Poker, amazingly enough, can get boring from time to time, especially during tournament play. This means it is fertile ground for some crazy proposition bets and during the televised poker boom, there were plenty of cameras around to capture the action. But crazy prop bets have been going on far longer than that. It’s rumoured that Winston Churchill once offered Lloyd George a bet for the Prime Minister’s job during a round of golf (Churchill lost). So here’s a look at five of the maddest proposition bets ever made.
Gary McCord Pelican Shot
We start outside the world of poker, and instead go with golf. Tin Cup is hands-down the best golf movie ever made. It also has the incredibly useful distinction of being one of very few films that illustrate both kinds of prop bet. The first, the rigged bet, occurs in the scene where McAvoy (Kevin Costner) challenges Simms (Don Johnson) to see who can hit the ball furthest with a 7-Iron. The second bet takes place in a crowded bar after a day at the US Open, and this time, Simms bets McAvoy that he can’t hit the ball out the bar, over a lake and into a post with sufficient force that the pelican sitting atop it flies off.
This is based on a real event that took place in Pensacola, Florida, when Gary McCord and several other players were bored during a rain delay. “There was nothing to do but gamble,” McCord complained. The others bet McCord that he couldn’t hit a ball out of their apartment, over the lake and scare off the pelican, but he did, and he still claims it as the best shot he ever played. McCord, who was hired as an advisor for Tin Cup, plays himself in the film, and you can see him in that scene annoying Kevin Costner’s character by narrating the shot into a soda pump as if on live TV.
Amarillo Slim Goes to Jail
Amarillo Slim was probably the greatest proposition bettor of all time. Tin Cup borrows two of his exploits for their film. The first is winning a game of golf using everyday garden tools – which Slim did against Evel Knievel. Hitting a ball the furthest with a 7-Iron is also based on one of Slim’s bets, but when the skinny Texan did it, the bet was to drive a ball further than a mile. To win the astonishing sum of $1 million, Slim drove out to a frozen lake and walloped the ball with a hammer.
One of Slim’s most audacious bets involved a gangster. This gangster had been caught speeding, and he and his goons thrown in the local jail. The local sheriff was a friend of Slim’s and gave him a call, telling him what had happened. Most people might want to steer clear of a situation like this, but Slim was not most people. He raced down to the jail and begged to be locked up with them. With nothing better to do, they spent the night making prop bets, one of which included a fly. Each of the five men had a sugar cube on them, and they bet $50,000 on which cube the fly would land on first. Slim, being a canny old soul, had moistened his sugar cube with a licked finger and the fly came straight to him.
Mad Mickelson
One of the biggest prop bets in history is probably taking place right now. Phil Mickelson is playing Tiger Woods in Las Vegas for $9 million this weekend. This is not part of a tournament but is for charity – although the charity aspect is probably being used as an excuse to televise this audacious game. The side bets will be part of the televised show, and things have already started, with Mickelson claiming he’ll birdie the first hole for $200,000.
It’s no secret that Phil Mickelson will gamble on just about anything, and also made a cameo in Tin Cup. Of course, any break in filming is an opportunity to part a sucker from their money, and Mickelson is always game for that. He was bet that he couldn’t put his shoulder against a tree (which was a tall pine), drop a ball and then hit the ball over the tree. When the pot had reached $1,200, Mickelson took his shot. While the ball was still in the air, he leaned down, picked up his winnings and walked off. Here’s hoping he comes off looking that cool this weekend.
$1,000 worth of Maccy Ds
We move from no meat to, well, quite a lot of meat. In May 2017, poker pro Mike Noori was bet $200,000 at 5/1 odds that he couldn’t eat $1,000 worth of McDonald’s food in 36 hours. There were additional stipulations: he could not spend more than $200 on salads, he had to eat at least $50 in burgers and a minimum of $300 in hot food. The difficulty with this bet – aside from the fact that he would be eating a lot of horrible fast food in a very short space of time – was that while not exactly being at the top of the list of most nutritious meals, McDonald’s food is incredibly cheap. For example, if this lunatic’s account is to be believed, buying the entire McDonald’s menu of 42 different sandwiches and burgers only costs $141.33.
Noori, it turns out had a plan. It’s just that it wasn’t a very good one. He spent his first $95 on huge amounts of guacamole and apple pie. The guacamole would be distributed throughout other meals, while the pie would be mashed into one meal (but not blended, that would be against the rules). Evidently, even this was too much for Noori’s stomach to handle, because he ducked out of the bet having only gotten a tenth of the way. At least he managed to raise $14,000 for charity.
Brian Zembic Goes Bust
Brian Zembic is a gambler, magician and professional blackjack and backgammon player. He is also no stranger to a prop bet. He once spent the night under New York’s 59th Street Bridge sleeping amongst vagrants with $150,000 in cash strapped to his leg. He has lived out of a bathroom for a week. But the stupidest bet he’s ever taken (his words) took place in 1996 when a friend bet him $100,000 that he wouldn’t get breast implants and keep them in for a year. Zembic’s response? Hold my beer…
Sure enough, Zembic went through with it and became the proud owner of a pair of 38Cs. His friend wasn’t unhappy with the result, claiming that it was worth every penny just for the laugh. But the curious thing is that all this happened 22 years ago… but Zembic still has his fake boobs. It doesn’t hurt that he gets $10,000 for each additional year he keeps them, but Brian claims he’s got used to them.