The Biggest and Most Famous Casino Wins in History

For most people, a trip to the casino is a form of entertainment where the dream of a life-changing win is part of the thrill. These stories of incredible luck serve as a testament to the unpredictable nature of gambling. These are the stories of ordinary people and high rollers who experienced a once-in-a-lifetime win.

The Megabucks Jackpot: A Software Engineer’s $39.7 Million Win

The stuff of dreams became reality for one man at the Excalibur casino. A 25-year-old software engineer from Los Angeles decided to play the famous Megabucks slot machine while waiting for a basketball game to start. After feeding about $100 into the machine, he hit the jackpot of a lifetime. The life-altering sum was so huge that it was structured as an annuity, casino paying him $1.5 million a year for 25 years. The winner chose to remain anonymous, and his story remains the ultimate testament to the incredible, albeit minuscule, chance of hitting it big on a slot machine.

Beating the House at its Own Game

Not all legendary wins come from pure luck. In an incredible run, Don Johnson managed to beat several casinos at blackjack for casino more than $15 million.

He didn’t use card counting to achieve this feat. His strategy was to leverage his status as a whale to get better rules. These negotiated perks, including a generous loss rebate, effectively tilted the odds in his favor. By combining these advantageous rules with perfect basic strategy, he was able to shift the mathematical edge slightly in his favor. After his epic winning streak, casinos became much more cautious about the deals they offered high rollers.

The Double Megabucks Winner

The odds of winning a major lottery-style jackpot are astronomical, but winning it twice seems impossible. Yet, that is precisely the story of Elmer Sherwin, a veteran of the Second World War. His first jackpot was for $4.6 million, hit on the opening day of The Mirage. He traveled extensively with his winnings but never gave up on his dream of winning again. His persistence paid off in 2005 when he hit another Megabucks jackpot for over $21 million. Sherwin generously donated much of his second win to charity, including relief efforts for Hurricane Katrina victims.