Pilgrim’s Progress Dwyte Pilgrim Rises From Unknown to WSOP Circuit King to Player of the Year Contender in Two Years

Some top poker professionals achieve success so quickly via one big win that they appear to have come out of nowhere, and we wait for them to validate that initial victory with additional strong performances. Thanks to the increased media attention that poker has received since 2003, we have been able to watch some players enter the spotlight. Few players have done so more dramatically than Dwyte Pilgrim.
In the last two years, he has built his poker career piece by piece on the tournament circuit. Since January 2008, Pilgrim has scored 40 live-tournament cashes, made 20 final tables, won eight tournaments (including two World Series of Poker Circuit gold rings and one World Poker Tour title), and racked up $1.5 million in tournament earnings. He was a major contender in the Card Player Player of the Year (POY) race throughout 2010, either leading it or residing in the top 10 for 12 months.
During his successful run, Pilgrim has developed a cult following within the poker community, with many players counting themselves amongst his fans. He has developed an alter ego thanks to his confident personality and a string of catchphrases that hint at a poker Muhammad Ali. This persona stays hidden most of the time, but when the bright lights of a final table and the accompanying television cameras are on, so is the behavior that makes Pilgrim unique. He doesn’t scream, “Float like a butterfly, sting like a bee,” but he will be the first to let you know that he is about to “shock the world,” as he put it when he won the WPT Borgata Poker Open in September. It was his biggest win to date, and it came in the largest WPT event of all time (1,042 players).
Card Player recently sat down with Pilgrim for a lengthy conversation that served as a retrospective view of his last two years. He loves talking poker and reflecting, and making predictions on his new career.
Leaving the Real World Behind
Ryan Lucchesi: What were you doing before you started playing poker?
Dwyte Pilgrim: Before poker, I was a loan officer in Long Island. Before I became a live poker player, I was an online junkie. I played tournaments and sit-and-gos, but for low stakes. I was just learning the game, and then started playing with friends in a couple of home games in Brooklyn. Then, I started playing with some of the executives at First Republic [the bank company where he worked]. I realized that I could beat the game.
I started to live in the Taj Mahal in 2007. I used to play there every day and grind it out. That was definitely my first major live experience. We were a bunch of guys who were really going out there and trying to make a living. There was no more joking around; you had to go out there and grind it out. The overhead is really high when you are staying at the casino. I lived there six days a week for roughly 10-12 months, and then I moved to Harrah’s when the [World Series of Poker] Circuit event came to town in December 2008.
In my first 10 tournaments in December at that series, I cashed in four of them. I took seventh place in both a $2,000 event and a $5,000 event, so they were big events. After that, I took a little time off from December until March, because I wasn’t really a tournament grinder yet. In March, the Circuit came back, so I went back to Atlantic City, but I still wasn’t a guy who was traveling the tournament circuit. I was basically waiting for them to come to me. I played my next 10 tournaments at the Circuit at Caesars. I was up and down, and cashed once, but won my first gold ring.
RL: How much anxiety did you feel upon leaving your job to play poker full time?
DP: I had a really cool boss. He told me that if I thought I could do it, to start slowly but surely, so I started by going on weekends when I had some time off to see if I had what it took. It got to a point that he would allow me to take an extra day off so that I could take weekends to go down to Atlantic City. One day when I was in Atlantic City, I got up and thought I had a good chance out there. That is when I went to my boss and let him know that I was going to leave.
He said, “If you think you have what it takes, you need to take a shot. You need to live life with no regrets; you’re real young, and you don’t want to be saying, ‘I wish I had gone for it when I was 25.’” That’s when I went to try to make it happen. I made the transition from grinding on weekends to staying the whole time. But it wasn’t all great at first. I actually had to return to work, because different things happened. I took some losses in cash games, and I took some losses online.
