Ranking the Biggest Gambling Losses of All Time – The Mattress King and More

Humans are an odd species. We believe in stuff like beginner’s luck and the luck of the Irish. We almost instinctively root for the underdog. And yet, with a mixture of awe and admiration, we watch a high roller place an impossible bet and lose.

Naturally, no one can ever entirely avoid loss while gambling, but we can ensure it happens less frequently simply by honing our gambling skills at one of the best online casinos.

Below you’ll find some people for whom losing big was just a part of their day. Indeed, they also had won, some quite impressive sums. But while those wins might have funded entire hospital wings or college adjunct chairs, they will be forever the biggest gambling losses they are remembered for.

And before you argue that the worst gambling losses are your own, review the hapless losers listed below. Every one of them would beg to differ.

Also known as the Suitcase Man, William Lee Bergstrom first appeared at the Horseshoe in 1980, wearing a cowboy hat and carrying two suitcases.

One suitcase was empty, and the other held $777,000 in cash. Bergstrom would later confide in the Horseshoe’s manager—Ted Binion—that he had borrowed the money from a bank to purchase gold but had instead decided to risk it on a single roll of the dice.

However, he obtained the money, Bergstrom exchanged the cash for chips, then bet the entire $777K on the Don’t Pass line. He watched the shooter as she rolled a six, then a nine, then a seven.

She had lost—which meant that Bergstrom had won. He exchanged his $1.5 million in chips for cash, loaded it into his two suitcases, and left the casino.

He visited the Horseshoe on other occasions, betting smaller amounts still in the hundred-thousand-dollar range, and he won more often than he lost.

In November 1984, Bergstrom again showed up at Binion’s Horseshoe with $770,000 in cash and $300,000 in cashier’s checks. Bergstrom again bet the Don’t Pass line by changing cash and cashier’s checks for chips.

But luck wasn’t with him this time, and the shooter’s first roll was a seven—a win for the shooter but a million-dollar loss for the Phantom Gambler.

His final big gamble moved him to the top of the list of biggest craps losses ever.

Incidentally, three months later, Bergstrom’s body was discovered in his room at the Marina Las Vegas (now part of the MGM Grand Hotel & Casino), dead from an apparent drug overdose.

According to the Los Angeles Times, Bergstrom left a suicide note that requested he be remembered as the “phantom gambler of the Horseshoe.”

Want to stay out of the headlines like Bergstrom? Check out the top craps mistakes to avoid.

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Not all the biggest casino losses in history have dramatic stories with tons of details. I mean, not many other gamblers will commit suicide and say that they want to be known as “The Phantom Gambler” in their note.

There are crazy stories, but it’s hard to get the full details for all of them. One of these stories is about Shoeless Joe. No, this isn’t the Shoeless Joe Jackson from the 1919 Black Sox scandal. This Shoeless Joe was just a homeless man from Las Vegas.

I’m willing to bet that you didn’t think a homeless man would pop up on the list of the biggest casino losses ever. To be fair, if someone has a lot of money to gamble, they probably aren’t homeless.

As you can probably guess, he lost it all in the same night. You can learn a lot from moments like this. If you win a bunch, it’s probably a good idea to stop playing right then and there, especially if you’re homeless.

Shoeless Joe’s game of choice was blackjack. Ironically, the house edge in blackjack is better than most games in the casino.

One of the biggest losses at the casino happened to Robert Maxwell.

Born in Czechoslovakia in 1923 as Ján Ludvík Hyman Binyamin Hoch, Ian Robert Maxwell was a decorated British officer, a media mogul, and even a member of Parliament. His life story could serve as fuel for any number of biopics.

Once Maxwell had built his media empire, he was regularly seen in various casinos, winning regularly bet huge amounts in casinos—winning £750,000 here, losing £400,000 there.

But he wasn’t just a gambler. He was also the consummate host, holding extravagant parties at his Oxford mansion for days. And he was, of course, quite generous to numerous charities.

He was rumored to occasionally urinate from his roof’s edge onto passers-by below while waiting for his helicopter to arrive.

So, well-rounded in both disposition and humor was our Maxwell.

How do you lose that much that fast? Well, it helps if you place bets on multiple roulette tables simultaneously—which is precisely how Maxwell did it.

He was playing three roulette tables at once at the Ambassadeurs Club in London. The Ambassadeurs Club, by the way, is where James Bond first uttered the most famous self-introduction in cinematic history: “Bond. James Bond.”

No reports exist about what he may have done immediately after the loss, but I guess he asked for directions to the stairwell leading to the casino’s roof.

If you want to not blow your money on roulette like Maxwell, be sure to read our guide to playing roulette.

Jim McIngvale definitely makes our list when looking at some of the biggest gambling losses in history.

The Mattress King of Houston, Texas, is notorious for his massive sports wagers and his $1.5 million bet on the favorite, Epicenter, to win.

His profit would have been minor due to the short odds offered on the favorite, but when you’re dealing with more than a million dollars, it wouldn’t have been insignificant, either.

Unfortunately, the 80-1 long shot in the 2022 Kentucky Derby—Rich Strike—crossed the wire first, and McIngvale’s $1.5 million went who knows where.

If you want to place some wagers like McIngvale – okay, not exactly like him – be sure to visit the top Kentucky Derby betting sites.

There have been a lot of golfers with gambling problems throughout the years. Phil Mickelson is probably the one most people think about. His losses are rumored to be around $40 million worth, but that’s over the course of several years.

If you’re looking for the biggest loss in gambling, I’d say that John Daly might have Mickelson beat.

We don’t exactly know how much Mickelson would lose in one sitting, but we do know that Daly lost $1.65 million playing slot machines in just five hours.

