Noteworthy Gamblers With Horrible Luck

Portraits of Unlucky Casino Gamblers

Gambling, by its nature, creates two very distinct categories of gamblers, winners and losers. Hollywood, who loves a winner and loathes a loser in 99.9% of cases, almost celebrates losers when it comes to gambling.

So, why is it that we feed on the misfortune of the down on their luck punter?

Maybe it’s because most of us can relate far more to Clark Griswold than Rusty in Vegas Vacation. Here are five noteworthy gamblers with horrible luck.

Charles Barkley

Charles Barkley is a very public figure, and his gambling woes are well documented. Barkley had an illustrious NBA career over 16 seasons and is a double inductee into the Basketball Hall of Fame.

Despite all of his success on the court, Barkley never won an NBA Championship. He did everything in his power, including changing teams several times.

Unfortunately, Barkley had a huge roadblock on his path to a title, Michael Jordan, a.k.a. The Best to Ever Do It.

NBA Player Charles Barkley

Barkley didn’t have much luck off the court either. Sure, he had millions of dollars and a lifestyle many dream about, but I attribute that to hard work and talent.

I’m referring specifically to the casinos. Barkley has admitted to having gambling losses in excess of $10 million in the 1990s.

Charles noted a specific session at the blackjack table in which he went home $2.5 million lighter in the wallet. He was also spotted playing roulette for $50k per spin at Las Vegas casinos.

By 2008, the horrible luck had really caught up to Barkley. He now had accrued over $20 million in losses.

Things were so dire that Wynn Las Vegas filed a complaint against “Sir Charles” over an unpaid $400,000 gambling debt.

Barkley has been very public about his woes and faces them head-on. Today, Barkley claims to have his gambling under control, but his golf swing is still a disaster.

Harry Kakavas

Harry Kakavas might be the biggest casino loser of all-time. As you’ll find with many of the gamblers on this list, he was extremely successful, perhaps even a little lucky in life.

Kakavas made over a billion dollars selling luxury real estate on Australia’s posh Gold Coast.

Of course, you can’t lose massive amounts of money if you don’t have a ton of cash to burn in the first place.

Some poor schmo will probably spend his last $5 on a scratch-off today and lose everything he has. Still, we don’t necessarily consider that horrible luck. However, if you have billions and lose millions, it’s somehow horrible luck.

You’re probably wondering just how much Kakavas lost in casinos. Well, it’s estimated to be in the range of $1.5 billion.

Yes, billion with a “B”!

Pro Gambler Harry Kakavas

Kakavas is rumored to have once lost $164 million on a spectacularly poor trip to Las Vegas playing baccarat. Harry allowed his gambling to get so out of hand that he actually went to jail for defrauding a corporation out of $500k to fuel his gambling habit.

Kakavas took the step of adding himself to the self-exclusion list at the Crown Casino as a last-ditch effort to help curb his problem gambling.

By 2004, Kakavas was back at the tables. He was spotted in Las Vegas playing in the high limit rooms, and the Crown Casino wanted their VIP back. Their efforts to secure the casino whale were successful, and Kakavas ultimately lost over $11 million.

Kakavas later sued Crown Casino, among others, for exploiting his gambling problem for a profit, and while the judge agreed, Kakavas wasn’t returned any of the money he lost.

This is a cautionary tale of what can happen when a problem gambler doesn’t seek some form of help.

It doesn’t matter whether a player is wealthy or not. $ 10 million or $30k look the same when the counter reaches zero.

Arnold Rothstein

Arnold Rothstein is a legend in gambling circles. He’s lauded as a pioneer in bookmaking but was also a prolific poker player.

Rothstein amassed a fortune at the poker table. At one time, he was worth over $50 million, which was in the 1920s.

That’s over $750 million in today’s dollars, pretty impressive.

Rothstein was the Black Sox Scandal mastermind in which the Chicago White Sox through the 1919 World Series. The book “EightMen Out,” which was adapted to the big screen, focuses on the scandal and resulting legal case.

However, it wasn’t the Black Sox Scandal that led to his demise. He beat any charges against him in court. It wasn’t until later that he openly admitted his role.

Black Sox Scandal Vintage Photo

In the late 1920s, Rothstein went on a long losing streak and began to have financial hardships.

In the fall of 1928, Arnold lost over $300k in a poker game. Rothstein refused to pay the debt, contending that the game was fixed.

Less than a month later, Rothstein was invited to another poker game in town. No doubt hoping that his horrible luck would turn around, Rothstein jumped at the chance to play some cards.

Rothstein was fatally shot after arriving at the game, retribution for not paying his $320,000 debt. Rothstein stayed gangster to the bitter end and refused to rat on the subject that delivered the fatal shot.

Michael Vick

Michael Vick had a charmed life. He was the 1st overall draft pick by the Atlanta Falcons. He had all the money and accolades he could dream of and made a 13-year career for himself in the NFL.

Vick played in NFC Championship games, Pro Bowls and was considered for league MVP. However, Vick lost everything and not in the way you may think.

Vick was arrested for founding and funding a dog fighting operation. I won’t get into specifics because it’s explicitly barbaric, but suffice it to say the animals are treated in a reprehensible manner.

In fact, so egregious that the 10-year prison term Vick received seemed a little light at the time.

Ex NFL Player Michael Vick

Vick’s case shows that there’s much more than money to be lost when gambling goes wrong. I’m not saying that Vick was necessarily unlucky for the mess in which he found himself.

I’m just pointing out his brilliant fall from grace. You have to have some bad luck to go from NFL stadiums to federal prison. No?

Vick owned his mistakes and has made every effort to right the wrongs he’s done. For starters, the Atlanta Falcons sued to have a large portion of his signing bonus returned and won.

The courts sided with the team, and Vick was ordered to pay back nearly $20 million. Vick was forced to sell a huge chunk of his possessions to make good on the debt, but he got it paid off.

Michael Vick fundamentally reformed his stance on animal abuse and specifically dog fighting. Vick has become an advocate for animals’ ethical treatment and has even lobbied before the Pennsylvania State Senate on their behalf.

Vick made some horrible choices as a young adult, but Vick has shown a vast transformation through his prison sentence and return to the public spotlight.

His story shows what is possible when today’s cancel culture isn’t in full effect. People can make impressive strides to overcome their shortcomings and promote actual change in the world.

Jack McCall

Even if you’re not familiar with the name Jack McCall, you’ve almost certainly heard of him. McCall is the man responsible for bringing us the Dead Man’s Hand, Aces, and Eights.

That’s right; Jack McCall murdered Wild Bill Hickok over losing a real money poker game.

The trouble began when McCall drunkenly lost all of his money to Wild Bill in a Deadwood saloon. Hickok suggested that McCall stop playing poker altogether.

Hickok presumably felt bad for Jack, or perhaps he was feeling generous and offered to buy McCall a meal and some cash. McCall accepted but considered the gesture an overt insult.

Wild West Poker Player Jack McCall

The following day, McCall walked up behind Hickok and fired a single shot to the back of his head, killing him instantly.

McCall claimed the murder was retaliation for Wild Bill, killing his brother and was acquitted. Unfortunately for McCall, he couldn’t leave well enough alone and began bragging of the murder.

McCall was retried and found guilty. His punishment for the boastful tongue was hanging.

After losing all of his money to Wild Bill, McCall was hung seven months later.

McCall lost not only all of his money but his life for his gambling blunder. That’s some horrible luck.


Gambling is meant as a form of entertainment. These cautionary tales about gamblers who lost big show what can happen when horrible luck hits.

Keep these five noteworthy gamblers with horrible luck in mind the next time you get up from the table and head to the nearest ATM.