It is quite obvious that if you bet on a very rare possibility, you are likely to lose, but not always. You don’t know when your luck will kick in and earn you a million dollars. This has actually happened with people, but not all bets are just about money. People had bet crazily on wagers that had destructive consequences, huge embarrassments, bankruptcies, etc. Combining such instances and more, here is our list of 10 of the craziest bets of all time.

1 An overconfident Russian pilot, Alexander Kliuyev, bet his co-pilot, Gennady Zhirnov, in 1986, that he can land the plane blindly, without looking at the ground. He curtained all the cockpit windows and ignored all the alarms and warnings. The plane went upside down and crashed. Seventy out of 94 people were killed but the pilot survived.

On 20 October 1986, the Russian Aeroflot Flight 6502 was landing at Grozny Airport. The pilot, Alexander Kliuyev, had made a deadly bet with the first officer that he could land the plane without having any visual contact with the ground.

So when the flight was just two minutes short of landing, he ordered the flight engineer to close all the curtains over the cockpit windows boasting that he will use the instrument-only method to land the plane.

The alarms went off, the air traffic controller suggested switching the landing method, ATC suggested taking precautions, and a warning was issued at 200 feet of altitude. Alexander ignored and disagreed with every little piece of a hint of the destruction.

The plane went completely unstable, it reached the ground very quickly, and literally turned upside down after overrunning the runway and burst into flames killing 70 passengers.

The pilot didn’t die and was sentenced to 15 years in prison but was released after six years. The co-pilot, Gennady, tried his best to save people but was heavily injured and died of a heart attack on the way to the hospital. (1, 2)

2 Pete Conrad, the Apollo 12 commander bet $500 with an Italian journalist, Oriana Fallaci, who claimed that astronauts’ declarations during the Moon landing were scripted by NASA. Only to prove Oriana wrong, Pete uttered “Whoopee!” as his first word after setting his foot on the moon.

Pete was already irritated by the common public opinion that the astronauts are asked to speak only particular things during the missions. One such controversial speech was of Neil Armstrong when he said, “That’s one small step for a man; one giant leap for mankind.”

People thought that it was very odd for an astronaut to use such poetic words, but Pete knew they were his own. During an argument in an interview with an Italian journalist, Pete thought the best way to get rid of this by betting $500 that he would make up his word when he lands.

A few months later Apollo 12 was launched with Conrad as the commander. The flight had to face a temporary power cut-off because of a series of lightning strikes.

Five days later, the spacecraft reached the moon, and when Pete stepped down the Lunar Module’s ladder, the first thing he said was, “Whoopee! Man, that has been a small one for Neil, but that’s a long one for me.”

He sure won the challenge, but very unfortunate for Pete, Oriana never paid him his $500. (1, 2)

3 Sir Richard Branson, the founder of Virgin Group, and Tony Fernandes, the owner of Air Asia, bet over the winner of the 2010 Formula One Grand Prix in Abu Dhabi. The loser had to be dressed and served as a stewardess on the winner’s airline. Branson lost the bet and actually completed the task. 

Mr. Branson mentioned that he and Tony both had a Grand Prix team. In the 2010 Finals in Abu Dhabi, Tony made a wager that his team, Lotus will finish before Branson’s team.

They also decided the loser will dress and serve as a stewardess. Branson was pretty confident and also excited to win the bet and see Tony in the Virgin Atlantic stewardess outfit, but the race turned out very unfortunate for him.

Branson took the humiliation and dressed like a female flight attendant on the flight to Malaysia from Australia with lipstick and a red skirt. Richard also shaved his legs but not his beard and wore tights for his stint.

Richard rather took up his task in a rather funny spirit. He purposely spilled a tray of drinks over Tony. In the end, both of them and everyone on the flight seems to have a pretty good time.

The incident attracted public attention and raised more than $300,000 for the charity that both Virgin Australia and Air Asia support and is run by the Starlight Foundation. (1, 2)

4 In 1956, just for the sake of a barroom bet, a pilot named Thomas Fitzpatrick stole a plane from a New Jersey aeronautics school and landed it in front of a New York City bar where he had earlier been drinking and made the bet. Two years later, he stole another plane from the same place and landed it in Amsterdam because another bar patron didn’t believe his first story to be true. 

On the night of 30 January 1956, Thomas was drunk in a New York City bar when he bet that he could travel from New Jersey to New York in just 15 minutes. He actually did it by stealing a plane from Teterboro School of Aeronautics in New Jersey at 3 a.m.

He took the flight without light and radio and landed right in front of the New York bar in St. Nicholas Avenue near 191st Street where he had been drinking. He was fined $100 for his illegal act.

This was not enough for Thomas. A couple of years later, he repeated the same scene on 4 October.

Again drunk, he stole a plane from the same place but landed on 187th Street in front of a Yeshiva University building in Amsterdam when another bar patron doubted Thomas’ previous feat to be true. Thomas was sentenced to six months of prison by Judge John Mullen for the entire incident. (1, 2, 3)

5 The professional golfer Rory McIlroy was just 15 years old in 2004 when his father bet £200 ($341) that Rory would win the British Open sometime within the coming ten years. The odds for him to win were just 500-1 but Rory won the tournament in 2014 making his dad $171,000 richer. 

Gerry McIlroy made the bet with the bookmaker Ladbrokes Plc which stated that the odds of winning such a wager are as low as 500-1.

The stakes might seem to have put pressure on the 25-year-old Rory, but as he mentions, “The bet was not a regular conversation topic at the dinner table,” but he knew about it very well.

Rory’s father had invested in his victory from an early stage, but he didn’t remind Rory of it frequently, even though Rory was a prodigy in himself and everyone believed in him.

Unfortunately for Ladbrokes, they didn’t see that coming. For the company, such a loss is extremely rare, but they did pay Rory’s dad $171,000 for it. (1, 2)