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. While most wins are modest, every now and then, someone defies the odds in spectacular fashion, walking away with a fortune that becomes the stuff of legend. Let’s look at a few legendary tales of astonishing casino victories.

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

The largest slot machine jackpot in history was won in March 2003 at the Excalibur Hotel & Casino in Las Vegas. A young programmer from L.A. put some money into a Megabucks machine to kill time before a game. After feeding about $100 into the machine, he hit the jackpot of a lifetime. The win amounted to an incredible $39.7 million, paid out over 25 years. He wisely opted to keep his identity private, becoming a legend in the process.

Beating the House at its Own Game

Some of the most famous wins are a result of skill, strategy, casino and negotiation. In an incredible run, Don Johnson managed to beat several casinos at blackjack for more than $15 million.

He didn’t use card counting to achieve this feat. Johnson, a savvy businessman, negotiated special rules with the casinos before he even started playing. These negotiated perks, including a generous loss rebate, effectively tilted the odds in his favor. This combination of perfect play and casino negotiated advantages gave him a small but crucial edge over the house. 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. But that’s exactly what happened to World War II veteran Elmer Sherwin. He first won $4.6 million on a Megabucks machine in 1989 at the grand opening of The Mirage. He traveled extensively with his winnings but never gave up on his dream of winning again. Incredibly, 16 years later, in 2005, at the age of 92, he did it again. He won a staggering $21.1 million jackpot on another Megabucks machine at the Cannery Casino. Sherwin generously donated much of his second win to charity, including relief efforts for Hurricane Katrina victims.