Gambling can lead to some crazy outcomes and situations. When money is on the line, people can do ridiculous things, leading to plenty of unbelievable gambling stories. And the myths of winning, like Do You Have a Better Chance at Winning With Higher Bets? Or What’s the Secret to Winning Big? are always being asked to find the real truth to winning.
And sometimes the craziest bets can be the best, or at least most interesting. Check out 10 of the Craziest Gambling Bets below.
Famous Gamblers
1) It’s almost impossible to decide which of legendary gambler Archie Karas’ bets was the craziest. The man came to Vegas with $50 in his wallet and grew that stake to a staggering $17 million over the course of three years. Whether he was playing pool or poker, Karas’ three-year streak is widely regarded as the most insane in Las Vegas history. By the end, after being banned from the poker tables at most casinos, Karas was just taking $100,000 bets on single dice rolls. And yet, just a year after that, he’d lost it all the same way he earned it.
2) In 1979, El Cortez owner Jackie Gaughan decided to start taking bets on where space station Skylab’s wreckage would fall to Earth when it re-entered the planet’s atmosphere. Jackie laid odds on everything from New York City to the El Cortez itself (which paid out at 10,000 to 1), but the final resting place of the downed satellite turned out to be in Australia.
3) Ted Forrest, a World Series of Poker winner, is well known as a gambler. However, this bet was not about cards. Instead, he bet with another famous poker player, Mike “The Mouth” Matusow, that he could lose an enormous amount of weight. Matusow challenged Forrest to say he could not get below 140 pounds (from Forrest’s weight of 188 pounds). Not only that, but Matusow also bet $2 million. Forrest eventually did get below 140 pounds, 138 to be exact, and won the bet.
The Friendly Skies
4) Richard Branson of Virgin Airlines fame and his friend AirAsia CEO Tony Fernandes made a bet. Both owned Formula One auto-racing teams that were in the 2010 Finals in Abu Dhabi. Tony wagered that his team, Lotus, would finish before Branson’s team. The wager – The loser would dress and serve on the plane as a flight attendant.
The bad news? Branson lost. He paid the price of the wager on a flight to Malaysia from Australia with lipstick and a red skirt (and shaved legs!). However, he kept his beard. On that flight, Branson purposely spilled a tray of drinks over Tony. The good news? The entire incident raised more than $300,000 for the charity that both Virgin Australia and Air Asia support, the Starlight Children’s Foundation.
5) In the early days of FedEx, Frederick Smith, the founder and CEO of FedEx, was desperate to make his new company succeed. After three years of starting up, the company was losing $1 million monthly. Smith tried everything but eventually looked for Lady Luck’s help. Taking the remaining money from the company’s accounts ($5,000), he went to Las Vegas to play blackjack. Smith must have hit some lucky cards because he left the casino with over $30,000, enough to give FedEx time to grow. FedEx started with 186 deliveries on day one. Now? About 17 million per day!
Insanity
6) The Man Who Got Breast Implants on a Bet – This one, of course, is almost mythic by now, but we couldn’t include the craziest bet ever made, bar none. Magician and high-stakes gambler Brian Zembic bet in 1996 that he would get breast implants and keep them in for a year for $100K wager. The craziest part of this story is that Zembic apparently became so enamored with his “additions” that he never had them removed.
7) Some people come to Vegas to find a mythic transformation, to leave behind everything of their old life and be born again in the fires of chance. Ashley Revell sold everything he owned, emptied his bank account, and put every penny he had—$135,000—on red. One spin of the wheel later, and he’d doubled his money. He gave a $600 tip to a dealer and walked out of the casino a rich man.
8) After losing a wager, a New Zealander changed his name to “Full Metal Havok More Sexy N Intelligent Than Spock and All The Superheroes Combined With Frostnova.” The name is 99 characters long, so it technically fits New Zealand’s Department of Internal Affairs’ 100-character maximum limit. Mr. Frostnova applied to change his name back in March 2010 by paying the required fee, but he only found out that his request was accepted five years later when his passport expired.
A Visit from Lady Lluck
9) Ashton Griffin laid out 3:1 odds on himself of being able to run 70 miles on a treadmill in 24 hours, meaning if he had lost, he would have paid out 3x the bet. By some miracle, he pulled this off, won $300K, avoided having to shell out $900K, and finished the 70 miles with 45 minutes to spare!
10) The bet is one of my favorites. It took place at the Borgata Hotel Casino in Atlantic City in 2009. Patricia DeMauro was playing slots at the Borgata in Atlantic City, while her friend John Capra played poker. While taking a break, Capra taught Patricia how to play craps. That same day, DeMauro, starting with $100, proceeded to roll the bones for over 4 hours. It was a record of 154 times in a row against seven and won. Patricia, the “gambling granny,” was the epitome of beginner’s luck.
Share Your Stories
What was your craziest bet? Let me know in the comments.
Gamblers will be on most anything, thanks for the stories they were great.
Would love to see Branson in heals and lipstick losing that bet lol
4 hrs on a craps table is absolutely insane, I wonder how many times they changed the dice. My husband who’s Not a gambler rolled 30 minutes his first time and the table was wild.
I agree about gamblers betting on anything. For me, my biggest gambler was shooting craps on a cruise ship for three hours all by myself! My arm was sore, the dice were starting to fly off the table, and my belly was sore from reaching over the table for the dice (I’m only 5 feet 4). But it was still fun!