The Biggest Casino and Gambling Wins of the 21st Century

Posted on February 25th, 2015

big jackpot winAs the remote and land-based gambling industry has evolved in recent times, so too have the average earnings and jackpots. This was showcased spectacularly last year, when professional poker star Phil Ivey won a staggering $9 million during a major tournament in April. This is the single biggest casino win of the last 15 years, and it underlines just how far the industry has come in a relatively short period of time.

Ivey’s win is by no means the only big success of the 21st century, however, as other gamblers have also managed to win big across a range of platforms. So let’s take a look at three more of the biggest casino wins ever from the last 15 years: –

Cynthia Jay (won $34,959,458.56 in 2000)
The 21st Century hadn’t started that long ago when Cynthia landed this big win. Perhaps the most recounted gambling success of all time, Cynthia Jay’s story reads like a tragic fairy-tale from a different era. A cocktail waitress at the impressive Monte Carlo casino in Vegas, she decided to kill some time between shifts by playing the Megabucks progressive slot machine. To her surprise she won big on her ninth pull, earning a staggering jackpot of $34,959,458.56 and recording the single biggest slot win in history. This story had a tragic and unexpected ending, however, as Jay was paralysed and her sister killed in a collision with a drunk driver just seven weeks later.

Elmer Sherwin (won $21 Million in 2005)
Another Megabucks winner, Elmer Sherwin also has the distinction of winning two large jackpots within the space of 16 years. His original success when winning $5 million in 1989 was dwarfed by his efforts in 2005, however, as he claimed a staggering $21 million jackpot and brought his lifetime earnings up to $26 million. With the odds of winning once on this machine registered at an unfavourable one in fifty million, Elmer achievement in succeeding twice defines both logic and belief. I guess he was just born lucky.

Don Johnson (won £15 Million in 2011)
While Elmer’s success was down to opportunism and luck, professional gambler Don Johnson adopted a strategic approach to earn casino success. More specifically, he toured around American casinos playing his game of choice (Blackjack), targeting outlets with favourable house rules, odds and minimal numbers of decks. During this time, he also struck up friendships and regular interactions with dealers, lowering the odds further by negotiating guaranteed paybacks. This gradually increased his probability of winning, with the result that Johnson won an impressive $15 million from three casinos during a six month period in 2011.

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