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

We now have detailed biographies on people involved in all aspects of gambling. We address those who have won big, and those who have lost it all. We’ve written about those who have found legitimate ways to win, those who have cheated and those who have engaged in outright criminal behavior.

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.”

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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.

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 Money

We all know that pro sports players earn a lot of money. Some of these players get so much money for their talent that it doesn’t seem like they could ever spend it in one lifetime. Although that seems like the way it is to us average citizens, it happens to be a real problem of professional sports players winding up down and out and in a financial mess. There is actually a high percentage of pro sports players that don’t know how to curtail their spending and they wind up spending themselves right into court to file for bankruptcy. If you have ever wondered who some of the biggest spenders were that found themselves broke and in the poorhouse, keep reading to see who the 20 top high paid athletes who went completely broke, are.

20. Vince Young

As a former star quarterback for the Tennessee Titans, Vince Young would have, and could have been living on easy street, but that was not to be. Only seven years after signing on with the pro NFL team, Young was in court filing Chapter 11 bankruptcy. Ronnie Peoples, Young’s former financial advisor, claimed that Young spent his money faster than he made it. He received one of the highest paid, Rookie contracts, receiving a $26 million contract with the Titans, and as Peoples explains it, he blew through his money recklessly. He would purchase extremely high-ticket items, including a $176,000 Ferrari, and had no means to pay for it. His bankruptcy petition showed that he and his wife had assets that worth between $500,000 and $1Million, yet had liabilities that were in between $1Million and $10Million. He has not been with the National Football League since 2011.

19. Mike Tyson

Mike Tyson is one of the biggest names in the boxing arena. He has won multiple championships and made a fortune, boxing. His career was tainted by many different issues, including battles with drugs and alcohol. He was involved with multiple women, and in those relationships, had five children. Tyson not only had a love for boxing, but he had a love for spending his money frivolously, and because of that, he hit rock bottom financially, and eventually made the announcement in 2003, that he was destitute – completely broke, with no money in the bank. On the flipside, Tyson said that despite having no money, he was completely happy. He claimed he was happily married to a woman he didn’t deserve, Lakhia Spicer, had a daughter with her and four other children with other women, whom he loved, and was just happy to be given a second chance at life.

18. Diego Maradona

One of the world’s greatest soccer players, Diego Maradona, hails from Argentina and played in four World Cups in four consecutive yeas. He finally won the championship in 1986, scoring the most controversial goals in the history of soccer. He made a great living, playing pro soccer, unfortunately, Mardona had a history of not paying taxes and the Italian Tax Authority caught up to him in 2009 and demanded that he pay a $54 million, back tax figure. This put Maradona in the poor house and he was force to file bankruptcy.

17.John Daly

One of the most recognized names in pro golf, is John Daly. He was a household name for years in the sport, and he made a substantial amount of money playing. He had many championships under his belt and was one of the highest earners of any player. In an interview, he discussed his financial issues and the vices he dealt with, one of which was gambling. Daly admitted that he lost an enormous amount of money gambling, and the figure he gave, astounded everyone. He claimed to have lost more money than many golfers made in their career, stating that over the years, he lost about $98Million and only won about $45, which meant that he only truly won about $50Million. Due to his gambling addiction, Daly went broke and is one of the top 20 highest paid sports figures to lose their money.

16. Dennis Rodman

Former NBA player, most recognized for his time on the Chicago Bulls, though he played short stints with various other teams. He is remembered as one of the most flamboyant and distracting players in the NBA and now, is remembered as one of the NBA players who wound up going broke, to add to his list. He went to court to file paperwork, claiming that he could not make his back child support or spousal support payments due to being sick and broke. He owed a whopping $800,000 in back child support, and $50,00 in back spousal support. Although he didn’t earn what some NBA players may earn in their career, Rodman had an incredible wealth between his NBA contracts and many other ventures he embarked on, including TV shows, ads, endorsements, and movies.

