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7 craziest gambler stories in history

Russian Roulette
Russian Roulette. Photo/Freepik

From ancient Rome to modern-day Las Vegas, gambling has been a part of human culture for centuries. However, online casinos have become more popular today as they offer more flexibility. Unlike their land-based counterparts, they also feature exciting offers like 25 free spins on registration no deposit.

From gamblers who landed live-changing winnings from just a few bucks to those who spent their entire fortune and ended up with astronomic debts, this article will explore some of the craziest exciting gambler stories you’ve ever heard.

A Casino

A Casino. Photo/The Plaid Horse

Ashely Revell: All or Nothing

Born in 1972 in Kent, England, 32-year-old Revell was already a professional gambler when he decided to make what would become one of the biggest and craziest bets in history. In 2004, he sold everything he owned, from his house and car to clothes, and took his life savings of $135,300 to Las Vegas. He then walked into the Plaza Hotel and Casino and placed all the money on a single spin of the roulette wheel.

Revell’s bet was for the colour red, and he watched as the ball spun around the wheel before finally landing on red 7. He won, and his initial bet doubled to $270,600. As expected, Revell’s story quickly became a sensation in the gambling industry. The story was even featured in a television documentary called “Double or Nothing,” which chronicled his journey to Las Vegas and his daring decision.

However, it is noteworthy that while Revell was lucky enough to win his bet, many others who took similar risks were less fortunate and lost it all.

Akio Kashiwagi: The Trump-Linked Whale

Akio Kashiwagi’s is one of the darkest gambling stories in history. Kashiwagi was a wealthy Japanese businessman with a penchant for high-stakes gambling. Known as “The Whale” in Las Vegas, Kashiwagi was famous for his love of baccarat, and he would routinely bet $100-200,000 on each hand.

In 1990, Kashiwagi arrived in Las Vegas to play at the Trump Plaza casino, one of the three casino sites owned by the former POTUS, Donald Trump. Much to Trump’s disappointment, Kashiwagi left the casino with $6 million in winnings after a series of high-stakes baccarat games. However, the businessman offered the Japanese whale a double-or-nothing offer to double $12 million or lose everything. Kashiwagi accepted this deal, but luck didn’t smile on him the second time, and he left the Trump casino with $10 million in debt.

Sadly, Kashiwagi was found dead in his home in 1992, having been brutally murdered. His death remains a mystery, but many suspect it was related to his gambling activities and the large sums of money he owed to casinos and loan sharks.

Archie Karas: From $50 to $40 Million

Born in Greece in 1950, Archie Karas moved to the United States in the 1960s and became obsessed with gambling. In December 1992, Karas moved to Las Vegas with only $50, a journey that would become the most incredible rags-to-riches gambling stories in history. In Vegas, he borrowed $10,000 from a friend and began playing various casino games at high stakes. After making millions of dollars, Karas played poker at the highest of stakes with the globally renowned high-rollers. Some of the biggest names he played include:

  • Stu Ungar
  • Chip Reese
  • Puggy Pearson
  • Johnny Moss
  • Doyle Brunson
  • Johnny Chan

By 1995, he had racked up almost $40 million in winnings. Although his story ended with a series of unfortunate bets that saw him lose nearly all his fortune, Karas remains a legendary figure in the gambling world today with a record of an unmatched gambling winning streak known as “The Run.”

Fred Smith: Blackjack Saves FedEx

Federal Express, known today as FedEx, a company that revolutionized the package delivery industry, currently has around 300,000 employees worldwide. However, the billion-dollar company may not exist today without what is now one of the most exciting gambling stories ever. Fred Smith established the Federal Express Corporation in 1971. However, the company got into financial trouble in 1973, with just $5000 in its account and a $24,000 fuel bill. To avoid liquidation, Fred took the $5000, headed to Las Vegas and wagered the whole amount on the blackjack casino game.

Luckily, Fred turned a $27,000 profit after his bets, pushing the company to $32,000 worth, enough to cover the fuel bill and keep business moving. While the money didn’t solve all of Fred’s problems, it prevented the company from liquidating until it could secure some major investments a few years later.

Considering that FedEx is worth over 50 billion dollars today, Fred’s story will remain one of the most exciting gambling stories ever.

Don Johnson: $15 Million in Six Months

Card gaming

Card gaming. Photo/PeakPx

Don Johnson’s journey is a perfect example of how to apply proverbs for gambling to achieve success. In 2011, Johnson decided to put his skills to the test, so he walked into the Tropicana Casino in Atlantic City and sat at a blackjack table with a $100,000 buy-in. What followed was nothing short of extraordinary. Over the course of a 12-hour blackjack marathon in a single night, Johnson won $6 million from the casino.

While many people think Johnson is involved in card counting or some elaborate fraud, his success is mainly due to his ability to negotiate favourable rules with the casino, proving the truth of the proverb, “If you play the game by the rules, you will never get cheated” and reducing the house edge to 0.263% instead of 0.5%. Also, he was able to convince the Tropicana casino to offer him a 20% discount on losses of at least $500,000. These, combined with his expertise in the game, allowed Johnson to win millions of dollars over months.

Jon Heywood: From £30 to a £13.2 Million Jackpot!

Jon Heywood’s story is the only online gambling story on our list, but this doesn’t make it any less crazy or exciting. In 2015, he became a millionaire just 25 minutes after he opened an account at Betway online casino. With £13,213,838.68 winnings, Jon entered the Guinness World Records as the “biggest jackpot payout in an online slots game.

The British Lance Corporal had seen a TV ad about a progressive jackpot Mega Moolah slot game and decided to try his luck with £30. After a couple of £0.25 per spin bets, fortune smiled on him, and he set a winning record that has not been matched till today.

Jon’s story shows that shocking gambling stories can also happen at only online casinos and not only land-based ones. So watch out every time you play at your favourite online Canadian casinos.

Patricia Demauro: 154 Lucky Rolls!

Bored by her usual slot games, Grandmother Demauro walked into the Borgata Hotel Casino in Atlantic City and sat at a craps table. What happened next is one of the most shocking gambling stories in history. Demauro proceeded to roll the dice 154 times without crapping out. Below are some key points that make Demauro’s story exceptional:

  • The odds of achieving this result are estimated to be 1 in 1.56 trillion
  • She was a newbie to craps and had only played the game once
  • Her winning streak generated massive media attention
  • Her run continued for four hours and 18 minutes
  • She broke a 20-year-old world record for longest consecutive craps rolls set in 1989.

Today, Demauro’s story serves as a reminder that the impossible can become a reality in the gambling world.

Honourable Mentions

The table below shows some honourable mentions of the craziest gambler stories we couldn’t cover in this article:

Gambler Story
Kerry Packer $20 million in 40 minutes
Charles Barkley Over $30 million in total losses
William Lee Bergstrom $777k on one throw of the dice
Brian Zembic Man Breast Implants for $100k


Whether you are playing at a land-based or online casino, the gambling world is full of fascinating stories of people who have won big or lost everything. From the man who bet everything he owned on a single roulette wheel spin to the whale who racked up $10 million in debts after a life-changing win, these stories showcase the highs and lows of gambling.

It’s noteworthy that for every success story, countless others involve astronomical losses. So while it can be tempting to chase that big win, it’s crucial to always gamble responsibly.

Teresa is a journalist with years of experience in creating web content. She is a wanderlust at heart, but an outgoing sports writer with focus on tennis, athletics, football, motorsports and NBA.

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