Given the varying and intriguing history of gambling across the world, it’s perhaps no surprise that there have been several wild tales as a result of the betting and casino industry. Truth is always stranger than fiction, as they say! For many people, discovering more about these crazy stories while playing online casino games and looking for online bonuses at BonusFinder is an engaging addition to gameplay. That’s why we’ve collated a few of the wildest gambling tales ever below. Enjoy!

The Crazy Case of Ashley Revell

Very few gamblers wouldn’t react to the name Ashley Revell. Especially the name Ashley Blue Square Revell. Revell was a keen gambler from Britain who in an act of what can only be described as pure madness, decided to sell everything he owned worldwide. How much money did he get? Nothing short of £76,840! Which is around $150,000 in money today. To increase his funds further, Revell negotiated one of the weirdest deals with the online betting site, Blue Square… changing his name legally to Ashley Blue Square Revell.

After securing this money, Revell went to the Plaza Hotel and Casino in Las Vegas where he put everything (yup, every single penny) down on red. Luck was in his favour though as the ball landed on 7 red, doubling his money instantly. If Revell had lost, his crazy antics would no doubt have gone down in the history of the worst gamblers of all time. And the reason he needed the money and sold everything in the first place? For gambling purposes, obviously! Today, Ashley runs a company that produces human-readable QR codes with a slogan that reads ‘Remember the impossible.’

Akio Kashiwagi vs. Donald Trump

Yes, you read that right. This next story features none other than the former President of the United States, Donald Trump. The tale takes place in the 1990s when a Japanese real estate investor called Akio Kashiwagi was a big name in the gambling industry; Kashiwagi was considered one of the biggest high rollers in the world, routinely engaging in high-stakes games of baccarat and dropping upwards of $200k on a single hand! Very quickly Kashiwagi garnered the attention of Donald Trump, back then also an infamous casino owner and big-league who convinced Kashiwagi to pay him a visit to Atlantic City.

Trump naturally expected to see a big windfall from the Japanese gambler’s visit. However, Kashiwagi quickly took the house for a lot of money – $6 million exactly. Unsurprisingly, Trump was left far from impressed and proposed a double-or-nothing offer, propositioning Kashiwagi to come back and bet $12 million – or lose the six. Not only did Kashiwagi lose all of the money, but he also left Trump that day with $10 million owed to the house from the debt he had found himself into from multiple other casinos across the globe. But the story doesn’t end there. In the weirdest twist of fate, Trump would never see a dime of Kashiwagi’s money as a few years later, he was brutally murdered with a samurai sword. To this day, the case remains unsolved. 

Michael Jordan’s Baggage Bet

As famous faces go, Michael Jordan is one of the biggest celebrities to be shrouded in crazy gambling stories. One of the sadder and darker tales is that Jordan’s father, James, was murdered over his son’s gambling debts – a story that has been “affirmed” by former Mafioso, Michael Franzese. Couple this with Charles Barkley’s statement that Jordan would often bet a hundred dollars a hole during a game of golf, and it’s easy to see just how many crazy stories linked to gambling are associated with MJ’s name. However, the tale of Jordan’s baggage bet is much lighter.

After landing in Portland with the Bulls, Jordan was standing around waiting for his luggage with the rest of his team when he threw $100 down and challenged anyone to bet against his bags coming out first. Nine of his fellow players put their money down, not put off by Jordan’s title of the greatest player of all time. Suddenly, Jordan’s bags came out first on the belt. Everyone was shocked, grumpily handing over their wagers. But Jordan’s win wasn’t actually in the hands of lady luck – it was in the hands of the baggage handler Jordan had previously bribed a baggage handler to ensure his wager was a winner.

FedEx: From Zero to Hero

You’ve heard of FedEx, right? The American billion-dollar shipping and logistics company that in 2022 had an annual revenue of $93.5 billion before the 4th quarter? Thought so. Well, they weren’t always doing so good. Back in 1974 – just three years after Frederick W. Smith first founded the Federal Express Corporation – the company had just $5,000 in its company account. In other words, it was almost on the precipice of being totally dissolved. So, Smith decided to let fate decide the future of FedEx instead. 

Smith took the remaining 5k and flew to Las Vegas to lay everything on the line – or on the blackjack table. He’d hoped for at least $24,000 to pay the company’s fuel bills but ended up leaving with a staggering $32,000. This was enough to not just keep the company alive, but lead to an investment offer that would help him to raise $3.5m in profit just a few years later. In a quote from an essay by Smith that Forbes published in 2017, he said “No business school graduate would recommend gambling as a financial strategy, but sometimes it pays to be a little crazy early in your career.”

Final Word

From the intense to the down-right bizarre, these wild gambling stories show that the world of casinos is far from what it seems on the surface. Perhaps the best way to minimize anything as crazy happening when you gamble is to try and gamble responsibly. Choosing your bets wisely and more, choosing where you bet with the utmost wisdom, can mean you won’t end up as another story on this list.