The 8 biggest gambling losses in history

Despite the increasing flock of bettors into the gambling business, the risk involved is still very significant. Everyone who sits in front of a slot machine or at a blackjack table is aware of the risks involved with gambling. Not only that, but the bookmakers bank on this fact, as there are many more chances of losing than there are of winning in betting.

For lack of a better description, one can say that gambling is a ‘rollercoaster’ of wins and losses. Sometimes, bettors get into winning streaks, and naturally, they become emboldened to wager more. As the stakes rise, the size of losses potentially becomes devastating. This article discusses some of the largest gambling losses of all time.

1. Archie Karas – $40 million

Archie Karas goes down in history as one of the most thrilling rags-to-riches gambling stories. When he moved to Sin City in 1992, he had only $50 in his pocket. From one poker game to another, he gambled his way into tournaments and cash games.

While his fame grew in Las Vegas, he could now apply for loans, which he used to get himself a seat at the top poker tables with the pros. In no time, Karas’ bankroll was running into millions. For a gambler who came from nothing, this fortune quickly got to his head, and when the ovation was loudest, Archie Karas changed his strategy.

He probably was not familiar with the saying, “If it’s not broken, don’t fix it.” Well, his fixing did fix a hole in his pocket as he abandoned poker for more chance-based games like craps and baccarat. He lost over $40 million as a result.

2. Maureen O’Connor – $13 million

Rarely will you find a female gambler making headlines, but Maureen O’Connor did more than that as she made history. As the mayor of San Diego, she was a formidable leader.

Tragically, she lost her husband after about two decades of marriage. One thing led to another, and she found herself staking on sporting events. This new adventure might have been a way to escape from her personal tragedy, but it quickly became lucrative. She won almost $1 billion from betting.

Unfortunately, the losses came just as quickly as the wins, and she soon resorted to taking money from anywhere possible. It got so bad that O’Connor took huge sums from her late husband’s foundation. In all, she lost close to $13 million to sports bets.

3. Harry Kakavas – $20.5 million

The case of Harry Kakavas is a unique one with a very long losing streak. Within just 16 months, he lost close to $20.5 million at the Melbourne Crown casino. Like many gamblers, he could have walked away when the net loss was not so astronomical, but addiction is usually stronger than logic. As they say, “Leave when the ovation is loudest.” But perhaps better advice for gamblers is, “Leave when the woes are minimal.”

When he took the casino to court, accusing them of taking advantage of his addiction, the judge was quick to strike out the case.

4. Terrance Watanabe – $127 million

Unlike most passionate gamblers, Terrence Watanabe did not have to go into this risky business as he had inherited a company called Oriental Trading in 1977. He sold this company for a considerable sum in 2000 and then went into betting. For Watanabe, this might have been done out of boredom, adventure or any factor other than necessity.

Unfortunately, he lost about $127 million to two of the most popular casinos in Vegas. After the devastating loss, he sued the casinos but only extended his run of losses to the courtroom.  He has almost paid off all his debt but still faces felony charges for the ones left.

5. Charles Barkley – $30 million

Charles Barkley is a famous American basketballer who became even more known for his gambling escapades. Even while he played for the likes of the Phoenix Suns and other NBA teams, Barkley was always open about his betting habits.

He is one of those big-minded gamblers who expect to come back with huge wins after every trip to Vegas. As a result, Barkley ended up losing all of his net worth – $30 million at the time.

6. Michael Vick – $20 million

This former NFL player’s gambling was quite unique as he was not involved in regular sports betting. Instead, Michael Vick ran the Bad Newz Kennel, an illegal dogfighting ring. Vick was the one funding the gambling part of this venture, and his career went south when word got out.

First, the NFL suspended him for ethical violations and breaching the rules of the league. Sanctions also came from his club, mandating him to pay $20 million from the bonuses he received. The matter went to court, and he was made to pay the club the full amount.

7. Frank Saracakis – $13 million

Frank Saracakis is another gambler who had a wealthy background as he inherited the Greek Automobile Company. He got attracted to the game of roulette when he visited London in 1995 and lost $13 million in one go.

8. Bruno Venturi – €650,000 

This is not the biggest gambling loss, but it’s significant considering it was caused by a software bug. Bruno Venturi was able to win €650,000 from Eurobet UK, but he could not withdraw his money.

Eurobet UK claimed the website suffered from a glitch and therefore did not charge Bruno for five of his bets. Upon going to court, judgment was in favor of the betting platform, and Bruno lost out completely.


So much fortune has been made through gambling, and much more has been lost in this venture. The cases mentioned above show just how quickly the winning streaks can become losing runs. It is even more difficult to throw in the towel at the most logical time when one has a gambling addiction.

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