The Wildest Bets Ever Placed that Shouldn't have Won

Gambling is a hobby that, when done rationally and in healthy doses, provides a very positive form of entertainment for many people. Yet sometimes, people get a little too daring with their gambling and place more risk on a bet than they probably should. In this article, we'll tell the stories of some of the wildest bets ever placed, both inside and outside of casinos, that miraculously ended up winning (but probably shouldn't have). It is often said that fortune favors the bold, and surely these gamblers will be grateful that luck happened to be on their side!

Crazy Bets That Won

Double or Nothing Roulette Bet

Nobody should ever bet their entire life savings on a single roulette spin, but that's exactly what Ashley Revell did in 2004. After selling all of his possessions, then 32-year-old Revell took his sum of $135,300 to the Plaza Hotel & Casino in Las Vegas. All the cameras were rolling as British TV channel Sky One filmed the bet that would become one of the most famous bets in history. In dramatic fashion, the croupier explained the rules to Revell who pushed his chips all-in on Red. When the ball finally settled on its final spot, Revell's face lit up. It was Red 7--Revell doubled his life savings and walked away with $270,600!

For the record, Revell was playing at an American Roulette table, where there are 18 red numbers, 18 black numbers, and two green numbers (zero and double zero). This put his probability of doubling his money at 47.37%. Needless to say, this was an extremely risky bet that nobody in their right mind should be making! However, while it seems like a lot was at stake, many have noted the amount of media attention the event garnered. Some people speculate that it was all a setup - a publicity stunt to affect people's psychology who didn't know any better to make larger bets. Win or lose, Revell was probably going to make up a lot of the money through the various interviews about the event. So was the entire spectacle real or staged? It's difficult to know for sure, but this is without a doubt one of the wildest bets ever placed at a casino that probably shouldn't have won.

Blackjack Keeps FedEx Afloat

Today, we all know FedEx as a multi-billion dollar delivery services company. Many large corporations in the United States come from humble beginnings, but FedEx had a particularly rocky start. With only $5,000 left in cash, FedEx founder Fred Smith needed to scramble to find a way to pay for a $24,000 jet fuel payment. Today, he could've just played at a USA no deposit casino (okay, perhaps he'd need a little more luck there), but in a move that would save his company, Smith boarded a flight to Las Vegas where he would win $27,000 in profit at the blackjack tables. The following Monday, his board was stupefied at the $32,000 sitting in FedEx's bank account. They were shocked that Smith had potentially gambled away FedEx's future, but the move ended up putting them back in business.

We don't know exactly how Smith played his cards, but it doesn't take a casino genius to know that turning $5,000 into $32,000 is an extremely unlikely event, even with counting card techniques. The probability of winning one blackjack hand is around 46.36%. We can assume that Smith required at least one stretch of ten consecutive wins to achieve his mighty sum, which by itself is a probability of just 0.05%! Crazy as this bet was, it was all Smith needed to keep FedEx afloat. Soon after the big gamble, Smith would successfully raise $11 million dollars, and FedEx became profitable in just its fifth year of operation. Who knows how things would've turned out had Smith not taken his company's funds to Vegas?

The Suitcase High-Roller

William Lee Bergstrom has many nicknames: he's known as both the Suitcase Man and the Phantom Gambler. This was well before the evolution of no deposit bonuses. These titles don't come for free - Bergstrom was known as a highroller who frequented Las Vegas with huge bets. One day in 1980, Bergstrom arrived at Binion's Horseshoe Casino in Vegas with two suitcases, one filled with $777,000 and the other empty. He had picked Binion's Casino for a reason: they had a policy where they would match any first bet 100% on any game. Indeed, Benny Binion came for the occasion and matched Bergstrom's $777,000 with $777,000 of his casino's own. With $1,554,000 in chips, Bergstrom headed over to the craps table and bet the whole lot on a single roll of dice, and subsequently won of course! Binion congratulated Bergstrom on the win and helped him load up his empty suitcase with his winnings, and Bergstrom left without a word, cementing himself as the Suitcase Man and the Phantom Gambler.

Once a highroller, always a highroller. Bergstrom couldn't stay away from the allure of Vegas after his huge win and continued to place wild bet after wild bet. He would later place wagers of $538,000 and $1,000,000, again on single dice rolls, and win and lose those bets respectively. Anytime he made one of these crazy bets, it was often his life on the line. Some of Bergstrom's bets included borrowed money, and his plan B to losing was to commit suicide. Unfortunately, his $1,000,000 loss along with a personal breakup led him to take his own life in 1985, but not before solidifying himself as one of Las Vegas's most remarkable stories.

Craps Table

Lucky Not Seven

The term "Golden Arm" is reserved for the luckiest craps players who roll dice for over an hour without losing. If this is true, then Patricia Demauro has the most Golden Arm of all time. In May of 2009, Demauro walked into the Borgata in Atlantic City, New Jersey with a measly $100 and would pull off the greatest streak of craps wins ever. For a ridiculous 4 hours and 18 minutes, Demauro rolled the dice 154 times without a single loss, which is still the world record to this day. What's even more remarkable is the fact that she stuck with the same bet every single time: that the dice would not result in a seven. When she finally lost, she was celebrated with champagne and quickly made headlines as everybody's favorite "grandma gambler."

