High-Stakes Addictions: How Celebrities Lost Fortunes Gambling

Being a famous millionaire sounds like a dream, doesn’t it? You have a ton of money in the bank, people adore you, and you’re living on easy street.

The names on our list range from A-listers and NBA icons to actors who made headlines for all of the wrong reasons. Some emptied their bank accounts, others got caught up in lawsuits, and some deny there was ever a problem to this day.

Gambling addiction can happen to anyone, even those who live in gated mansion communities and have an Oscar on their mantle.

Why Celebrities Are Drawn to Gambling

Big money, bigger egos, and snap-your-fingers access to the world’s most exclusive tables? It’s not rocket science or a mystery why some celebrities fall into a gambling trap.

Most of them live in high-adrenaline worlds to begin with. Add fame-induced dopamine rushes to the equation, and gambling just turns into another way to chase that very same high. Private jets, secret poker rooms, and VIP hosts make it even easier to lose track of just how far things are going.

Psychiatrists who specialize in addiction say that gambling lights up the same reward pathways in the brain as drugs or extreme sports.

Dr. Timothy Fong, co-director of UCLA’s Gambling Studies Program, told The Guardian, “Gambling becomes an escape, a distraction, or a thrill that mirrors the lifestyle they’re used to.” And that line between recreation and compulsion? It ceases to exist.

That’s the basic backstory of how it happens. And now for some real-life celeb cautionary tales. All of them illustrate how messy and destructive gambling can be, and it doesn’t matter how many awards or endorsement deals a person has.

Celebrity Gambling Disasters: 7 Shocking Stories

The following are seven very real and pretty shocking tales of celebs who went too far with gambling. Some of them are still millionaires and escaped relatively unscathed, and others weren’t so lucky.

1. Ben Affleck – Blackjack Obsession

Ben Affleck has been really open about a lot in his life, including his battles with alcohol, his rough patches in romantic relationships, and his blackjack habit. In 2014, he was booted and banned from the Hard Rock Casino in Las Vegas for counting cards. It’s not technically illegal, but it’ll get you persona non grata fast. His BFF Matt Damon made a movie about it called Rounders–was that a coincidence? Hmm…

“I took some time to learn the game and became a decent blackjack player. And once I got good, the casinos asked me not to play anymore.”
—Ben Affleck.

Affleck later confirmed it himself, saying that he studied the game, practiced strategy, and became “too good” for the casino’s liking. His skills weren’t random by any means, and he reportedly took blackjack seriously and considered it a mental challenge. But even a skill-based approach doesn’t mean it was a healthy habit.

Besides his blackjack drama, Affleck’s larger struggles with addiction point to the way gambling can overlap with other compulsions. He’s been in and out of rehab over the years, suggesting that his relationship with gambling was probably only one part of a cycle of behavior that he’s tried to manage.

• Estimated losses: Unknown, but the ban itself suggests there was heavy spending and high-stakes play.
• What Went Wrong: Affleck’s need for control and to master the game eventually turned into an obsession.

2. Charles Barkley – $10M Lost at Casinos

Iconic basketball player Charles Barkley has never been shy, and that extends to his gambling history. The former NBA MVP and current broadcaster admitted to blowing through more than $10 million in casinos. He told ESPN point-blank: “Do I have a gambling problem? Yeah. But I can afford to gamble.”

That quote aged pretty poorly. At one point, he was sued by a Vegas casino for not paying back $400,000 in gambling markers. Barkley said he didn’t gamble for the money; it was the competition and the excitement that kept him coming back. But the financial hole he dug for himself was pretty deep.

“I’ve lost a million dollars at a time on three or four occasions.”
—Charles Barkley.

He says that he eventually slowed down, especially after he was hit with legal trouble and hard conversations with friends. But his openness and willingness to talk about it give us an inside look at how gambling addiction operates in people who have seemingly unlimited funds.

• Estimated losses: Over $10 million.
• What Went Wrong: Barkley’s competitive streak didn’t stop when he left the basketball court. It followed him into the casinos, but the stakes were different.

3. Tobey Maguire – Poker Scandal

The OG Spiderman didn’t just love poker—he was really good at it. Maybe a little too good for a game that was operating outside the law.

Tobey Maguire got caught up in an underground poker ring that was run by Molly Bloom (it was turned into a movie written by Aaron Sorkin called Molly’s Game) in the early 2010s, which was oozing with scandal. The games included lots of A-listers, hedge fund managers, and one major Ponzi schemer—Bradley Ruderman—whose stolen investor money ended up in the pot.

“The underground poker ring was invitation-only—and dripping in cash, crime, and celebrities.”
—Tobey Maguire.

Maguire reportedly made hundreds of thousands from the games, but that money got him sued by Ruderman’s victims. He eventually settled, but the whole thing exposed a side of celebrity gambling that most people never see: high-stakes games in penthouses, insulated from the public and run like private clubs.

According to court documents, Maguire wasn’t only a player, he was a regular winner and a calculated competitor. That, combined with the fact that the money he won was technically stolen, added some extra messiness to the whole saga.

• Estimated losses: He reportedly profited over $300,000 but had to pay an undisclosed amount to settle the lawsuit.
• What Went Wrong: Even when you’re good at gambling, getting entangled with criminals and lawsuits can put your name on the wrong kind of headlines.

