Cigar Aficionado

Poker has its perks. For Shaun Deeb, a 33-year-old pro from Upstate New York, the game has provided plenty. He’s reaped loads of money, public acclaim and four World Series of Poker bracelets. But despite his baby-faced appearance, he’s also known for aggressive play, abrasive behavior and a knack for remorselessly pissing off his opponents.

A new Land Rover is parked in Deeb’s garage at home and a splashy Audemars Piguet is wrapped around his wrist. To finance those goodies, Deeb has made some $7 million playing online, more than $7 million in live tournaments and around $6 million in cash games. Nevertheless, as of 2018, Shaun Deeb still felt incomplete. It wasn’t for a lack of money or attention or a place at the table of elite pros.

It was a banner.  He wanted his face on a banner. More specifically, a World Series of Poker Player of the Year banner. 

These 40-or-so-foot-long hanging hallmarks, featuring the faces of 14-years-worth of winners, are displayed prominently inside the World Series of Poker tournament rooms every year. 

In previous years, Deeb was pretty much taunted by the mugs of buddies such as Jason Mercier, Frank Kassela and Ben Lamb looking down on the high-stakes proceedings. Player of the Year status is achieved by earning more tournament points—calculated through a formula that takes into WSOP tournament buy-ins, field sizes and finishes—than any other player. Deeb decided in 2018 that he would do his best to his friends up there.

As is usually the case for Deeb, he succeeded. So when he and thousands of other poker lovers rolled into the Rio for the start of the Series in May, Deeb got to see his face bannered as the 2018 Player of the Year.  

“I thought about it every World Series, and thought about the fact that I did not have a banner,” he says. “Then I played some tournaments in 2018, made some final tables and realized that I had a good shot at winning. That’s when I decided to go for it.”

Deeb got his banner by cashing in 20 events the year before last, taking down more than $3 million in WSOP earnings and managing to win two WSOP bracelets in the process. While World Series bracelets are obviously coveted, snatching up those diamond-studded bands does not rank as his biggest accomplishment. Actually, he is made proudest by a pair of tournaments that he did not win. 

In the midst of playing a Texas hold’em event known as the Big Blind Ante (so named because the player in the Big Blind antes for everyone at the table in an effort to speed up action), he was faltering and looked likely to bust out. Already chasing Player of the Year and not wanting to lose an opportunity to garner points, Deeb entered a second tournament (Deuce to Seven Lowball) while still hanging in on the first. Then he got onto a good run in the Big Blind contest and began accumulating formidable chip stacks. Suddenly, he had to play both tables at once as each event rumbled toward its conclusion. 

Not exactly blessed with a sprinter’s physique, the burly Deeb desperately charged from one table to the next, doing his physical best to avoid missing hands and having his chips blinded down. 

“For the first time in 10 years, I was running. Those tournament tables had to be two-tenths of a mile apart,” Deeb says, sounding out of breath merely from the recollection. “I kept winning all-ins on the Deuce to Seven and got to three handed on the final table there.” Deeb wound up finishing third in that one and 16th in the other. “Cashing both of them”—for a total of nearly $50,000, with a shot at taking home two bracelets in one day—“was a bigger accomplishment than winning Player of the Year.” 

Presumably, he’s kidding. And, of course, the money that season was hardly inconsequential. As Deeb puts it, “The summer of 2018 was when I used a bodyguard to fly home with me from Vegas. I was traveling back with a load of cash. People get killed for a lot less.”

In January 2019, with Deeb’s Player of the Year status still fresh, he travels to Paradise Island in the Bahamas. Far from being a man on vacation, the pasty skinned Deeb is there to play in PokerStars Caribbean Adventure, a series of tournaments held at Atlantis Bahamas casino and sponsored by the online site. It is the night before the start of the Main Event, a $10,300 buy-in tournament with a first prize that will top out at $1,567,100, and Deeb appears hungry in more ways than one. 

Wearing khaki colored shorts and a bright red T-shirt, the baby-faced Deeb appears in the lobby of Atlantis. He taxis from there to Graycliff, arguably one of the best restaurants on the island, which boasts a significant feature: a cigar roller who makes fresh torpedoes for smoking after dinner. 

He settles down at a table inside the venerable restaurant, situated on the ground floor of a home that had once been a refuge for pirates. Starting in on his cocktail, an amaretto-based drink dubiously dubbed The Godfather, Deeb says that he owes everything to his grandmother. She taught him how to play poker and was a devoted gambler herself.  

“When I was eight or nine, people asked me what I wanted to do when I grew up,” Deeb recounts. “I said I want to own a casino. They thought I was a little weird.”

By the time Deeb turned 16, his ambition seemed less off-kilter. The year was 2002. The movie Rounders had already lit a Texas hold’em fire, but the real accelerant would be Chris Moneymaker, a rank amateur who outplayed a raft of seasoned pros in 2003 and won the World Series that year. 

Deeb competed in his first poker tournament atop a pool table in the home of his cousin’s friend. He got the bug and went on to spend six months running 30-people tournaments, composed mostly of fellow high school students, in his parents’ house. 

Tables stretched from the basement to the kitchen and the game’s host was a monster. 

“It was self-dealt and a blast,” he re. “Over the course of six months, I won seven times. Those are ridiculous results for 30-person tournaments. I had no idea how to play but I went all-in all the time and people folded.”

