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5 Crazy Bets You Won’t Believe People Made

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5 Crazy Bets You Won’t Believe People Made


The world of gambling sometimes seems wider than the world at large. Everywhere you look there are opportunities to wager. Sports. Horses. Dogs. Slot machines. Table games. Poker. And those are just the legal games of chance that any Tom, Dick, and Harry can indulge in when they have a little extra money in their pocket and wish they didn’t. If you look to the illegal gambling options, there’s a whole new universe of exciting and usually horribly cruel ways to double or triple or lose your money.

Take Cockfighting, dog fighting, and all manner of other underground games that would be illegal in a casino. It seems the law is a capricious master, because in the same states where it is illegal to sit down at a poker table, it is completely legal to bet on the seemingly arbitrary outcome of a horse race. But that is neither here nor there – the wagers that I detail in this list are the sort undertaken by the gambler who doesn’t get a rise out of betting tens of thousands of dollars anymore. For them, taking a 75% chance to double $50,000 is routine. They need more sauce on their gamble-steak.

The world of gambling indeed seems limitless, as are the things hardcore gamblers are willing to bet on. The father of the science of criminal profiling was originally tasked with investigating illegal gambling.

He tells the story of a gambler he’d arrested several times. It was raining and the criminal was sitting in the back of the squad car, cuffed, ready to be taken away. The officer asked the criminal, why did he keep doing it? Why, after getting in so much trouble, didn’t he just give it up? The criminal replied that the cop didn’t get it and never would. You pick one of these rain drops and I’ll pick another and we’ll bet on which one reaches the bottom of the window first.

The five points on this list are some of the biggest and weirdest gambles that anyone has ever taken and, surprise surprise, most of them were perpetrated by professional gamblers. Read on, and be amazed.

Ivey And Negreanu vs. Everyone

Phil Ivey should be a familiar name to anyone interested in the world of gambling. Considered by some to be the world’s best poker player, Ivey’s gotten himself into all sorts of wagering-related shenanigans. Not content with poker, he plays baccarat. Not content with baccarat, he tosses dice. Not content with dice, he makes prop bets. Once, he famously flipped coins with another poker player for $10,000 a toss. Not really a gamble as, statistically, it was very likely the two would end up even in the end. But right now Ivey and fellow poker legend Daniel Negreanu are betting all takers that one of the two of them will end up in the first place at the world series of poker this summer.

It was Negreanu, a player with a voodoo-like ability to read people’s hands, who announced the bet with his tweet. If you want in on the action, it’s an even money bet with the minimum wager being $5,000 and the maximum being $1,000,000. If one of them wins a bracelet, you lose. Otherwise, you collect. If you want in, email pattylandis@hotmail.com, but don’t be surprised if you lose that money. Ivey and Negreanu are two of the best and most experienced players in the game.

A prop bet that you will win or lose in a tournament is not uncommon, but challenging the world? It takes serious cajones to risk that much cash.

Grey Vs. Lederer And The $10,000 Hamburger

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Here’s a more playful bet, and one that I would not have made. No matter who you are, everyone loves a good burger. And this bet proves that even vegetarians can’t resist the lure of burnt cow carcass. Howard Lederer, poker pro, is a vegetarian. David Grey, poker pro, likes to give people shit. So he bet Howard that he couldn’t eat an entire hamburger. The bet was $10,000.

David Grey ought to have realized that no true vegetarian could refuse all that lettuce and down went the burger, and up went Howard’s bankroll. Later on, Lederer offered Grey the chance to win back his money. He bet Grey that he couldn’t eat some olives. Grey refused the offer.

Just goes to show you, Grey didn’t care about winning the wager… he wanted to make a vegetarian eat meat. Evil masterminds, those poker players.

Man On The Moon? I’ll Give You 1,000:1

Moon-Landing

Ever have faith in the promise of a US President? One enterprising Brit, David Threlfall, believed in JFK’s promise that he would land a man on the moon. He wrote to William Hill, a famous bookmaker, that he would like to bet a man would be on the moon before the first of January, 1970. The bookie gave him 1,000:1 odds on his ten pounds bet and the wait was on, and it wasn’t a long one.

David made his wager in 1964. In the course of the next five years, it became obvious that either the USA or the USSR was going to get a man on the moon or bankrupt themselves trying, and people starting popping out of the woodwork to buy David’s wager off of him at a discount in the hopes of cashing in. It was to no avail. David has faith in JFK’s 1963 speech and stood firm on his bet.

In 1969 Neil Armstrong took one small step for man, and one big step for David Threlfall’s wallet. David was handed a check on the spot, bought a sports car and lived happily ever until he died in a crash.

The Bathroom Bedding Bet

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Ever been on vacation and thought to yourself, man, I wish I could stay here forever? Well some young poker players felt that way and were discussing how they believed they could stay on the Bellagio premises for an entire month. And so one poker player, Andrew Robl, bet another, Jay Kwik, that he couldn’t spend that month in his room. In the bathroom. Without leaving. For 30 days.

Evidently Andrew hadn’t counted on Jay being a veteran of several high security prisons’ solitary confinement cells (maybe). Kwik set himself up with a twelfth television set, called room service every day and made good on the wager. Or he would have if Robl had let him.

Andrew Robl was worried enough that Jay would win that he bought him out of the bet early. Supposedly Kwik was given $40,000 for his effort. Not a bad ransom to get out of the tub.

30. Quails In 30 Days

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Put this one under #richpeopleproblems. If you haven’t heard of Phil Ivey, maybe you have heard of Doyle Brunson, probably the most famous professional poker player of all time, and the winner of the first two World Series of Poker tournaments. Needless to say, Grampa Poker has tons of cash and the willingness to bet it. But it was before he was a legend that Doyle says he was offered $20,000 to eat a quail a day for thirty days. If he failed, he paid.

The stipulations were that it must be a freshly killed game bird, and the meat ended up being too gamey for the soon-to-be famous Texas Dolly. He gave up after 17 days, saying, “The quail looked liked the size of a turkey,” by then.

It turns out that this quail a day bet is actually kind of popular and inspired by the bible! In Numbers 11, god punishes the picky Israelites for complaining about the monotony of mana by raining quail down upon them and nothing else. Well the good lord is obviously not an American because several of us hardy folk have taken the quail challenge… and won!

The trick seems to be to get the frozen variety, and not chow down on the spicier wild game. Now go make some money!

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