Five of the Craziest Gambling Stories in History


They say that fortune favors the bold, and the following stories are bolder than a Doritos commercial from 2006. If you like to think you like to push the luck envelope, then see how well you match up with some of the craziest and most daring bets that have ever been made.

1. Ashley Revell Bets His Life on One Roulette Spin

We all reach a point in our lives where we say to ourselves, “I think I will throw down my entire life savings on a single roulette spin in Vegas—wait, sorry, that is completely wrong. Hardly anyone does that, which makes the following so exciting.

In 2004, a young British man by the name of Ashley Revell decided to give his family and friends a heart attack by doing just that. And in the spirit of realism, you can endure the hair-raising stress by watching the video to see how it all plays out.

2. The Largest, Most Precise Novelty Bet in History

In 1989, an unknown Welshman walked into his local bookie and wagered £30 that a number of highly precise events would transpire before the year 2000:

  1. Singer Cliff Richards being knighted: 4 to 1
  2. The Irish pop band U2 remaining as a group: 3 to 1
  3. The soap opera Eastenders still being aired on BBC: 5 to 1
  4. Neighbours still being shown on British TV: 5 to 1
  5. Home and Away still being an active TV show: 8 to 1

Remember in Back to the Future II when Biff travels back in time to give himself the answers to all future sporting bets? This novelty bet is kind of like that: it’s so precise that it’s almost suspicious—then again, given the traditionalist nature of British media, perhaps it’s it should simply be regarded as the most astute pop culture bet ever made.

3. FedEx Owner Bets the Company’s Payroll on Blackjack

FedEx was a bit of gamble to begin with. Started with CEO Fred Smith’s entire four million dollar inheritance, it was a “make it or beak it” situation from day one, and with the company both on the edge of bankruptcy and the precipice of big time success, Fred did what any shrewd businessman would do: he took the company’s payroll, flew to Vegas, and threw it all down on a blackjack table.

Today FedEx is a 29 billion dollar company. Not a bad payoff, all things considered.

4. First High Stakes Play: $777,000

In the 1980s, casino owner Benny Binion opened up the Horseshoe Casino in Las Vegas, and unlike the other casinos as the time, Benny’s casino would accept a bet no matter how large. Not too long after the casino opened, a man by the name of William Bergstom decided to put Binion’s claim to the test. He placed a single briefcase down on the craps table. Two rolls of the dice Bergstom was a $770,000 richer. Two more visits to the Horseshoe saw him successfully win on multiple bets in excess of half a million dollars.

What makes this win truly crazy is the down spiral: in 1984 Bergstom would return to the Horseshoe, and after losing a million dollar bet, and then a bet comprised of the remainder of his cash, he would be found dead in a Las Vegas hotel of an apparent suicide.

5. Johnny Moss Can’t Pass up 15-1

Part of being a great gambler involves knowing the difference between a pretty good bet, and a great bet. The following story is in no way an example of that distinction.

The well-known tale is as follows: poker legend Johnny Moss was standing outside of a bar talking to a man who claimed he had never lost a fight in his life. Naturally when Moss got a proposition from one of his friends that he would receive 15-to-1 on his bet if he could knock out the self-professed fighting expert, he agreed instantly.

The result: Moss would get his body and face filled in with a barrage of punches and end up going to the hospital for a couple of broken bones. Not only did he lose the bet, he didn’t even come close to winning. (Not) surprisingly, Moss didn’t have any regret in the slightest: “15-to-1 was too good to pass up,” he said when it was all over.