Poker a Nice Fallback for Law Student

Leo Wolpert lost on
Leo Wolpert lost on "Jeopardy" but is a winner when it comes to playing poker. (By Jeff Brushie -- Wsop/impdi)
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Friday, June 19, 2009

When Leo Wolpert was a senior at Thomas Jefferson High, his quiz bowl team lost in the first round of Mac McGarry's "It's Academic."

"I was absolutely devastated, crushed," Wolpert told me. "I probably cried like a little girl afterward. I was just in a rage."

When Wolpert was a freshman at TJ, he was cut from the baseball team.

"That was another devastating moment," Wolpert recalled. "This interview is all about me getting crushed and devastated."

And when he lost to Ken Jennings on "Jeopardy" during college, he left the studio in a similar state. I mention those incidents merely to demonstrate that Leo Wolpert does not take kindly to losing. The first time the 26-year-old from Fairfax played poker, after his freshman year at Michigan, he lost $50 in a half-hour, at an age and income level when losing $50 meant something.

"Again, was devastated," he said. And as with these other cases, Wolpert then dedicated himself to making sure that loss wouldn't happen again. He knew that poker was about skill, was "beatable," and he wanted to learn how. So he started reading books. He started playing for extremely small stakes online, buying into sit-and-go events for $20 or $30 at a time. He got to computer science grad school at Virginia and kept inching his way along the online poker trail, until one day -- when he didn't feel like studying -- he entered a $600 event and wound up with a five-figure payday.

That was in the spring of 2006. Three years later, a lot has changed in Leo Wolpert's life. He developed a fascination for the law, which was spurred by reading a blog entry about a Fourth Amendment case. He dropped out of comp-sci school. He became a professional poker player. He took the LSAT, entered law school at Virginia, and got a summer internship with the ACLU of Nevada.

And this week, between writing memos about civil liberties, he borrowed a few thousand dollars from a poker-playing friend, entered a World Series of Poker event, made it to the final pairing of the heads-up no-limit Texas hold 'em event, endured a final match that lasted more than eight hours, and won a WSOP bracelet, walking away with more than $650,000.

Then he went to a nice dinner with friends, watched some TV, fell asleep, and reported for work at the ACLU the next morning.

"I'm going back [to school] in the fall, for sure," said Wolpert, who had never won a live tournament before. "It's not like the money is gonna last forever. U-Va. is a fun school, and I really do enjoy learning about the law."

Wolpert isn't sure what he'll do with the money. He drives a 2000 Toyota Camry, but it still works fine. His mom thinks he needs a watch, "but I tell her I have a cellphone, I don't need a watch." He hasn't yet treated his office mates to lunch, but "there will be many lunches on me, for many different people," he promised. He still wants to be a lawyer, although in these uncertain times, it's always good to have a backup plan.

"With the economy as it is," he noted, "it's definitely nice to have poker to fall back on."

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