Lights, Camera, Gamble! Top 5 Celebrities Who Lost Big
Lina Almans
09 June 2022
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For some celebrities, the thrill of gambling has become a full-blown addiction, and they are willing to do almost anything to indulge in their passion. Here are the top five celebrities who have lost large sums of money:
Celebrity | Occupation | Biggest Failure |
Drake | Musician | Lost $27 million |
Michael Jordan | Basketball player | Lost $5 million |
Ben Affleck | Actor | Lost $400,000 |
Pamela Anderson | Actress | Lost $250,000 |
Tobey Maguire | Actor | Paid $80,000 to keep his name clear |
The Night Drake Lost $27 Million

Drake is no stranger to gambling addiction and has lost millions of dollars in high-stakes games. He lost $27 million in a single night while gambling with French Montana on Twitch, and he’s also lost hundreds of thousands of dollars in other high-stakes games. Drake has also lost approximately $300,000 after betting on F1 pilot Charles Leclerc not coming first in the Formula 1 Spanish Grand Prix.
Ben Affleck’s Blackjack Ban: Too Good to Play

Ben Affleck’s well-known gambling habits have landed him in hot water, resulting in a ban from playing blackjack at the Las Vegas Hard Rock Casino. His skills at the game were deemed “too good” by security, leading to his expulsion. His addiction to gambling spiraled out of control, nearly leading him to rehab.
Affleck’s gambling losses have also been significant, as he lost a staggering $400,000 in a high-stakes poker game with other celebrities, including Tobey Maguire and former Yankee slugger Alex Rodriguez.
Michael Jordan: The $5 Million Craps Disaster

Michael Jordan, the basketball legend, is infamous for his lavish spending on gambling. There’s an urban legend that his initial retirement was actually a ban imposed by the NBA due to his excessive gambling.
In Las Vegas, Jordan’s biggest gambling loss was at the craps table, where he lost a staggering $5 million in a single night. As someone who’s fiercely competitive, Jordan was probably more disappointed about the loss than the actual financial impact.
Pamela Anderson’s Big Losses

Pamela Anderson, famous for her roles on Baywatch and Playboy magazine, has a long history of high-stakes gambling. In fact, Anderson once lost significant amounts of money during these games, including a stunning $250,000 in a poker game at the Mirage Hotel and Casino in Las Vegas.
Tobey Maguire’s Illegal Poker Ring Scandal

Tobey Maguire’s involvement in an illegal poker ring with other celebrities, including Ben Affleck, caused quite a stir in the gambling world. Maguire won approximately $300,000 from a man who had stolen money from investors to fund the games. However, his participation in the illegal gambling ring didn’t go unnoticed, and Maguire ultimately had to pay $80,000 to keep his name out of the lawsuit.