My overhead was so high, living in Atlantic City, that it was better for me to go back. By the time I went back, there was nothing there for me. The lifestyle had me at that point. I was trying to put myself in a position to be a prime-time poker player, because I realized that once you get to that level, you’re able to make a lot of money and have fun with what you’re doing. I needed to make that happen.
Rookie of the Year
RL: How would you sum up the experience of improving your game and taking it to the next level on the WSOP Circuit?
DP: On the WSOP Circuit, there are lots of different games, more types of people, and lots of different traps that you need to avoid. There are lots of different styles that you learn by playing against those different people. Those guys don’t have as much skill or experience as the top pros, but they are putting their money out there and trying to put together their game, as well. So, I just tried to read the players, see what was going on, and make the best guess that I could, because everything you do in this game is an educated guess.
I’m always trying to acquire information from everybody, and see what’s going on. I’m trying to figure out what my opponent is thinking, and when I’m in a hand with that person, I’m drawing on all of that information to make the best decision to win that pot. So basically, I’m trying to learn from all of the mistakes that everybody is making.
You definitely see a lot of people you grind with, have played a lot of hands with, and played a lot of games with. Everybody plays the $500 and $1,000 events, except for maybe the top pros in the world. The Circuit now has a great $1,600 event that has brought a lot of players in. You’re learning to deal with these guys so that when you meet them on a bigger stage or in a bigger game, and things mean more, you have that information from before, and can put them on a profile.
RL: How do you think your first two years of live play compare to some of the other poker greats out there?
DP: If you look at my record, everything speaks for itself. My first year, I was Rookie of the Year [his own title, not an official award]. I came in and won two Circuit rings, and was the WSOP Circuit Player of the Year, and there was no person who came in with me that year who was better than me.
In 2010, my second year on the Circuit, I came out and actually went after winning Player of the Year. There are not a lot of guys who come to the Circuit, win Rookie of the Year, and then the next year go after Player of the Year. If you look at the combination of those two years, I think I’m one of the strongest guys on the Circuit. You know that the numbers don’t lie. I made about $1.6 million on paper, 40 cashes, and 20 final tables. I think my progress is faster than the average player. Right now, I’m three years ahead of where Phil Ivey was at the start of his career.
I’m not talking about the one-hit wonders who were set up after one big win with their bankroll; I’m talking about the guys who did it the other way. I was a grinder to build my bankroll, and now I’m in a position to show the world that I’m one of the great players.
A Perennial Player of the Year Contender?
RL: You were in the Card Player 2010 Player of the Year race from day one of the year. At times, you led it, and at other times, you were challenging the leader. Was there constant pressure on you?
DP: As you said, I was the only one in the Player of the Year race from the start of January. On Jan. 9, I won a $500 event, and then on Jan. 13, I won a $300 event, and then on the 16th, I was second in a $1,000 event, so I had a sick run. I actually said that I was going to go for Player of the Year. I didn’t wake up one morning after a big score and say, “Hey, I’ve got 2,500 points, so maybe I’ve got a chance.” I said I was going to do it from the beginning of the year. I put my mind to it, and then kept playing.
I’m going to try to do this for as long as I can. I feel like I’m going to be in the top 10 in the Card Player 2011 Player of the Year race. I’m going to try my best to put myself in that position. I’m going to try to win it this year [at the time of this writing, two major tournaments remained on the 2010 POY schedule], and try to win it again next year.
RL: When some players get involved in the POY race, they push themselves to play as many events as they can, but you are so used to playing in a lot of events that this pace appears to be normal for you. Is that a big advantage?
DP: If you look back at 2009, I played just as many events, but not as many $10,000 events. I was still trying to watch my bankroll at that point. In the last two years, I think I have the most POY points if you combine 2009 and 2010. I think I have the most final tables in the last two years, as well, and my number of cashes also would be up there. When you have the most final tables, cashes, and Card Player points, that’s showing consistency. All through my career, I have been a consistent player. I feel like I’ll have an even better chance in 2011. I feel like my game is at a very high level, and that is going to show in 2011.
