Biggest Sports Betting Losses Ever

By in Sports & Betting on
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Sports Loss MJ Dollar Burning

Sports betting in the United States is big business. An estimated $150 billion exchanges hands every year on anything from a $10 bet between friends to bets in the millions at prominent sportsbooks.

Unfortunately, these bets can often go south for some punters.

Today, we’ll look at some of the biggest sports betting losses in history.

Air Jordan Shoots an Air Ball

It’s no secret that Michael Jordan loves to gamble. Many have stated over the years that the greatest basketball player of all time takes his gambling to excess.

Jordan’s first retirement from the game for one season is widely believed somewhat of a lowkey suspension that the star was forced into due to his gambling troubles. Of course, the only people who seemed to know the truth were Michael Jordan and commissioner David Stern.

Michael Jordan Seems to Put Action on Nearly Anything

For instance, Jordan would often play rock, paper, scissors for over $100k per round. Or there was the time when Team USA was coming back from winning Olympic Gold in Barcelona, and MJ bet over $30,000 that his luggage would be the first off the plane. Jordan later fessed up to paying the airport staff to make sure his bags arrived first. Ruthless.

Michael Jordan also loves golf. In fact, his love of the sport may rival his love of gambling. So, it’s no real surprise that the two would often intersect.

The biggest loss we’ve been made privy to was over $1 million. Since, MJ himself has confirmed that he’s played for over $100k per hole, it’s easy to rack up such significant losses.

This particular bet was made public by Richard Esquinas in his book about not only his gambling addiction but that of a former friend (or soon to be a former friend) Jordan. I suppose throwing one of the most famous athletes of all time into your book will undoubtedly encourage sales.

In his book, Esquinas states that Jordan lost a total of $1.2 million over a 10-day golf trip. Furthermore, the businessman goes on to detail how Jordan flatly refused to pay the seven-figure sum, and Esquinas was left with little choice but to accept a fraction of the amount.

Jordan has denied the charge that he lost that amount to Equinas and pointed out that perhaps things were exaggerated to sell books.

“Vegas Dave” Loses a Million on MMA

Dave Oancea is well-known for his behemoth wagers. He goes to exhausting lengths to make sure as many people as possible hear all about his massive bets with a taste for longshots.

Vegas Dave made one of the best sports bets ever when he picked the 2015 Kansas City Royals to win the World Series after only 1 week of play that season. The win netted him over $2,000,000.

If you’re going to fly that close to the sun, you’re definitely going to get a burn from time to time.

That’s precisely what happened in 2016. Vegas Dave bet $1 million on the fierce Meisha Tate to dispatch bantamweight rival, Amanda Nunes.

Things did not unfold in favor of Tate or Oancea that night. Less than 4 minutes into round 1, Nunes had submitted Tate and doused Dave’s hopes of a huge win.

Vegas Dave seemed to shrug off the million-dollar loss, though. Like the saying goes easy come, easy go.

Jim McIngvale Doubles Down on the Houston Astros

McIngvale is somewhat of a local celebrity in the Houston, TX area. He reminds me of one of the personal injury attorneys you see on TV at 11 AM when you’re home on a random Tuesday.

Mattress Mack is beloved in his community and for a good reason. McIngvale has opened his doors for those displaced by hurricanes. The same hurricanes that had other prominent businesses and mega-churches turning people away.

Mattress Mack seems to be an all-around great guy despite his fatal flaw. He loves the Houston Astros. His affection for the team is so great that he placed at least three bets with different sportsbooks on his favorite team to win the 2019 World Series.

The three bets totaled over $5 million, with the largest wager being $3.5 million at the Scarlett Pearl in Biloxi, MS. This was reportedly the largest sports bet ever placed in the state and garnered national attention.

You may think that Mattress Mack is just another greedy businessman looking to cash in on an easy bet. However, that’s not the case at all. You see, Jim owns Gallery Furniture in Houston, TX.

Why does the fact that he owns a furniture business have any bearing on his massive bet? Because Mattress Mack is a man of the people. In 2017, he ran a promo through his incredibly busy business.

If the Houston Astros won the World Series that year, he’d refund all mattress purchases over $3k. The 2017 Astros defeated the Dodgers in seven games to become world champions, and McIngvale was reportedly out over $10 million.

That’s literally tons of mattresses he’d have to eat the cost of. So, with Mack being savvy in business and having some understanding on how to market himself, he ran the same promotion in 2019.

However, this year he decided to hedge that bet with a bit more on the line. So, he placed $5 million to help absorb some of the bite.

The Washington Nationals took care of the Astros in game 7, and Mattress Mack lost the $5,000,000. It may be a small price to pay to insure against the millions he could have been out had Houston won.

Betting With Your Life

You’ve probably never heard of Matthew Webb. Frankly, I had never paid much attention to the name until a recent conversation. Captain Matthew Webb rose to fame way back in the 1880s as the first person to successfully swim across the English Channel.

Webb took on a career as a professional gambler by betting on himself against the public. He once won what could be considered a yearly wage by swimming for an astonishing 74 consecutive hours. To be clear, that’s over three straight days in the water without sleep. It’s a pretty incredible feat if you ask me.

Captain Webb would often travel, performing all sorts of incredible tasks for adoring fans. Once, he floated in a tank of water for a record-shattering 128 hours.

Matthew Webb was also a writer and published author. His book, The Art of Swimming, was prevalent in its time. Webb copyrighted the title for merchandise use. The biggest bet of Webb’s life and perhaps the biggest loss in sports betting history came on July 24, 1883.

The money he had accumulated was beginning to dwindle, and Webb decided to go all-in with one epic stunt. He had secured a $10,000 bet that he could successfully swim across the Whirlpool Rapids below Niagara Falls.

On the morning of July 24th, 1883, Webb entered the water from a small boat. The banks of the river auspiciously filled with curious and concerned onlookers. Many of them considered the attempt to be nothing short of suicidal. Webb successfully negotiated the first section of the swim. Unfortunately, upon entering the dangerous whirlpool section, Webb was never to be seen again.

I encourage all of you to think of Captain Matthew Webb when you suffer a demoralizing loss. We’ve all been there, and thankfully, we’re all still here. Even Mattress Mack, that lost $5 million on a baseball game, lived to fight another day.

The next time someone is lamenting you with their betting woes or asks about the worse loss you’ve ever incurred, I encourage you to share the story of captain Webb and remind others that it’s only money.


Betting on sports can bring a rush like no other fix in the gaming world, but with that incredible high of winning comes the crush of defeat.

Most of the gamblers on the list of biggest sports betting losses can be found on another equally important and far more satisfying list. That’s the list of biggest wins of all time.

Remember, if you have it to gamble, you’d better have it to lose.

Michael Stevens

Michael Stevens has been researching and writing topics involving the gambling industry for well over a decade now and is considered an expert on all things casino and sports betting. Michael has been writing for since early 2016. ...

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