Top 10 Craziest Bets


From the outrageous to the hilarious and the downright unthinkable, there have been some crazy bets made over the years. We’re not just talking about backing a few dark horses, but everything from betting on your own life to changing your anatomy. Join us as we count down ten of the craziest bets ever placed.

10. Hold Me in Your Arms


Sometimes the craziness of a bet isn’t measured by the decisions of the outcomes, but by the randomness of it. Back in 1989, a Welshman (and evident visionary) took to the bookies for a 5-fold accumulator on things that would remain the same until the year 2000. His list? The soaps Home and Away, Neighbours and Eastenders would all still be on the air, Cliff Richard would be knighted, and the band U2 would still be together. These are quite bold claims given that there was a solid 11 years to go, but it is the seemingly arbitrary nature of the bet that makes it so amusing. Nonetheless, it turned out to be a solid $50 investment, returning a whopping $320,000 to start the new millennium in style.

9. All or Nothing


When you hear of people going all in, it usually means they’re putting in all the money they have on them. For Ashley Revell, the term was a bit more literal – he put every single item he ever owned on the line and span the roulette wheel in an attempt to double up, or potentially lose everything he ever had.

In a television programme made to follow his high-risk journey, Revell discussed his vision before going around and selling off everything he owned, eventually raising around $135,000. There was only one suitable location – Las Vegas – so he jetted off with the cash and took to Plaza Hotel & Casino to put it all on black. In a drastic change of heart, Revell switched his money to red at the last minute in what turned out to be the best decision he ever made. The ball landed on 7 red and Revell was left with $270,600. He tipped the dealer the additional $600 and with his newfound wealth he started his own online poker company.

8. Swimming in Money


When a man has swam across the English Channel, he has certainly earned the right to declare himself an excellent swimmer, but Matthew Webb learned the unfortunate lesson that this doesn’t make you invincible. In 1875 Webb became the first ever individual to successfully complete the feat of crossing the Channel, but the achievement went to the ex-Navy man’s head when he took on a $10,000 wager that he could swim straight across the volatile Whirlpool Rapids by Niagara Falls. It was a disastrous decision which everybody knew would end horribly, but you have to admire Webb’s confidence and resolve. We salute you, Captain.

7. What a Boob


You’ve probably already heard the well-publicised story of Brian Zembic but it’s so outlandish it deserves a mention. A fervent gambler, Zembic’s buddies challenged him to something particularly out of the ordinary that would make most men balk – for the fee of $100,000 he would have to have false breast implants for a full year. Zany Zembic accepted the unprecedented prop bet, and actually went through with it. It’s not the first time a recognisable face has got involved in a huge wager; boxer Floyd Mayweather reportedly gambled $10 million on the 2014 Super Bowl, so maybe these mad bets have something to do with being famous.

Although a crazy decision, it turned out to be a nice little earner for the Canadian. In addition to the 6-figure windfall from his friends, he became a bit of a celebrity and featured in the book ‘The Man with the $100,000 Breasts and Other Gambling Stories’. A lot of money, but still not the breast decision ever…

6. A Game of Two Halves


In the modern world of in-play betting, you can have a punt on just about anything in football (soccer). From the next goal scorer to the body part they use to knock it in, seemingly nothing is off limits. Scouser Adrian Howard took it to the next level, though, betting specifically on Xabi Alonso to score from his own half in the 2005/06 season. It is audacious to expect a goal from your own half, let alone to name the specific player to do it, and so the bookies happily took his $355 at odds of 125-1.

Miracles do happen. Against newly-promoted Championship side Luton Town, Alonso smacked a cheeky attempt from 70 yards out having spotted the keeper off his line. The ball flew in and Mr Howard picked up a spiffing $45,000. “I’ve never placed such a large bet before but I had a feeling about it” he said. Next time you have a feeling, let us know Adrian!

5. We Gonna Party Like It’s Your Birthday Suit


Check out any of rapper 50 Cent’s many CD album covers and you’ll no doubt find many of Eminem’s protégé baring his chest for all and sundry. Whilst it is fairly common for rappers to show off their abs, it is much rarer for them to venture into X-rated pictures, yet that is precisely what the G-Unit frontman risked when he gambled a picture of his manhood on the outcome of a football game.

In one of many crazy bets by Fiddy, the Shady Aftermath superstar found himself talking to somebody by the name of @mybestassets on social networking website Twitter. It was she who put the bet to Fiddy, tweeting “Lets bet. If the Giants lose the Superbowl, u must post ur d**k on the twitter. If they win, I’ll post my boobs & face. Bet?” Ferrari accepted but, when he won, @mybestassets quickly scarpered. We doubt he would’ve paid up, either.

4. The Mayweather Mystery


This one has been denied, so the man in question must be taken with a pinch of salt, but we still suspect there may be a hint of truth in it.

It was widely reported before, during and after Super Bowl XLVIII that Floyd Mayweather placed a wager of no less than $10.4 million dollars on the Denver Broncos to beat the Seattle Seahawks. As it turns out, the Seahawks slaughtered the Broncos 43-8 leading to a massive loss, if rumours are to be believed. Mayweather came out to deny the allegations and stated that if he was to bet it would more likely be the Seahawks that saw his money. However, he didn’t refute the claims until after the game was over, leaving many to speculate that this was simply a face-saving tactic.

3. Shocking Result


There’s nothing wrong with a bit of friendly banter with couples, but we sense this one got a bit out of hand. When the Green Bay Packers took on the Chicago Bears one couple made an audacious bet; the supporter of the losing team would be TASERED by the winner!

The pair had been drinking in a local bar when the boozy wager was placed. John Grant was supporting the Packers and his wife the Bears, with the former taking the win at 27-20. Apparently Mrs Grant assumed that her husband would never follow through with the actual taser, but he had other ideas.

After the game the two stepped outside into the alley and Mr Grant proceeded to zap his wife not once, not twice, but an astonishing three times. Mrs Grant decided things had gone far enough and promptly called the police to put an end to proceedings.

2. “House” Your Luck?


Football has a sense of tribalism which makes it easy for supporters to get carried away, as in the case of a couple of keen football fans in Uganda.

With Arsenal riding high at the summit of the Premier League and Manchester United undergoing an identity crisis under new manager David Moyes, Henry Dhabasani was pretty confident when the Gunners were due to face the Red Devils despite it taking place at Old Trafford. So much so, that he put his house on the line. Fellow Ugandan and die-hard Red Rashid Yiga took him up on the offer and, perhaps even more shockingly, staked both his wife and a Toyota car (clearly, his wife wasn’t enough…)

Ex-Arsenal legend Robin van Persie nodded home the only goal of the game for United to take all three points and leave Dhabasani cursing his luck as he packed up his things to make room for the Yigas – though we wouldn’t bet on the wife sticking around for much longer after that stunt.

1. Magnificent Seven


In what is now widely referred to as Frankie Dettori’s Magnificent Seven, the bookies endured an unprecedented upset with the pint-sized Italian winning all seven of his races at Ascot. For those who aren’t fans of the sport it may be difficult to comprehend the magnitude of achieving such a feat, but despite the fact that it was seemingly impossible it not only happened, but several shrewd punters got a piece of the action.

One such man took odds of 25,000/1 on Frankie winning all seven races and saw a return of half a million pounds. One poor lady bet 75 cents on each race netting $30 but didn’t think to back an accumulator of all seven – the latter would’ve seen her walk away with over $18,500.

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