Four Famously Crazy Bets

Many consider the “gambling spirit” to be a pure expression of adventure. Sometimes though, someone will come along and place a bet that is just so insanely daring that, whether they win or lose, they end up becoming the stuff of folklore.

1. The Bet That Saved FedEx

Most people are probably familiar with the world-famous, billion dollar courier company FedEx. Not many people know, however, that its founder, Fred Smith, once almost gambled away the very future of his successful company at a blackjack table in Las Vegas.

In a last-ditch effort to save his company from looming bankruptcy, Smith gathered their remaining $5000 and went to Vegas. He could have lost it all but instead managed to win $32,000. This was just enough to save FedEx, which now earns more than $25 billion a year!

2.The Drunken Pilot

US marine pilot, Thomas Fitzpatrick, is remembered for more than his larger-than-life ego and wild drinking habits. As the story goes, while drinking with friends, hewagered them that he could fly his plain at night, with no radio or lights, from New Jersey to New York, and land it on the street in front of the pub without problem.

They all thought it was a joke, until he landed a stolen plane infront of the pub on 187th street the following night. Everyone, including the owner of the plane, was apparently so impressed and amused by his stunt to that he was let off with a mere $100 fine.

A few years later though, Fitzpatrick made the exact same bet, and did it again!It’s unknown how much he made from these crazy bets.What is known though, is that the airplane owner and law enforcementweren’tso impressed the second time round, and he ended up serving 6 months in prison.

3. An Almost Impossible Record

Patricia Demauro will be remembered in gambling history for achieving something that should be virtually impossible. In May 2019, while on holiday at the Borgata Casino in Las Vegas, she decided to buy into a game of craps for $100 dollars.

What followed was the longest streak of successful rolls without “sevening out” (rolling a seven), in all of the history of craps. Demauro rolled against the seven an incredible 154 times, which took 4 hours and 18 minutes, a new Guinness World Record. The final amount that she won was never disclose by the casino, though it was apparently enormous, and it was only her second time playing!

4. The Suitcase Man

The story of William Lee Berstron, aka. the Suitcase Man, or Phantom Gambler, is a legendary, though ultimately tragic one. In 1980, long before you could play at Black Lotus online casino, he showed up at the Horseshoe casino in Vegas with two suitcases. One with $777,000, and one empty.

He staked it all on craps, won a shot at 7, instantly doubling his money, then filled up the second suitcase with his winnings, and promptly left. Three years later he did the same thing, winning $500,000. His third attempt, however, failed, losing him everything, after which he sadly committed suicide.

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