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Shaun Deeb Looking To Lose His Way To A Million-Dollar Payday

Six-Time WSOP Bracelet Winner Talks Poker And Prop Bets

by Julio Rodriguez |  Published: Oct 04, 2023


Shaun Deeb was just 16 when he fell in love with poker, hosting tournaments at his home in New York. It wasn’t long before he was focusing more on cards than school, and Deeb found himself quickly rising the ranks among the best online players in the world, reaching the peak of no. 1 in 2009, according to PocketFives.

In the live arena, Deeb has done most of his damage at the World Series of Poker. Not only is he in an elite group of just 22 players with at least six gold bracelets, but he is consistently one of the best performers each summer in the WSOP Player of the Year race. In fact, since 2015 Deeb has finished in sixth place or better six times!

In total, the 37-year-old has racked up more than $13.5 million in live tournament earnings during his career, to go along with millions more won online.

Deeb finished in second place in this summer’s WSOP POY race, but also has four other wins in 2023, putting him in the top 20 of Card Player’s year-long POY race as well, which is sponsored by Global Poker.

His latest run is made even more impressive when you consider that he has done it while also working on a weight-loss prop bet with high-stakes businessman Bill Perkins that will earn him a seven-figure payout if he can shed enough pounds by next summer’s series.

Deeb recently appeared on the Poker Stories podcast. Highlights appear below, but you can listen to the entire episode on the Card Player website, YouTube, Spotify, or any podcast app.

JR: It’s been a great year for you as far as results go. Not only did you win another bracelet this summer, but you also have four other wins this year, including a $25,000 high roller in Florida, a $5,000 event in Texas, a $10,000 H.O.R.S.E event in Las Vegas, and even a $1,700 WSOP Circuit main event back home in your native New York.

SD: That circuit win is actually the reason why I got the weight loss prop bet. There was a video taken by my close friend DJ MacKinnon making fun of me on the stage for eating chicken fingers. Matt Glantz tweeted it out, and the butterfly effect of that resulted in the bet.

JR: What exactly are the terms of the bet?

SD: The initial bet was he laid $1 million to my $100,000, [betting against] me getting to 17% body fat, by any means necessary. So that means I’m allowed surgery, steroids, [prescription drugs] … anything I can do to get there.

Part of the reason I have this ridiculous beard and hair is because I figured out that that’s going to be beneficial to me to have some extra fat free pounds. So, at the final weigh in, I’m probably going to make my hair into dreads for a few extra pounds. When it comes to those last few pounds of cutting, being able to get one or two extra pounds and still qualifying with the same body is going to be beneficial for sure.

That’s probably going to be my favorite moment, shaving my head and beard, because I f***ing hate it. I’m sure it helps a little in the workouts to get a little more sweat, but I can’t wait to get rid of this.

JR: You’ve lost over 50 pounds since the bet started and still have until the start of the 2024 WSOP.

SD: It’s good, but I’m not as far as I wanted to be. My goal is to win the bet by December because I just really want to get done with this. It’s such a time commitment not only to me, but to my family. It’s so difficult. People always talk about how difficult it is to stay healthy while traveling for poker, because it is.

JR: It seems like it helped you out this summer considering you cashed 24 times (second most to Mike Holtz’s 25 cashes), won your sixth career bracelet, and finished second overall in the WSOP Player of the Year race.

SD: Unfortunately, you are wrong. I actually had my worst series financially ever. I had about $650,000 in buy-ins, and I only cashed for [~$470,000].

Obviously, I won a bracelet, and I came close to winning POY, which are my main two goals, but I [didn’t run as well] in the high buy-in events and that is going to affect the bottom line a lot. But I’m also okay with losing money because I know that there are some events where I’m playing a minus EV strategy to increase the EV of bracelets or POY.

I actually had to miss the last five or six events because my best friend Dan Weinman was going deep in the main event. Spoiler for those who didn’t watch it, he won.

(Editor’s Note: Weinman credits Deeb for convincing him to come back to Las Vegas to play in the main event after he had left the series early to go back home to Atlanta, Georgia.)

So that was an amazing experience. I took two days away from poker and the diet to celebrate and party because that truly is a once-in-a-lifetime moment. To be there with someone I’m so close with, someone who I helped motivate, reminding him just how f***ing good he is. And now the whole world gets to see what I’ve seen in him from the first day I met him.

JR: Did you have a little piece of his action? Enough to get you unstuck for the summer?

SD: Yeah, I had a significant piece. Dan and I do a 10 percent swap in every event. Then when he was three-handed, he decided to sell some equity at ICM. I knew the skill edge he had, so I bought some more.

My personal cut ended up being the single biggest score of my career, which is just insane. Watching my friend win while also having a sweat was my favorite moment out of my 20-year poker career.

JR: And that’s not the first time we’ve seen you on the rail sweating the main event final table.