To get a sense of how unlikely this is, the probability of rolling a seven in craps is 1 in 6, or around 16.7%. That means the probability of not rolling a seven is 5 in 6, or 83.3%--pretty good odds. But to do it 154 times in a row? The probability of doing that falls to 1 in 1.56 trillion, which is less likely than pretty much any lottery game. The casino has never disclosed how much money Demauro won that night, but she definitely got a payday out of just a small $100 buy-in. Will anyone top Demauro's historic craps run? The numbers will say otherwise, but crazier things have happened!

If you want to prepare yourself better and leave nothing to chance, have a look at this article and find out more about online gambling strategies.

A 50-Word Classic Based on a Bet

Did you know that Dr. Seuss's classic children's book "Green Eggs and Ham" was actually written on the basis of a bet? While this may not be one of the wildest bets on this list, the story behind it is still quite remarkable. Upon his successful release of a few children's books, most notably "The Cat in the Hat" in 1957, Bennett Carf, co-founder and publisher at Random House, struck a $50 bet with Dr. Seuss in 1960 that he couldn't write a book with 50 unique words or less. Of course, Dr. Seuss stepped up to the challenge and came up with "Green Eggs and Ham," which became an all-time bestseller, selling over 200 million copies to date.

Go ahead and re-read the childhood classic - it truly is formed with just 50 unique words. Not only that, 49 of them are monosyllabic, with the only exception being the word "anywhere." Paradoxically, perhaps this crazy constraint actually helped Dr. Seuss produce a better book than he would have otherwise. By limiting himself to 50 words, he would have to dig deep into his creative toolbox to finish the book. And while the bet was only for $50 (equivalent to roughly $450 today), multiple generations of young readers would benefit from it.

The Mysterious Sir "Let It Ride" Bet

Sir "Let It Ride" is perhaps one of the most infamous MLB and overall sports bettors of all-time. Nobody knows exactly who he is, but he made headlines announcing his crazy bets on Twitter. RJ Bell, an odds provider for the Associated Press, confirmed rumors of a particular Las Vegas high roller who was going all in on bets during the 2017 World Series. Five games into the series, the Astros were winning three games to two against the LA Dodgers, and this mysterious bettor had already won 5 for 5 betting on the moneyline. With $8 million already secured, he did the unthinkable and bet everything on the Dodgers to win game 6, truly "letting it ride" which earned him his nickname. With closing odds of around -126, Sir Let It Ride was set to win another $6 million if the Dodgers came out on top... which of course they did by winning.

Now $14 million in the green, the whole world was waiting to see whether Sir Let It Ride would continue into game 7. Ultimately, he sat out of the sportsbooks and walked away. In typical sports betting at Betway Casino or other sites, a win rate of around 55% is considered excellent and you'll likely come out profitable with those odds. Winning 6 for 6 in such a large-scale event such as the World Series with millions of dollars on the line is just wild. It does appear that Sir Let It Ride does have a knack for picking the correct side of sports matches, as RJ Bell also reported that he is undefeated in his UFC bets as well. We'll never know if Sir Let It Ride would've tacked more onto his $14 million payday in game 7, but we're breathing a sigh of relief that he didn't lose it all.

All in on Dogecoin

All-In on Dogecoin Bet

One of the more recent headlines in the finance world is Dogecoin millionaire Glauber Contessoto. The 33 year old self-proclaimed Reddit trader claimed that he had become a millionaire in just 69 days by investing in the cryptocurrency Dogecoin, widely considered a "meme" investment even by Dogecoin's creators themselves. Yet, in a similar move to Ashley Revell, Contessoto threw his entire life savings into the joke coin against the warnings of friends and family. He went all-in on $DOGE at a price of $0.045 with around $250,000, which included borrowed money from credit cards and margin trading. Not long after, the price of $DOGE would skyrocket, and he found himself with nearly $2,000,000 just a couple months into this investment.

Contessoto called the move a "calculated risk" that has obviously paid dividends for him. However, the journey is not over, as Dogecoin is still a very volatile asset which can jump upwards of 15% or 25% in either direction on any given day. Elon Musk's timely appearance on Saturday Night Live did cause the coin to dip 25%-30%, devaluing Contessoto's portfolio by hundreds of thousands of dollars. But Contessoto still believes whole-heartedly in Dogecoin and is still holding on. Dogecoin today is far below its all-time high of $0.74 a coin, but only time will tell to see if Contessoto has a right to be bullish.

For most people, trying to become a millionaire overnight on the back of a risky bet just doesn't end up working out. For every success story like the ones from this list here at, there are hundreds of others who make the same bet and fall completely short. Though we all love offline and real money online gambling, it's important to keep our expectations in check and accurately assess risks versus rewards. But these are undoubtedly crazy stories that prove that anything can happen.