Biggest Blackjack Losses of All Time

Blackjack, Lost, Cards, Chips, Table, Money

Looking for a list of the biggest blackjack losses ever? You’re in the right place. In this post, I show you some staggering losses at the 21 tables that will make you rethink chasing losses.

Some of these stories are well known, and others I found digging through popular internet forums. The confessions of dealers are a real gold mine when it comes to these stories.

I start with the smallest and work my way up to the biggest loss ever on blackjack. I also cover one big loss on online blackjack, complete with video footage.

Unknown Player Loses $209,000 at the Tables

  • Who: Unknown
  • Loss: $209,000
  • Location: Undisclosed

Some of the best stories I read about the biggest blackjack losses ever come from anonymous dealers at undisclosed casinos. You can find these stories on forums and dedicated blackjack sites. Some probably aren’t true, but I’m sure a good chunk of them did happen.

Futher Info:

This dealer tells how he clocked in, and a player told him he was already down $100k. He then watched the same player bet $500-$1k per hand, playing two hands at a time until he had lost a total of $209,000. The dealer says it was mostly $100 bills, and it took him forever to count.

More entertaining still is that he supposedly just shrugged it off like it was nothing. Some people really do have money to burn!

A Rookie Dealer Tells of a Staggering Loss on Reddit

  • Who: Unknown
  • Loss: $350,000
  • Location: Undisclosed

The internet is full of unbelievable stories from everyday people. Digging through forums like Reddit and Quora can provide hours of entertainment. I typed in ‘huge blackjack loss’ and found the following story on this thread.

A rookie dealer described how he was assigned to a private table where a high-roller wanted to play blackjack. The person walked in with a duffel bag containing $350,000 cash and began to bet $35,000 per hand on blackjack.

Within minutes, the high-roller had burned through his entire stack and was broke. He then left without even tipping the dealer.

Shoeless Joe Learns That the Tables Can Turn Quickly

  • Who: Shoeless Joe
  • Loss: $1.5 million
  • Location: Las Vegas
One of the biggest blackjack wins in history was collected by an unidentified homeless man known as ‘Shoeless Joe’ turned walked into a Vegas casino with $300 and won $1.5 million.

Sadly for Joe, he lost everything. Observers say his blackjack strategy was clumsy, involving reckless splitting and doubling down. This may be one of the most tragic large blackjack losses because the guy clearly could have used the money.

Charles Barkley Lost It All – $2.5 Million in a Single Session

  • Who: Charles Barkley
  • Loss: $2.5 Million
  • Location: Unknown

Basketball legend Charles Barkley was renowned for his gambling problem. He lost a total of $30 million, his entire fortune, betting on sports and playing blackjack.

However, Barkley once lost $2.5 million in a single blackjack session. This is officially one of the biggest blackjack losses ever. We don’t know much more about that, but the amount alone is staggering.

Kerry Packer Loses $10 Million in One Night

  • Who: Kerry Packer
  • Loss: $10 million
  • Location: MGM Grand

Kerry Packer is an Australian businessman and a living legend on the global blackjack scene. He’s known for playing eight hands at a time and once won $40 million in a single night.

Naturally, lady luck being fickle, Packer also has the biggest blackjack loss ever to his name. He is said to have lost $10 million in a single night at the tables. Yikes!

Online Player ‘Yassuo’ Loses $30k in 10 Minutes

  • Who: Yassuo
  • Loss: $30,000
  • Location: Online

$30,000 isn’t the biggest loss on this list, but it’s the speed at which it happened that’s startling. This seemingly ordinary player lost $30k in just 10 minutes, making this one of the biggest blackjack losses ever streamed.

Playing in what looks like Evolution’s Salon Prive studio for high rollers, ‘Yassuo’ has a violent reaction when he gets yet another bad hand. It just keeps getting worse from there.

It’s an insane story and a great example of why you should always gamble responsibly.

Play Real Money Blackjack Online

Playing blackjack online is the easiest way to enjoy this game. By utilizing bonuses and playing with an effective strategy, you can make sure you don’t lose big like some of the players on this list.

Visit the best blackjack casinos online here if you want a good place to try the popular card game. There are lots of game variants, and you’ll enjoy fast, secure payouts when you win big.

Petko Stoyanov
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About Petko Stoyanov
My name is Petko Stoyanov, and I've been a gambling writer for more than ten years. I guess that was the natural path for me since I've loved soccer and card games for as long as I can remember! I have a long and fairly successful history with English Premier League betting and online poker, but I follow many other sports. I watch all big European soccer leagues, basketball, football, and tennis regularly, and I keep an eye on snooker, volleyball, and major UFC events.