The Best Gambling Stories That Are Almost Too Crazy to Believe – Gambling Sites

Many seasoned bettors have enoughcrazy 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, Im not short on betting anecdotes. But today, I wont be talking about my experiences.

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

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

4. When Going All-In Pays Out

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 todays money) to show for it.

That wasnt 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, youre probably wondering why Revell needed the money.

Well, it was for gambling purposes. Clearly.

Revell took his cash to the Plaza Hotel and Casino in Las Vegas, which was filmed as part of a Sky TV documentary namedDouble 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?

Winning money is an art; like with most arts, connoisseurs have a lasting fondness for the greats. Of course, amassing stacks of money is one thing. But holding onto it is what separates the red-handed vulgarians from the masters that stand tall in the...

3. Trump-Linked Whale Meets a Grizzly Death

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

In the 1990s, a Japanese real estate investor namedAkio 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.

Kashiwagis 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 bossesespecially those of the ilk of former President of the United States, Donald Trump.

It wasnt 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 gamblers excessive betting habits. Things didnt work out that way, however.

Remember that scene from Scorceses 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 murderedin his home, having been stabbed up to 150 times with a samurai sword. The case remains unsolved and is widely considered one of thecrazy gambling stories of all time.

2. Lady Luck Saves FedEx from Collapse

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 foundedFederal 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 companys fuel bills. In one of the best stories about gambling youll ever hear, he managed to do better, leaving with $32,000.

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, FedExs annual revenue was $93.5 billion before the 4th quarter. Considering that, its easy to see why this is among the top tier ofcrazy gambling stories.

1. Michael Jordans Bribe Nets Him Some Cash

Jordans craziest gambling story? There are a few to choose from.

The man is a walking book of thebest gambling stories in sports. Some of them are a little darker than others. For example, the theory that Jordans father, James, was murdered over his sons gambling debts. One that was affirmed by former Mafioso, Michael Franzese.

Jordansinsane stories about gambling arent 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 MJs constant thrill-seeking nature.

Back when I would play, it was pretty much even [between me and MJ]. But I tell you what, and I apologize to Michael for saying this wed be playing golf with certain people, and wed be playing a couple of hundred dollars a hole. But hed be playing some guy for $100,000.Charles Barkley Former NBA Player

Perhaps the one story of Jordans 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. Jordans 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.

Best Way to Avoid Bad Gambling Stories of Your Own

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

Some were intense. Ill give you that. Downright bizarre, too. But while many of thecrazy stories involving gambling are humorous, its no laughing matter when you find yourself down a couple of hundred. Or with silicone breasts.

The best gambling story is probably one that doesnt require retelling.

See that quote up there? Thats wise.

What does it mean, you ask? Well, most nutty stories about gambling typically involve something going awry. When I bet, I certainly dont want that. Instead, Id 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, choosingwhereI bet with the utmost wisdom. One of the smartest things to do when preparing to gamble? Locating the very best casinos. Ill leave you with the best the internet has to offer below.

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The Best Gambling Stories That Are Almost Too Crazy to Believe - Gambling Sites