Daly said he lost $55 million in gambling over the years. You would think that Daly would be the one people mostly think about when it comes to golfers with gambling addictions, but it’s not.

Professional golfers can make unreal amounts of cash. Daly isn’t considered one of the best golfers ever by any means, but he has won a decent amount for himself.

Like all gamblers, Daly was just hoping to end up with some big slot wins, but obviously, it didn’t work out.

Is it the biggest loss in casino history? Not by a longshot.

Daly isn’t the only professional athlete on the list. NBA legend Charles Barkley joins him, who has had his fair share of gambling problems.

Chuck has lost around $20 million in his lifetime, which is a third of his net worth. His biggest gambling loss in history was worth $2.5 million in one blackjack session.

Barkley has also said that he’s lost around $1 million between 10 and 20 times. There’s a good chance we should see his name on this list a lot more than once, but we don’t exactly know how large his other losses were.

He would enjoy a variety of games at the casino. Blackjack tore him up for the $2.5 million, but Chuck also played baccarat, roulette, and other games.

He’s not completely done with gambling, but he’s much better about it nowadays. Keep in mind, “doing better” does not mean winning a lot. Barkley is simply only betting money he can afford to lose, which is ideal.

One of his most recent bad bets was for the Portland Trail Blazers to win the Western Conference. He put up $100,000 and was asking for a refund within the first couple weeks of the season.

Hopefully, we don’t see him on the list again and his $2.5 million blackjack loss remains his worst in one session.

Kerr Packer is no stranger to throwing money at some horses. In fact, he has the biggest loss in gambling history when it comes to horse racing.

Still, the size of this particular wager is enough to put the Australian media mogul near the top of just about anybody’s Biggest Losers list.

Australia’s answer to Houston’s Mattress King, Kerry Packer was well-known in the Land Down Under for his huge sports wagers.

He would regularly wager millions on a single horse race, so this particular wager of $4.9 million on the outcome of the prestigious turf handicap known as the Sydney Cup (Group 1) is hardly extravagant or even out of character.

In any case, the twist to this story is that Packer (along with business associate Lloyd Williams) had a horse in the Sydney Cup—Major Drive. At the start, Major Drive’s odds had shortened to 3/1, but he wasn’t the favorite.

Still, when the race concluded, Major Drive had indeed crossed the finish line first.

Unfortunately, before the race, Packer had decided not to bet on his horse but to bet seven million Australian dollars on the favorite—Myocard.

Myocard came in second, making this the most money lost gambling for Packer.

Want some skin in the game when it comes to betting on horses? Start off with our detailed horse racing betting guide below.

It takes money, guts, and a particular flair for failing BIG to make it TWICE in a list of biggest gambling losses ever.

Well, Jim McIngvale has said fair in spades. If you’re looking for the most money lost gambling, Jim McIngvale is way up there.

Even before his $1.5 million loss on his Kentucky Derby bet, McIngvale blew $9.5 million on a series of bets on the 2022 Super Bowl (Los Angeles Rams vs. Cincinnati Bengals).

And this wasn’t even one of his biggest gambling losses.

That said, it was a gutsy move, and not wagering on the big game is also difficult to do. I’m sure you can probably refrain from laying nearly $10 million on the Super Bowl winner, of course.

Regardless of the sum you risk, just make sure you’re using the best betting sites out there.

If just under $10 million wasn’t shocking enough, wait until you hear about Frank Saracakis.

His most money lost gambling in a day was a whopping $13 million. Frank’s game of choice was roulette and he played at London’s Crockford’s Casino.

Kerry Packer also played at the Crockford’s Casino, so maybe that’s a place to avoid. If some of the biggest losers ever played at their casino, it’s probably best you played elsewhere.

I’d recommend the best big win casinos online before heading to that spot.

Saracakis was a billionaire who inherited the Greek Automobile Company. That certainly helped fund his play, but it seems as if he would have been better without it.

Although Saracakis’ $13 million is arguably the most money ever lost gambling, there’s one person that has him beat.

That’s right, the biggest gambling loss in history belongs to Jim McIngvale. The Mattress King is a triple threat when it comes to losing big wagers.

You might say he is the Prince of Wails in the gambling world. The Boss of Loss. The Duke of DOH! Am I on a roll or what?

Okay, how McIngvale managed to lose that much money required nearly a month’s worth of traveling via private jet to place his bets.

Always a clever promoter of his furniture store chain, McIngvale had publicly promised to refund up to $3000 to customers who bought mattresses from his stores if the Houston Astros won the 2019 World Series.

They didn’t, of course, losing 6-2 in game seven to the Washington Nationals. So McIngvale had to kiss more than $13 million goodbye.

But at least he didn’t have to refund all those mattress purchases. He made the top (or bottom, in this case) of my list of the biggest gambling losses ever.

I don’t think even Charlie Sheen would call that winning.

Everyone knows that a bet is a risk and that sometimes the risk results in a loss.

Still, it’s human to stand in awe when another member of our species wagers an enormous amount of money on a single spin of the roulette wheel or a single throw of the dice.

Oh, one last thing: While losing big on a single wager is both impressive and horrifying, losing millions—even billions—over a lifetime of gambling is another kettle of fish entirely.

Of course, these are just the worst stand alone gambling losses I could find.

It’s entirely possible there are other staggering gaffes that haven’t been documented. I wouldn’t even be surprised to see some of the biggest online gambling losses ever in the next few years, given the rise of mobile betting.

Maybe these gamblers would have had more luck had they read this online casino tutorial.

Footnotes:

• CBS News provided the story about the 2019 World Series.
• Phantom Gambler details are from the LA Times.
• History provided the Black Sox scandal from 1919.