3 of the Biggest Casino Wins of the 21st Century

Free Casino takes a look at three of the biggest casino wins to have hit the headlines since the turn of the century

3 of the Biggest Casino Wins of the 21st Century

Professional gambler and poker star Phil Ivey hit the headlines in April last year, after winning a staggering $9 million at a tournament in April. This is far from the biggest casino win of the last fifteen years, however, as the increased prevalence of online gaming has added diversity to the gambling industry and enhanced each players’ chances of winning big. 

With this in mind, let’s take a look at three of the biggest casino wins to have hit the headlines since the turn of the century: 

Cynthia Jay ($34,959,458.56 Million in 2000)

Working as a cocktail waitress at the lavish Monte Carlo casino in Las Vegas, Cynthia Jay was used to watching high-rollers ply their trade in the quest for a fortune. She could never have imagined that she would achieve fame and fortune herself, at least until she decided to take a shot at the popular Megabucks slot machine game. On the ninth pull, she claimed a staggering $34,959,458.56 million jackpot and stunned those watching into silence. This represented the largest Megabucks jackpot in history, although tragically it not herald the dawn of a new and exciting life for Cynthia. Just seven weeks later her sister was killed and she was left paralysed after a collision with a drunk driver, and to this day she asserts that she would give all her winnings back in exchange for the ability to walk or the return of her sisters’ life.

Don Johnson (£15 Million in 2011)

If there was ever an exercise in strategic gambling, it was provided by Don Johnson in a six month period during 2011. Playing blackjack, he targeted casinos with favourable house rules and tables with an optimal number of decks, before developing a rapport with dealers and lowering the odds even further.


Essentially, he raised his probability of winning in increments, before aggressively negotiating guaranteed paybacks of up 20% at individual tables. This led to Johnson’s glorious period of success, which generated earnings of $15 million from three casinos in a little under half a year and made headlines all around the world.

Elmer Sherwin ($21 Million in 2005)

While he may not have achieved the single biggest win in the 21st century, Elmer Sherwin will always be unique the world of gambling. This is because he is distinguished by the fact that he has won two major jackpots on the same slot machine game, claiming total prizes of $26 million across 16 years. After winning a cool $5 million on the Mega Millions (Megabucks) lottery game in 1989, he repeated the feat again in 2005 and earned a further $21 million The odds of hitting the jackpot once on this machine is a prohibitive one in fifty million, but Elmer has achieved this twice in a single generation. He was also one of the first Megabucks jackpot winners, and his name will always be synonymous with luck and beating the odds.