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A Poker Life: Jesse Sylvia

by Julio Rodriguez |  Published: Apr 02, 2014

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Jesse Sylvia had been playing poker as a successful, yet anonymous cash game grinder since 2008, but his runner-up finish in the 2012 World Series of Poker main event for a $5.3 million payday thrust him into the unfamiliar territory of the poker spotlight.

After a year of trying to add to his resume on the tournament circuit, the 28-year-old is now planning to get back into the cash-game scene and perhaps consider an entirely different career altogether.

Growing Up On The Island

Jesse James Sylvia was born Feb. 26, 1986 in West Tisbury, Massachusetts. Though he shares his name with an infamous American outlaw, Sylvia admits that it was unintentional.

“When my parents were at the hospital and signing the birth certificate, the nurse recommended giving me a middle name because otherwise, it would be a lot of paperwork to add it on later,” Sylvia said. “My uncle Jimmy was there and joked that my middle name should be his name, so they gave me the middle name James. It wasn’t until a week later that they realized what they had named me.”

Sylvia grew up in Martha’s Vineyard, an affluent summer community located south of Massachusetts. As a full-time resident, however, Sylvia and his younger sisters Randi and Nica did not grow up with silver spoons in their mouth.

“The vineyard is a very polarized place,” he admitted. “There are the rich summer home owners who are in million-dollar mansions on the beach, and then there are the year-rounders like me, who basically work for the rich people. For instance, my mom was a florist who would take care of the flowers for all of the couples who were planning a destination wedding on the island. In the winter, there are about 20,000 people who live there. In the summer, there’s upwards of 150,000 people walking around and a lot of activity.”

Sylvia grew up extremely competitive, jumping from sport to sport each season as well as fixating on computer and board games.

“I realized in high school that I was more partial to games that involved your brain, probably because I wasn’t the tallest or the strongest of my friends,” Sylvia recalled. “I hated losing. I remember one summer that I spent obsessing over a computer version of the game Risk.”

When Chris Moneymaker burst onto the scene in 2003, it made sense that Sylvia, then a senior in high school, would gravitate towards poker.

“My friend Hans would always have games in the studio apartment above his parent’s garage. We all got really into it, but after graduation, I was the one who kept playing.”

Poker Beginnings

After high school, Sylvia left Martha’s Vineyard for California Lutheran University in Thousand Oaks. There he studied hard to earn his undergraduate degree in math, with a minor in psychology. But mostly, he studied poker.

“I found a bunch of college home games pretty quickly, but when I found out that you only had to be 18 to play in some of the casinos, I was making the road trip as often as I could,” Sylvia admitted.

Sylvia was experiencing a new world of firsts and quickly realized that his first debit card would allow him to put money into an online poker site. Soon, he was playing nearly every day.

“I would deposit $50, run it up to a few hundred and then lose it,” he said. “I did this a few times and then the summer after my freshman year, I decided to really work on building a bankroll. I deposited $100 and very slowly built it up to $8,000. At the end of the summer, I lost $5,500 in like one night. That was a tough lesson to learn.”

Six months before graduation, Sylvia chopped up the Sunday Million on PokerStars, giving him the bankroll he needed to become a professional poker player. He completed his classes and moved to Boston to continue the grind.

A Move To The Desert

Though it was an online poker tournament that funded his start, Sylvia believed that cash games were a safer investment of his time and resources.

“After I chopped the Sunday Million, I decided to make a decision about my poker career. I looked at the tournament and saw 8,000 players and told myself, ironically enough, that I would never get that lucky again. I needed a more consistent form of income, so I devoted my time to learning how to play cash games.”

Sylvia continued to grind online and improve as a cash-game player. A month before Black Friday, he moved to Las Vegas to continue his career.

“My timing couldn’t have been any worse,” he said. “I was finally starting to make good money online. In February of that year, I had my biggest winning month ever for something like $50,000. Then it all got shut down.”

After honing his skill online, Sylvia was forced into the live cash games in Las Vegas.
“Ultimately, I think it was good for me as a player overall because playing live forced met to meet and interact with other poker players. As a result, my game improved dramatically. It got to the point where everything we did resulted in a poker discussion. A hand will inevitably pop up and we will begin dissecting lines.”

The Perfect Tournament For A Cash-Game Pro

Though Sylvia still believed cash games were a better use of his time, he wasn’t about to miss the 2012 World Series of Poker main event.

“I was playing very few tournaments throughout the year, but the WSOP main event is perfectly designed for cash-game players. The stacks are deep and the structure is slow enough to allow for a lot of play. Even though it’s not my usual game, I know my edge in that tournament is too big to ignore.”

Sylvia entered the tournament in the middle of a small downswing, but never thought about skipping the event.

“The cool thing about the WSOP is that you could be in the middle of the worst run of your life, but one tournament can turn it all around and make it the best summer of your life.”

After navigated his way through a field of 6,598, Sylvia found himself at a final table featuring three other friendly faces.

“The whole time I’m thinking, I just made the final table with Russell Thomas, who used to be my roommate, and Greg Merson, who is staking my current roommate and who almost moved in with me, and Jeremy Ausmus, with whom I played nearly every day. All of those players in that tournament and I just so happened to have three of the final tablist’s numbers already in my phone. I thought that was a pretty remarkable story that probably didn’t get enough attention.”

When all was said and done, Sylvia, who up until that point had been a local anonymous cash-game grinder, wound up with a 44.71 percent chance of winning the tournament. It was essentially a coin flip for all of the marbles, but the poker gods weren’t kind and he had to settle for the $5,295,149 second-place prize.

A Tournament Circuit Victory Lap

A couple of weeks after the final table, a production company sent Sylvia a message asking if he was interested in appearing on an episode of MTV’s True Life: I’m A New Millionaire. Sylvia, and his girlfriend Ashley, were in the middle of a cross-country road trip when they agreed.

The film crew followed the couple to some of the major highlights on their around-the-world trek that included the Bahamas, Australia, Los Angeles, New Orleans, and Paris, even documenting the house hunting trip Sylvia took for his mother back in Martha’s Vineyard.

Though he enjoyed the attention and had a blast with his travels, Sylvia knew that he couldn’t continue his jet-setting poker tournament lifestyle forever.

“I traveled a lot in 2013,” he said. “One thing I realized is that the rake of traveling and playing tournaments is ridiculously high. Unless you are a sicko like Vanessa Selbst or Jason Mercier, it’s really hard to overcome those expenses. If I have a 50 percent ROI (Return On Investment) on a $10,000 tournament, but $4,000 is spent on travel and hotel accommodations, then I’m better off staying home and playing cash games to make more money.”

Moving Forward

In addition to being more choosey about his destination tournament stops, Sylvia wants to continue being a positive ambassador for the game. He believes that it is up to poker professionals to help the game grow.

“What does it mean to be a good poker player?” he asked. “Be friendly to amateurs, take off your headphones and interact with the new players. Talk about anything but poker. It’s a competitive game, obviously, but the games are getting tougher because we are creating an uninviting environment for beginners. The number one reason why the games are dying is the recession, but we can still do our part.”

Though he loves the game more than ever, Sylvia admits that he’d like to venture into a different line of work in the future.

“Poker is the greatest game ever made. There are so many variations of it that I can be learning the game for the rest of my life. However, I would love to pursue a career as a film writer. I had planned on going to film school, but the main event presented me with some opportunities that I had to take. One day I’ll make it happen. I’d like to leave behind something a little more meaningful that just a bunch of numbers listed next to my name in poker earnings.” ♠