10 Crazy Huge Gambling Wins

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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 in history.

She married her boyfriend Terry Brennan two weeks later. Seven weeks after that, she’d never walk again.

A drunk driver with 16 prior arrests slammed into Cynthia’s Camaro while it sat at a stoplight. The accident killed her sister and paralyzed Cynthia from the chest down. Instead of traveling the world with her new husband, she found herself confined to a wheelchair, unable to even feed herself or comb her own hair.

The drunk driver, Clark Morse, received a minimum of 28 years in prison for his crime. Cynthia says she’d give all her winnings back if she could only walk again or get her sister back.

9 The Beginner’s Luck Craps Roll

Craps looks mighty intimidating to non-players. It’s a fast-paced game with many betting options, and if you don’t know what you’re doing, you can drop money fast. Then again, you could just pick up the dice, throw them randomly for four hours, and win big anyway.

In 2009, grandmother Patricia Demauro approached a craps table at the Borgata in Atlantic City for only the second time in her life. Her friend played briefly, and then Demauro took the dice in her hands. She won 154 consecutive throws. She never revealed how much she won, but she bought in for $10, and even the most conservative of betting strategies would have returned 50 times that amount.

8 The MIT Students Who Beat The System

The 2008 movie 21 is a fictionalized tale of college students who use math to devise a formula to win in blackjack. The true story didn’t play out exactly like in the film, but the basic message is accurate: The geeks beat Vegas.

The team used card counting, a technique that reveals whether upcoming cards are primarily high or low. When players expect high cards, they should raise their bets. Despite what movies like Rain Man suggest, you don’t have to be a genius to count cards, and counting a dozen decks is no harder than counting one. But if you raise and lower your bets correctly and win a lot of money, the dealer may notice, and the casino may ask you to leave.

The MIT gamblers got around this problem by working as a team. A few members would count cards and signal the counts to a third member, who’d bet big exclusively at high count tables. Then other members would simply distract the dealers with huge bets of their own, ignoring the count and roughly breaking even.

The team won big. Over their years of play, they pulled in millions. They even formed an investment company just to handle their bankroll.

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