Biggest Gambling Losses: Gamblers Who Lost It All

Biggest Gambling Losses: Gamblers Who Lost It All

It takes time to go from zero to hero, but the opposite is much, much faster.

And in the world of gambling, all good fortune can change in a matter of seconds.

Check out our list from bottom to top of the people who lost everything gambling, suffered the biggest gambling losses in history, as well as their personal struggles.

10. Erick Lindgren (E-Dog)

Age: 45

Nationality: American

Profession: Professional poker player

Total Amount Gambled: $10,3 million

Debt: more than $12 million

Game: Poker, Fantasy Football

A two-time World Series of Poker champion who earned more than $10 million during his career has collapsed along with his poker cards fame after he began betting heavily on fantasy football and sports. Because of his gambling habits and addiction to it, he ended up in a rehab clinic after he mentally collapsed. In 2011, he not only lost it all, but he was also left with more than $2.5 million in debt.

Struggling to gamble in poker with what appears to be his way out of poker debts, he failed once more in 2015, filing for bankruptcy. As a result, he is being sued for millions of dollars by PokerStars, the successor to Full Tilt Poker. In addition, Lindgren is still in debt to his fellow players and the IRS – for failing to pay the tax on his winnings.

9. David Rheem (Chino)

Age: 41

Nationality: American

Profession: Professional poker player

Total Amount gambled: $11.3 million

Debt: undisclosed

Game: poker

Despite winning over $11.3 million in tournaments, he is left with nothing but debts after a successful gamble on his way to fortune and fame. The Amount owed to institutions and co-players by this professional is still unknown. Rheem owed and still owes so much money that rumours circulated he was not only a debtor but a swindler as well.

His admission to owing many co-poker players even resulted in his Epic Poker League membership being placed on probation. The three-time WPT champion is one of those people who lost everything by gambling, despite having made his fortune in the same way.

8. Michael Vick

Age: 41

Nationality: American

Profession: Retired NFL quarterback, Fox Sports studio analyst

Total Amount gambled: undisclosed

Debt: $19.9 million, paid off fully

Game: Dog Fighting

Vick was sentenced to 23 months in prison for his direct involvement in dogfighting, high-stakes gambling, and brutal executions of dogs. Not only that, but as soon as his crimes were revealed, his NFL team, The Atlanta Falcons, demanded nearly $20 million in reimbursement from a $37 million pre-delivered bonus, which was also approved and supported by a court rule. In addition, he declared bankruptcy in 2008 while still in prison. 

After serving his sentence, he returned to the NFL and paid off all of his debts. He also advocated for legislation that would create federal misdemeanour penalties for those who watch illegal animal fighting and make it a felony for adults to bring children to rights.

7. Charles Barkley (Sir Charles)

Age: 59

Nationality: American

Profession: Retired NBA player, TV Sports analyst

Total Amount gambled: $30 million

Debt: $400,000, paid off fully

Game: Baccarat, Roulette, Dice, Blackjack, Betting on Sports

The ace of the Phoenix Suns and a Hall-of-Famer, Charles Barkley, is one of the most famous gambling addicts and he did not replicate his on-court success in managing his bankroll and finances. Instead, he could gamble almost everything he earned during his long and successful sports career, mostly in Las Vegas casinos.

Despite his openness about his gambling addiction, his obsession with casino games caused him to be one of the biggest gambling losers, despite remaining cool and excited to play another round to this day.

6. Stu Ungar (The Kid)

Age: deceased (1998, 45 years)

Nationality: American

Profession: Professional poker, blackjack, and gin rummy player

Total Amount gambled: $30 million

Debt: undisclosed

Game:  Gin rummy, Poker, Blackjack, Horse and Sports betting

Stu entered the gambling world at a young age, becoming one of only two people to win the World Series of Poker three times and owning five WSOP bracelets. His outstanding maths skills and photographic memory served him well in defeating opponents with such dominance and aggressive tactics that no one wanted to play against him.

Then there were the years spent battling cocaine addiction and compulsive gaming. He was still winning, but he was spending a lot more money on horse and sports bets. His personal life was in shambles; his adopted son had committed suicide, and his daughter was the only thing keeping him connected to the outside world besides addiction. He was struggling with debts and visible physical manifestations of his abuse when he won the WSOP in 1997, earning the nickname “The Comeback Kid.” Ungar passed away with no assets to his name.