15. Sheryl Swoopes

It is estimated that Sheryl Swoopes had a total earning of $50Million during her professional career with the WNBA. NBA players have one of the biggest problems with overspending, and are a sport that experience a large number of their players that wind up having to file for bankruptcy. Swoopes was one of the biggest faces used to represent the WNBA and her incredible earnings did not last her lifetime. She claims to have had terrible representation and made bad investments, as well as she has said that she also played a role in her loss of money. Swoopes wound up having to sell Olympic medals and her Naismith trophy in order to satisfy creditors, which also included a $250,000 debt to the IRS.

14. OJ Simpson

If you don’t recognize the name from pro football, surely you know the name from the big murder scandal and trial of the century with accusations and charges that Simpson murdered his ex-wife and her boyfriend, Ron Goldman. He had a net worth of $11Million, but for obvious reasons, with a murder trial and all the legal fees that go with it. He was ultimately found not guilty in the murder charges, but was found responsible for the killings in a civil suit and was ordered to pay compensation and punitive damages to the Goldmans that totaled $33.5Million. Today, Simpson sits in jail on unrelated charges, as a broke man.

13. Leon Spinks

Former heavy weight boxing champion, Leon Spinks. had earned approximately $4.5 million during his career. When he defeated Muhammad Ali in 1978m his career hit a high, but less than twenty years later, he was broke and homeless. He had admitted to spending frivolously and squandered his earnings away, mostly on drugs, as well as he had many run-ins with the law. He was last reported to be working as a janitor at a YMCA in Columbus, which is a far cry from a number one position in a pro sport.

12. Dorothy Hamill

The 1970’s were a big time for ice skating and for a girl named Dorothy Hamill. Dorothy went to the 1978 Olympics and took home the Gold medal. She later took a position in the famous, Ice Capades in the 1980’s and was one of the most iconic skaters in the sport’s history. Sadly enough, after all the money Hamill earned in her career, endorsements and other ventures, Hamill was filing for chapter 11 Bankruptcy in 1991 and had sunk to a financial disaster of being broke. She had spent a lot of money on multiple ventures, and later spent more on court costs fight for custody of her daughter, along with money battling depression, and money on medical costs when she was diagnosed with breast cancer.

11. Lawrence Taylor

Lawrence Taylor had a good thing going with his NFL career until he got himself into a boatload of trouble with his finances. He is known to have had a severe drug problem and spent a lot of money on drugs, sniffing and otherwise. He also was a very big spender, spending his money foolishly on all kinds of things that he could not afford. Taylor also reportedly was in big trouble with the IRS for filing a false tax return and furthermore, he was sued for child support, all while allegedly shelling out $300 to an underage prostitute. Taylor pretty much earned his right to be broke, according to reports throughout his ordeal.

10. Darren McCarty

Known for his time on the Detroit Red Wings pro hockey team, McCarty made some poor business deals during his career and wound up having to file for bankruptcy a few years ago, causing him to lose his, over $15 million, that he earned during his professional career. He claimed that $6 million of what he owed was to creditors and despite having been a very successful hockey player, just a few years into his retirement, McCarty found himself bankrupt and not in near the financial position he had grown accustomed to.

9. Travis Henry

The NFL running back who played for multiple teams, had a big financial downward spiral and a lot of it had to do with having nine children by nine different women. Some of the children were born in close proximity to each other. The situation put him into financial ruin and he wound up broke just by having fathered so many children with so many women.

Celebrities Who Lost It All Gambling Winnings

8. John Arne Riis

The young soccer player had to file bankruptcy and found himself in a dispute with his former agent, Einar Baardsen, over what is said to be, poor management of his money and how it was invested. It was reported that he owed over 100,000 pounds in debt, although it has been reported that he earned 50,000 pounds a week. The agent stopped representing this pro soccer player in 2005, and the matter was still in the works to be resolved, but until it becomes resolved, Riis has been listed as one of the pro players who have gone completely broke.

