Biggest Gambling Loss In History

As an experienced player, regardless if you gamble at online casinos, land-based establishments, or simply with friends, you realize that some days you gain and other days you lose. 

When you gamble sensibly, you should be aware of many aspects of the casino, such as knowing the boku casino list. However, some players are not that diligent, and there have been instances of truly incredible defeats throughout history.  

We present to you the 5 biggest gambling losses of all time, as well as the circumstances of their occurrence.

5. Maureen O’Connor: $13 million

Maureen O’Connor is a single female on this list, but what’s even more interesting is that she was the mayor of San Diego when she made her major gambling loss! 

13 million dollars sounds impressive, but since she lost more than $1 billion in gambling, it’s absolutely remarkable that she managed to control her losses so well. O’Connor was apparently seriously addicted to gambling, as she had to borrow $2 million from her second husband’s charity fund to blow it on video poker. 

However, we would fail to recall O’Connor simply because of her significant casualties. She had a good run as mayor and has achieved a lot in her job with a lot of commitment and recognition. She also paid off her gambling debts quickly, which is a big feat.

4. Harry Kakavas: $20.5 million

Following the example of Maureen O’Connor, former Australian billionaire Harry Kakavas lost $20.5 million, which is genuinely a minor sum provided that he lost $1.43 billion. His losses accumulated over two years, from 2012 to 2013, solely at the Crown Casino in Melbourne.

However, it is apparent that Kakavas suffered from an addiction to gambling that started long ago. In 1998, he was sentenced to four months in prison for swindling a major Australian corporation out of $220,000, employing the money to finance his gambling addiction. 

Harry thought he’s done with his visit to the Corona Casino and forbade himself to play there. However, he couldn’t stay away from baccarat games and then got caught playing millions in Las Vegas. At that time, the Crown Casino is said to have lured Harry to its tables, which would have led to additional costs. So is Corona justified? We reserve the right to draw our own conclusions. 

3. Charles Barkley: $30 million

Charles Barkley is presumably the most well-known person on this list. In contrast to the above two, the 11-time NBA All-Star was not a typical gambler. 

Regardless of his huge fortune as a basketball player, he lost almost all of his $30 million fortune. Always a gambler, Barkley confessed to spending $2.5 million in a one-time blackjack game. However, even though Barkley definitely had troubles, he seemed to derive more pleasure from the gambling than many other players mentioned here. 

He frequented many various casinos and relished a broad range of games, from baccarat to blackjack, craps to roulette. For him, it was not about winning a bunch of money, but more about the excitement of the game. He realized that losing was an integral aspect of the experience.

2. Archie Karas: $40 million

Archie Karas stands as a prominent player in history, and even though he was among the most notable losers in the game, he has the status of the longest and biggest winning series in the entire gambling industry. 

It is often said that when his bankroll reached 7 million dollars, he merely laid the cash on the table and expected his rivals to come up to him. His favorite games were poker, baccarat, and dice.

However, this streak of uninterrupted victories had to end sometime, and Karas placed increasingly unreasonable bets, haggling with the casino to allow him to bet much more than the limit. In 3 weeks, he lost all his winnings down to the last million. 

1. Terrence Watanabe: $127 million

Terrence Watanabe was the kid of a profitable businessman who succeeded to the Oriental Trading Company when his father passed away in 1977. Nevertheless, he was more into gambling than entrepreneurship and disposed of the company in 2000 to focus his efforts on baccarat and blackjack. 

In 2007, Watanabe embarked on a one-year gambling trip to Vegas, mainly to Caesar’s Palace Casino. He wagered a whopping $835 million and lost $127 million. Watanabe’s crushing losing record is believed to be the largest that Las Vegas has ever witnessed.

Watanabe was not just a gambling addict. He was said to drink two to three bottles of alcohol daily, and reportedly consumed harder drugs such as cocaine. 

Watanabe still faces a $225,000 fine from Caesars Entertainment Corporation, which owns Caesars Palace, for enabling him to keep gambling while drunk. Watanabe remains in debt of $15 million and risks imprisonment if he fails to compensate for it.

Interesting Related Article: “What is Responsible Gambling?