Professional Gambler Phil Ivey banked $9 million in April 2014, but his was hardly the first or largest major win. Though the house has a substantial edge, a few gamblers have been able to strike it big. 10 The Tragedy Of The Big Megabucks Hit Cynthia Jay was a cocktail waitress at the Monte Carlo casino in Las Vegas. On January 26, 2000, while celebrating her future mother-in-law’s birthday, Jay took a shot at the Megabucks slot machine, a state-wide lottery jackpot that had rolled over for quite a while. On her ninth pull, she won $34,959,458.56—at the time thelargest Megabucks jackpot … Continue reading 10 Crazy Huge Gambling Wins