5. Leonard Tose

Age: deceased (2003, age 88)

Nationality: American

Profession: Owner of Tose Inc

Total amount gambled: $40 – $50 million

Debt: over $50 million, paid off fully

Game: Gin, Blackjack and other casino games

Leonard Tose is a perfect example of a successful business story that went horribly wrong because of poor gambling and alcohol abuse. His inherited successful trucking business was worth $20 million per year. An avid football fan, he began investing in the NFL Philadelphia Eagles, which paid off until he bought out the team entirely in 1969 for $16.1 million.

After losing $25 million in various Atlantic City casinos, Tose was forced to sell the Eagles for $65 million. This, however, did not put an end to his tribulations. His gambling losses continued, and multiple lawsuits from well-known casinos reduced his fortune. During his final years, the rest of his material belongings were confiscated because of unpaid taxes. After five marriages, he died alone in a Philadelphia medical centre at 88.

4. Archie Karas (The Greek)

Age: 71

Nationality: Greek-American

Profession: Professional poker player

Total Amount gambled: over $45 million

Debt: /

Game: Pool, poker, baccarat, craps

The man who pulled off the greatest winning streak in history (named “The Run”) climbed his way up to his millions out of a passion for the game, asserting he never cared about the money. He arrived in Las Vegas in 1992 with only $50 and a $10.000 loan from a fellow gambler. Karas turned the loan into $30,000 in winnings and could pay off his debt in a matter of hours. Nobody wanted to play poker with him because of his unrivalled reputation. 

He lost a $30 million fortune in just a few weeks, losing $11 million on baccarat and another $18 million on craps tables. Then, he went back to Greece for a “quick break,” only to return to Vegas and continue his losing streak, costing him the rest of his millions and making him one of the biggest gambling losers of all time.

3. Maureen O’Connor

Age: 70

Nationality: American

Profession: Teacher, Politician, Mayor of San Diego

Total Amount gambled: 1 billion

Debt: $2.1 million

Game: Video poker

In contrast to her family’s inability to afford basic food for the table, this capable and well-educated woman becomes San Diego’s first female mayor and an avid gambler.

Her addiction became so severe after her husband died in 1992 that she had to withdraw money from charity funds entrusted to her by him. In 2008, she arranged a series of transfers totalling $2,088,000 from the foundation to her personal account. Over nine years, it is estimated that she spent approximately $300,000 on bets every single day. According to IRS records, O’Connor won more than $1 billion in casino winnings between 2000 and 2009, but she also reported losses that exceeded her wins. However, it’s amazing how she could limit her losses to around $13 million.

2. Harry Kakavas

Age: 55

Nationality: Australian

Profession: Real Estate Agent

Total Amount gambled: $1.48 billion

Debt: $1 million, paid off fully

Game: Baccarat

Kakavas, dubbed the “highest of high rollers,” made his fortune by selling luxury properties for multimillion-dollar sums. He has a bad gambling habit and has often requested self-exclusion orders because of his gambling addiction.

However, from 2012 to 2013, Harry lost close to $30 million gambling at casinos. He eventually sued the Melbourne Crown Casino for ‘unconscionable conduct,’ claiming they exploited his gambling addiction over 16 months. The court reasoned that because Mr Kakavas had not gambled at various times, he could control his desire to gamble. – he was the one who entered the gaming venue. He will be remembered as one of the gamblers with the most money lost gambling.

1. Terrance Watanabe

Age: 60

Nationality: American

Profession: Ex-President of Oriental Trading Company

Total money gambled: $825 million

Debt: $15 million, settled

Game: Baccarat, Blackjack

Terrence completely ignored the fact that he continues to spend as if the well has no bottom and suffered one of the worst gambling losses. Despite inheriting a multimillion-dollar company, he sold his entire stake in 2000. Years of bad luck and compulsive gambling contributed to his extreme loss of more than $800 million in less than a year in 2007, resulting in the largest loss in the history of $127 million. 

He reached a massive civil and criminal settlement with Caesar’s Las Vegas in 2010. His main point is that the casino allowed him to gamble while under the influence of alcohol, which is against the law. An out-of-court settlement was reached, and they dropped all charges. Watanabe is said to have paid $100,000 of his debt. Regulators fined Caesars Entertainment $225,000 in March 2013 for failing to prevent Watanabe from gambling while visibly intoxicated.

Wrapping Up

Some gambled their way to fortune, while others gambled their way to ruin. They all had one thing in common, though: an uncontrollable gambling addiction and passion that eventually led to their demise.

If there is anything to be learned from the biggest gambling losses, it is to think of gambling as entertainment, to only gamble with money you can afford to lose, and never drink or use drugs while gambling.

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