Ranking the 4 Craziest Gambling Stories of All-Time

Many seasoned bettors have enough crazy gambling stories to fill a warehouse.

I have a few of my own that I have shared over the years. From entering a casino with less than ten bucks and leaving with just short of $3k to watching a croupier lose his mind and punch a player, I’m not short on betting anecdotes. But today, I won’t be talking about my experiences.

Instead, I’ll be regaling some of the best gambling stories of all time. These accounts include insane wagers, outlandish bets, and even a gruesome murder. 

If you’re looking for unbelievable tales to share with your poker buddies, start with the craziest gambling stories of all-time.

One of the best stories about gambling ever emerging from Britain relates to a guy named Ashley Revell. In absolute chaos, the quirky Englishman took the ballsy decision to sell everything he owned worldwide, with £76,840 (around $150,000 in today’s money) to show for it. 

That wasn’t enough for the Brit, who then legally changed his name to Ashley Blue Square Revell. In agreeing to do so, the Blue Square online betting site paid him. This contributed to an increase in the spare cash he had.

Now, you’re probably wondering why Revell needed the money.

Revell took his cash to the Plaza Hotel and Casino in Las Vegas, which was filmed as part of a Sky TV documentary named Double or Nothing.

Not for a mammoth gambling session, however. The gutsy gambler instead decided to put it all down on red and see what happens. Well, he was lucky as the ball landed on 7 red, doubling his money instantly.

A brave move. Had he lost, would he have been in the same league as some of the worst gamblers of all time?

When it comes to truly insane gambling stories, this one is up there.

In the 1990s, a Japanese real estate investor named Akio Kashiwagi was an enigmatic figure in the gambling world. Rumored to have been linked with the Yakuza, the uber-wealthy businessman was considered one of the biggest whales in the world. 

Kashiwagi’s game of choice was baccarat. He routinely engaged in high-stakes games, dropping upwards of $200k on a single hand. Naturally, players like the Tokyo-based magnate are desirable customers to casino bosses—especially those of the ilk of former President of the United States, Donald Trump.

It wasn’t long before Trump convinced Kashiwagi to pay him a visit in Atlantic City.

As the owner of three casinos, the former president expected to see some cash hit the coffers due to the Japanese gambler’s excessive betting habits. Things didn’t work out that way, however.

Remember that scene from Scorcese’s 1995 epic, Casino? The one with the Asian businessman who initially takes the house for a lot of money? That was based on Kashiwagi.

Kashiwagi took the former POTUS for $6 million, which reportedly left Trump far from impressed. So, being a businessman and all, Trump proposed a double or nothing offer — the Japanese gambler was to come back and bet $12 million or lose the six.

Not only did he lose all of the money, but he also left with $10 million owed to the house. It later turned out that he was already deep in debt to casinos in other parts of the world.

Trump would never see the money repaid. Kashiwagi was brutally murdered in his home, having been stabbed up to 150 times with a samurai sword. The case remains unsolved and is widely considered one of the crazy gambling stories of all time.

From a harrowing tragedy to something a little more upbeat.

Well, that is unless you have a rabid hatred for FedEx. Which so many people do. Nonetheless, this is one of the best gambling stories I have ever heard.

In 1971, Frederick W. Smith founded Federal Express Corporation. Known today as FedEx, it is a billion-dollar company that operates in over 200 countries worldwide. However, just three years after its launch, the company was screwed. With just $5,000 in the company account, it was destined for the scrap heap.

That was until Smith decided that divine intervention was needed. So, he grabbed the remaining 5k and took a plane to Las Vegas as you do. 

Smith wasted no time getting down to business, setting up shop on a blackjack table. To see his plan work, he would need to raise at least $24,000 to pay the company’s fuel bills. In one of the best stories about gambling you’ll ever hear, he managed to do better, leaving with $32,000.

The Founder of FedEx once saved the company by taking its last $5,000 and turning it into $32,000 by gambling in Las Vegas.

— Did You Know? (@Know) July 7, 2013

With the funds, Smith had enough to keep the company alive. This led to attracting investment that would help him to raise $3.5m in profit just a few years later.

In 2022, FedEx’s annual revenue was $93.5 billion before the 4th quarter.  Considering that, it’s easy to see why this is among the top tier of crazy gambling stories.

Jordan’s craziest gambling story? There are a few to choose from. 

The man is a walking book of the best gambling stories in sports. Some of them are a little darker than others. For example, the theory that Jordan’s father, James, was murdered over his son’s gambling debts. One that was “affirmed” by former Mafioso, Michael Franzese.

Jordan’s insane stories about gambling aren’t all dark, however.

The Chicago Bulls legend is known to enjoy a bet. From playing $100,000 holes in golf. Charles Barkley, another basketball player with a penchant for gambling, has previously spoken out about MJ’s constant thrill-seeking nature.

Perhaps the one story of Jordan’s I enjoy more than any other is the baggage bet one. As it goes, the Bulls had landed in Portland and were waiting for their luggage. Jordan threw $100 down, challenging anyone to bet against his bags coming out first.

Naturally, the odds for this prop were heavily against the greatest player of all time. Nine of his fellow players put their money down, only to lose it all. Jordan’s bags indeed came out first.

It was no matter of luck, however. He had previously bribed a baggage handler to ensure his wager was a winner.

Having run through four of the best gambling stories of all time, your synapses might be firing.

Some were intense. I’ll give you that. Downright bizarre, too. But while many of the crazy stories involving gambling are humorous, it’s no laughing matter when you find yourself down a couple of hundred. Or with silicone breasts.

See that quote up there? That’s wise. 

What does it mean, you ask? Well, most nutty stories about gambling typically involve something going awry. When I bet, I certainly don’t want that. Instead, I’d prefer a nice, normal, nothing-out-of-the-blue run when playing my favorite games.

The best way to ensure that is by choosing my bets wisely and more, choosing where I bet with the utmost wisdom. One of the smartest things to do when preparing to gamble? Locating the very best casinos. I’ll leave you with the best the internet has to offer below.