7. Lenny Dykstra

This former pro baseball player for the Mets, Lenny Dykstra, not only went broke, but he went to jail. He spent three years in the state penitentiary for grand theft auto. He had filed for bankruptcy in 2009, saying that he owed more than $31 million with only $50,000 worth of assets. After he filed for bankruptcy, the Federal prosecutors claim that Dykstra went and sold about $400,000 worth of his possessions from his $18.5 million mansion that was bought from pro hockey payer, Wayne Gretzky.

6. Johnny Unitas

The Baltimore Colt’s quarterback, Johnny Unitas filed Chapter 11 bankruptcy in 1991, and he and his wife filed for protection against creditors being able to come in and seize personal accounts and property in order to repay debts they owed. Unitas was said to be in debt of $3.2 million dollars and was having to work with banks and creditors to try to settle his debts, but in the end, he wound up broke and in financial ruin after all was said and done.

5. Rollie Fingers

As a free agent, Rollie Fingers played pro baseball for the Milwaukee Brewers in the 1979’s and in 1978, he filed bankruptcy with reports of desperately needing cash to pay for his rent and food for his 4 children. He made a series of bad investments and was involved in business scams that caused him to lose his $1.1 million. He is only one of many pro sports players to lose all they made and become broke, including losing his line of Arabian horses he had purchased and owned until the bank stepped in and sold them for $5,000 to help pay off the debt he owed.

4. Deuce McCallister

Deuce McCallister had a promising NFL career playing for the Saints. He made tens of millions during the years he was the running back for the team, however, like many other pro sports players, McCallister made some poor investment choices that wound up costing him millions and left him a financially ruined man. The home he lived in was seized by the St. Charles Parish Sheriff’s Office and was auctioned off. He was also sued by the bank that held his mortgage, Whitney National Bank, who claimed he owed $1.8 million on the mortgage. He also lost his Nissan dealership in Jackson, Mississippi when they filed for bankruptcy. The financial situation he was in, left him reeling and scrambling to just stay afloat.

3. Mark Brunell

Mark Brunell made about $50 million playing for the NFL on the NY Jets. In the end, Brunell had about $5 million in his account with about $25 million in debt. It is said that Brunell had a lot of bad luck with real estate investments and bad business choices. He bought a lot of Whataburger franchise restaurants where 5 of the 9 went belly-up. He did not have good luck with investing and was the biggest role of his financial downfall.

2. Warren Sapp

Celebrities Who Lost It All Gambling Casinos

One of the most acclaimed names in the NFL, Warren Sapp has one of the most memorable bankruptcy stories ever. Sapp had to sell off all of his belongings, and it was a lot. Sapp earned $82,185,056 during his NFL career, at the end, when filing for Chapter 11, his bank account was like many other people’s in the real world, with $826.04. At an auction at his $4.1 home, all of his expensive taste items were being auctioned off. It was hard to imagine how someone so famous and wealthy, could wind up with so little. Well, that is, until you saw his huge, expensive tennis shoe collection, lion-skin rug, among other high-cost items found throughout his home. He clearly had more expensive taste than he could afford.

Celebrities Who Lost It All Gambling Losses

1. Evander Holyfield

Evander Holyfield is one of the most decorated pro boxers in the history of the sport. He has claimed many championships and had an extremely successful career. He earned millions upon millions during his career, but eventually began to have some financial difficulties that started with child support issues that later turned into a major downward spiral for the boxer. He was forced to sell his million dollar mansion that was sold for $7.5 million. This barely touched the surface of what he owed because he owed the bank more than twice that much, and was in debt with the IRS for more than $200,000. His financial situation became public and the world watched as he went through his financial desperate situation and was forced to sell off all of his worldly possessions in an effort to try to help his grim debt situation. Holyfield is one of the top pro sports players that wound up completely broke and destitute.