Prop Bet Evolution

Say what you will about him as a person, and there are plenty of bad things to mention, but Thomas “Amarillo Slim” Preston was a great story teller, and probably an all-time prop bettor. He was certainly the most famous gambler in the world all the way up until 2003 when Chris Moneymaker won the World Series of Poker main event.
He was famous for all kinds of things, including being a regular guest on The Tonight Show with Johnny Carson. I was at the front of the line to read his book Amarillo Slim in a World Full of Fat People in which he details many of his famous prop bets.

He beat a pool hustler in a game of pool with a broomstick, won a game of ping pong against a world champion with a frying pan for a paddle and then with a coke bottle for a paddle, and many other legendary bets. People have kept up his tradition of being savvy prop bettors over the years. I remember a poker player booking a prop bet that he could live in a Bellagio hotel bathroom for 30 days, Bill Perkins betting Antonio Esfandiari that he couldn’t get around the Atlantis resort for his trip only by doing lunges, and Bill Perkins again betting Dan Bilzerian he couldn’t ride a bike from Las Vegas to Los Angeles in 48 hours. Bill Perkins has said about those bets that he didn’t mind losing the money as long as it caused his opponents plenty of pain. Now, Perkins is using his money, and that pain to make people’s lives better and he’s helping prop betting evolve in the meantime.

In March of 2017, Bill and some other poker streamers were on a boat playing poker and someone in the stream’s chat room asked about the Staples brothers’ weight. Jaime Staples weighed 305 pounds at the time and his brother Matt weighed 134. He laid them 50-1 odds that they couldn’t weigh the same amount by the end of the year and they snapped up the bet for a total of $3,000.

Then, a couple of weeks later, Perkins was on the 2+2 PokerCast talking to Adam Schwartz and Terrence Chan. Naturally, the subject of prop bets came up and Adam jokingly asked how much he would bet on Adam making it to 150 pounds by the end of the year, being at almost 230 at the time. Perkins offered him a five-figure freeroll and it was off to the calorie races for Schwartz.

In the course of that conversation, Perkins made some interesting points about why he has decided to make these bets and freerolls over time. First of all, he sees money as a resource to create the only real thing he cares about in life, fun. Sure, he works hard, but he likes to use the money he makes from that to facilitate fun in many forms. He finds it fun to make these bets, so he does it. Secondly, he realizes that at the same time he can have some fun making these bets, he can help someone else greatly improve their life. As Staples said in an interview not long after they made their bet, “For me there’s no downside. If I fail, then I lost $3,000, I’m embarrassed and the poker world can laugh at me. But say I lose like 90 lbs and Matt gains 20 lbs then we fall short of the goal, that’s not a loss. I’ll be in much better shape and it only cost me $3,000.”

Both prop bets are close to coming due and will be right down to the wire it looks like. Schwartz has come down to around 170 pounds as of this writing and has two full months to lose 20 more pounds and keep it off. In a nice stipulation to the freeroll, Perkins is requiring Schwartz to weigh in weekly over the next two months of the year at 150. The last public update from the Staples brothers I was able to find was at the end of August when they were within about 80 pounds of each other. Since then, Jamie seems to have slimmed down even more and is looking good.

One of my favorite things about being around professional poker players is that when someone says something outlandish in a group, they will be forced to back up that statement with hard earned cash or quit talking nonsense. Adam Schwartz was a little peeved at himself for asking about getting to 150 pounds by the end of the year, but he’s since admitted to his life being much better since taking on the challenge. Prop betting has evolved from an opportunity to take advantage of suckers, to a way to cause pain for your opponents, to a way to improve your friends’ lives and Bill Perkins is at the forefront of that evolution in recent years. ♠

Gavin Griffin was the first poker player to capture a World Series of Poker, European Poker Tour and World Poker Tour title and has amassed nearly $5 million in lifetime tournament winnings. Griffin is sponsored by HeroPoker.com. You can follow him on Twitter @NHGG