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Capture The Flag: Bill Perkins

Hedge Fund Manager Discusses Prop Bet Gone Wrong For Poker Pro Antonio Esfandiari

by Brian Pempus |  Published: Mar 16, 2016


Hedge fund manager Bill Perkins has been cashing in high buy-in poker tournaments for a handful of years now, but the pressure he has put on some people in the form of prop bets has given the Texan a special place in poker. He once bet someone $500,000 that they wouldn’t get a tattoo of Perkins’ choosing on their back. Perkins lost that one.

The 47 year old had the money to spare, however. In addition to managing Houston-based energy hedge fund, Skylar Capital, Perkins is a film producer, helping make the movies After.Life (2009), Unthinkable (2010), and The Baytown Outlaws (2012). It’s been a diverse career for the man who studied electrical engineering at the University of Iowa.

When he’s away from business these days, Perkins plays in some of the richest private cash games in the country and also makes appearances at the World Series of Poker. His largest score was for $1.9 million at the final table of the 2013 WSOP $111,111 buy-in One Drop High Roller. Also at that final table was Antonio Esfandiari, who in January won a strange bet from Perkins that generated some controversy.

During the annual PokerStars Caribbean Adventure tournament stop in the Bahamas, the two men agreed on a bet that called for Esfandiari to lunge everywhere he went for two days. The bet was scheduled for the early stages of the PCA main event, one of the flagship poker tournaments of the year.

In an effort to win the bet, Esfandiari decided to urinate in a bottle underneath the poker table rather than lunge all the way to and from the bathroom. The move got him disqualified from the tournament and drew a lot of criticism from the poker community.

Card Player had the chance to talk to Perkins about the prop bet, as well as how his poker game has improved over the years. He’s still a recreational player, but he is always trying to improve, as he no longer wants to be the hyper-aggressive guy who plays like he just wants to gamble.

Brian Pempus: First off, can you talk about how your poker game has improved over the years?

Bill Perkins: I would have to say that, you know, taking it a little more seriously, being able to improve hand selection, understand table perceptions, awareness of what is going on at the table, and dialing down the, “Hey, let’s get lucky and have fun.” It has vastly improved my game over time. I am still able to enjoy the game and the social aspects of it, but I take it a little more seriously and take my strength, which I consider to be aggression, and use that in a style of play that works much better than before.

Pempus: Have you noticed some of your most frequent opponents changing the way they play against you?

Perkins: Yeah, you know, given that my hand selection has changed and I am able to come in with a wider range than they are, but not necessarily sending out these glaring signals that completely give away my hand. So, I think there is a little bit more of trepidation with calling light [against me] or just playing any two cards in position against me.

Pempus: I want to ask you about this really great hand you played last summer in the Super High Roller Cash Game. You picked off a $127,000 bluff on the river against Jean-Robert Bellande. You had a pair of aces with a very low kicker. ADiamond Suit 5Diamond Suit were your hole cards. Can you go through what you were thinking and tell me if that was one of the biggest bluffs you’ve ever picked off in a cash game?

Perkins: I’m trying to think. If it’s not the biggest, then it’s in the top five for me. As the hand was progressing, I felt like I had the best hand just based on how it was played preflop. I felt like if Bellande had a stronger hand, he would have represented it earlier. I didn’t understand his action on the flop. He was firing and I was in position on him. He kept firing, and he didn’t appear to be afraid of anything, which meant that he must be on a draw or not paying attention. Now Bellande is a pretty good player, right? He didn’t seem to be afraid, at all. The timing of his bets, the way he was putting them out there, I felt like he had the super nuts and I was dead, or he was on a draw and he may have got there [on the river].

Pempus: Yeah, the river card completed a flush draw on a board reading ASpade Suit 9Spade Suit 2Club Suit 4Diamond Suit 10Spade Suit.

Perkins: Yeah, I felt that…does he have a set? Was he afraid of a draw? The timing of his bet, the way he was punishing it, was too strong and not considering what I could have had. If he had A-K, it wasn’t like he had two pair. It felt like there was zero consideration for my hand, which felt like he was trying to get me off it. I don’t think I was a genius on this hand. It just felt awkward the way he was betting. I feel like Bellande is bluffing 33 percent of the time when he put me all-in, he had to (laughs). If he had a real hand and he was trying to get some money out of me, would he go after all of my chips? There were a lot of things that didn’t make sense to me. At the end of the day I was like, “F-ck it, I call.” I think I was getting myopic in my thought process and going that way. No new thought was coming into my mind other than “call,” so I did.