Early on, Deeb learned a cornerstone of poker strategy: aggression pays. By age 18, he was cutting his teeth on the tournament tables of a local casino and chatting up serious players who were his own age. He added refinements to his strategy and won what would prove to be a life-changing game of Monopoly with a bet of $30 riding on it. Deeb was playing against a pal. Their friendly wager was designed to add a little juice to a kids’ board game, but it did a lot more than that.

Deeb won and his opponent must have been caught short. “He paid me the money via an transfer on PokerStars,” says Deeb who opened an on the site. “This was 2004 or 2005. I ran that 30 bucks up to my current bankroll, never went broke and never had to deposit a dollar. I played online every day and played in $50 buy-in home-game tournaments.” 

By the time Deeb enrolled in college, higher education never stood a chance. Poker fit his personality way better than English class did. “I always had a fast mind,” he says, working his way through a platter of lobster ravioli as he orders a medium-bodied cigar for after dinner. “I’ve always been hyperactive in my thinking and poker allows my mind to move as fast as I want it to. Verbally I can talk fast but still get out only so many ideas at a time. With poker I can get out as many as I want to.”

He quit college during his freshman year, with the intention of moving home to grind at online poker. Clearly his parents were not thrilled. His grandmother, though, who was known for playing poker in the casinos until past 2:00 in the morning, stood behind him all the way. 

“She saved me,” says Deeb. “My grandmother told my parents I’m smart and that I will figure it out. Poker was not looked down upon but my parents thought it was a phase.”

Deeb knew it wasn’t: “I dropped out of college, went home to my parents’ house and just stayed in bed all day, playing online poker.” 

Along the way, Deeb’s unquiet mind helped him to do something spectacular. While it was fairly normal for young, winning players to leverage their advantages by multi-tabling—that is, playing as many as eight tables at a time—Deeb took it to the next level. He began playing 40 tables simultaneously. 

“To stay engaged, I needed to be constantly making decisions,” he says. “I was a trial-and-error, high-volume guy, but, by playing so many tables at once, I figured out people’s strategies and how to go against them. I played 200 tournaments a day back then and you couldn’t avoid me. My ROI was 100 percent. I had hundreds of $1,080 wins over the years. I made 20 bucks every time I bought in.” And he bought in a lot.

Successful as Deeb may have been, his parents really got the message after he was recruited by 2004 WSOP champion Greg Raymer to play in a PokerStars sponsored event called the World Cup of Poker. It was a team tournament airing on network television. The Deebs watched as Shaun was called in to close out the tournament. An announcer made it clear that Deeb, thanks to his prodigious online play, had evolved into a more experienced player than Raymer. “I knocked out the last three guys, including Daniel Negreanu, and won us a bunch of money. It was a turning point in of my parents and my poker career.”

But if Deeb managed to enhance his game through the modern technique of online poker, he has cultivated an image at the table that owes more to the flamboyance of  Puggy Pearson than to the inscrutable nature of Tom Dwan. 

“I am a cocky asshole,” Deeb happily its, now out on the front deck of Graycliff, lighting up his cigar. “I am always needling, always shit-talking, always making jokes. I’ve always had confidence. Even if you are better than me, I will find my way to reduce your edge.”

Most notoriously, he’s infuriated opponents by slow-rolling them—that is, taking an extraordinarily long time to call an all-in bet, despite having an unbeatable hand, in order to put opponents off their games and on tilt. Deeb particularly got under the skin of Mike Matusow during a taping of the televised Poker Night in America. 

There were a pair of 5s on the board and Deeb had two more in his hand. Unquestionably, four of a kind would take the pot. At the end, Matusow had zero-percent chance of coming out on top. Deeb realized this and very intentionally slow-rolled him. Matusow was clearly annoyed. 

“He threatened to punch me in the face. I just cracked up laughing. The producers thanked me for getting such a memorable reaction out of him, and it has gotten tons of views on YouTube.” 

At 33 years old, Deeb is a family man. He tries to limit his traveling so he can spend more time with his wife and kids who camped out with him in Vegas while he labored to nab Player of the Year last summer. 

A day after dinner at Graycliff, during a break in action at the PokerStars tournament, where Deeb is hoping to get deep and have a shot at the first prize of more than $1.5 million, he debates with himself on whether or not to stick around if he busts out.  

“The 25K [a so-called high-roller tournament with a buy-in of $25,000 and a field of seasoned pros] does not look profitable for me,” he says, acknowledging that there is a new crew of young, highly competitive players who have benefited from software that has taught them to engineer each hand optimally. “I’m not sure if I will stick around.”

Deeb is only talking about leaving the Bahamas, but, having already made his bones and his money at poker, he could be talking about exiting the game as well.

“Seven years from now, when I turn 40, I’d love to be done with poker as a full-time occupation. I am looking for ive cash flow,” he adds. “I don’t see myself being a nine-to-five guy.”

Deeb busts out of the tournament way earlier than hoped. He winds up finishing in 118th place and takes home $18,460 (profit there of just $8,160 for the event) on top of the $86,060 he took down for third place in a Pot Limit Omaha tournament on this trip, which adds up to be pretty tidy for a week’s worth of work. He winds up forgoing the $25,000 event after all, and decides to board a plane for the next flight home instead.

“Poker is a psychological game,” he says. “People are trying to keep their heads together. As soon as you become emotional, you start ignoring the math. And when that happens to an opponent, it’s a good thing for me.”