Lost Bets – Biggest Losing Wagers in the History of Gambling

Article by: Nicholas Crouch - Casino Еxpert

Date Published: 21/04/22

Gambling is risky, which means players can experience huge wins and losses. However, some players take such significant risks that they lose millions in a single bet. We will look at some of the most famous lost bets in the history of gambling and learn from their mistakes.

What Are the Biggest Losing Bets

As mentioned above, lost bets are just unsuccessful bets. While most players can shrug it off and try again, some have lost so much that they have become cautionary tales for all types of gamblers. We will go over the important details of these stories, giving insight into who these players are and what led to their monumental losses. The paragraphs below also contain information on their preferred gambling games and how to mitigate losses. You can use the quick navi below to navigate through this blog and find any details you require. So, let’s dive into the biggest casino losses:

Top 10 Losing Bets List

1. Jim McIngvale ($9,500,000)
2. Fouad al-Zayat (£23,200,000)
3. Michael Jordan ($1,200,000)
4. Harry Kakavas ($20,500,000)
5. Terrance Watanabe ($127,000,000)
6. Robert Maxwell (£1,500,000)
7. Dave Oancea ($1,000,000)
8. Steve Richards (£30,000)
9. Charles Barkley ($2,500,000)
10. Kerry Packer (£8,000,000)

1. Jim McIngvale – Mattress Mack’s Mishap

Some people are just born unlucky as evidenced by Jim McIngvale and his series of losing bets. McIngvale is well-known as “Mattress Mack” due to his ownership of the furniture company Gallery Furniture. He frequently enjoys betting on sports, to the point he sometimes makes promotions, offering rebates for his customers if his pick wins.

Unfortunately, McIngvale is also infamous for his bad luck and losing millions on sports bets, including baseball and horse racing. The most significant of his lost sports bets is the $9,500,000 wager on Cincinnati Bengals winning Super Bowl LVI. He had placed an initial $4.5 million for Cincinnati to win at 4.5 odds and an additional $5 million right before the big game against the Los Angeles Rams.

With the potential of earning $21 million, this was the biggest bet in Super Bowl history and, indeed, the most significant sports bet made through mobile betting sites. Despite his loss, McIngvale is not discouraged and claims to enjoy the added thrill, having moved on to other great gambling exploits.

2. Fouad al-Zayat – The Gambling Whale

Some high rollers are called “whales” due to their huge spending habits, betting thousands or even millions on games. Fouad al-Zayat, a Syrian businessman and investor, was one such player and was a regular at Aspinalls, a casino in Mayfair, London. With more than 600 visits across 12 years, he enjoyed a similar experience to the best high roller online casinos.

Unfortunately, Fouad al-Zayat was not a lucky gambler. He frequently lost bets gambling on various games, including £500,000 on blackjack and of the £91.5 million he wagered over the years, £23,200,000 were lost. His losses would become so great that the casino once sued him for £2 million, plus costs, due to unpaid debts.

Although he won the court appeal, claiming the casino had given him an illegal credit under the Gambling Act, his luck in life would run out. Until his death in 2018, Fouad al-Zayat had been involved in various controversies and corruption scandals, such as an attempt to sell a jumbo jet to the Iranian government, despite US trade restrictions.

3. Michael Jordan – Golf and Gambling

Not even celebrities are immune to gambling and lost bets, as evidenced by Chicago Bulls’ ace: Michael Jordan. MJ needs no introduction, having become a cultural icon in the 80s and 90s. He is also considered one of the greatest basketball players in the game’s history.

A lesser-known fact is that Michael Jordan is incredibly competitive and frequently enjoys gambling. Jordan certainly enjoyed the thrill, whether playing cards with friends or a simple bet on rock paper scissors. However, his gambling has also sometimes caused him problems, such as when he played at casinos in New Jersey before the big playoffs in 1993. He even had to cover $53,000 in casino losses the previous year.

However, his biggest lost bet comes from his golf match against Richard Esquinas. Jordan enjoys golfing and frequently competes with friends by betting large sums on winning holes. After ten days of golfing, Esquinas claims Jordan owed him around $1.25 million but paid only around $200,000. Esquinas would publicly reveal this story in a book about his personal gambling problems, which soured his relationship with Jordan.

4. Harry Kakavas – Gambling with Billions

High rollers may enjoy the chance for bigger prizes and benefits at land-based casinos, similar to online casino bonuses, but they also run the risk of losing it all. Harry Kakavas is one such gambler, having once defrauded an Australian company in 1998 and using the money for gambling activities. This event would land him in jail for four months.

