People have made proposition bets, or prop bets, since the year dot. Humans have placed wagers on each other since they could first communicate. These bets are made for entertainment purposes, although some of them can grow quite large. Poker players are natural gamblers, so it makes perfect sense that poker players have made some of the craziest and most iconic prop bets of all time.

Amarillo Slim was a top-level poker player but is arguably better known for his love of prop bets. Amarillo Slim won four World Series of Poker bracelets during his career, but his famous prop bets put his name into the minds of the non-poker-playing public.

Amarillo Slim was a very intelligent man, especially when it came to making bets. Whereas some people would simply get their hands on the best online sports betting bonuses and take a punt on a team or sporting event, Amarillo Slim put a great deal of thought into the prop bets he made with friends and anyone who was prepared to put their money where their mouths were.

Racing a Horse!

For example, legend has it that Amarillo Slim claimed he could outrun the champion racehorse Seabiscuit over 100 yards if he could choose the track. Obviously, Amarillo Slim had a long line of people queuing up to bet against him, but they were left with egg on their faces when he selected a 50-yard course. In the time it took the jockey to slow the horse and turn it around, Amarillo Slim had sprinted to an impressive victory.

Amarillo Slim’s table tennis bets are what he is best known for outside of poker. He bet Bobby Riggs, a renowned tennis champion, that he could beat him at ping-pong if he could choose the bats. Several months later, Amarillo Slim took on Riggs in a game of table tennis where the duo used iron skillets to play! Amazingly, Amarillo Slim repeated the hustle against a Taiwanese ping-pong champion using Coca-Cola bottles.

Other Impressive Prop Bets

Amarillo Slim’s fellow poker player, Titanic Thompson, who hosted the first-ever World Series of Poker, was another prop bettor who always had an angle. He once bet he could throw a walnut over a building but failed to disclose that he had weighted the walnut with lead. Thompson bet he could drive a golf ball 500 yards using a hickory-shafted club. At the time, golf pros could only drive 200 yards, so Thompson had plenty of takers for his seemingly impossible bet. Thompson won the bet because he waited until the winter months, headed to a frozen lake, and hit the ball across it. The ball bounced and rolled along the ice before resting more than 500 yards away!

A little more recently, in 2011, high-stakes poker pro Ashton Griffin accepted a prop bet that tested his physical endurance. Some of his friends clubbed together and bet $300,000 that Ashton could not complete 70 miles on a treadmill in 24 hours. Then 22 years old, Griffin went out partying the night before embarking on the challenge, but it did not hinder him because he completed 70 miles with 45 minutes to spare.

Another physical challenge happened in 2016 and involved the social media star and self-proclaimed playboy Dan Bilzerian. Hedge fund manager Bill Perkins bet $600,000 that Bilzerian could not cycle from Los Angeles to Las Vegas, a 300-mile journey in 48 hours. Bilzerian had not been on a bicycle for many years, so he spent more than $150,000 preparing for the challenge, including convincing now-disgraced cyclist Lance Armstrong to train him. Amazingly, Bilzerian completed the epic ride with 15 hours to spare.