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From Mac McGarry to World Series of Poker

(Courtesy WSOP/IMPDI)

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, Wolpert left the studio in a similar state.

"I could never beat Ken to the buzzer," he said. "Timing is 90 percent of the game. He started kicking my ass, and I just started kind of choking almost, the Jeopardy equivalent of poker's tilt. I couldn't think straight at all, I was mashing the button, thinking, 'This is gonna be embarrassing.' "

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 still meant something.

"Again, was devastated," he said. And as with these other cases, Wolpert then threw himself into making sure that loss wouldn't happen again. He knew that poker was about skill, was "beatable," and he wanted to learn "not to suck," as he put it. So he started reading books. He started playing for extremely small stakes online, first depositing $50, then eventually buying into sit-and-go events for $20 or $30 at a time.

He graduated from Michigan, 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 in which the Supreme Court had sided with police. He dropped out of comp-sci school, became a professional poker play, moved back home to Fairfax with his parents, then moved into D.C. with a buddy who had pointed out that "we're 24, living with our parents, this is kind of pathetic." He traveled to Australia, Barcelona, and the Bahamas to play poker. He took the LSAT, entered law school at Virginia, and got a summer internship with 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 Hold'em event, and won that 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'll save the partying for Friday or Saturday," said Wolpert, who had been fueled by pretzels, popsicles and a latte during his title run. "I was so tired. I would have had one or two drinks and fallen asleep in my seat. That wouldn't be fun for anybody."

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 cell phone, I don't need a watch," he said. He hasn't yet treated his office mates to lunch, but "there will be many lunches on me, for many different people," he promised.

I asked why he went the ACLU route this summer instead of pursuing a paying gig; "To be honest, if I really wanted to make money, I just wouldn't get a job and would just grind online for 80 hours a week," said Wolpert, who configured a 30-inch monitor so he can play 12 online tables at once. "I wanted a job where I'd be doing work I actually believed in. I'm not lock step with the ACLU on all their opinions or beliefs, but I agree with the majority of them, and it really feels good to help defend people's rights. Even if I'm doing it for free, it just feels great knowing I'm helping protect the Constitution."

A few more things you should know. Wolpert is, of course, playing in the Main Event. He's a Wizards and Caps fan. He played defensive end at TJ, and won a couple of national championships with the Michigan quiz bowl team. He says he's "not even nearly the best poker player in my high school class," that "it's not even close." (He graduated with the legendary player Di Dang, with whom he regularly played pickup hoops at TJ.) And he's definitely heading back to Charlottesville, bracelet or no.

"I'm going back 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....It's not super competitive like some other schools, it's not drab and boring. A lot of our competitive impulses get taken out on the softball field instead of in the classroom. It's just a really good place to go to school, and poker may not last forever. A JD from U-Va.'s a great thing to have."

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

By Dan Steinberg  |  June 19, 2009; 10:44 AM ET
Categories:  Weirdness  
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Seems like a pretty humble, well-balanced guy, unlike a lot of the guys playing poker for even a part-time living. Now he has a decent bankroll to fund his playing and with a bracelet he will get invitations to tournaments all over the place. The downside is that there are so many a**holes on the WPT circuit which is why I stay at $5/10 online games where I can make enough to nicely supplement my income and the occasional table in Las Vegas.

Posted by: skipper7 | June 19, 2009 11:56 AM | Report abuse

Sometimes I wonder why all the famous alumni of my high school are poker players.

Posted by: the_slammer | June 19, 2009 12:23 PM | Report abuse

@the_slammer: I don't. We're geniuses...might as well make some cash in the process.

Posted by: sprinter319 | June 19, 2009 8:21 PM | Report abuse

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