Wagering was always part of human society and throughout history, many people have seen great winning potential in the most bizarre scenarios. Although many people may consider this type of betting rather absurd, there are some really foolhardy bettors who have managed to come up with truly outrageous wagers and, surprisingly enough, they won impressive amounts of money.
Let’s take a trip back in time and meet history’s most audacious fortune-hunters and their baffling, shocking and ridiculous bets.
1. Mirror, Mirror On the Wall, Who’s The Ugliest of Them All?
Going back to the 17th century, we find John Heidegger, a Swiss opera manager who moved to London as a young man and managed to quickly gain the not-so-flattering reputation of being the ugliest man in the country. Soon, this claim was challenged by none other than Lord Chesterfield, who claimed that he could easily find an uglier individual. Heidegger, however, was so confident in his absolute repulsiveness that he immediately accepted the bet.
Chesterfield eventually managed to find a woman in the slums of London, so ugly that for a moment it looked like a sure win. When Chesterfield arranged a meeting between the two individuals, he fully expected to win the bet. Unfortunately for him, just before adjudication, Heidegger made an unexpected move, grabbing the woman’s hat and placing it atop his own hideous head. The sight was so exceptionally abominable that the woman fainted. This made Heidegger the undisputable winner of the bet.
2. The ‘Heavy Weight’ Chase and a Clever Bet
Let’s move forward to the 18th century England where another strange bet was placed. This time, an obese butcher named Mr Bullock challenged the Lord of Barrymore to a race. As expected, a tremendous sum was placed on the outcome. Being the athletic and very confident type, the Earl of Barrymore immediately accepted the rotund butcher’s bet. Since the odds were obviously in Barrymore’s favour, Bullock demanded a few conditions for a fair stake.
First, he demanded a 35-meter head start. Secondly, he was to choose the course of the race. Obviously, the overly confident Barrymore immediately accepted the terms. But there was a catch.
Mr Bullock requested that the race be held in an extremely narrow street in London and the head start meant that he was always in the lead as his bulky physique prevented Barrymore from getting ahead of him. Clever, right? As a result, the butcher was declared a winner and walked away with the huge prize to go along with his huge girth.
3. Only A Very Creative Mind Could Have Hatched This Wager
Well, actually two very creative minds. It was the beginning of the 20th century when the Earl of Lonsdale and his good friend John Pierpoint Morgan placed a bet stating that no man could travel around the world, on foot, without being recognised. But they didn’t stop there. The man had to push a baby stroller, wear a metal helmet, sell postcards of himself wearing a suit of armour, change his pants only once during the journey and find a wife along the way too. And of course, go the entire expedition without being recognised once (yes, let that sink in for a while).
Surprisingly, there was someone willing to accept the bizarre challenge for a solid £21,000 prize. His name was Harry Bernsley, a local showman.
His attempt was sadly ended by the outbreak of WW1 after 6 years in which Bernsley claimed to have made it through Italy, Ireland, Turkey, Japan, China, India, Canada and America. The man didn’t walk away empty-handed, as Morgan and Lonsdale awarded him £4,000 for his efforts.
4. “If He Wins, It’s His Funeral”
We all have to face death at one point in our lives so why not make it interesting? This was the case with a witty 91-year-old man named Arthur King-Robinson, who was determined to avoid a £3,000 inheritance tax on his estate by wagering his own death. The man bet £500 on 6:1 odds that he would die by the end of that year. It was a surprise when this morbid bet was actually accepted by the popular bookies William Hill who commented: “If he wins, it’s his funeral.” But regardless of the outcome, Arthur had basically nothing to lose. He eventually survived the year, avoided the tax but lost the £500 wager. Oh well, at least he’s healthy.
5. Is There A Bet On His Cup Size Yet?
Moving on to Canada where Brian Zembic a rather eccentric individual with a taste for ridiculous wagers won a $100,000 bet for getting breast implants. Yes, breast implants, and he had to keep them for 1 year. Apparently, Brian became very fond of his newly acquired assets and decided to keep them. Permanently. As he mastered the art of outrageous bets, he recently won $15,000 for living in a men’s restroom for an entire month. Good thing he had a couple of ‘ways’ to avoid boredom.
Creativity is limitless, especially when it comes to betting and it often gives us a reason to chuckle. If you fancy some more outrageous betting stories, stay tuned for The Strangest Bets in History – Part Two.
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