The Worst Lost Bets in History

by Tim | Feb 01, 2023

The Worst Lost Bets in History

Gambling is all about taking calculated risks in the hope that those risks will (literally) pay off. And it’s the anticipation of finding out whether or not Lady Luck has smiled upon you that makes this popular pastime so exciting. The glee that floods you when you win is incredible, but there’s no denying that a loss (especially a sizeable one) can sting!

Some of the worst lost bets in history have unsurprisingly been placed and lost by men and women who at least started out as wealthy individuals. While some bettors’ losses were well in proportion to their enormous personal fortunes, others lost out on the good life because they just didn’t know when to stop. Our list of the world’s worst bet losses is both a sobering tale of caution and an entertaining read. Whether you fancy a game of poker or love to play some of the best online slots in the UK, at the end of the day, it’s all fuelled by our love of dancing with Lady Luck.

Terrance Watanabe – £91.6 million

Over the course of a lengthy gambling binge, American businessman Terrance Watanabe reportedly lost a staggering £91.6 million at two Las Vegas casinos in 2007. Watanabe inherited his father’s global company in 1977 but just couldn’t get enough of the baccarat and blackjack tables. Adding to the catastrophe, Watanabe refused to pay a portion of the money owed, resulting in him being charged with four felony counts. He hit back saying that the casinos in question were working hard to fuel his addictions in an attempt to keep his money flowing. Regardless of the outcome of his legal battles, his bad luck and problem gambling set him on one of the biggest losing streaks by an individual in Vegas history, swallowing most of his personal fortune.

Kerry Packer – £30 million

Although the Australian billionaire Kerry Packer had one of the worst betting records in history, he managed to keep his considerable losses in proportion to his wealth. At the time of his death in 2005, Packer’s personal wealth was estimated to be around £3.5 billion. As a recreational gambler, it’s believed he once lost close to £30 million in a year – the biggest gambling loss in the history of English casinos. It wasn’t all bad luck for Packer, though; he reportedly also won £24 million while playing at the MGM Grand in Vegas!

Charles Barkley – £14 million

The 11-time NBA All-Star basketball champ, while a winner on the court, has had a string of hair-raising losses at the tables. Barkley’s recorded betting failures include £1.8 million in a single blackjack game, and £73,000 when the Falcons lost their 28-3 lead to the Patriots in the 2020 Super Bowl championship game. It’s an open secret that the 1993 MVP gambled away most of his £22 million fortune during his 16-year professional sports career, although the baller would only admit in 2015 to losing about £14 million over the years.

It shows that whether you play blackjack at the tables or live roulette online, even real champions find it hard to keep it recreational or know when to stop! 

Harry Kakavas – £11 million

As far as gambling losses go, Harry Kakavas’ are pretty troublesome! Not only did this Australian real estate tycoon have a run of bad luck that was undoubtedly cringe-worthy, but he also went to jail in 1998 for defrauding a large Australian corporation of more than £160,000 which he used to bankroll his gambling habits. After Harry’s prison spell, he still hadn’t learned his lesson and returned to the tables. When his debts began to mount again, he took the casino to court because he believed it had taken unfair advantage of him, knowing he had a gambling addiction. The full extent of Harry’s gambling came out as a result: he had a total gambling turnover of £1.1 billion and £11 million worth of losses. A ruling was passed down in an Australian court in 2013, which stated that casinos did not have a duty to protect gamblers from their own bad habits.

Maureen O’Connor – £9.4 million

Maureen O’Connor was the mayor of the Californian city of San Diego from 1986 to 1992. Married to a fast-food tycoon, she seemed to have the world at her feet, but she just couldn’t stop gambling, admitting to a court that she had bet about £800 million over the years. By 2013, her gambling debts amounted to £9.4 million, and she blamed her bad behaviour – including stealing from her husband’s charitable foundation – on an earlier brain tumour. O’Connor, who died in 1992, was quoted as saying, “I came in as a maverick, and I will go out as a maverick.”

