Biggest Gambling Wins (and Losses) in History

Gambling is a pendulum; sometimes you win, and sometimes you lose. But unless you are playing with especially large amounts of money, chances are you can quell these losses without issue.

But what about those who couldn’t? What about those who lost everything, or won an insane lottery? Read on as we go through the biggest gambling wins and losses in recent history.

The 6 Biggest Gambling Wins in History

Sometimes you win and sometimes you win big. Here are the biggest wins in gambling that we know of.

1. $39.7 Million at Excalibur Casino in Las Vegas

In 2003, a 25-year-old software engineer thought he would just put $100 into a Megabucks machine for fun, only to be shocked when he won $39.7 million dollars in just a few minutes (after 3 $1 bets).

While the man decided to remain anonymous, we know he was from Los Angeles and only in town for March Madness. He played the Megabucks machine at the suggestion of his uncle, and we hope he shared the prize with him.

2. $34.9 Million at Desert Inn in Las Vegas

Before it was torn down in 2001, a cocktail waitress won an astounding $34.9 million dollars playing the Megabucks slot machine at Desert Inn in 2000. Afterwards, the cocktail waitress, Cynthia Jay-Brennan, made plans to marry her boyfriend and travel the world.

Sadly, just six weeks later, she was hit by a drunk driver in a crash that killed her sister and left her paralyzed. While she was glad to be alive, she unfortunately spent most of her winnings on her medical care and is still paralyzed today.

3. $27.6 Million at Palace Station in Las Vegas

In 1998, a retired flight attendant changed her life when she won $27.6 million at a Megabuck slot machine in Palace Station Casino (noticing a trend?). While she did initially plan to only spend $100, she had to pay almost $300 before winning the $27 million.

We don’t know her name, but we do know she was one lucky lady, as she had apparently won $68,000 just a few months before. Although we don’t know much about her time after winning, she was 67 years old in 1998, so we assume she has passed on to the next life by now.

4. $22.6 Million at Bally’s in Las Vegas

Another crazy story, Johanna Heundl stopped by a Megabucks machine to play a quick $170 before breakfast. Imagine her surprise when she won a $22.6 million jackpot instead.

Johanna was visiting Las Vegas from California at the time, and was 74 years old when she won in 2002. As such, we assume she has joined the other Megabucks winner (the retired Flight Attendant) in the winner’s afterlife.

5. $21.1 Million at Cannery Casino in Las Vegas

Elmer Sherwin is a famous Las Vegas resident, mostly because he won major jackpots not once, but twice in his life. His first win came in 1989, when he took home $4.65 million for a $3 bet at The Mirage Casino. The real win came in 2005, however, when he was 92 years old and won the $21.1 million Megabucks jackpot at Cannery Casino.

Elmer has passed on, but before his death, he donated much of his fortune to charity.

6. $22 Million at MGM Grand Casino in Las Vegas

You might think these are out of order, but Kerry Packer famously had to bet over $250,000 USD in order to win his $22 million at the MGM casino, which we are pretty sure is just perseverance, not luck.

However, he did win some other smaller bets in addition to the Megabucks jackpot, increasing his net worth to $40 million by the time he left the casino. His luck wasn’t to last, though, and he ended up losing 15 million pounds in a London casino just a few years later.

The 3 Biggest Gambling Losses in History

You can’t always win, however, so here are some of the largest losses to remind you of the dark side of gambling.

1. $15.43 Million - Jim McIngvale

Sports betting can go wrong quickly, especially when you make a, $10 million dollar bet on a team in the Super Bowl along with numerous other side bets. Jim McIngvale found this out in 2022 when he lost $15.43 million in a matter of minutes after the game ended in favor of the Rams.

Lucky for McIngvale, he owns Gallery Furniture, and the massive loss was likely a blip on the screen for him, especially after winning $75 million on a World Series bet later in 2022.

2. $40 Million – Archie Karas

The reason Archie Karas is below our friend Jim is because he didn’t lose $40 million at once—no it took him three full years for his losses to reach this staggering amount.

At first, Archie Karas was living the Vegas dream, arriving in the city with $50 in his pocket and quickly transforming it into $40 million in 1992. His winning streak in poker, pool, and dice games was widely known, and he was even featured in the Guinness Book of World Records.

It wouldn’t last, though, and after an $11 million loss on craps and a $17 million loss on Baccarat, he was broke by 1995. Although he would continue gambling, the rest of his life was plagued with legal issues as he was caught cheating in casinos across the country. Archie Karas passed away in 2024.

3. $204 Million – Terrance Watanabe

Similar to Karas, Watanabe didn’t lose his fortune all at once. Rather, he made a series of bad decisions that led to the loss of his fortune. It’s important to note that he amassed the money from the sale of Oriental Trading Company, which he had inherited in his parents’ death.

It took him an entire year to lose the $204 million fortune in Las Vegas, and it resulted in him being banned from most casinos—including the famed Wynn Casino. Harrah’s also struggled to cut off his gambling, but they couldn’t afford to as he was 6% of their gambling revenue during the year he spent in Vegas.

He later tried to sue Harrah’s, stating he only continued gambling due to being provided painkillers and alcohol, but he did not win the case.