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, casino 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 stuff of dreams became reality for one man at the Excalibur casino. 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 total prize was a staggering $39.7 million, a sum so large that the casino agreed to pay it out in 25 annual installments of about $1.5 million. 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.

Don Johnson: The Man Who “Broke” Atlantic City’s Blackjack Tables

Some of the most famous wins are a result of skill, casino strategy, and negotiation. Between 2010 and 2011, a man named Don Johnson went on an unprecedented winning streak, taking three Atlantic City casinos for a combined total of over $15 million playing blackjack.

His secret wasn’t card counting in the traditional sense. His strategy was to leverage his status as a whale to get better rules. These included a 20% “loss rebate” (where the casino would refund him 20% of his losses if they reached a certain amount), the ability to bet up to $100,000 per hand, and favorable rules like splitting and casino doubling down on any four cards. 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.

Winning the Jackpot… Again

To hit a huge jackpot once is a miracle; to do it twice on the same machine type is beyond belief. 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. A true philanthropist, he gave a significant part of his second win to those in need.