After years of self-exclusion, Kakavas would again try his luck at the Crown Casino in Melbourne and ended up with some of his biggest gambling losses. Between 2005 and 2006, he spent $1.5 billion and lost $20.5 million at the casino’s baccarat tables. Becoming outraged at such a shocking loss, Kakavas attempted to sue the casino in 2007 for exploiting his gambling addiction, using various benefits to keep him playing.

Several gruelling years of court battles later, the Australian court ruled in the Crown Casino’s favour, stating that as Kakavas could previously refrain from gambling, he could make rational decisions and was not being exploited. Fortunately, Kakavas has recovered from his loss and addictive habits and now continues selling real estate on the Gold Coast in Queensland.

5. Terrance Watanabe – The Biggest Blackjack Bust

Becoming the president of a company is usually a sign of outstanding achievement and further success. But for Terrance Watanabe, it was just another way to fund his gambling activities. Although Watanabe inherited the Oriental Trading Company from his father in 1977, established in 1932 and is one of the US’s first wholesaling companies, he was seemingly not interested in managing it.

In 2000, Watanabe sold all his shares and stepped down as president, focusing entirely on his gambling habits. He would spend years gambling at various casinos in Vegas until 2007, at which point he had biggest gambling loss of $127,000,000 after wagering close to $825,000,000. Some reports state that he would gamble all day and even lose up to $5 million in one day.

He is also reported to have been allowed to break casino rules and play with up to three hands in blackjack, which is forbidden, unlike games at blackjack casino sites. After failing to sue Caesar’s Palace to avoid paying the debt, he would be charged with four felony charges for attempting to defraud and still owes $15 million.

Meanwhile, Caesar’s Palace was fined $225,000 for allowing Watanabe to gamble while drunk, while Watanabe has received counselling and quit gambling.

6. Robert Maxwell – Wheel of Fate

Having lived in poverty, only to become a Labour MP and own a multi-media empire, it might seem as if Robert Maxwell had achieved the dream. However, Maxwell faced numerous debts underneath the glamour, even selling off his company Pergamon Press to cover some of them. To earn back some of his money, he began gambling at London casinos.

However, even in gambling, Maxwell was met with failure as he achieved one of the biggest losing bets in the history of gambling. Within three minutes at the Les Ambassadeurs, he would lose £1,500,000 after betting on multiple wheels. That is why it is always important to have a proper strategy before playing roulette at roulette casino sites.

After this spectacular loss, Robert Maxwell would spiral further into debt and try everything to keep his empire afloat. Unfortunately, after becoming incredibly paranoid and isolationist, he would accidentally drown during a trip with his yacht. He would be declared bankrupt with £400 million in debts after his death, while his family attempted to preserve his companies.

7. Dave Oancea – Vegas Dave’s Lost MMA Bet

Sports betting, especially through online betting sites, features a wide range of sports, including MMA. David Oancea, better known as “Vegas Dave”, is famous for his successful sports bets, such as predicting two consecutive Super Bowl winners. He also won close to $200,000 after predicting Miesha Tate would become the new UFC Women’s Bantamweight Champion, among other MMA bets.

As such, it is no surprise he bet on his favourite to defend her title at UFC 200 on the 9th of July 2006. While it was initially believed that Tate would fight Ronda Rousey, she instead had to face Amanda Nunes. After just three minutes into the first round, Tate lost the title, and Dave lost his bet of $1,000,000.

Despite the loss, similar to Jim McIngvale, Oancea did not regret his bet or blame Tate and proceeded to enjoy the rest of his night. These days, Vegas Dave continues placing bets on various sports while operating his successful sports betting consultation company.

8. Steve Richards – Win Some, Lose Some

Not all lost bets in gambling are spectacular tales of high rollers, debt and court battles. Steve Richards, a 56-year-old roofing contractor, is an average man passionate about gambling. He typically bets every week and even managed to win £38,000 from a £10 bet on a Premier League match.

Feeling emboldened by his win, Richards bet £30,000 that Wales would beat Australia in the Australia Tour 2013 rugby match. Alongside other players, Richards anticipated the match and was hoping to get an even bigger payout than his previous win. Unfortunately, luck was not on his side.

Wales would lose to Australia 26 to 30, and Richards lost most of the money from his previous victory. However, it was not a total loss as he refrained from betting all the money he had won and was not sad about losing. He still enjoys betting on sports and continues supporting Wales in rugby matches.

9. Charles Barkley – Six-Hour Blackjack Loss

Charles Barkley is another NBA MVP with a history of gambling. The former Phoenix Suns player is an admitted compulsive gambler who has lost around $10 million playing blackjack at casinos or betting on sports. He even claims to have won $700,000 after predicting Indianapolis Colts’ victory at Super Bowl XLI.

