The Craziest Wagers the World Has Ever Known

Date Created: Apr 17
Written by Jerico

Human beings have always been drawn to gambling. Even in ancient history, we are sure to find stories of people betting on a wide variety of things. Although some people may say gambling is a complete waste of time and money, many people engage in it surely for entertainment and relaxation, while others are serious gamblers looking to win big every time they make a wager.

Most of those who gamble, whether casually or for high stakes, in land based casinos or on online casino games, make sensible wagers. They consider all the odds and try to visualize the outcome of every possible wager before they part with any of their money. Additionally, most sensible gamblers don’t spend too much money on a single wager, nor do they bet on seemingly impossible odds because gambling may be risky business, but it usually involves making educated guesses.

Once in a while, though, people make bets that leave most of us shaking our heads in bewilderment. These are the kinds of bets that don’t seem to make any kind of sense, no matter how long we think about it, or from how many angles we try to view the odds.

But, believe it or not, these bets do happen from time to time. Here are a few examples:

Crazy Bets People Won

Making unbelievably outrageous bets would be worth it if you actually won. Then people might not think you were so crazy, after all. Here are some of the world’s most outrageous bets that people actually won:

1. Brian Zembic’s Breast Implants

Brian Zembic was a known gambler and magician, and those who knew him knew that he loved taking on outrageous bets. But perhaps the most outrageous bet he has ever made was the one in 1997 when, at a restaurant in Europe, the girlfriend of one of his friends flaunted her boobs. Zembic casually said he would probably get as much attention as she’s getting if he had boobs like hers.

Upon hearing this claim, and knowing how much Zembic loved bets, one of his friends then asked if he would be willing to actually get a boob job done for a certain amount of money. He agreed to do it--and keep the boobs for at least a year--for $100,000. Being the notorious gambler that he is, he not only won that bet, he even got the surgery for free!

Zembic went to a New York plastic surgeon who was also a known gambler and told him about the breast implant bet. They played backgammon, where Zembic won $5,000, thereby getting the surgery for free. He ended up learning to appreciate his new boobs and kept them not for the one year that was originally agreed upon, but for almost 20 years!

2. Welsh Gambler’s Prediction

Back in December 1989, a Welsh gambler made what at that time seemed like outrageous predictions. It was at the Ladbrokes betting shop in London where the gambler predicted that in the year 2000, Bono and his band, U2, would still be going strong. He also said that in that same year, the soap operas Home and Away, Eastenders, and Neighbours will still be on the air. Finally, he predicted that Cliff Richard will be knighted before the end of the millennium.

The year 2000 came and those who took the bet were astonished to realize that all of those predictions had come into fruition. The Welsh gambler may have had to wait a little bit more than a decade to claim his winnings, but $320,000 is certainly nothing to complain about.

3. Green Eggs and Ham

Almost everyone has heard of Dr. Seuss and his popular book, Green Eggs and Ham. What a lot of people may not know is that the book was the result of a bet. In 1960, Random House co-founder Bennett Cerf bet Dr. Seuss (legal name: Theodore Geisel) that he couldn’t write a book using only 50 distinct words or fewer. Dr. Seuss took him on and the rest, as they say, is history.

The bet was only for $50, but that was a considerable amount at the time, equivalent to about $382 today. Geisel came up with Green Eggs and Ham, which contains exactly 50 distinct words. The bad news was that Cerf never held up his end of the bargain, as he did not pay the agreed on $50. Considering how popular the book became and how much he earned from it, though, it’s safe to say Geisel has forgiven Cerf for not paying up.

4. Betting It All

Are you willing to wager everything you own in a game of roulette? Apparently, English gambler Ashley Revell was. In the year 2004, Revell sold everything he owned, including his clothes. He then wagered $135,300 on one roulette spin at the Plaza Hotel & Casino in Las Vegas. If there ever was a make or break bet, this sure was one.

Fortunately for Revell, that wasn’t a night when he would lose everything he had. The roulette ball landed on 7 red, doubling Revell’s money. With the $270,600, he went on to set up his own online poker company. The company may have gone out of business in 2012, but Revell has since multiplied the original amount he wagered. That bet even became so famous that it inspired Simon Cowell to set up the game show "Red or Black?".

5. Betting on a Goal

People bet on sports outcomes all the time, but it isn’t all the time someone bets on a specific outcome from a particular player. That is exactly what Adrian Howard did when he bet $355, predicting that Xabi Alonso will score from his own half in one of the games during the 2005/06 soccer season. It’s crazy enough to expect anyone to score a goal from his own half of the field, but crazier still to name the specific player to do it.

