A Poker Life: Jason Wheeler

In the last eight years, Jason Wheeler has earned nearly $10 million in live and online poker tournaments, but none of that would have happened had he not lost his job during the financial crisis of 2008. The 39-year-old Chicago native was on the fast track, working in the banking industry, but after being laid off, he went all-in on poker.

He now spends the majority of his time traveling from one tournament stop to the next, looking to add more accolades to his poker resume. Most recently, he won his first WSOP Circuit ring by taking down the Bally’s main event in Las Vegas.

Here is his story.

A Self-Proclaimed Nerd

Wheeler grew up in Riverdale, a small community on the southern edge of Chicago. In his teens, he stayed out of trouble by focusing on his hobbies such as chess and computers.

“I was kind of a nerd growing up,” Wheeler admitted. “The first thing I was really into was chess. I played on a team in high school and ended up as the team captain. During the summer I actually tried to play chess semi-professionally, just to see what would come of it. I would drive all around the Midwest to these tournaments and I did really well. But at the end of the summer, after expenses, I had only ended up with about $6,000. I knew then that chess wouldn’t be the profession for me. There just wasn’t enough money in it.”

With competitive chess in his rear-view mirror, Wheeler was accepted to the University of Illinois where he planned on majoring in computer science.

“I had been into computers for a while, even before most people had access to the internet,” he said. “When I got there, however, I realized that I was too much of a personality to be behind a keyboard all day. I switched to business during my second year and after graduation, I went into business consulting.”

Poker Beginnings

Wheeler took a position with a financial services firm, which mainly focused on process improvement for the banking industry. It was a good job with a six-figure salary, and his background with both computers and business made him an excellent project manager. In 2004, however, he discovered poker after his company relocated him from Chicago to San Diego.

“The Moneymaker boom made home games very popular, so we started doing that,” he recalled. “My buddy Kevin kept winning, even with garbage hands, and that really opened my eyes to how the game could be played.”

Eventually, Wheeler moved his game online and quickly found success. He still had his day job, but he was beginning to win pretty big at night too. He had already cashed out somewhere in the neighborhood of $25,000 and had another $25,000 still on the site.

By 2007, however, he had spent his winnings and lost his bankroll. The negative experience made him swear off poker entirely until the economy took a turn for the worst and he lost his job.

“I ended up getting laid off in April of 2008,” Wheeler said. “We had been doing layoffs for months and I had survived a number of cuts, but then I got the call from my boss that I was being let go. They gave me $6,000 for my trouble. I knew I couldn’t get a similar job because everything I had done up to that point was for banks and the banks were hurting, so I put that $6,000 online and went back to sit-n-go’s. I played something like 30,000 sit-n-go’s on Full Tilt, running that money up to $70,000.”

After spending the rest of the year playing sit-n-go’s, Wheeler decided that in January of 2009 he would use his new bankroll to play tournaments. Much to his dismay, his results were terrible. The rest of the poker world had gotten much better during his time off.

“I didn’t get frustrated, I got pissed off. I signed up for every training site I could find and stayed up for 34 hours straight watching videos. I think some players watch the videos and then try to copy what they see. My approach was to watch the videos and then come up with a way to beat what I saw. Within two weeks, I had completely retooled my game. By February, I was crushing everything. I won close six figures in a couple months, put some money away and went to Vegas for the summer with $25,000.”

A Real Professional

Despite all of his time in the poker world, Wheeler still hadn’t made the annual pilgrimage to the desert for the World Series of Poker. He had high hopes, and even set a goal of winning enough to get himself a new car.

“In my first two weeks, I final tabled a couple tournaments at the Venetian and had won $50,000,” he said. “I had met my goal, so I called up my girlfriend and told her I was coming home. Then I called my buddy Kevin, who was the guy who used to beat me back in the home games, and told him I had won $50,000. He then asked me if poker was my hobby or if it was my job. Hobby? I had just won $50,000! Of course I’m a professional. He said, ‘well, if you’re going home during the WSOP, then you’re not a real professional.’”

