Law Student Finds Time for Big Poker Payday

July 1, 2009

It was back during his days as a professional poker player that Leo Wolpert first started to think about becoming a lawyer.

Leo Wolpert '11 (photo courtesy of IMPDI)

"I spent a lot of time on the Internet reading Supreme Court opinions and that kind of thing. I would get outraged about some decisions I thought were kind of wrong," said Wolpert, 26. "If you're not fighting for your civil liberties, who is?"

So last year, the Northern Virginia native decided to give up his lucrative gambling career and begin a legal education at the University of Virginia. All-night poker games gave way to study sessions, and he made the transition with relative ease.

"It was great. I even somehow started getting up early and getting to class, " he joked. "The professors were great and they were engaging enough to make me want to go."

Besides, you can still make some poker money on the side, as Wolpert found out in June when he took home $652,682 for winning a World Series of Poker event in Las Vegas.

The rising second-year student is living in the city this summer while he works as an intern for the Nevada affiliate of the American Civil Liberties Union. The location is no coincidence; Wolpert has lived in Las Vegas for each of the past two summers, and is staying with friends from his poker days while he works for the Nevada ACLU, an experience he said he's enjoyed so far.

"Typically I'm doing the kind of stuff that interns do: a bunch of legal research, plus helping to write memos and motions and that kind of stuff, " Wolpert said.

He decided to enter the World Series of Poker tournament on a whim after seeing a friend fare well in a similar competition. "A bunch of my friends I'm staying with are all excellent tournament players, and that kind of made me want to catch the bug again and play tournaments, " he said.

The tournament was heads-up, which means contestants only play one other player at a time. The players face off in games of no-limit Texas Hold 'Em until one is out of chips, and the winner advances to the next round.

The tournament started on a Saturday, and when the marathon final match was over the following Tuesday, Wolpert was the owner of a new World Series of Poker championship bracelet.

"I just played pretty well, " he said. "I kept my cool and didn't make any giant mistakes. When I made mistakes, I tried to keep them small. I got lucky in a bunch of crucial spots. You've got to get lucky in some of those spots to win a tournament like that."

The final round, which was a best-of-three, took almost eight hours total, Wolpert said. It was an endurance contest that required sustained mental focus.

"I had to steadily drink coffee the entire time, because I was exhausted and I needed that caffeine fix, " he said.

A few co-workers from the Nevada ACLU came down to watch the finals and cheer him on, he said.

"We are happy for Leo that he won, but even happier that he has been a part of our legal team for the summer, " said Maggie McLetchie, a staff attorney at the Nevada ACLU. She said interns such as Wolpert help the organization take on important cases that they wouldn't otherwise be able to work on.

"We were impressed from the start with Leo's legal skills and his commitment to civil liberties, " McLetchie said. "Indeed, after his big win he came right into work the next morning raring to go."

As for similarities between poker and the law, Wolpert said analytical skill and logic are required for both, and that the perception that poker is strictly a game of luck is not accurate. Though luck plays a big part in one hand or one game, people who play the percentages will win over time, he said. 

"In poker there's a huge skill edge. Sometimes people will win a hand as a 3-1 underdog, but that still means that 75 percent of the time they are going to lose. But if you put your money on 75 percent every time, you're going to get a decent return over the long run."

Law School professor Josh Bowers, who taught Wolpert this past year, said he has a keen analytical mind that will serve him well both as a poker player and a lawyer.

"I congratulate Leo both on his stunning accomplishment and for the good work he's doing this summer at the ACLU, " Bowers said. "That said, he is never welcome to play in any of my friendly games. The embarrassment would be too great."

The World Series of Poker event win was also a redemption of sorts. In 2004, Wolpert appeared on the TV quiz show "Jeopardy!," only to become one of a host of challengers swept aside by long-running champion Ken Jennings.

Wolpert knew of Jennings' string of victories when he arrived to tape the show in August of 2004, but didn't know if Jennings was still a contestant, because of the delay between taping and airing.

"It was like I thought I was going to show up and play two average guys in basketball for some money, and one of the guys turned out to be LeBron James," Wolpert said.

The stinging defeat — he ended the game with $1 — was partially mitigated by the fact that the show aired around the time of the 2004 presidential election, and "most people probably weren't watching," Wolpert said. Still, it was in the back of his mind when he got to the finals of the poker tournament.

"I decided when I got this close this time, I wasn't going to let myself lag or make some ridiculous play that I didn't have confidence in. I wasn't going to make stupid plays, " he said.

Despite the big win, Wolpert has no immediate plans to return to the ranks of professional poker players. He said his poker winnings help him finance law school, and that he may even splurge on some personal items. No flashy cars, though.

"My car is alright. I might get a watch, but I'm not really a watch person. If I treat watches as badly as I treat sunglasses, it'll be a bad investment. I think I will get some fitted golf clubs. That's really the only thing I've thought of so far."

Founded in 1819, the University of Virginia School of Law is the second-oldest continuously operating law school in the nation. Consistently ranked among the top law schools, Virginia is a world-renowned training ground for distinguished lawyers and public servants, instilling in them a commitment to leadership, integrity and community service.

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