Because of the total outrageousness of his prediction, bookies were more than happy to take Howard on. The odds for the bet was 125-1. Then Lady Luck smiled on Howard during a game against Luton Town. Alonso saw that the Luton Town keeper was off his line, so he sent the ball flying into the goal from 70 yards out, and Howard went home $45,000 richer.

Crazy Bets People Lost

Not all outrageous bets have happy endings, which is quite understandable, expected even. Considering that the odds are out of this world, one can’t really expect every single person who makes crazy bets to end up on the winning end. Here are a few wagers that people most likely regretted ever making:

1. Betting Against Yao Ming

It’s difficult to understand how this bet could ever have made sense to him, but when NBA star Yao Ming signed with the Houston Rockets, Charles Barkley bet against Yao scoring more than 19 points in one game. The wager was made after TNT’s Kenny Smith predicted that Yao would do just that. Barkley disagreed with Smith’s prediction, and the bet was on!

What made this wager so much fun for those who witnessed it is that there was no money involved. Rather, the bet was for the loser to kiss the winner’s behind.

So, when Yao Ming scored 20 points against the L.A. Lakers, did Charles Barkley end up kissing Smith’s derriere? Well, almost. Smith must have taken pity on him; he had Barkley kissing a donkey’s backside, instead.

2. Homeless

If you’re being sensible, you probably won’t bet your house on anything, unless you have more than one, that is. So a Ugandan man named Henry Dhabasani probably wasn’t thinking clearly when he wagered his house away. He was so sure Arsenal would beat Manchester United when Manchester was obviously struggling under the leadership of David Moyes that he made a bet with his neighbor.

Dhabasani ended up getting evicted from his own house when Van Persie scored the game’s only goal, getting Manchester the win. Now here’s something even crazier than Dhabasani betting his house: His neighbor bet not only his house, but also his car and wife! But, then, he ended up winning, so perhaps HE wasn’t so crazy, after all.

3. Squandering a Student Loan

Besides your house, one thing that may not be a good idea to wager would be a loan that’s supposed to help you achieve your dreams. Other than the fact that you definitely will have to pay the loan, regardless of how you used the money, there’s also the fact that your future most likely hinges on you having that money.

A student learned the hard way that it’s a bad idea to bet student loan funding on anything. The student was so sure Angola was going to win the African Cup of Nations that he put all 4,400 British pounds of his funding on a bet. Seeing that the score was 4-0 in favor of Angola, with 11 minutes remaining, it did seem like a safe bet. But sometimes, things just don’t go your way. Mali made an unbelievable comeback within those 11 minutes, and the student lost his student loan funds.

4. Tasered

What happens when a couple backs opposing sporting teams? You can expect an argument to ensue, right? And maybe making bets isn’t even such a crazy idea. At least, not if it’s all for fun and the bets are reasonable. But, what if the bets are taken way too far? That’s exactly what happened with Nicole and John Grant.

Nicole is a die-hard Green Bay Packers fan whereas her husband John roots for the Chicago Bears. There wouldn’t have been a problem with the two of them being loyal to these opposing teams, if the bets hadn’t gotten out of control. They made a bet where the loser gets tasered.

Well, the Chicago Bears won, and Nicole probably ended up being endlessly teased about her loss, but surely her husband didn’t really taser her, right? Wrong. He not only tasered her as a consequence, but he actually did it THREE TIMES. She called the police and got him arrested. Maybe we shouldn’t take our sports too seriously, eh?

5. Challenging the Niagara

Michael Webb made history in 1875 when he became the first man to successfully swim across the English Channel. The sad thing is that the feat that made him impressive also proved to be his downfall. He became so caught up in his success and so impressed with his own abilities that he decided to bring it to the next level. He decided to challenge the Niagara.

To be specific, Webb took a $10,000 bet that he can successfully swim across the Whirlpool Rapids at the Niagara Falls. Countless supporters crowded around the area on the scheduled day to bear witness to Webb defying the odds once again. But the rapids will not be defied. Webb started out strong, but it did not take long for the rapids to drag him under. His body was recovered four days later.

As most professional gamblers know, higher stakes usually deliver more life-changing results. This may be why people who gamble not just for fun, but for the winnings, tend to put up bigger wagers than casual gamblers. And high stakes gamblers are usually the ones who go home with the biggest payouts.

However, it is also important to bear in mind that when you gamble in the high stakes, the life-changing results can go either way. So, regardless of how high the stakes are, and no matter what you are willing to risk, you have to make sure you’re still making level-headed decisions. This isn’t to say you shouldn’t bet huge amounts or your precious possessions on anything, simply that you should only do so when you have a realistic chance of winning.

Be careful not to let emotion get in the way of good judgement, as in the case of Michael Webb. Remember, the most successful high stakes gamblers, whether they do these wagers in casino games online or in other ways, aren’t those who bet the highest amounts, but those who make the most well thought-out and educated guesses.