Top 10 Craziest Bets!

The best bonkers bets ever!


We’ve all made some crazy bets in our lives, but this list really takes the biscuit! It’s a long read, but we think it’s worth it. Here are our top ten favourites…


10) Way back in the 18th century, the Earl of Barrymore was challenged by a butcher, named Mr Bullock, to a 100 yard race. The Earl loved an outlandish bet and this was one that he felt confident that he could easily win. He was an athletic man renowned for his running prowess, whilst his opponent was rotund and described as having an ‘inhealthy complexion’. So the wager was made for a hefty sum, but Mr Bullock demanded to have a few conditions put in place first. The Earl felt it fair to level the playing field, so he agreed to the bulky butcher’s request for a 35 metre head-start and also that he could choose the course for the race. Maybe because he was over-confident or simply because he hadn’t done his homework, but the Earl didn’t bat an eyelid when Mr Bullock asked for the race to be held in Black Lion Lane in Brighton. So what chance did the beefy butcher stand against the sporty Earl? Well, it seems Mr Bullock had a good brain in his head, as the course that the butcher chose had the distinction of being one of the narrowest roads in Britain, with some areas only being a metre wide. The head-start that he had secured himself meant that he was out in front and then, when the Earl caught up, he realised that the butcher’s girth would not allow him to pass in the alleyway. As a result, the Earl had to admit defeat as the butcher walked his way to victory and bagged the cash prize. It seems a fit mind can help to win races too!

9) A favourite children’s book by the world famous author, Dr Seuss (Theodor S. Geisel), was written because of a bet. After Dr Seuss had published The Cat in the Hat (which contained 225 unique words), his editor and the co-founder of Random House, Bennett Cerf, bet him that he couldn’t write a book that contained even fewer words. So in 1960 the bet was made for $50 that he couldn’t write a book with fifty or fewer distinct words. Dr Seuss produced the book Green Eggs and Ham, which contains exactly 50 unique words, which meant that he won the bet. Cerf never paid up, but as Green Eggs and Ham became Dr Seuss’s best-selling work, he made a pretty penny anyway!

8) Back in the early 1960s the famous bookies, William Hill, were taking bets on whether a human would set foot on the moon during that decade, with odds of 1000/1. So in 1964, David Threlfall from London, placed a bet of £10 that it would happen. At that time, £10 was about twice the average weekly wage, so it was quite a gamble. However, it paid off as he was able to collect winnings of £10,000 when Neil Armstrong took that small step and stood on the moon! Spokesman for William Hill, Graham Sharpe, said: “Plenty of other customers took advantage of what now seem almost literally lunar-tic odds. We paid out over £100,000 and were perhaps the only people not entirely delighted to see that particular feat of human exploration and ingenuity achieved.” Since the pictures emerged of Armstrong on the moon, there have been various conspiracy theories that have tried to refute that this event actually occurred. Never one to miss an opportunity to offer a unique bet, William Hill are now offering odds of 500/1 that the US Government will officially admit that the moon landing was faked!

7) Stu Unger, AKA ‘The Kid’, was perhaps one of the best Poker players in the world ever. He started very young, playing Gin Rummy, but he quickly discovered that he had a unique gift for both Blackjack and Poker. At just 27 years old, he won the World Series of Poker in 1980, then went on to win again in 1981 and finally in 1997. He was famous for his genius card-counting abilities, and in 1977, his talents were seriously put to the test by Las Vegas casino owner and poker player, Bob Stupak. Stupak challenged Unger to a wager that he thought was impossible, betting him $100,000 that he couldn’t count down three decks worth of a six deck shoe (a gaming device used in casinos to hold multiple decks of playing cards) from memory. The cards were dealt in a row and Unger got all of them right, not missing any of the 156 cards, thus winning him the ‘impossible’ bet!

6) Back in 1989, the year 2000 seemed like an age where we would all be riding in hover cars and eating space food. A man from Wales was convinced that certain things would remain the same though, so he took out a 5-fold accumulator wager at a local bookies, based upon what would happen in Y2K. At 8 to 1 odds, he bet that the ‘Home and Away’ would still be on the air; at 5 to 1 odds, he said that ‘Neighbours’ would still be showing, at 5 to 1 odds, he said that ‘EastEnders’ would still be on, at 4 to 1 odds, he wagered that Cliff Richard would get knighted, and at 3 to 1 odds, he thought that the band U2 would still perform together. In January 2000, he returned to the bookmakers to collect almost £200,000 after all those things came to pass. What a way to start the new millennium – that’s one New Year he’ll never forget!

5) Just how far would you go for a bet? Gambler Brian Zembic had taken part in a lot of crazy bets, such as, living in a friend’s bathroom for a month for $7,000, and sleeping under a bridge with $20,000 in cash strapped to his ankle for a week, but in 1997 Zembic proved that he would take things to the extreme to win a wager. He accepted a bet from a friend for $100,000 that he would not get breast implants and keep them for one year. He explained how the wager came about, saying, “It was about 1997-ish, I was in some restaurant in Europe and I was with two friends and his girlfriend at the time was flaunting her boobs and I said to my friend: ‘If I had boobs like hers I could get just as much attention as she would.” Desperate to prove his friend wrong and land himself a giant win, Brian opted to go under the knife and became the proud owner of 38C breasts. However, as implants are expensive, Zembic managed to secure himself a free operation through another bet. “I knew a plastic surgeon that was also a gambler in New York, so I went to his office and I said: ‘Can you put boobs in me?’ And all he said was: ‘This is for a bet, right?’ I played backgammon with him for an hour; I won $5,000. Boom, surgery was for free, and I woke up with boobs.” Zembic won the bet, but perhaps the weirdest thing of all is that he kept the boobs after the year was up as he had grown attached to them! Apparently it didn’t even hurt his chances with the ladies either, saying, “I guess the boobs really intrigue them.” It’s only nearly 20 years later, in 2016, that Brian has taken the decision to get the implants removed. He was scared about how he would look without them, saying, “When I take them out, they really are going to look like wet socks with nipples in them and that’s what I’m more afraid of.” He recently appeared on the reality TV series ‘Botched’, to see if the show’s LA-based surgeons, Dr. Terry Dubrow and Dr. Paul Nassif, could remove the boobs for him. Now a father to a teenage daughter, it seems that Brian might have participated in enough wild bets for one lifetime, saying, “The other day someone bet me that I wouldn’t cut off my own penis, but I’ve since decided I’m not going to do it. I’ve learned that money isn’t everything.”

