5 Betting Losses That Will Make You Feel Better

Pile of Money on Fire With a Sportsbook Background

If you’ve ever gambled, it’s a near certainty that you’ve suffered plenty of crushing losses. A dramatic last second layup that leaves you one-point shy of covering, that garbage time touchdown that pushes it from the under to the over, the dealer somehow getting a blackjack on your biggest hand…the list goes on.

If you feel like you’ve been a victim of bad betting karma, you aren’t alone. In this article, I’ll lay out 5 examples of betting losses that will help you feel better about your own.

1 – The GOAT Goes Down

Michael Jordan is undoubtedly (sorry, LeBron people) the greatest basketball player of all-time. His relentless competitiveness was an invaluable asset for his game throughout his career. Unfortunately, this same competitive spirit didn’t always help outside the lines.

A golf-lover and gambler, Michael Jordan was known to wager huge amounts of money on the course despite not being the most talented player. His betting buddy Richard Esquinas recounted one time he’ll remember more than any other.

Esquinas said that Jordan went on a 10-day “golf betting binge” in September 1991. When all was said and done, His Airness found himself down nearly $1.2 million. The good news? He was apparently able to get some back on the course, and eventually talked down his debt to $300,000.

How did he get down that much in the first place? By placing historically-high bets on each hole, of course. It’s been said that it was no big deal for him to throw down $100,000 on a single hole.

While MJ never backed down to anyone, perhaps golf was not his best game. As it stands today he’s worth more than a billion dollars, so I’d say he can lose a few more $100,000 holes and still come out okay.

2 – Rap Battle

Long-time producer, music executive, and rapper Birdman is an avid sports bettor. Unfortunately for him, betting on the Super Bowl has been somewhat of a challenge.

As a New England Patriots fan, he certainly had good reason to be feeling confident about his chances going into Super Bowl XLVI. He was so confident, in fact, that he was prepared to put down $5 million on the game. One sportsbook challenged him to do it but he backed down.

Profile of Rapper Birdman

Instead, he placed a $1 million wager on the game. This time he didn’t place it with a sportsbook, but rather went head to head with fellow rapper 50 Cent.

The game ended with a New York Giants victory and 50 Cent took the million from Birdman. And his bad luck did not stop there.

In Super Bowl LII, which featured the Patriots and the Eagles, Birdman challenged another rapper to raise the stakes. He bet AR-Ab $100,000 that the Pats would take down the Eagles.

Of the many comeback drives Brady put together over the years, this would not be one of them. Birdman lost the $100k, and presumably has stopped betting other rappers.

3 – The Whale of Whales

Over the years I’ve read about plenty of high-rollers who have suffered big losses. These people are the ones who keep casinos in business, and the ones who act as a warning to others that gambling can end very badly.

One such man was Terrance Watanabe. An American businessman who had developed quite the fortune, in the hundreds of millions, also had a penchant for taking risks in Las Vegas. Unfortunately for Terrance, he wasn’t a very good gambler.

Most casino whales prefer to play games where some skill is involved, such as blackjack or baccarat. Not Terrance Watanabe. He actually preferred to wager his money on games that were purely based on chance.

Gambler Terrance Watanabe in Court

Casino management, who were probably his biggest fans, referred to him as a “house player.” This means that he actually liked playing the games that had a higher house edge. Meaning he was betting on games that he knew were tipped in the casino’s favor.

Now before I get into the exact dollar figures Mr. Watanabe burned through, it’s important to get some context on his mindset during all of this. Today, he claims that he is a compulsive gambler, and that casinos like Caesars Palace knowingly took advantage of him and his condition.

Additionally, he has alleged that casinos provided him with drugs and alcohol in order to keep him gambling, and losing, as long as possible. Somewhat surprisingly, the gambling regulators actually took his side and fined Caesars Palace $225,000 for their misconduct.

That fine might seem significant, but when you consider the amount of money Terrance Watanabe lost, it’s a drop in the ocean. The final total of his losses added up to nearly $112 million per the Wall Street Journal.

4 – Vegas Dave

With a nickname like Vegas Dave, one has to assume that big losses are just going to be part of the experience. This sports bettor, whose actual name was Dave Oancea, was known for being showy with his gambling on social media.

Unfortunately for Vegas Dave, he was about to get a big dose of harsh reality in 2016. He took a $1 million bet on female MMA fighter Miesha Tate at UFC 200. As Tate squared off against Amanda Nunes, things went south quickly for both Tate and Dave.

Profile of Vegas Dave

It only took a little more than three minutes for Tate to fall to Nunes, costing Dave a cool million dollars. Following the defeat, his social media posts seemed to focus more on his concern for the health of Tate, who had broken her nose during the fight.

I’m sure that playing off a million dollar loss as the second thing on your worry list sounds good, but my guess is that the loss hurt more than any broken nose.

5 – The Daredevil

The betting losses described above are significant, but ultimately nothing that really surprises anyone. To find something a bit more unique, let me take you back to the good old days of 1883.

Daredevil, and self-professed compulsive gambler Matthew Webb had built a name for himself after becoming the first man ever to swim across the English Channel.

Webb was unique in that he was able to make enough money to support himself by betting against the public on swimming challenges that he would perform. For example, he once won a bunch of money by swimming for 74 hours straight.

Photo of Daredevil Matthew Webb

Although he was British, he spent quite a bit of time in America as well. In 1881, he took up residence in America and won a few challenges that paid him fairly well, but it wasn’t quite enough to fully support himself at that time. So, he did what any reasonable gambler would do – he put his life on the line and bet on himself.

This time, he decided to take bets on whether or not he could swim through the whirlpool found at Niagara Falls. The dollar figure he would receive if able to complete the challenge was $10,000. Keep in mind this was pre-1900, and that amount of money was enough to last him awhile. It would be roughly worth $400,000 today.

On July 24th, 1883, Webb dove in to attempt the challenge. He was never seen again.


As long as gambling is available, you can bet there will be individuals who are willing to risk it all in hopes of a huge payout. In Matthew Webb’s case, he paid the debt with his life.

These examples of extreme gamblers should make everyone else aware just how quickly things can turn for the worst if you aren’t careful. My guess is that these people weren’t exactly keeping a close eye on their bankroll.

Although you probably won’t ever have $100 million to lose, let these people be a cautionary tale to always bet within your means.