casino in Australia’s High Court, saying that they took advantage of his impulsive gambling habit. However, he also lost the case as the judge believed that Harry was an adult and could make logical decisions. 

In addition to losing millions in gambling, Harry lost his real estate business gradually. He was also imprisoned for four months for doing fraud with a well-known Australian corporation of $220,000 and using it to support his gambling addiction. 

4. Charles Barkley

Charles Barkley

He is unarguably one of the leading names on the list, and who doesn’t know this famous 11-time NBA All-Star? But while Charles is well-known for its basketball tactics, he is not a responsible gambler. To your surprise, Charles almost lost $30 million in wealth via gambling. 

You might be amazed to know that Charles once crashed out $2.5 million in a single game of blackjack, making him one of the most irresponsible and impulsive gamblers of all time. However, what makes Charles Barkley different from others on the list is the fact that he usually enjoys playing these games and has never shown any regret for such massive losses. Over the years, Barkley gained knowledge about gambling and started playing it responsibly. He also took a break from all of these for a while and then began his journey with bets he could afford. 

All in all, Charles is one of those gamblers who have learned from his mistakes and protected himself from losing everything in gambling. 

5. Maureen O’Connor

Maureen O’Connor

Last but not least, the name on our list of celebrity curses is Maureen O’Connor. Although she is the only woman gambler on our list, she is equally notable for her impulsive gambling and has lost millions of dollars for placing rigorous bets. She is known to be the mayor of San Diego at the time when she lost $13 million in the casino. 

While she sharted placing bets with $1 billion throughout her gaming sessions, she still somehow managed to lose around $13 million in the end. O’Connor’s gambling addiction is something out of control, and she has to borrow $2 million from the charity foundation to pay the money she lost in the video poker.

While she did a good job as a mayor, she was not a responsible gambler and lost a whopping amount of her wealth in the casinos. However, later on, she learned about responsible gambling and left this game for good. 

Summing Up

That’s all about the most noteworthy casino losses. We hope our guide has helped you know the fate of those who play impulsively and have no control over their emotions. Gambling is addictive, therefore, gamers are suggested to keep their emotions in control and place bets mindfully. Stop playing if things are not going as intended, and stay safe. 

Posted by
Bobana Hemun

My name is Bobana Hemun, I graduated from the Faculty of Medicine in Novi Sad. I am a professional occupational therapist. I used to work at the Oncology Institute of Vojvodina, after which I set my sights on the SEO world. I enjoy spending my free time relaxing with yoga, hiking in nature, or taking care of my plants.