What are Some of the Craziest Bets in History?

Trying one’s luck has been more than a welcome pastime for many people throughout history. People have placed bets on absolutely everything, sometimes beating some extraordinary odds and getting rich with a single stroke of luck.

It’s always tempting to make a crazy bet in the hope that your life will change in a blink of an eye. Some of the craziest bets happen when friends enjoy one drink too many, while others are motivated by a much nobler goal. Either way, you need to do something remarkable if you want to place one of the craziest bets in history.

From landing a plane in the middle of the city to tasing your other half for losing a bet, the internet is filled with excellent and interesting betting stories. However, once money enters the game, the thrill becomes higher and the stories even crazier. Let’s look at some numbers, shall we?

  • The odds of winning a jackpot are one in 292 million.
  • The largest recorded bet at a casino is $777,000 (worth $2.4 million today).
  • The highest bet placed on the flip of a coin is $100 million.
  • The highest bet on sports was $5.9 million on an NBA match in 2013.
  • The biggest win on the smallest bet was £1 million on a £0.50 bet.

Silly Bets that Made Sense (and Dollars)

  1. A Welshman won £194,400 for betting on U2 still performing, Cliff Richard being knighted, and three TV shows still being on air in 2000.

(Sports Information Traders)

In 1989, a Welshman placed an 11-year long bet. He bet £30 in the hope that several things wouldn’t change by the year 2000. With this multi-leg bet he predicted that U2 would still be performing, TV shows Home and AwayNeighbours, and EastEnders would still be on air, and that the singer Cliff Richard would receive a knighthood. We probably don’t have to explain betting odds and how they work to show how insane this bet is.

Eleven years later, the lucky (or perhaps psychic) Welshman took home £194,400, beating crazy odds of 6,479-1.

  1. Anything-for-a-bet man gets breast implants for a bet worth $100,000 and lives with them for almost 20 years. 


Brian Zembic is famous for accepting all types of bets and doing pretty much anything to win them. We’re not even sure he knows how to read betting odds – he seems to be simply addicted to the high-risk experience!

The most ridiculous bet he took, according to him, was in 1997, when he agreed to have breasts implanted and live with them for a year. In return, he would get $100,000.

Zembic was smart about it; he found a plastic surgeon who enjoyed trying his luck, too, and then beat him at backgammon to get the pair for free. He then lived with the implants for not only one but almost 20 years, which surely tops the list of crazy things to do for bets. Even though someone bet him $10,000 to take them out in 2014, he only did so in 2017, at the request of his daughter.

Zembic’s story was featured in a book of classic gambling tales. He was a guest on several shows and to date remains one of the world’s most famous bettors.

The Luckiest Casino-Goers

  1. A reality TV contestant once won $135,300 on an all-in bet.


Ashley Revell, a participant in a reality TV series called Double or Nothing, decided to sell everything he ever owned, including his clothes, raising $135,300. He headed to Las Vegas with that money, where he put it all on a single bet on a roulette wheel, making this move one of the most famous crazy casino bets.

Luckily for Ashley, he won and doubled his money. After this stroke of luck, he used that money to open an online poker company, which unfortunately did not have as much luck – it went belly-up in 2012.

  1. The largest-ever successful bet of $777,000 (worth $2.4 million today) was doubled in a single attempt.


The largest recorded bet in the history of casino gambling history goes to William Lee Bergstrom, who walked into the Binion Horseshoe casino with two suitcases – one carrying $777,000 and the other empty.

He put the $777,000 on “don’t pass line” and won, doubling his money. He stashed the winnings in the empty suitcase and simply left. At this point, Bergstrom became one of the celebrities of crazy bets. He tried his luck again, three years later, with a bet of $538,000, which he also won. The same day, he won an additional $117,000. His luck ran out when he attempted to double a $1 million bet, and his story ended tragically.

  1. A woman beat 1.56 trillion odds by consecutively rolling the dice 154 times before getting the number seven.

(Online Bingo)

Patricia Demuro’s case should be the definition of beginner’s luck in every dictionary. While she wasn’t technically a first-time player, her second attempt at the craps table was astounding.