SD: I’ve coached players at the final table like seven other years. Guys like Cliff Josephy, Ben Lamb, Jay Farber, Tony Miles. But this experience was different, hanging out every night and talking through hands.

JR: Although you needed Dan’s score to turn a profit, you did finish second in the POY race, in which you have an incredible record. In the last eight years, the worst you’ve finished was 56th…

SD: I wasn’t even trying that year. (laughing)

JR: And you had a 23rd-place finish in 2017. But every other year since 2015 you’ve made the top six, with the overall win in 2018. Was it tough coming up short this year?

SD: Ian Matakis had an insane year. I don’t think people know how difficult it is to do what he did, especially on the volume he played.

(The Minnesota pro cashed 22 times, with six top-nine finishes and a bracelet win en route to the POY title.)

Obviously, I wish he didn’t have this outlier year because it would have been cool to have won the banner the same year my best friend won the main event, and also tie up with Daniel [Negreanu] for two POY wins. I’ve come so close so many years. But it was a great battle. I think he’s a great up-and-coming player and I’m happy for his success.

JR: You also won your sixth bracelet, which only 22 players have ever accomplished in history. (Deeb is also the third youngest with six, just slightly older than Brian Hastings and Jason Mercier.) Phil Hellmuth says that you are probably his top competition when it comes to the bracelet count.

SD: I love bracelets. They’re what got me hooked on poker. But I have shifted a little bit where I think that bracelets are not as important as Player of the Year. I’ve kind of stolen some of Phil’s ideas, actually. Like the way he promoted the [bracelet race] from early on in his career. That’s why I’ve been [promoting] the Player of the Year [competition].

I like that it’s only given out once a year. Nowadays it feels like there’s 600 or 700 bracelets given out every year. It’s a lot easier to win one. But POY is about putting in the time and effort. Putting in the work. Playing every event.

I just love the WSOP for how much volume I can play. The prize pools are great. I love the mixed games, and even the no-limit and PLO events are great. Making a final table still makes you so f***ing motivated.

JR: You definitely can’t fake an entire summer, and your summer must have felt like twice the work considering the seven-figure bet you have on the line.

SD: If I win this bet, it will just prove how ridiculous my life has been, how far above expectation I’ve ran on everything I’ve done.

A lot of people consider me to be one of the best poker players, but I just think I’m one of the hardest working poker players. And that’s not hardest working by studying in the lab. I’m talking about hardest working by putting in volume.

I have all those wins because I go to the stops and I play well, but I know that the game is going to pass me by one day. There’s a bunch of up-and-coming kids like Ian who are studying the game.

I really love it when people come to visit me at my house and see what my day-to-day is like, because it’s so different from what people assume. When I’m not playing poker, I’m trying to be a dad and a husband and make [investment decisions].

JR: You’ve had a few million-dollar scores throughout your career, although not in prop bets but in tournaments. Do you feel any nerves when the prize pool gets big, or is it just another final table?

SD: I think I do a really good job of ignoring the money on the line, and I’m not the best ICM player. A lot of these big scores I was the chip leader most of the final table, and that tends to be how I play most of my tournaments. I’m a foot-on-the-gas type of player.

I’m good at figuring out the psychology of people in the moment. I can just tell based on timing or intuition if they’re in the mood to make a big call or a big fold. I’ve made a lot of great reads throughout my career, and I’ve also looked like an idiot on many hands, but it’s worked out more times than it hasn’t.

JR: You mentioned not being afraid to look silly making a move in a game, but you also really don’t care what others think about you when it comes to be outspoken on issues in the poker community.

SD: People have gotten to the point where they realize I’m a no bullshit kind of guy. I would never lie to someone to give someone an answer they want to hear. I’m very opinionated when it comes to controversial topics, but I also have a lot of logic behind my opinions.

I’ve always cared about poker’s long-term growth, and I have done a lot of things in my career that have hurt my individual earn because of my morals and ethics. I love having that reputation for being ethical in poker, because that is one of the hardest images to maintain. I love that I have the respect of my peers. I love that casual players even know that I’m a respected voice in the community. It’s because I care so much and because I want to see people get as much enjoyment out of the game as I have throughout my career.

I’m so excited for the future of poker. I think we’re hitting a boom that is going to be bigger than Moneymaker. The numbers keep getting bigger and operators keep getting better. The game is booming internationally and there are so many new regions of the world that are [just starting to play.] There are so many great ambassadors helping new people find the game.

Maybe one day we’ll get the real sponsorship we should have, where money gets added to prize pool and leaderboards and different things like that. Then you’re going to see massive growth.

We’re so f***ing close to being a big and respected industry. That’s always been my goal since I got into poker, is for more people to know that it’s a respectable skill game and for more people to fall in love with it just like we all have. ♠