$105 million Lost in 6 Hours! 5 Historic Gambling Losses That Make Drake’s Bets Look Like Pocket Change
The TL;DR
- The biggest gambling losses dwarf Drake’s high-profile bets, with the largest recorded loss reaching nearly $1 billion by Australian property developer Harry Kakavas
- Terrance Watanabe’s $204 million loss in 2007 represented 6% of casino owner Harrah Entertainment’s annual gambling revenue, highlighting the extraordinary scale of high-roller losses
- Archie Karas experienced gambling’s extreme volatility, turning $50 into $40 million before losing it all within three years
- Celebrity gamblers like Charles Barkley ($25 million in losses) and businessman Jim “Mattress Mack” McIngvale ($15.4 million) demonstrate gambling problems affect people regardless of fame or wealth
- These massive losses often involve common patterns: escalating bets, chasing losses, and casinos providing special treatment that encourages continued gambling
Gambling has existed in many forms for centuries, from dice games and card tables to modern online casinos. While some players win big, others lose far more than most people earn in a lifetime.
This article explores five of the most significant gambling losses ever recorded. These are not just stories of bad luck—they involve complex behavior, legal disputes, and financial consequences.
Each case involves a real person who lost tens or even hundreds of millions. In one case, the total almost exceeded $1 billion over the course of just one year!
| Gambler | Amount Lost | Timeframe | Primary Games | Aftermath |
| Harry Kakavas | ~$1 Billion | 2005–2006 | Baccarat | Lost lawsuit, diagnosed pathological gambler |
| Terrance Watanabe | $204 Million | 2007 | Slots, blackjack, baccarat | Legal issues, VIP treatment, substance claims |
| Archie Karas | $40 Million | 1992–1995 | Poker, craps, baccarat | Lost entire fortune, legendary cautionary tale |
| Charles Barkley | $25 Million | 1990s–2000s | Casino, sports betting | Public admission, responsible gambling advocate |
| Jim McIngvale | $15.4 Million | 2022 | Sports betting | Business losses, continued high-profile bets |
The Biggest Loss In Gambling History: Harry Kakavas ($1 Billion)
Image Credit: Gold Coast Bulletin
Harry Kakavas made millions selling properties on Australia’s Gold Coast before losing nearly $1 billion at Melbourne’s Crown Casino. Between 2005 and 2006, he gambled away approximately A$1.47 billion (about US$984 million).
Kakavas mainly played baccarat, a simple card game where players bet on which hand will get closest to a total of nine. The game moves quickly, making it possible to place many high-stakes wagers in a short time.
In May 2006, Kakavas lost A$164 million (around US$105 million) in less than six hours. He sometimes bet A$300,000 on a single hand.
After losing his fortune, Kakavas sued Crown Casino, claiming they took advantage of his gambling addiction. The High Court of Australia ruled against him in 2013, finding that he understood the risks he was taking.
Key facts about Kakavas’s losses:
- Diagnosed as a pathological gambler
- Lost A$164 million in a single six-hour session
- Unsuccessfully sued the casino for exploiting his addiction
- Represents the largest documented casino loss in history
Inside The Most Money Ever Lost at a Casino: Terrance Watanabe ($204 Million)
Image Credit: Advocate.com
Terrance Watanabe inherited and later sold the Oriental Trading Company, a party supply business. In 2007, he lost $204 million gambling in Las Vegas, mostly at Caesars Palace and The Rio.
His losses were so massive they made up about 6% of the annual gambling revenue for Harrah’s Entertainment, which owned both casinos. This level of spending was extraordinary even among high-rollers.
Despite losing millions, Watanabe received VIP treatment from the casinos. They provided him with luxury suites, private gaming areas, and personal attention to keep him playing.
The story took a legal turn when Watanabe was charged with failing to pay $14.7 million in casino markers (lines of credit). His legal team claimed casino staff gave him alcohol and prescription painkillers while he gambled, raising questions about responsible gaming practices.
Watanabe’s case highlights how Las Vegas establishments treat their biggest spenders and the ethical questions that arise when someone loses such enormous sums of money.
The Rise And Fall: Archie Karas’s $40 Million Loss
Image Credit: Hendon Mob
In 1992, Archie Karas arrived in Las Vegas with just $50 in his pocket. Over the next three years, he turned this tiny sum into $40 million through what gamblers now call “The Run.”
Karas started out as a pool shark, but built his fortune playing poker, craps, and baccarat. He dominated poker tables and took on some of the best players in the world, often winning hundreds of thousands of dollars in single sessions.
“Money means nothing to me,” Karas once said. “I don’t value it. I’ve had all the material things I could ever want.”
But the games that made him rich eventually broke him. First, he lost $11 million playing craps. Then he dropped another $17 million on baccarat. By 1995, his entire $40 million fortune was gone.