Demuro pulled off the most successive dice rolls ever by sheer luck, rolling it 154 times in a row without hitting a seven once. This streak of luck came at genuinely funny odds: one in 1.56 trillion, and it’s estimated that Demuro took home approximately $100,000 that night.

Who Says Sports Is Just For Entertainment?

  1. A gambling genius once placed a long-term, £1,500 bet on Roger Federer winning Wimbledon seven times by 2019.


When Roger Federer won his first Wimbledon championship in 2003, a man named Nick Newlife decided to bet on him for the long haul. Newlife placed a £1,500 bet that Federer would win Wimbledon at least seven times by 2019. At the time, the odds were 66-1.

Federer turned this bet into reality seven years ahead of time, when he won the title for the seventh time in 2012. Unfortunately, Newlife passed away in 2009, so he never got to enjoy the £100,000 in winnings from the mother of crazy sports bets. However, he donated the betting slip – along with his estate – to Oxfam International, an organisation that works to end poverty.

  1. A golfer’s father won £150,000, by betting on his teenage son to win the British Open.


Gerry McIlroy, a Northern Irish golfer, saw extreme potential in his kid, Rory McIlroy. When Rory was barely 15, Gerry and his three friends each placed a £100 bet, which put some pressure on Rory to win the British Open by the end of 2015 so that they could collect. Rory delivered a year before the bet was off, and his father and his friends collected about £50,000 each.

  1. An unlucky student lost his £4,400 tuition betting on the African Cup because of a last-minute twist.

(The Sportster)

The African Cup of Nations cost an unlucky young student his scholarship, as he bet his whole student loan funding of £4,400 on a bet that Angola would win against Mali in the championship.

While not the biggest bet ever lost, it was probably the biggest one possible for the young student. Initially, it seemed like a safe bet, since Angola was winning 4-0 when he placed it, but his luck turned dramatically; Mali made an incredible comeback, costing him his scholarship funds. On the other hand, the odds were so slim that even if he won, he would have won a mere £44. It’s really important to actually find good betting offers and consider the odds before you gamble with something as important as your scholarship. Here’s hoping a career involving math was not in this kid’s plan for his future.

  1. One man’s 15-year-long bet on his grandkid earned him £125,000.

(The Guardian)

Young football star Harry Wilson made his debut in the world of professional football representing Wales at the young age of 16. His grandfather, Peter Edwards, foresaw this 15 years ago and placed a bet worth £50 that his grandson would one day play for Wales, creating yet another entry in the book of crazy football bets.

Fifteen years later after a win of £125,000, Peter is now happily retired, and his grandson didn’t let him down.

“I’ve retired one year early. I have come home now and will not be going back. Not bad for a daft bet,” Peter said of his crazy prediction.

If you like football betting sites, this story could inspire you to try your luck with more unusual bets.

  1. Two lucky people won £550,000 when Frankie Dettori won the “magnificent seven.” 

(Finance Monthly)

Jockey Frankie Dettori made history in 1996 when he won seven consecutive races in a single day. To this day, he is the only jockey to have succeeded in doing so. The odds of this happening were 25,051 to 1, and the day justifiably became known as Dettori’s “magnificent seven.”

On that day, he also made two lucky people very rich. While they placed a couple of crazy little bets, these two took an astonishing £550,000 home with them.


What was the biggest bet ever?

Throughout history, plenty of massive bets have been made, some worth millions of dollars. The highest recorded sports bet was placed on an NBA game and was worth $5.9 million.

What are good bet ideas?

This is extremely subjective, so it really depends on what you’re into and how big a risk you’re willing to take. A good bet should challenge you and motivate you to achieve a particular goal. But, of course, the best bet is one that wins.

What is the most money won on a bet?

It is safe to say that one of the craziest bets was winning a lucky £1 million on a £0.50 bet. This happened when 60-year old Fred Craggs chose eight long-shot horses and bet on them in an eight-play accumulator.

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Silly Bets that Made Sense (and Dollars) The Luckiest Casino-Goers Who Says Sports Is Just For Entertainment? FAQ
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