The strangest bets in history

One of the smartest bets in history happened during the 18th century when a butcher by the name of Mr. Bullock challenged the Earl of Barrymore to a footrace, with a sizeable wager placed on the result. Barrymore found the butcher’s suggestion hard to resist, as the butcher was fat and unhealthy, while he was at the peak of fitness.

The butcher had two demands, however. The first was that he be given a 35-meter head start in the race, and the second that he be allowed to choose the course for the race. The Earl of Barrymore, being a good sport, agreed to these conditions and the date for the race was duly set.

But, the butcher had planned his wager carefully. He arranged that the race be held in Black Lion Lane – one of the narrowest streets in Britain. On the day of the race Mr. Bullock was duly given his head start, and as could be expected, the Earl of Barrymore soon caught up with his portly opponent.

However, this was where the Earl ran into trouble, as the narrow street made it impossible for him to pass the butcher. With no way into the lead, the Earl of Barrymore had to make do with second place and Mr. Bullock landed himself a princely payout.

The Ugliest of Them All

Although this unusual story doesn’t involve sports it does deserve a mention as one of the oddest bets of all time. During the 1600s there lived a Swiss opera manager by the name of John Heidegger, who had the reputation of being the ugliest man in the country.

However, one Lord Chesterfield took it upon himself to dethrone Heidegger as the ugliest person in the land, and was prepared to wager Heidgegger that an even uglier person could be found. Heidegger accepted the wager and Lord Chesterfield went about his search for a person uglier than the Opera master.

Chesterfield eventually succeeded by sourcing a truly grotesque woman from the slums, and gleefully arranged to have Heidegger meet up with her so that he might concede defeat. A large crowd gathered to witness the showdown, and were duly impressed with the ugliness of Lord Chesterfield’s selection.

However, before the adjudication could take place, Heidegger stepped forward, removed the woman’s hat and placed it on his own head. The gruesome sight of Heidegger in a hat was more than the woman could take, and she promptly fainted, leaving Heidegger substantially wealthier and with his unsurpassed reputation for ugliness intact.

The Newport Novelty Bet

The majority of online sportsbooks offer novelty bets on current affairs. While these bets are a fun diversion, they seldom form the basis of a sound betting strategy. Yet in 1989, an anonymous Welshman generated one of the biggest payouts in history by betting on the outcome of several unrelated events.

The Welshman, a man of modest means, placed an accumulator bet which included bets on Cliff Richard being knighted before the turn of the millennium, U2 staying together past the turn of the millennium and both Eastenders and Neighbours remaining part of the BBC programming schedule until at least the year 2000.

Once he had placed all these bets at cumulative odds of 6,479/1, the Welshman paid £30 into the pot, and the incident was promptly forgotten.

However, 11 years later the Welshman reappeared at the same betting shop with a threadbare betting slip and a request that his accumulator be paid out. Every one of the man’s selections had won, earning him a payout of  £194,400 the largest novelty odds payout in history.