I’m All In: Some of the Craziest Bets Ever Made

Most sensible gamblers like to weigh up the odds, and consider whether they think a particular potential outcome is likely before parting with their money. Others, it would appear, are much less cautious, and never far away from a bet that strikes as plain crazy. Whether it’s a matter of life and death for a few thousand, or picking that unlikeliest of sporting outcomes at 25,000/1, there are plenty to stories of crazy bets come good, as well as those that have gone bad. Here are a few of our favourite crazy bets, some of the most unbelievable wagers of all time.

Some Things Never Change

Sometimes, crazy bets seemingly have no rhyme or reason to them, like this incredible bet taken by a Welsh gambler back in 1989. He stuck down the equivalent of $50, a lot more money then than it even is today, on a bet that attempted to predict how the world would look in the year 2000, on a few strange bases. Firstly, that the band U2 would still be together – check, the band are still going strong today, a further 17 years after the 11 years out when he placed the bet. Secondly, that soaps Eastenders, Neighbours and Home and Away would still be broadcast – they are, again, even to this day. He also incredibly predicted that Cliff Richard would be knighted before the millenium, which he was, completing an unbelievable crazy bet at astonishing odds.

At the turn of the millenium, as the gambler watched his results confirmed, he walked away with a cool $320,000 for his troubles. Not a bad bet, though few would have called it at the time. Just an example of what can be achieved with a bit of blue sky thinking…or maybe a crazy attitude to gambling your own money.

Sink or Swim…

In 1875, a man by the name of Michael Webb made history when he became the first man to swim the English Channel. This is no mean feat, and even today, is considered an impressive display of physical endurance, strength and resilience to cover the distance. Buoyed by his initial success, Webb cast his eye to opportunities further afield – namely, the treacherous Whirlpool Rapids at Niagara Falls. Confident of his ability to recreate the feat, he took a bet in the sum of $10,000 that he couldn’t make it – a staggering amount of money in the late 19th century.

With the pressure on, Webb attempted the crossing – widely thought to be impossible for a human swimmer to traverse safely. Unfortunately for Michael Webb, his crazy bet didn’t come good, and he suffered a rather drastic fate at the hands of the rapids. Commendable courage, or sheer gambling madness? You decide.

‘Money’ Mayweather

There’s something of a legend that does the rounds about boxer Floyd ‘Money’ Mayweather, who is well know to be a gambler. Since the event, Mayweather has denied ever placing the bet, although there are a number of reliable sources who testify to the veracity of the rumours. The story goes that Mayweather fancied a punt on the Super Bowl XLVIII, where the Denver Broncos faced off against the Seattle Seahawks. Mayweather reportedly stumped up $10.4 million on the Broncos, who were widely anticipated to run out as winners.

Unfortunately for Mayweather, the Broncos were battered by the Seahawks, who won with an emphatic 43-8. This would have cost Mayweather his stake, not to mention a world of embarrassment.

Since the event, Mayweather has denied the bet every happened, and said that is he was to bet on that game, he would have backed the Seahawks anyway. Whether or not you believe the rumours is up to you.

Lucky 7s

When jockey Frankie Dettori ran out 7 winners at Ascot, he completed one of the most impressive sporting achievements ever to have been recorded. An unprecedented outcome, few could have predicted that he would go on to win each of the races he entered, and in the process, cement his name as a true legend of the sport. Unfortunately for the bookies, there were a few plucky punters who took a stab at the impossible, and backed Dettori to go all the way, with significant winnings as a result.

The odds on offer before the event got underway stood at 25,000/1. One punter was recorded as backing this outcome, walking away with in excess of half a million when Dettori came good. An elderly punter backed Dettori in each of the seven races at £0.50 but didn’t back the accumulator, so walked away with something like £25 for her troubles (she could have potentially won nearly £15,000). It just goes to show that just sometimes, crazy bets can actually pay!