Shock the World
RL: What emotions did you feel when you won the WPT Borgata Poker Open?
DP: There were a lot of different emotions going through me, since that tournament put me into first place in the Card Player POY standings at that time. It wasn’t just a final table or a WPT title, or a regular big tournament; there were other aspects that made it even bigger for me. It was the biggest prize pool I’d ever played for, and the biggest field I’d ever gone through, so it just meant so much to me. I feel like it was the steppingstone for me to start my second career.
I believe my first career was great, and now I’m trying to start a second one on the second level, with $10,000 and $5,000 events, and things like that. I feel like it was a good way to get my bankroll firmed up, and now I’m ready to play with the big boys.
RL: Would you agree that television cameras heighten your personality?
DP: When I’m at a televised final table, it is time to put on a show. I had been bottling it up before that, and wasn’t as animated up to that point. But once it gets to that big production, it’s bigger than me, it’s bigger than that final table. It’s for the world to watch. You want to have something that the world wants to watch; you don’t want to see guys just flipping over their cards.
When you watch my game, you’re going to be like, “Damn, this should have been the play-in for $100 million, because these guys are giving me a real show.” I’ve seen a lot of shows, but haven’t seen my show yet. I know what I brought, and I think it’s going to be one of the best shows out there.
RL: What did you bring to the table that other players out there don’t in that situation?
DP: I think I just did whatever it took, and I brought something extra out of everybody else who was there, and made it a show. I think you’re going to see the energy. You’ll see what I was feeling as I was going through it. You’ll see the different mind games, and will see how many different styles I have. I had to switch it up and play many different psychological games to get me to where I was, and at the end of the day, to make it happen.
RL: Your persona has caught on in the poker community as a kind of cult-classic figure whom people love to watch. What do you think goes into that?
DP: I play so many games that it all depends on what is going on at the table. Some guys will be like, “Dwyte Pilgrim is a real solid player,” while some guys will be like, “Dwyte Pilgrim is real aggressive.” Some guys will be like, “Dwyte Pilgrim is real tight,” and some will be like, “Dwyte Pilgrim is a maniac.” Some guys will be like, “Dwyte Pilgrim is a real nice guy to play with,” while other guys will be like, “Dwyte Pilgrim is a jerk.” It’s a game in which you have to bring many different faces, and have to be able to adapt to a lot of different situations.
You can’t be friendly with everybody; you can’t have top respect for everybody; you can’t be playing around with everybody, because not everybody is going to do the same with you. So, you have to analyze the situation you’re in and bring the face that you need to go to the next level. At the end of the day, I can say that I’m a stand-up guy. I play to win, and I bring my A-game.
RL: What are some of your best catchphrases?
DP: I always say, “Shot in the dark,” because when I started playing, it was a very dark scene for me, and the light at the end of the tunnel wasn’t really there for me yet. I had to actually make that light. I had to keep breaking pieces off to see a little bit more, and that is why that is one of my favorite phrases.
One of my other favorite phrases is, “When life gives you champagne, you make rosé.” Life has given me champagne, so my goal is to turn it into rosé and have a little bit more fun and a little bit more success.
One of my great phrases is, “24 hours from greatness.” We’re all trying to become living legends. I feel that at any time when I am in a big game, I could be 24 hours from greatness.
“Shock the world” was a good catchphrase at one time. They called me the minor-league player of the world at that time, and said it was my time to shock the world against major-league players.
RL: What are your future plans and goals in poker?
DP: I’m going to be in the Poker Hall of Fame. I’m going to put together year after year of great, great stats. I think my ambition is going to take me over the top. I want to be great. It’s not just about this year; I want to be great every year. I have the time to dedicate myself to this, and I will put it all into being one of the best in the world. I want people to say, “Dwyte Pilgrim is one of the best poker players in the world.” ♠