Pempus: Yeah, it was still a great call. I was wondering if that is another thing you’ve improved on over the course of your interest in poker, being able to break down situations where someone’s range is really polarized.

Perkins: Yes, especially in cash games. There are a lot of good starting hands, but even if you do have one it’s still hard to make a pair. It’s not easy to get the nuts. Understanding what players would be afraid of in the hand and their betting patterns can give you information. I am not the best at this, but I have been in situations where calling with third pair or no pair when I think it’s the best hand is a good spot. It’s not like I am 100 percent right, but that is now a part of my game. There wasn’t enough of this [kind of thinking] before.

Pempus: Hearing you break down a hand, obviously poker is a game of skill. Do you think business schools in the U.S. should offer some courses in poker and its parallels to the business world? I know some places already do, but do you think more should consider poker as a learning tool?

Perkins: I think it is an excellent learning tool, especially the deeper thinking of what people have. You’re in an asymmetric information negotiation session, right? And people are fighting over a pot, so there is a lot to be learned here. I am sure game theory classes have this. Understanding people’s risk tolerance, what are their tendencies, I think all these things could help.

Pempus: I want to ask you about prop bets. I know you have a lot of fun with those. Could you talk about your recent lunging bet with Antonio Esfandiari that went a little bit awry for him?

Perkins: To play poker and walking lunge from the tower [where he was staying] was almost a physical impossibility. I actually gave him a break and said his knee could touch the ground, but actually your knee shouldn’t. Technical details aside, any step he had to take had to be a lunge, for two days. One day he just stayed in his room (laughs). I actually gave him a bus pass to go to where the tournament was, but there was still a very long hallway, at least 100 yards, over 300 lunges I would say. Antonio being Antonio, he had to win the bet at all costs. He had a plan for everything in order to win the bet.

I knew from going to the gym and doing lunges, once you sit down and then you have to lunge to and from the bathroom during breaks, it would interfere with his [PCA] main event. He had a plan for that. He had towels and a water bottle for him to relieve himself without having to get out of his chair. It was pretty much impossible for him to play the tournament and lunge back and forth to the bathroom, and lunging in the bathroom would have been a disaster. So, I think Antonio got a little myopic and didn’t look at the big picture of what was going on here and what he would have to do to win the bet. I didn’t think he would do that. I thought he would just lose the bet. But he tried to win and play poker at the same time. I think the tournament staff did exactly what they should have done, which was boot him out. They showed mercy on him, and I think he deserves a pass. He apologized, he immediately realized that he had made a mistake. His ego in wanting to win the bet got in the way and he admitted it. He donated the proceeds to charity. There was some chatter about did he really send it, but I sent the money directly to the charities he chose, so he definitely paid. In the end, I don’t think he was classy in his actions to win the bet, but I think he had humility in his willingness to admit a mistake. I was very proud of him in the end.

Pempus: Would you say this was one of your better prop bets in terms of you having a big edge? It seems like you had him drawing dead because you knew much better than he did how hard lunging is.

Perkins: Yeah, I think this is up there with the “no sex of any kind” for one year bet, which [Antonio] bought out of two weeks later (laughs). I think he lasted nine days. This was full entertainment value, and I thought he would have had to go through extraordinary measures to win. I think other people would have given up. What was more important? Playing poker or winning this bet? I thought I had a massive edge. He got a little short-sighted. I think he wishes he never had made that bet. I think if he had to do it all over again he would have paid the bet or negotiated out of it. Yeah, it was probably the best edge for me other than the sex bet. Antonio was getting engaged that year, so I knew he had no shot (laughs).

Pempus: We talked about your poker game getting better every year, but would you say your ability to make your friends sweat in prop bets is also improving?

Perkins: Yeah, I try to think of ones that are possible. Ones that are impossible are no fun because you want to see an attempt, but you want ones where you can get an edge. The bets that you can accomplish only by doing ridiculous things can be fun. I would say that in one out of every four prop bets, a charity is involved. There is a good cause attached to 25 percent of our ridiculousness.

Pempus: After the lunging bet, did Antonio say he was going to sit out from prop bets with you for awhile?

Perkins: (Laughs). No, he didn’t, but he should. We always want to punish each other. ♠