Gambling has long been a high-risk, high-reward pursuit, creating stories of both astonishing wins and catastrophic losses. Whether in casinos, sports betting, or stock market speculation, some individuals have walked away with life-changing sums, while others have seen fortunes vanish in a single night.
This article explores the most legendary gambling victories and devastating losses in history, highlighting the unpredictable nature of luck, skill, and sometimes sheer recklessness.
Biggest Gambling Wins in History
1. Archie Karas – The Greatest Streak Ever ($40 Million Win)
Archie Karas, a Greek-American gambler, pulled off one of the most legendary gambling runs ever recorded. In 1992, he arrived in Las Vegas with just $50 in his pocket. Borrowing $10,000 from a friend, he turned it into $17 million playing poker and pool hustling.
Karas then took his winnings to the high-stakes tables at Binion’s Horseshoe Casino, where he played poker and dice against some of the world’s best gamblers. Over a three-year period, he amassed a staggering $40 million fortune, earning him a reputation as an unbeatable high-roller.
However, as we’ll see later, Karas’ luck eventually ran out in one of the biggest losing streaks in history.
2. Elmer Sherwin – Twice-Lucky Megabucks Winner ($25 Million and $21 Million Wins)
Elmer Sherwin defied all odds by winning the Megabucks jackpot twice in his lifetime—an event so rare that it is almost mathematically impossible.
- In 1989, at the age of 76, Sherwin won $4.6 million at the Mirage in Las Vegas. Instead of blowing his fortune, he wisely saved and donated much of it.
- In 2005, at the age of 92, lightning struck twice when he hit another Megabucks jackpot worth $21 million at the Cannery Casino.
Sherwin spent the rest of his life donating to charities, proving that sometimes, gambling winnings can be life-changing in the best way.
3. Don Johnson – The Man Who Beat Atlantic City ($15 Million Win)
Don Johnson, a professional gambler, took advantage of casino promotions to legally outplay the house.
In 2011, Johnson negotiated favorable blackjack rules at three Atlantic City casinos, securing a deal where he received a 20% rebate on losses over $500,000. With a highly skilled team and expert card counting, he managed to win $15 million over six months from Tropicana, Borgata, and Caesars.
His success was so devastating that Tropicana banned him from playing blackjack altogether.
4. Kerry Packer – The Billionaire Who Broke Casinos ($30-$40 Million Win)
Kerry Packer, the Australian media mogul and billionaire, was known for placing astronomical bets.
One of his most famous gambling wins occurred in 1995, when he reportedly won between $30 million and $40 million playing baccarat and blackjack in Las Vegas.
Packer was famous for tipping casino staff lavishly, often leaving $1 million tips for dealers and waiters. However, as we’ll discuss later, even he wasn’t immune to devastating losses.
5. A British Soldier’s Roulette Miracle ($270,000 on a Single Bet)
In 2004, British soldier Ashley Revell sold everything he owned—his house, car, clothes, and possessions—to fund a single spin of the roulette wheel in Las Vegas.
With $135,300 in hand, he placed it all on red at the Plaza Hotel & Casino. The wheel spun, and the ball landed on red 7, doubling his money to $270,600 in an instant.
Rather than pressing his luck further, Revell wisely cashed out and used the winnings to start a business and live a comfortable life.
Biggest Gambling Losses in History
1. Archie Karas – The Greatest Fall in Gambling History ($40 Million Lost)
After his historic $40 million win, Archie Karas believed his luck would never run out. Unfortunately, it did—spectacularly.
Over the course of two years, Karas lost every penny of his fortune, gambling at high-stakes poker, baccarat, and dice games. He tried to recover, but his losses kept mounting until he was completely broke.
His story remains one of the most extreme cautionary tales in gambling history.
2. Terrance Watanabe – The Man Who Lost $127 Million
Terrance Watanabe, a wealthy businessman, lost a staggering $127 million in just one year at Caesars Palace and the Rio Casino in Las Vegas.
Between 2007 and 2008, Watanabe was gambling at an extreme rate, reportedly betting $5 million per day on blackjack and baccarat. His losses were so massive that they accounted for 5% of Caesars Entertainment’s annual revenue that year.
He later sued the casino, claiming they had encouraged his gambling addiction by providing alcohol and prescription drugs.
3. Harry Kakavas – The Real Estate Mogul Who Lost $1.5 Billion
Harry Kakavas, an Australian real estate tycoon, lost an estimated $1.5 billion playing high-stakes baccarat in a series of disastrous gambling sessions between 2005 and 2008.
At one point, he was betting $300,000 per hand and reportedly lost $164 million in just 14 months. Kakavas later sued the Crown Casino, alleging they had exploited his gambling addiction, but the court ruled against him.
4. Kerry Packer – The $60 Million Meltdown
While Kerry Packer enjoyed massive wins, he also suffered devastating losses.
On one occasion, Packer lost $60 million in a single gambling spree over a weekend in Las Vegas. According to reports, he bet $250,000 per hand in blackjack at multiple tables and quickly ran into a brutal losing streak.
Despite the loss, it barely dented his billion-dollar fortune. However, it remains one of the largest known casino losses in history.
5. Michael Jordan – The Gambling Addiction That Cost Millions
Basketball legend Michael Jordan is known for his ultra-competitive nature, which extended beyond the court into gambling.
Jordan reportedly lost millions betting on golf, poker, and casino games. One of the most infamous stories involves a 1993 golf bet, where he lost $1.25 million to a businessman named Richard Esquinas.
His gambling habits were so controversial that some speculate his first retirement from the NBA in 1993 was secretly a suspension due to his gambling debts (a theory never proven).
Gambling history is filled with incredible wins and devastating losses. Some individuals, like Don Johnson and Ashley Revell, walked away with fortunes, while others, like Archie Karas and Terrance Watanabe, lost everything.
These stories serve as powerful reminders that gambling is unpredictable, and even the luckiest streaks can turn into crushing downfalls. Whether it’s a billionaire high-roller or an everyday player, one truth remains: the house always has the edge in the long run.
For those who gamble, the best approach is to enjoy the thrill responsibly, knowing that luck can change at any moment.
