• Celebrities Who Lost It All Gambling Casinos
• Celebrities Who Lost It All Gambling Winnings
• Celebrities Who Lost It All Gambling Losses

All the gamblers on this list have had to think ‘what if’ when reflecting back on their careers. Each of these players was up big at some point and lost everything. Ungar is arguably the best all-around gambler ever. But sports betting and cocaine proved to be powerful addictions that he couldn’t overcome. Here are 25 examples of rich and famous celebrities who lost all of their money at one point in their careers. Some of them managed to bounce back, while others remain in financial trouble.

Celebrities Who Lost It All Gambling Casinos

Professional athletes can make millions of dollars through lucrative contracts — and sometimes billions when you add in endorsement deals — but despite their high paychecks, many end up going broke. According to a 2009 report by Sports Illustrated, 78% of former NFL players have gone bankrupt or are under financial stress within two years of retirement, and within five years of retirement, an estimated 60% of former NBA players are broke. Similar fates have befallen professional baseball, golf and hockey players as well.

But where exactly do those millions go? GOBankingRates is breaking down exactly how 25 athletes lost millions of dollars, with some falling from the top of their game to financial rock bottom.

Last updated: July 28, 2020

Did former poker organizer Molly Bloom witness the biggest gambling loss ever?

The film adaptation of Bloom’s 2014 memoir hit U.S. theaters on Christmas Day, and to promote the project Bloom has been making her interview rounds. In a recent chat with Ellen DeGeneres, Bloom revealed the biggest poker loss she ever saw first-hand.

“I saw someone lose $100 million in a night,” Bloom told DeGeneres.

“$100 million?” DeGeneres asked incredulously.

“$100 million,” said Bloom, “and he paid the next day.”

Bloom said the buy-in for her most expensive and exclusive games, which ran in L.A. and later New York City, was $250,000. That was presumably the minimum buy-in. According to Bloom, it wasn’t unheard of for someone to lose an entire buy-in in the first few hands of the evening.

“This game was populated by some of the world’s most famous, wealthiest, and most powerful men,” she said in a Business Insider interview. “My regular game in New York City was a $250,000 buy-in, no limit. So people were burning through that, a lot of times in the first 30 minutes.”

The $100 million loss raised a lot of red flags for her. The game, which took a rake, eventually fell into the cross-hairs of federal prosecutors in the early 2010s.

“When you watch that, as an owner-operator of a game, you realize that these numbers are incredibly unsustainable, incredibly unhealthy,” Bloom recounted. “So, I was not happy about this loss. It brought me no joy or adrenaline. I recognized it as really unhealthy and unsustainable.”

Celebrities in her games, which kicked off around the height of the poker boom in the mid-2000s, included Alex Rodriguez, Dan Bilzerian, Leonardo DiCaprio, Ben Affleck, Matt Damon, Toby Maguire and Nick Cassavetes, as well as billionaires such as Alec Gores and Andy Beal.

Beal, as the poker community knows, etched his name into poker history thanks to his losses between 2004-2006 against the “Corporation,” which was a group of bankroll-pooling poker players that included the likes of Phil Ivey, Jennifer Harman, Doyle and Todd Brunson. Beal lost more than $16 million alone in a heads-up match versus Ivey.

Bloom took a plea deal and received probation in 2014 for her poker games, which were linked to a wider illegal gambling operation involving Russian organized crime. A lawyer for the former Olympic-class skier said she profited $1 million for her work hosting the games.

That’s a pretty small sum considering the amount of money exchanging hands.

Celebrities Who Lost It All Gambling Winnings

None of the aforementioned celebrities and businessmen were accused of any wrongdoing. However, Maguire was sued in 2011 over his winnings in the game, because one of the game’s participants, businessman Brad Ruderman, was orchestrating a Ponzi scheme. The government said that Ruderman lost about $25 million of investor money in the poker games.

Celebrities Who Lost It All Gambling Losses