It was the tough love Wheeler needed to hear. Sure, he could play it safe, take his profit and go home happy. But if he really wanted to make it as a poker pro, he needed to be willing to put it all on the line and see just how his game stacked up.

Wheeler called his girlfriend to tell her the news that he was staying in Vegas, and then he promptly lost back half of his winnings with a bad run. Things quickly turned around, however, and by the end of the summer, he had notched four WSOP cashes, including a runner-up finish in a $1,500 no-limit hold’em event for a huge $418,122 payday.

“From that point on, I was a professional. It felt like I was a part of the club and I was meeting all of these other players. I didn’t feel like an unknown outsider anymore.”

Online Vs. Live

For the next couple of years, Wheeler continued to rack up big scores online. He even got to see the world as he won tournament packages online for live European Poker Tour events. Although he managed a few final-table finishes in spots like London, Prague, and San Remo, it was with online poker that Wheeler was truly dominating. Unfortunately, Black Friday forced him to take his game abroad.

“Everybody says Black Friday was bad for them, but it was particularly devastating to me because of how well I had been playing at that time,” he said. “I felt like everything clicked right at the beginning of 2011 with my game and, for four months, I was on fire. I think I won something like $400,000 in those months leading up to Black Friday.”

With money tied up online, Wheeler quickly relocated to Mexico, where he could continue grinding away. His hot streak continued and by the end of the year, he was crowned the Card Player Online Player of the Year, which was a remarkable feat given the interruption he endured with Black Friday.

To date, Wheeler has earned nearly $7.2 million online despite maintaining regular appearances on the live tournament circuit. Lately, however, he has cut back on his volume.

“I used to go home between tournaments to play online,” he said. “Before, I almost never missed a Sunday. Missing a Sunday for me is like the most religious person in the world not going to church. With only one major player in the market, there have been a lot of changes recently that make playing online less attractive. My attitude has finally changed this year to the point where if I miss a Sunday, it’s not a big deal.”

Of course, it helps that Wheeler’s live game has been remarkably consistent over the last few years. In April of 2013, he won a preliminary event at EPT Berlin for $91,045. In 2014, he scored a win at EPT Vienna and final table finishes in Barcelona, Florida, London, and Prague.

In 2015, he had good finishes in the Bahamas, Los Angeles, and Monte Carlo and even won an event at the WPT Amsterdam for $140,317. He also made another WSOP final table, earning $112,339 for a fifth-place finish in the $5,000 event. The last 12 months has been even more rewarding, with three final tables in Malta and a win in Dublin. Most recently, he won the WSOP Circuit main event at Bally’s in Las Vegas for $323,236.

Moving Forward

It’s clear that Wheeler loves his jet-setting lifestyle, but he also believes that he has to strike while the iron is hot, and that means long days at the tables and living in hotel rooms out of a suitcase.

“If you are just occasionally playing poker to grind out a $30,000 or $40,000 profit, then you can do all of the things that the rest of society is doing. But if you are playing high stakes and have bigger ambitions, then those standard rules of life become almost impossible to follow. In my mind, there’s an environment that I can win in and create a future for myself, so I have to attack it now while it’s still there. If you are getting a 25 percent or better return in poker, it’s really hard to get that anywhere else. In two years, or maybe ten years, everything could change because of many different factors, so poker has to be my focus right now.”

The key, Wheeler says, is recognizing that poker is a unique profession and to stop trying to force it into the 9-to-5 box.

“At the end of the day, you have to understand that nothing poker players do is normal,” he explained. “The lifestyle isn’t normal at all. There aren’t many jobs in the world where you have to go put in 100 hours of work on a business trip, and the end result is you losing money.”

But despite his success and recent attention, Wheeler knows that his story could have easily ended up completely different.

“The best player in the world could be living in his mom’s basement after running really bad when he first started playing. If I lose a flip early on in that 2009 WSOP tournament that I finished second in, then maybe I go home, never turn pro, and go find a different job. It’s that fragile. The way I measure success is longevity. After a decade of playing, I’m really proud of the fact that I’m still here and I’m still relevant.” ♠