James “Mattress Mack” McIngvale – £8 million

In the US, the only thing more exciting than watching the Super Bowl is betting on it, as American businessman James McIngvale will agree! McIngvale, who’s also known by his nickname “Mattress Mack”, is the owner of Gallery Furniture, a furniture shop based in Houston, Texas. The brand is known to be extremely profitable, hence the reason he has so much extra cash to wager! 

According to reports, the mattress-selling mogul lost well over £8 million when he bet that the Cincinnati Bengals would stand victorious at the 2022 Super Bowl. Unfortunately for him, the team lost 20-23 to the Los Angeles Rams. McIngvale took a chance on the worst betting odds, with the Bengals being the underdogs for the third straight game in the 2022 NFL Playoffs, and the risk just didn’t pay off. Luckily, he wouldn’t have felt the need to spend too much time reeling from the loss. After all, Gallery Furniture is said to generate well over £50 million in annual profits!

Birdman – £870,000

Nobody can flash the cash quite like a rapper, and this was indeed the case with Birdman, a New England Patriots fan and seasoned gambler. The American musician went public with his intention to place a £3.6 million bet on his favourite team in the Super Bowl XLVI. But when it came time to put his money down, lucky for him, Birdman settled on the much smaller sum of £870,000, going up against fellow rapper 50 Cent, who bet on the opposing team (the New York Giants, who went on to win 21-17!) Birdman lost the bet… and a fair chunk of change.

Would you believe it, the loyal fan did it again six years later when he lost a £145,000 bet that the Patriots would win the Super Bowl LII. They lost to the Philadelphia Eagles 33-41.

William Bergstrom – £720,000

Man with head in his hands loses at a card game with casino chips and wallet in the foreground on a green felt table.

Texan William Bergstrom, who worked as an estate agent in Austin, made his way to Binion’s Horseshoe Casino, which these days is called Binion’s Gambling Hall & Hotel in Las Vegas, in September 1980. At the time, he was just 29 years old. He had two suitcases with him, which is why, as he preferred to remain anonymous, he was referred to as “The Suitcase Man”. One case was empty; the other held £562,000. The Texan went ahead and bet the entire contents of the full suitcase on one throw of the dice – and won. He put his original stake back into one suitcase and his winnings of £562,000 into the other, leaving the casino with two suitcases full of money!

In 1984, he visited the casino again, made a handful of wagers, which he won, and repeated this later that year in November. But things went a little differently this time. He repeated the original wager that had won him £562,000 more than three years before – placing a Don’t Pass bet (this is when the dice must land on 2, 3 or 12 after being rolled by the shooter to win) in a game of craps. This time, he upped the wager to £720,000 – but he lost! Could this have been one of the worst bets ever? We think so!

Responsible gambling

Now, we did warn you that there’d be some cautionary tales within this blog regarding the worst bets in history. Accordingly, we’d like to urge our readers to take stock of these stories and keep things in perspective when they decide to gamble.

Play the best online casino games responsibly at The Phone Casino and ensure that you know what to look out for in terms of the warning signs of problem gambling. Here are a few:

  • The inability to stick to specific limitations regarding how frequently you play or how much money you spend. 
  • Constantly thinking about gambling, planning your gambling activities and plotting how you’re going to get hold of the money you need to play your favourite games. 
  • Noticing how your bankroll is steadily increasing because you need to spend more in order to get the same thrill each time you log into an online casino or visit your nearest brick-and-mortar casino. 
  • Cancelling plans to socialise with friends or relatives because you’d prefer to gamble instead. 
  • Trying to cut back on how much money you spend, or how often you play, without success. 
  • Doing your best to hide your gambling behaviour and habits from concerned loved ones, such as lying about how much you’ve lost or playing in the middle of the night when everyone else is asleep. 
  • Feeling the urge to gamble to cope with negative emotions, like anger, sadness, guilt or loneliness. 

If in doubt, don’t be afraid to seek help! Remember, whether you prefer scratch card games or like to play online slots, you’ll always get more enjoyment out of the experience when you manage your time and bankroll responsibly. 

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