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7 Biggest Gambling Losses Ever

April 25, 2022

Written By,

Brijesh Mehta

If you’ve ever gambled, whether it’s in a live casino, a brick-and-mortar casino, or simply with friends, you’ll know that you either win or lose.

Losing money in a casino is nothing new; most players who become billionaires overnight go bankrupt in the blink of an eye. This is probably because most gamblers have no idea what their limitations are or when to quit in the gaming round.

7 Biggest Gambling Losses Ever

Even though every player’s bankrolls are different, it’s critical to set limits in the gaming world. Otherwise, all of the money will just flow to the casino operators.

When you sit down at a casino table, you’re constantly taking a chance, but significant losses are rare if you’re wise. If you play responsibly, you’ll always set a limit on how much you wager so you may enjoy yourself without losing more than you can afford. However, not all players think about playing responsibly; thus casino history has seen some truly massive losses of renowned players.

Here in this article, we present to you the list of gamblers who went from being wealthy to being careless loser gamblers. Continue reading to learn more about them so that you might be aware of your budget while placing online bets and will be a responsible player after knowing their story.

Let’s Begin!

1.    Maureen O’Connor: $13 Million

Maureen O’Connor is the only female on this list, and she was the mayor of San Diego at the time of her massive gambling loss!

She was from a very poor family that once couldn’t even afford a turkey for Thanksgiving. Later on, she married Mr. Peterson, a fast-food tycoon, and worked as a teacher before becoming the mayor of San Diego.

Maureen started gambling as an escape when her husband died in 1992, and she eventually won over $1 billion betting on sporting events. O’Connor’s gambling problem was so severe that she borrowed $2 million from her second husband’s philanthropic organization, only to blow it all on Video Poker.

It’s found out that she lost roughly $13 million over the years. Maureen was betting about $300,000 each day over nine years, based on her betting tendencies which made her a big-time loser in the end.

2.    Harry Kakavas: $20.5 Million

Former Australian billionaire Harry Kakavas lost $20.5 million. His losses were accumulated during a two-year period between 2012 and 2013, exclusively at Melbourne’s Crown Casino.

He even served four months in prison in 1998 for cheating a large Australian corporation out of $220,000 and using the money to finance his gambling addiction.

Harry, a regular at the Crown Casino, saw this as his lowest point and decided to stop gaming there. But he couldn’t stay away from the Baccarat tables and was later caught on camera in Las Vegas squandering millions. The Crown Casino allegedly attracted Harry back to their tables at that point, resulting in the losses.

3.    Charles Barkley: $30 Million

Well, we must say that the most well-known name on this list is Charles Barkley. Unlike the last two, the 11-time NBA All-Star gambled irresponsibly.

Despite his enormous success as a basketball player, he spent nearly his whole $30 million money. Barkley, who is known for his high-stakes gambling, has admitted to losing $2.5 million in a single Blackjack session.

He gambled in a variety of casinos and enjoyed a range of games, including baccarat, blackjack, dice, and roulette. He was more interested in the thrill of the action than in winning large sums of money.

Over the years, Barkley has picked up a few tips on how to gamble responsibly. He took a break from it for a while and, now that he’s back, he’s not gambling more than he can afford.

4.    Archie Karas: $40 Million

Archie Karas is one of the most well-known gamblers of all time, and despite being one of the worst losers in gambling history, he owns the record for the longest and largest winning ever.

He was penniless when he arrived in Las Vegas in 1992, with only $50 in his pocket. By early 1995, he had turned a $10,000 loan from an acquaintance into more than $40 million.

It is believed that once he had a $7 million bankroll, he would simply lay it down on a table and wait for an opponent to approach him. His favorite games were poker, baccarat, and dice. However, this tremendous winning run had to come to an end at some time, and Karas began to make increasingly uncontrolled wagers. Over the course of three weeks, he lost every last dollar of his earnings.

This guy is a legendary character in the casino world, having gone from being one of the largest winners of all time to one of the worst losses.

To be on the safe side, while playing online casinos, we always recommend players to make themselves familiar with the playing guides and to have a demo play before involving their real money. We have various articles written on the topic such as poker guides, teen patti tips and tricks, baccarat strategy, andar bahar winning tips, and many more so that players can enhance their winning chances. You may have a look at them in BetBarter’s blog section.

5.    Umar Siddiqui: $65 Million

Siddiqui is the former marketing manager of Fry Electronics who gambled away almost $65 million of the company’s money. He had a gambling problem and allegedly transferred a total of $70 million to the Venetian to gamble.

He was facilitated with luxurious amenities such as a private plane, a three-room luxury suite, and a large gaming credit by his company. When he declared bankruptcy a few years later, he had almost $120 million in gambling debt and owed his old company $65 million.

He barely had $80 at that moment, thus he was unable to pay off all this money back to the firm.

6.    Terrance Watanabe: $127 Million

Terrance Watanabe was a wealthy businessman’s son who inherited the Oriental Trading Company after his father died in 1977. However, he was more interested in gaming than in business, and he sold the firm in 2000 to focus on Baccarat and Blackjack games.

Watanabe went on a year-long gambling binge in Las Vegas, mostly at Caesar’s Palace, in 2007. He staked a whopping $835 million and lost $127 million.

Watanabe had a problem with more than simply gambling. According to witnesses, he drank two to three bottles of vodka every day and reportedly used more dangerous narcotics such as cocaine. Furthermore, Watanabe still has a pending amount of $15 million and risks jail time if he does not pay up the entire money.

7.    Harry Kakavas: $1.5 Billion

Harry Kakavas is arguably one of the perfect examples of how destructive a gambling addiction can be.

Kakavas had a total gaming loss of $1.5 billion in 14 months, most of which was lost at the Crown in Melbourne. From Melbourne to Macau to Las Vegas, he had some of the greatest losses known to any casino.

The most well-known example was when he lost $164 million in six hours while gambling away $300,000 every hand. He also lost $4 million in a single day in Las Vegas. The majority of the funds were borrowed, and he ended up being bankrupt and deeply in debt.

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Gambling is, in the end, a personal choice, but without control, it may lead to a darker side that is far from just being an enjoyable wealthy experience. These gambling loss stories are eye-opening for both pros and newcomers to the online casino world.

Given that gambling can either make or ruin a person, it is critical to understand certain financial limitations before a gaming session and never exceed them.

Forget the fun you see in the casino-based movies and online series and be cautious as in no time your enjoyment will turn out to be addictive.

If you are new to online casino gaming, you should always go for one of the best and trustworthy site to place your bet. For this and to keep you on the safe side, we highly recommend you to choose BetBarter India. Here you will be able to explore a variety of casino games such as online video poker, roulette, craps, blackjack, live dealer baccarat, and famous online slots.

Well, have a great time in an online casino, and have some fun from your monotonous life, but remember to bet responsibly!

Written By,

Brijesh Mehta

Brijesh Mehta is a content writer & strategist from India providing his top-notch skills & expertise in the Sports and online casino industry for more than seven years. He is an avid reader and creative writer who is fond of words and uses them to teach others about online betting and trending sports news through his in-depth guides.