Whenever there’s a score or a potential for a win, some people are going to perform better than others. There are those who are better at decision-making under pressure and those who just seem like they were born under a lucky star. Some people are better at winning, while others are better at losing.

Moreover, some people are natural storytellers, while others are characters that stories are based on. With that in mind and without further ado, here are the five most amazing high-roller casino stories ever told.

  1. Terence Watanabe

Being born into money doesn’t mean you’ll be able to make a name for yourself. However, with this kind of pedigree, you have several options. This is the story of Terence Watanabe, who became an heir to a large company but never saw himself in the corporate world. Instead, he tried his luck at the casinos across the globe.

The reason why he earned a place on this list is that no one can tell for sure how much money he lost at various casinos. The speculations range from $200 to $300 hundred million. All of this happened in the period of just five years. It’s understood that he lost $127 million in 2007 alone.

For a mere mortal, even one prone to risk, this would sound impossible, but when you consider that he had a habit of losing $5 million per day and that he virtually lived in Vegas, everything starts making sense.

  1. Archie Karas

Now that we’ve covered some of the biggest losses in recorded history let’s start with some of the most impressive gains ever. According to the legend, Archie Karas made $40 million even though he started with just $50.

He came from Greece in 1992 with just $50 in his pocket and started playing poker professionally. It’s also believed that he is the holder of one of the biggest winning streaks in the history of Vegas. According to some estimates, he couldn’t lose for three straight years.

Alas, casino stories seldom have a happy ending. This is something that the majority of casino quotes can confirm.

His luck didn’t take too long to turn, so, near the end, he ended up playing poker with $1 or $2 per hand. In fact, the thrill of winning can be so seductive that one just can’t stop. He lost most of his money in a matter of just three weeks. He lost $11 million playing craps and then $17 million more on baccarat.

While Archie left us in 2013, the legend about him will probably live forever.

  1. Adnan Khashoggi

While some gamblers are charming figures, Adnan Khashoggi was a notorious arms dealer. Near the pinnacle of the Cold War, it wasn’t too hard for him to profit from all the proxy wars that were taking place around the globe. This greed provided him with resources to fuel his true passion – gambling.

It is said that he used to play baccarat for $100,000 per hand. However, this is not all that he was famous for. He threw lavish parties, with call girls and celebrities attending. Unlike poor Archie, his wealth didn’t come from casinos, and it wasn’t as easy to exhaust his resources. His net worth in the early 80s was estimated at $4 billion.

Now, it’s no surprise that a person with a reputation for arms dealing and money laundering didn’t have a knack for fair play. Therefore, even though he was considered a whale, he had a bad reputation in many casinos. In the Ritz casino in London, for instance, he owed a debt of more than 3 million pounds. He refused to pay this debt for over 12 years until he finally did so.

  1. Charles Barkley

Like Michael Jordan, most former athletes usually keep their competitive spirit and proclivities for thrill-seeking. Some of them, like Charles Barkley, find it in casino halls. Now, while most pro athletes gamble, the thing about Charles Barkley is that he never even tried to hide the fact.

He was the one to openly talk about his ups and downs in casinos and wear all these stories like a badge of honor. Unlike some guests, Barkley was always the casino staff’s favorite. He’s always respectful and a proper class act. Moreover, he’s often praised as a generous tipper.

At one point, he set himself a stop loss at $200,000 so that he would never lose more than he could afford to. The crazy thing is that he actually managed to abide by his own rules. In this, he showed more self-discipline than the majority of others on our list.

The story about how he got started in this world is just as crazy. According to one interview, he set a goal to win $1 million dollars from gambling and vowed not to quit until he completed his quest. The rest is a well-known story.  

  1. Sultan of Brunei

This list wouldn’t be complete without at least one crowned head. Now, since the late Queen of England wasn’t known to be much of a gamble, we’ll have to settle for the ruler of Brunei – Hassanal Bolkiah. This monarch is estimated at $20 billion dollars, and he is probably the wealthiest passionate gambler in the world.

He often travels to Vegas and Monaco, but the majority of stories around him are shrouded in a veil of mystery. The most interesting story about him is that both his brother and one of his wives love playing themselves.

Keep in mind that Brunei has a $79,816 GDP per capita, which makes the monarch’s gambling habits feel much more ethical. He’s also known for his philanthropy and charity work, which is why he gets some leeway when it comes to his favorite pastime.

Wrap Up

In the end, the majority of these stories are impossible to verify. Some of them are factually correct, but we have no way of knowing if that’s exactly how things happen. Nonetheless, you should never let the truth get in the way of a good story.

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