Biggest losses in sports betting history: Almost $1 billion lost by one person

You might have heard about famous rapper Drake losing hundreds of thousands of dollars on bet over the years. His most recent being when he wagered $355,000 on Mike Tyson in his fight against Jake Paul, which took place on November 15, 2024, at the AT&T Stadium in Arlington, Texas.

Drake backed 58-year-old Tyson in his return to the ring. However, Tyson lost to 27-year-old Paul by unanimous decision, resulting in Drake losing his bet.

Surprisingly that doesn’t even crack the top 5 when it comes to the biggest losses in sports betting history.

Here are the five biggest sports betting losses in history:

5. Jim "Mattress Mack" McIngvale - $15.43 Million (2022) 

Jim McIngvale, better known as Mattress Mack, is a well-known sports bettor and the owner of Gallery Furniture in Texas. Despite hitting the jackpot in 2022, when he won $75 million after a successful World Series bet on the Houston Astros, he also faced significant losses.

That same year, McIngvale made two $10 million bets on the Cincinnati Bengals to win the Super Bowl LVI. Unfortunately for him, the Bengals lost, and he ended up with a hefty $15.43 million in total losses, which included poor bets on other NFL teams and college football.

4. Charles Barkley - $10 Million (2006) 

NBA legend Charles Barkley has long been known for his love of gambling. His habit started in the 1980s during his time with the Philadelphia 76ers. By the time he retired in 2000, Barkley’s gambling had become an issue. In 2006, he admitted to losing an estimated $10 million while gambling at casinos.

At one point, he was even sued by Wynn Las Vegas for $400,000 in unpaid debts, which he settled shortly after. Over the years, Barkley’s losses were mostly from high-stakes bets, with $25,000 per hand being a common wager. Ironically, he now sponsors a sportsbook, despite his gambling troubles.

3. Archie Karas - $28 Million (1995) 

Archie Karas’ story is a cautionary tale of extreme highs and devastating lows. In 1992, he arrived in Las Vegas with just $50, but within three years, he turned that into $40 million, thanks to his incredible poker and dice skills.

Known for "The Run," a winning streak that remains one of the greatest in gambling history, Karas lost it all in a matter of weeks. He lost $11 million at craps and another $17 million on baccarat, leaving him broke by mid-1995. Karas was eventually banned from all Nevada casinos due to his gambling behavior.

2. Terrance Watanabe - $112 Million (2007) 

Terrance Watanabe, heir to the Oriental Trading Company fortune, became a well-known high-roller in Las Vegas casinos. In 2007, he lost a staggering $112 million, with $94.1 million of that at Caesars Palace and $12.2 million at the Rio.

Watanabe’s legal team argued that the casinos had facilitated his addiction by supplying him with alcohol and prescription drugs, encouraging his gambling. He was later charged with unpaid debts, adding to his financial woes.

1. Harry Kakavas - $984 Million (2005-2006) 

The biggest sports betting loss in history belongs to Australian real estate billionaire Harry Kakavas. Between 2005 and 2006, Kakavas lost an unbelievable $984 million while gambling at Crown Casino in Melbourne. His losses included a single day in May 2006 when he lost $164 million in just six hours.

Kakavas sued the casino for encouraging his addiction, but the court ruled against him, determining that he was fully aware of the risks involved. His case has become a textbook example of how a high-stakes gambler can lose everything.

These stories show the extreme highs and lows that come with high-risk gambling, and serve as a warning to others who may be tempted to take similar risks. Always be guided by the gamble responsibly tag.