Unlike his fellow basketball star Michael Jordan, his gambling exploits are well-known, and he has even admitted to his biggest casino losses. One of these lost bets was during a six-hour blackjack session, where he would lose $2 500 000. He also had to settle an unpaid $400,000 debt to the Wynn Las Vegas in 2008.

While initially believing that he could manage the problem and that it was not hurting him, Barkley eventually decided to quit gambling entirely after paying off his debt in 2008. Although he enjoyed games, he has stuck to this promise. He is an excellent reminder that one must always play responsibly, even at the top online casinos in the UK or the in the USA.

10. Kerry Packer – The Influential Australian Gambler

Last but not least, on our list of the biggest gambling losses is Kerry Packer. He is well-known among Australians as a media magnate, with his Packer Family company owning the Nine television network and Australian Consolidated Press publishing company. Internationally, he is famous for creating the World Series of Cricket and influencing the sport itself.

Packer is also famous for being an exceptional high roller and often gambled, to the point where he had a private blackjack room at the Ritz Hotel. In this room, he ended up experiencing one of his biggest losing bets, with $19,000,000 in a single night. Other impressive losses include a three-day losing streak totalling £13.6 million on baccarat and £15 million after betting on four roulette tables at once.

Packer was furious when losing and ecstatic whenever he would win but kept playing all night. Due to his status as a high roller, he was well-liked at casinos and even received special benefits. Whatever the event’s outcome, Packer would always come back and enjoyed gambling until he died in 2005.

How to Gamble Responsibly and Minimise Lost Casino Bets

Before jumping into gambling, you must be aware that there is always a risk. Even the most responsible gamblers will sometimes experience lost casino bets. That is due to the inherent randomness of these games, even in table games such as poker and blackjack. However, it is always possible to control the amount you lose and avoing .

First, you should always make sure you play at reputable casino sites and check the RTP of your preferred game or the odds if you’re betting on sports. Next, you should plan your budget, which should be how much you are comfortable spending and plan a strategy if possible. That includes checking statistics and observing your available betting options.

Finally, remember that gambling is supposed to be fun above all else. You should always gamble responsibly and use the provided responsible gambling tools to avoid gambling addiction. Enjoy your time with your favourite games and contact customer support or a responsible gambling organisation if you require help to avoid your biggest gambling loss. Mind that many international online operators are also secure enough. The LeoVegas safety is excellent and the operator is regulated internationally.

Lost Bets Conclusion – Fun and Responsible Gambling

We hope you enjoyed our look into the most famous lost bets. As these stories show, it’s always important to plan a budget and play carefully. Whether you’re trying out the latest baccarat sites or placing bets sports bets, always remember to gamble responsibly.

Aside from helping you mitigate losses, trying out strategies can also be fun and allows you to experience new ways of playing your favourite games. Have fun with your preferred casino games or favourite sports event without having to worry about the biggest casino losses.

Lost Bets FAQ

Before wrapping up our blog, we will answer all your pressing questions about the lost bets. Learn more about the biggest gambling losses, how they happened, and how players dealt with the loss. You can also learn some extra details about the players themselves and how to mitigate losing bets.

1️⃣ Can I avoid losing bets?

While all players experience lost bets at some point, it's always possible to avoid huge losses by gambling responsibly. Make sure you plan out a budget and play within comfortable bet limits to avoid quick losses. Finally, always remember to contact customer support and use self-exclusion tools to combat gambling addiction if necessary.

2️⃣ Who has the single biggest lost bet?

Many players lost bets gambling over months, but Jim McIngvale would lose $9 500 000 on a single sports event. Although his initial bet was for $4.5 million, he was so confident in his pick that he placed another $5 million shortly before the big game. Unfortunately, this would become the biggest lost bets sports fans had seen.

3️⃣ Which is the biggest gambling loss?

The biggest gambling loss belong to Kerry Packer and his incredibly huge losses. While he would sometimes win, he would often lose millions, such as $19 000 000 on blackjack games in a single night. It is even said that he would place bets on multiple tables simultaneously and often play on his own.

4️⃣ How did the players handle their lost bets?

While some stories end tragically, many can recover from their lost bets gambling, such as Harry Kakavas. Initially, Harry was outraged at losing $20.5 million on baccarat tables and attempted to sue the casino for exploiting his gambling addiction. The casino did not rule in his favour, but he quit gambling entirely and now sells real estate in Australia.

5️⃣ What was Michael Jordan's biggest losing bet?

Although he did not lose it betting on sports or casino games, Michael Jordan is said to have once lost $1.25 million on golf. Jordan enjoys the thrill of gambling and would bet on anything, including that he could beat Richard Esquinas at golf. After several days of playing, he lost $1 250 000 against his friend.