4. Michael Jordan – Gambling Almost Everywhere

The GOAT of the NBA, Michael Jordan’s relationship with gambling is one of the league’s most talked-about “open secrets.” He famously bet thousands on golf rounds, high-stakes poker games, and reportedly on coin flips. In one of the wildest rumors, people speculated that his first retirement was connected to a quiet suspension for gambling, but the NBA has always denied it, so we cannot confirm this rumor.

“I can stop gambling. I have a competition problem.”
—Michael Jordan.

Jordan himself has shrugged it off. He once said, “I have a competition problem,” not a gambling one. But stories about million-dollar nights in Atlantic City and huge losses while on road trips during the playoffs don’t exactly scream that it was some harmless hobby.

And while Jordan is still massively wealthy—his 2023 sale of the Charlotte Hornets alone made him a billionaire—it’s pretty obvious that his gambling wasn’t just for funsies.

• Estimated losses: Rumored to be in the millions, though this has never been confirmed publicly.
• What Went Wrong: Jordan’s relentless drive didn’t stop after his basketball career ended, and gambling turned into another arena to try and win.

5. Pamela Anderson – Married a Poker Player Over Debt

In one of the absolutely most bizarre celebrity-gambling crossovers, Pamela Anderson reportedly married Rick Salomon, a professional poker player and infamous ex-boyfriend to Paris Hilton, so that she could erase a $250,000 debt she owed him from a game.

“I was playing poker one night…and I was down about 250 grand. He said if I made out with him, that would clear the [bet].”
—Pamela Anderson on The Ellen DeGeneres Show

Anderson later told Elle that the marriage was a way to “even things out” financially, though the relationship fell apart almost immediately. They divorced, remarried, and split again, and there were lawsuits and ugly public fights sprinkled throughout the drama.

Anderson has always been tabloid fodder (unfairly so), and this made them giddy, but underneath the story was the fact that gambling got personal, like, really personal. Anderson lost more than money; she lost her privacy (again) and her peace of mind.

• Estimated losses: $250,000 in poker debt.
• What Went Wrong: Gambling got personal and mixed up money and love into a big and messy knot.

• Estimated losses:

6. Nicolas Cage – $150M Career Wipeout

At the peak of his career, Nicolas Cage had enough money to buy castles, and he did! He reportedly earned $150 million between 1996 and 2011, but he was still in serious financial trouble thanks to bad investments, outrageous spending, and casino visits that bled him dry.

“I once won $20,000 in a casino, then gave it to an orphanage. I never gambled again.”
—Nicolas Cage.

He once described winning $20,000 in a casino, and then walking straight out and donating it to an orphanage. Sounds noble, right? And it was! But the affair was a lot messier than a donation. He owed the IRS millions, sold off his assets, and took every movie role that came his way just to stay afloat (there were some absolute B-movie bangers during that period, just saying).

To his credit, Cage has worked his way back financially with a string of indie roles and hits. But his story’s another reminder that Oscar-winning actors can burn through money at a terrifying pace when gambling is involved.

• Estimated losses: Part of a $150 million blowout that was tied to gambling and lavish spending.
• What Went Wrong: Cage’s love of risk and excess eventually caught up with him, and it cost him everything—until he clawed his way out of the financial hole he’d dug for himself.

7. Allen Iverson – ‘Broke’ Despite $200M Career

Allen Iverson was one of the most electrifying players the NBA has ever seen. But this baller couldn’t stop bleeding out money. He reportedly gambled away massive amounts and was banned from several casinos, including ones in Detroit and Atlantic City.

“Banned from multiple casinos and locked out of his own fortune until age 55.”
—Allen Iverson.

In court, he admitted that he couldn’t afford to pay back his debts, and at one point, a judge ordered that most of his money be held in trust to keep it from disappearing. Reebok reportedly created a $32 million trust that he can’t access until he turns 55, with the goal of saving him from himself.

Iverson is still a beloved figure in basketball, but his story shows just how fragile financial success can be even when you’ve earned hundreds of millions.

• Estimated losses: Unknown, but most of his $200M career earnings are gone.
• What Went Wrong: Iverson’s spending habits and gambling spiraled to the point that outside intervention was needed to protect what little was left.

The Dark Side of Glamour: Gambling Addiction is Real

All of the above stories point to a pattern: quick money, high stakes, and very few, if any, limits. For celebrities, gambling isn’t just accessible. It’s basically delivered to them with champagne bottle service. And when fun and addictive behavior intersect, it can have dire financial and emotionally devastating consequences.

Gambling addiction does not care how famous or rich you are or if you’ve won an Academy Award. It empties bank accounts, wrecks relationships, and leaves people stuck in vicious cycles of debt and secrecy. According to the National Council on Problem Gambling, an estimated 2 million adults in the U.S. meet the criteria for a severe gambling problem.

Conclusion: The House Doesn’t Care Who You Are

Celebrities aren’t just like us in most ways, but they are in one important area—they can lose millions the same way that non-famous people lose hundreds, and it happens one bet at a time. Fame can’t and won’t protect anyone from addiction, and the stories are proof that no bank account will be safe if gambling turns into a compulsion.

Want to know what this addiction looks like before it goes off the rails? You can check out How Gambling Addiction Starts: Early Warning Signs.