7 Of The Craziest Bets Ever Made
I’ve bet crazy at times, but I wouldn’t consider any of those bets as part of this post – 7 Of The Craziest Bets Ever Made. Today we take a break from the New England casino expansion to look at some of the craziest bets ever made. I’m not talking about taking insurance on a Blackjack hand, and I mean seemingly insane. I’m sure there are a lot more and a lot crazier!
It’s A Crazy World
A Run for His Money
1) Ashton Griffin laid out 3:1 odds on himself to run 70 miles on a treadmill in 24 hours. If he lost, he would have paid out 3x the bet. Ashton pulled this off by some miracle, won $300K, and avoided shelling out $900K. Furthermore, he finished 70 miles with 45 minutes to spare!
Easy Come, Easy Go – 7 Craziest Gambling Bets Ever Made

2) It’s almost impossible to decide which of legendary gamblers Archie Karas’ bets was the craziest. The man came to Vegas with $50 in his wallet. After arriving, he grew that stake to a staggering $17 million over three years. His gamers of choice were pool and poker. Karas’ three-year streak is the most insane in Las Vegas history. As a result, he was banned from the poker tables at most casinos. Instead, Karas settled for taking $100,000 bets on single dice rolls. Just a year after, he’d lost it all the same way he earned it.
Keeping Abreast of the Craziest Situation

3) Man Who Got Breast Implants on a Bet – This one is part of gambling folklore. Magician and high-stakes gambler Brian Zembic made a bet in 1996. Brian bet he would get breast implants and keep them in for a $100K wager for a year. The craziest part of this story is after the wager was paid, Zembic was so enamored with his “additions” he never removed them. Subsequently, this is one of the Craziest Gambling Bets Ever Made.
He Saw Red – One of the 7 Craziest Gambling Bets Ever Made.
4) Some people come to Vegas for a personal transformation. A change from their old life to be born again in Sin City. In 2004, Ashley Revell sold everything he owned to do that. In this case, he emptied his bank account and put every penny he had—$135,000—in red at the Plaza Hotel in Vegas.
One spin of the roulette wheel later, he doubled his money. Then, as a result of his win, he gave a $600 tip to the dealer and walked out a rich man.
Britain’s Sky One television filmed his bet as a short reality series, Double or Nothing, and E! featured it in the special THS Investigates Vegas Winners & Losers documentary.
One Man’s Trash
5) In Vegas, people will bet on just about anything. In short, El Cortez owner Jackie Gaughan started taking “astronomical” bets in 1979. The wager was that 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 El Cortez (which paid out 10,000 to 1). The final resting place of the downed satellite ended up being Australia.
Related Post – The lighter Side of Casino Gambling
Making $1 million from $5
6) Harold McDowell, 85, of Lakewood, New Jersey, shocked his wife when he won $1 million from $5.00 while gambling at the Borgata Hotel Casino in Atlantic City.
“I happened to be playing next to my wife. I had my back to her.” McDowell told The New York Post. “I turned around and said, “I just won a million dollars.” “She told me, “You’re full of crap.”
On Saturday afternoon, McDowell bet the $5 on a 6-Card Bonus on a Three Card Poker game. When the dealer laid out the cards, he was stunned to see a royal straight flush of diamonds. This hand was 1 in over 20 million odds.
It was an even sweeter win as far as gambling stories go because his wife was declared cancer-free the day before. She went through several surgeries and treatments for liver cancer while also dealing with colon cancer for years. “It must be luck of the Irish,” McDowell told The New York Post. “They’re both great news.”
“He bet $5.00 on the Three Card Poker “6 Card Bonus” bet and hit a six-card Royal Straight Flush of Diamonds for a $1,000,000 win. This was the first time this bet hit Borgata, and experts at wizardofodds.com confirm that the odds of hitting the Bonus Royal Flush are 1 in 20,348,320,” the Borgata Casino said in this Facebook post.
FedEx – Fueled By Vegas
7) When FedEx faced bankruptcy, its founder Frederick W. Smith took the remaining $5,000 from its account and went to Las Vegas. He came out with $32,000, enough to fuel the planes and keep the company running for a few days while they raised funds.
Smith invested his own $4-million fortune and raised $90 million in assets when he founded FedEx. After three years, the company faced losses of $1 million per month and bankruptcy. So he took what was left of the company’s funds, went to Las Vegas, and played blackjack, winning more than six times the amount. With the few days of respite the winnings brought the company, they could run the business and raise additional funds. By 1976, the company’s first profit was $3.6 million; four years later, it was $40 million, and as of 2018, its total assets amounted to $52 billion.
What are some of your craziest bets?