Karas’s story shows how quickly gambling fortunes can change. His dramatic rise and fall is one of the most famous tales in gambling history and serves as a powerful reminder of the risks involved in high-stakes play.
Celebrity Gambling Disasters: Charles Barkley’s $25 Million
Image Credit: NBA.com
Charles Barkley, the NBA Hall of Famer and TV personality, has been remarkably open about his gambling losses. He estimates he’s lost around $25 million over the years and was famously sued by the Wynn Las Vegas for unpaid gambling debts.
“I’ve lost a million dollars probably 10 to 20 times,” Barkley admitted in a recent interview. His losses span both casino games and sports betting, where people wager on the outcomes of sporting events.
Unlike some who hide their gambling problems, Barkley has discussed his experiences publicly. This openness has helped reduce the stigma around gambling addiction and encouraged others to talk about their own struggles.
Barkley’s story shows that gambling problems can affect anyone, regardless of fame or wealth. His willingness to share his experiences has made him an unexpected advocate for responsible gambling.
Notable aspects of Barkley’s gambling history:
- Lost approximately $25 million over his career
- Experienced million-dollar losses multiple times
- Speaks openly about his gambling problems
- Uses his platform to raise awareness about responsible gambling
When Promotional Bets Go Wrong: Jim McIngvale’s $15.4 Million Loss
Image Credit: Houston Family Magazine
Jim “Mattress Mack” McIngvale owns furniture stores in Houston, Texas. He’s famous for placing massive sports bets tied to his store promotions.
In 2022, McIngvale lost $15.4 million betting on sports. This included $10 million on the Cincinnati Bengals to win Super Bowl LVI (they lost to the Los Angeles Rams) and $6.2 million on college football bets.
McIngvale’s betting strategy is different from typical gambling. He uses hedging, where he places bets to protect against potential losses elsewhere. For example, if he promises customers refunds on furniture if a certain team wins, he bets on that team to cover the cost of refunds.
While this approach is part of his business strategy, it still carries significant risk. A single lost bet can cost millions, as McIngvale discovered when the Bengals lost the Super Bowl.
McIngvale has had big wins too—like a $75 million payout when the Houston Astros won the 2022 World Series. But his losses show that even carefully calculated bets can go wrong when the unexpected happens.
How Do Drake’s Losses Measure Up?
Image Credit: Adam McCullough/Shutterstock
While rapper Drake makes headlines with his million-dollar sports bets, his losses pale in comparison to the historic gambling disasters covered here. Drake has reportedly lost several million-dollar bets, including a $1 million wager on Argentina to beat France in regular time during the 2022 World Cup final.
Despite these notable losses, Drake’s gambling activities represent a different category altogether. His total reported losses likely fall under $10 million—substantial, but nowhere near the nine-figure catastrophes experienced by Kakavas or Watanabe.
Drake also differs from our most extreme cases in that gambling appears to be entertainment rather than compulsion for him. His high-profile bets often coincide with social media promotions and celebrity appearances, suggesting a calculated approach to his gambling activities.
When placed alongside history’s biggest gambling losses, Drake’s wagers—while impressive to average people—amount to little more than pocket change compared to the astronomical sums lost by the highest-stakes players in gambling history.
Warning Signs And Lessons From The Biggest Money Losses In History
These five historic gambling losses show several common patterns. In each case, the gambler increased their bets over time, often trying to win back previous losses—a behavior known as “chasing losses.”
Another common factor was the special treatment high-rollers received. Casinos provided luxury accommodations, alcohol, and other perks that encouraged continued gambling, even after substantial losses.
Warning signs of problem gambling:
- Escalation: Gradually increasing bet sizes over time
- Chasing losses: Betting more to recover money already lost
- Extended sessions: Gambling for longer periods than planned
- Financial strain: Borrowing money to continue gambling
- Emotional responses: Feeling anxious when not gambling
About 1% of adults in the United States experience severe gambling problems. These issues can lead to financial hardship, relationship problems, and legal troubles.
Many tools exist to help people gamble responsibly, including deposit limits, time limits, and self-exclusion programs. Self-exclusion allows people to voluntarily ban themselves from gambling at specific venues for a set period.
For more information on how to play responsibly and make informed choices, read our expert guide on responsible gambling.
FAQs About Historic Gambling Losses
Harry Kakavas’s nearly $1 billion losing streak between 2005 and 2006 represents the largest recorded gambling loss by one person.
High-stakes gamblers often have access to large credit lines and can place bets worth hundreds of thousands of dollars on a single hand or spin, allowing losses to accumulate very quickly.
Casinos are businesses designed to make profits, and high-rollers who lose large sums contribute significantly to their revenue. While many casinos have responsible gambling programs, they typically don’t intervene unless a player specifically requests help.
Losses of this magnitude are extremely rare and typically involve wealthy individuals with access to extraordinary credit lines and VIP treatment that isn’t available to average gamblers.
Title Image Credit: Adam McCullough/Shutterstock
