The Worst Lost Bets in History

by Tim | Aug 03, 2021

The Worst Lost Bets in History

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 staggeringly bad bets is both a sobering tale of caution and an entertaining read. Whether you fancy a game of poker or love to play roulette online, at the end of the day, it’s all fuelled by our love of dancing with Lady Luck.

Terrance W. – £91.6 million

American businessman Terrance W. reportedly lost a staggering £91.6 million at two Las Vegas casinos in 2007. Watanabe inherited his father’s global company in 1977, but couldn’t get enough of the baccarat and blackjack tables. His bad luck set him on one of the biggest losing streaks by an individual in Vegas history and swallowed most of his personal fortune.

Kerry P. – £30 million

Although the Australian billionaire Kerry P. 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, Kerry’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 Kerry, though: he reportedly also won £24 million while playing at the MGM Grand in Vegas!

Charles B. – £14 million

The 11-times NBA All-Star basketball champ, while a winner on the court, has had a string of hair-raising losses at the tables. Charles’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 just goes to show 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 K. – £11 million

Not only did this Australian tycoon have a run of bad luck that was undoubtedly cringe-worthy, 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 learnt his lesson and went back 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 in court – he had a total gambling turnover of £1.1 billion and £11 million 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. – £9.4 million

Maureen O. 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 Maureen just couldn’t stop gambling, admitting to a court that she had bet more 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. Maureen, who died in 1992, was quoted as saying, “I came in as a maverick, and I will go out as a maverick.”

Birdman – £870,000

Nobody can flash the cash quite like a rapper, and this was 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, 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 B – £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 B, 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!

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

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