Anchor ads are not supported on this page.

Crazy Gambling Stories You’ve Never Heard Of

Are you thinking of a trip to Las Vegas? Putting a few bucks on the craps or blackjack table can be quite a thrill. Or perhaps sports betting is a better option, and that overlooked underdog or sneaky parlay looks like a can’t-miss. These can be some fun options, but when it comes to gambling, some people take it to a whole different level. From massive lucky streaks to crazy wagers with friends, here’s a look at some of the craziest gambling stories in history.

Five Crazy Gambling Stories

Big Bucks for Fake Boobs

Brian Zembic, a high-stakes gambler from Winnipeg, Canada, would bet on virtually anything, including some cosmetic surgery in 1996. After an argument with a friend over the risks women faced when getting breast implants, Zembic agreed to get a pair of his own.

Advertisement - Continue Reading Below

If the newly-buxom bettor wore them for a year, Zembic would collect $100,000 ($190,000 in U.S. dollars) from his friend. At first, Zembic didn’t go through with the wager, but a stock market loss caused Zembic to search for a surgeon to perform the procedure.

The 38C implants were soon in place; his friend even offered to settle up early for $50,000. However, Zembic wanted to go the distance and completed the bet in October 1997 for his six-figure payday. He learned some things along the way, although he said this was the dumbest wager he ever accepted.

“This has been very educational for me,” Zembic noted in the book The Man With the $100,000 Breasts. “I feel I understand women a lot better. Having breasts gives you insight. You see what life is like for women. Taking hours to dress, worrying about how your breasts look. And you start to see what pigs we men are, the way we talk about breasts like they’re jewelry or a hat or something.”

Advertisement - Continue Reading Below
These are some of the wildest gambling stories to ever hit the internet.
(Photo by iStock)

Everything on the Line

Most gamblers head to Vegas with a modest bankroll, maybe a few hundred bucks—possibly a couple thousand. Visiting that ATM isn’t a great idea, but many players still make the trip. That slot machine has to pay out eventually, right? This is one gambling story that’s too incredible to be made up!

Ashley Revell isn’t like most gamblers. In 2004, over a round of beers with friends, the Englishman dreamed up the idea of putting everything he owned on the line in Las Vegas. That meant selling all his possessions – his Rolex, a BMW, golf clubs – everything. He hoped to gamble his entire bankroll on one spin of the roulette wheel.

Everyone has that one friend who gambles so much he barely makes it home with the shirt on his back. Would Revell literally be that guy? His bet gained considerable media attention, and Sky TV even filmed the roulette spin for a documentary.

Advertisement - Continue Reading Below

The Plaza in downtown Vegas agreed to take his $135,000 bet. On April 11, 2004, he put all $135,000 on red and waited for that ball to spin around the wheel – any black number or one of the green zeros, and he’d lose it all.

“The night before, I slept like an absolute baby,” Revell told the Telegraph in 2013. “There were no concerns whatsoever. Thinking back, it seemed crazy, but I was convinced I would win. I was literally going down there to collect my winnings.”

That’s exactly what happened. The ball landed on red seven, and the crowd erupted in cheers as Revell pumped his fists in the air.

“It was just a crazy time of complete happiness,” he said. “The whole experience taught me what is really important in life: it’sn’t Rolexes or flashy cars, but sentimental things.”

FedEx for the Win

Most Americans take it for granted when a FedEx package arrives. This multi-billion dollar company delivers everything imaginable, but efficiently shipping something quickly hasn’t always been easy.

In 1965, Yale undergraduate Fred Smith hoped to change that and wrote a term paper outlining his plan for time-sensitive shipments in airplanes. By the early ’70s, his company, Federal Express, hoped to revolutionize the industry with eight planes covering 35 cities.

However, the company soon became deeply in debt and was down to just $5,000 in the bank. A $24,000 jet fuel payment was due on Monday, or FedEx would go under. A loan from General Dynamics had fallen through, and faced with no other options, Smith grabbed that $5,000 and headed to Vegas.

“When I arrived back in Memphis on Monday morning, much to my surprise, the bank balance stood at nearly $32,000,” Roger Frock, one of Smith’s original managers, noted in his book Changing How the World Does Business: FedEx’s Incredible Journey to Success – The Inside Story. “I asked Fred where the funds had come from, and he responded, ‘The meeting with the General Dynamics board was a bust, and I knew we needed money for Monday, so I took a plane to Las Vegas and won $27,000.”

A session at the blackjack table saved the company. By 1976, FedEx had revenue of $71 million and a market capitalization of more than $65 billion.

$40 Million to Zero

Gamblers dream of a massive winning streak – hitting blackjack after blackjack, finding massive wins rolling dice, or hitting that 10-leg football parlay. Archie Karas has a gambling story that defied the odds back in 1992. He took his last $50 and a $10,000 loan from a friend into a run considered one of the greatest streaks in gambling history.

The Greek immigrant grew up in poverty and was never afraid of losing all his cash. A regular poker player in L.A., Karas headed to Sin City and began playing high-stakes poker, craps, billiards, and other games. That fifty bucks eventually went up to $7 million, and some big-money heads-up poker against some of the game’s greats like Stu Ungar, Johnny Moss, Johnny Chan, and Doyle Brunson later moved that to $40 million.

The three-year hot streak came to be known as “The Run.” But like any lucky streak, his good fortune came to an end in 1995. The high-stakes gambling results turned, and Karas sustained heavy losses, including $30 million at the baccarat tables. All the cash was eventually gone, but Karas had no regrets and passed away in September.

“You’ve got to understand something,” he told Cigar Aficionado in 2008. “Money means nothing to me. I don’t value it. I’ve had all the material things I could ever want. Everything. The things I want money can’t buy: health, freedom, love, happiness. I don’t care about money, so I have no fear. I don’t care if I lose it.”

Gambling in Las Vegas can be a fun and adventurous time.
(Photo by iStock)

The King of all Gambling Stories

Everyone at the craps table just seems to be having fun. When the numbers hit, look for plenty of shouting, high fives, and flowing cocktails. Players at Stanley Fujitake’s table had plenty of reasons to celebrate. This Hawaiian gambler walked into the California Casino in downtown Vegas on May 28, 1989, and dropped $5 on the pass line.

Most craps players seven out after a few rolls, and even great runs only last a half hour. However, Fujitake rolled for more than three hours without crapping out. Crowds gathered to take in the action, and bettors squeezed to get in bets.

“They had trouble keeping up with the chip payouts that night,” California dealer Guido Metzger said in 2014. “My table was empty. But at least 30 to 40 people were trying to place bets at his table. They couldn’t get fills to the table fast enough and had to start issuing scrip [casino credit] because not enough people were going to the cage and cashing in their chips.”

Fujitake’s massive streak ended after rolling 118 times for 18 pass-line winners. After starting out at the table minimum, he was betting the max of $1,000 when things concluded. He profited $30,000 that night, and the casino paid out $750,000 in winnings to players at the table.

BROWSE BY BRAND

MORE VIDEOS