4) 91-year-old Arthur King Robinson, a retired solicitor from Devon, placed a bet in 2005 that he would be dead by the end of the year. This rather morbid bet, made at bookmaker William Hill, cost Mr King Robinson £500 and gave him 6:1 odds. Not usually a betting man, he made the fatal flutter in an attempt to earn enough to cover the £3000 inheritance tax that his estate would have incurred, were he to have died by 6th December 2005. A William Hill spokesman said, “I thought I’d heard most things that people want to bet on after 30 years in the business, but one asking literally to place a dead cert was unique.” The bookmakers admitted that it was not the kind of bet they would normally take, but this was “one of those rare occasions.” “When Arthur contacted us and explained the circumstances surrounding his wager, we were so impressed at his ingenuity in solving his taxing problem that we decided to lay him the bet – after all, if he wins, it’s his funeral!” Fortunately the pensioner didn’t die, but he did lose his £500 bet. However, he still won out as he was able to dodge the inheritance by surviving the year as it was no longer applicable – so winners all round!

3) In 2007, Andrei Karpov from Murmansk, Russia, was playing a heated card game and when he ran out of money, he decided to put up the best collateral he could think of, his wife, Tatiana! Unfortunately Andrei lost to opponent Sergei Brodov. Tatiana was understandably furious about the wager and said, “It was humiliating and I was utterly ashamed. But as soon as my ex-husband did that, I knew I had to leave him.” Mr Karpov’s actions cost him very dear as Tatiana actually made good on the bet, left her husband, and rode off into the sunset with Sergei. Tatiana explained, “Sergey was a very handsome, charming man and I am very happy with him, even if he did ‘win’ me in a poker game.” Poor old Andrei ended up broke AND single!

2) Two-time World Series of Poker winner and Las Vegas resident, John Hennigan, made a bet with friends for $100,000 that he couldn’t leave the bright lights of Sin City to live in the sleepy town of Des Moines, Iowa, for six months. Being a regular high-roller in the casinos of Vegas, his pals knew that it would be a hard task for him, but they decided to test if his love of winning wagers was greater than his love for the Strip. Hennigan only lasted two days out in the Midwest before he backed out of the bet, missing out on a whopping $100k!

1) One of the craziest bets in recent times was made by 62-year-old Peter Edwards from Corwen, North Wales. As a proud grandfather to Harry Wilson, he saw something in the little lad that convinced him that one day he would be a football star. Even as a toddler, Harry was really keen on playing football and Mr Edwards said, “He used to chase the ball around the front room on his hands and knees even before he could walk, that’s what gave me the idea.” His idea was to place a £50 bet that the then-three-year-old Harry would one day play football for Wales. Bookies William Hill gave Mr Edwards odds of 2,500:1, but Peter felt confident that sometime in the future his flutter would pay off. Fast forward 13 years, when Harry was then a 16-year-old teenager, playing in Liverpool FC’s under-18s academy squad… In October 2013, the Wales National team played Belgium in a World Cup Qualifier. Late in the second half, in the 87th minute, 16-year-old Harry Wilson made his international debut, before the game ended as a 1-1 draw. Harry became a record-breaker that day, as he was the youngest person ever to have represented Wales in national play, at just 16 years and 207 days; snatching the title from football legend, Gareth Bale, who was 16 years and 315 days when he first played for the club. Harry’s achievements also meant that his grandfather’s belief in him paid off and Mr Edwards stunned the bookmakers by turning his £50 investment into a whopping £125,000! Peter said, “I retired immediately. I told my manager yesterday that if Harry plays I wouldn’t be coming back… This means I will be able to help Harry out. You can be quite sure that he will get a share of it… All he’s ever wanted to do was to play football — but the money means nothing to me. It’s the pride and enjoyment for Harry.” Peter’s wife, Dorothy, was also overjoyed at the outcome too, saying, “It was a historic moment and very a proud one for the whole family. We’re delighted for Harry and of course Peter’s bet makes it all the better – we had the champagne out last night. We all knew Harry would make it one day but no one expected it was going to be quite this soon. It’s great that he’s broken the record set by Gareth Bale – they are some really big boots to fill. He’s such a talented boy – he was kicking a football as soon as he was standing up. My husband always enjoyed a flutter on the horses and on the football and one day he just decided he was going to place the bet. It’s something which has really paid off now.” A spokesman for William Hill congratulated Mr Edwards on his win, saying, “Peter has been able to quit his job as a result of his amazing ability to spot fledgling talent earlier than almost anyone else we’ve ever taken a bet from.” We guess the moral of the story is, sometimes a leap of faith is totally worth it!