A Hard Way to Make an Easy Living

Chris Fitzgerald has always thrived on competition. When he was 10, his grandmother taught him how to play blackjack for pennies. In high school, he was a competitive golfer, and in college he jumped into the booming online poker scene.

“After a year, I was able to use it for some supplemental income,” Fitzgerald says, recalling that he’d play for a few hours four or five nights a week. “It wasn’t a significant amount of money, but enough to make life enjoyable in college. … When I graduated in 2007, I knew I wanted to give poker a shot before going to law school. I had some friends who were going to do the same thing, and at 21 years old, I figured now was the time to give it a try.”

His parents were a bit taken aback by the plan.

“I think a lot of people have a really negative view on what it means to play poker for a living. It is not deserved,” says Fitzgerald. “I don’t think it’s what my parents expected, to have me do something totally unrelated to what I’d spent the last four years working on. But they ultimately understood this was something I wanted to try, and they were supportive.”

For the next year, Fitzgerald played in cash games against scores of professionals and hobbyists alike. He treated the effort as a serious job, reading about the game and studying how to get better during his off hours. And although he says the gig was “far from glamorous,” he’s quick to add that it was one of the most enjoyable years of his life.

“I traveled with my friends, chose my own hours, and met so many interesting people,” says Fitzgerald. “But it’s been said that poker is the hardest way to make an easy living. That’s true. The fact that you could go in and spend several hours and do everything right and still lose money—that’s a hard thing to deal with. I think that’s why so few people succeed at it for the long term. It takes a lot of emotional discipline to withstand those swings.”

While his winnings were enough to keep playing, Fitzgerald had no illusions of making poker his life’s work; so after a year on the circuit he decided to fold and move to Boston to attend Suffolk University Law School, from which he graduated in 2012. When he settled into his first long-term role at a defense firm focusing on products liability matters, Fitzgerald started making connections between what it takes to succeed at the poker table and in the practice of law.

“The first thing, and maybe the most obvious, is the ability to read people and to pick up on passively conveyed information,” says Fitzgerald, who’s now a product liability and commercial litigator at Conn Kavanagh in Boston. “There are often moments in a case where I’ll speak with opposing counsel during a deposition break or over the phone. Small talk. But if I’m paying attention, I realize there’s valuable information everywhere. And it’s not nefarious—it’s just paying attention and understanding what motivates a person and what’s important to them.”

The second, more complex takeaway is the concept of expected value, which, in poker, involves assigning probabilities to various outcomes and assigning value to each of those outcomes. For example, imagine a player knows he has a losing hand, but there’s a $100 pot to win. If he bets $50 on a bluff and knows his opponent will fold 75% of the time, he’s looking at a positive expected value decision.

“When I started defending product liability claims, I noticed right away that clients wanted to know the likelihood of a defense verdict. How often do we win this case if we try it? Then, what do I think the verdict will be if we lose? Finally, what’s it going to cost from now until the day of the verdict? I realized they were asking for the same kind of analysis I did at the poker table,” says Fitzgerald. “Expected value is a tool in my toolbox, and when the rubber meets the road in a case, it’s incredibly helpful to be able to explain things to my clients through that lens.”

These days, Fitzgerald plays poker only occasionally—most of his free time is spent with his wife and their 2-year-old. But he looks back fondly on the experience.

“Playing professional poker was an experiment, and I wouldn’t do it any other way,” he says. “I learned a lot of valuable lessons that make me more effective for my clients.”