If there’s one thing celebrities aren’t short on, it’s money. And with that kind of cash, it’s no surprise that some develop a taste for gambling. For many, it’s just a harmless hobby—some even use their skills at charity poker tournaments. But for others, the stakes get a little too high, and the gambling habit turns into being part of a celebrities gambling addiction list. Careers, families, fortunes—nothing is off-limits when the betting bug takes hold.
So, let’s take a look at some of the largest cases of celebrities addicted to gambling.
1) Charlie Sheen
Charlie Sheen was the king of sitcoms, raking in millions playing the cool, carefree uncle on Two and a Half Men. His character was a gambler and womanizer—except, in Sheen’s case, he wasn’t acting. With a fortune of $150 million, you’d think he had money to burn, but it turns out most of it was going up in smoke at gambling. According to his ex-wife Denise Richards, Sheen was dropping $200,000 a week on gambling. His biggest bet? A cool $1 million on a boxing match. And while he won that bet, he later admitted he wasn’t even happy about it—a classic sign of a gambling problem.
2) Tobey Maguire
Tobey Maguire might be remembered as everyone’s favorite Spider-Man, but off-screen, he had a different kind of superpower—winning big at poker. The actor was a regular in high-stakes underground poker games, playing for serious money. In 2011, he even got sued for raking in over $300,000 in illicit poker winnings. Former TV producer Houston Curtis later claimed that Maguire was actually the mastermind behind these underground celebrity gamblers‘ poker rings. Guess Peter Parker had a bit of a wild side after all.
3) Michael Jordan
Michael Jordan isn’t just the GOAT of basketball—he’s also in the running for the GOAT of celebrity gamblers. Jordan bets on just about everything—sports, online casino table games for real money, even private golf matches. His biggest known loss? A whopping $1.25 million in a single round of golf. His gambling habits date all the way back to his NBA days, and some even speculate that his father’s tragic death was connected to Jordan’s betting debts. But with a net worth north of $3 billion, losing a few million here and there hasn’t exactly slowed him down.
4) Ben Affleck
Ben Affleck is no stranger to high-stakes poker and blackjack tables. Back in 2001, he had a brutal wake-up call after losing $400,000 in a single night. Realizing he had a problem, Affleck checked himself into rehab—but his love for cards didn’t disappear. In 2014, he made headlines again when he got banned from the Hard Rock Hotel and Casino for card counting. He’s tried to keep his gambling in check, but every now and then, the urge seems to hit him again.
5) Dana White
Dana White is best known for running the UFC, but outside the octagon, he’s also one of those celebrities addicted to gambling. After major UFC events in Vegas, White can often be found at the blackjack tables, making some truly wild bets. He’s lost as much as $3 million in a single night—but don’t feel too bad for him. He’s also won as much as $3.2 million in a single session. In fact, he’s won so much that certain casinos have actually banned him from playing. When the house is scared of you, you know you’re doing something right.
Which Celebrity Gambles the Most?
If there’s one celebrity who doesn’t hide his gambling habit, it’s Drake. The Canadian rapper loves to show off his massive bets on social media, and his love for gambling reportedly started during his Las Vegas residency. From roulette to sports betting, he’s played it all—sometimes with jaw-dropping amounts. To date, it’s estimated that Drake has lost around $7 million. And it’s one of the biggest celebrities addicted to gambling.
Know When to Walk Away
Gambling can be a thrill, but if even the rich and famous can lose big, imagine what it can do to the rest of us. No matter how much money you have, the house always has the edge, and when gambling stops being fun, the consequences can be brutal. So if you’re going to place a bet, do it for the fun—not because you’re chasing your next big win, or because you want to imitate famous people with gambling problems. After all, not everyone has the bank account of many celebrities addicted to gambling to fall back on.
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