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LL wasn’t in the car long with Ward 5 Councilmember-elect Kenyan McDuffie before the District’s newest elected official started talking about his “self-destructive” tendencies.

That’s a loaded term these days, considering the spectacular self-destruction of the last guy to hold the Ward 5 seat. Harry Thomas Jr. is set to report to federal prison soon, after pleading guilty to stealing more than $350,000 from the city.

But for McDuffie, who was taking LL on a brief tour of the old neighborhood haunts, it’s self-destruction of a much less worrisome, if more painful, kind. Like when he was a kid and jammed his finger playing basketball. After wrapping the finger in ice, McDuffie was so eager to rejoin the game that he sliced off the tip of a different finger in the door leading to his backyard. McDuffie also has ugly scars left from the time he cut his fingers on the sideview mirror of a parked car while he was playing football.

These days, voluntarily joining the current D.C. Council might well be considered a self-destructive tendency, too. McDuffie, who will be sworn in later this month, will be joining a legislative body filled with cold-blooded political operatives, smooth-talking lobbyists for well-funded interests and members who often actively hate each other. Throw in disillusionment over Thomas’ behavior, anxiety over the city’s demographic shifts, and ongoing federal investigations into Mayor Vince Gray and Council Chairman Kwame “Fully Loaded” Brown, and it’s a fraught time to be a politician in the District.

The big question is whether McDuffie—an affable, easygoing 36-year-old with no noticeable trace of cynicism—will thrive, merely survive, or get eaten alive in such an environment.

McDuffie obviously has high hopes for his service: While we were driving along neglected Rhode Island Avenue NE on our tour, McDuffie talked of wanting to make it a destination boulevard like what H Street NE is becoming. And he hasn’t been short on ambition in the past; he still remembers the August day in 1998 when he quit the Postal Service, leaving behind a secure government job with good money and benefits.

“My hand was quivering as I was handing in the papers, because I didn’t know what was on the other side,” McDuffie says. The postal employee who took the papers asked McDuffie if he was sure he knew what he was doing.

“No, not really,” McDuffie remembers thinking.

But the leap of faith paid off. McDuffie enrolled at UDC, then transferred to Howard University, where he graduated in 2002. After seeing his two older brothers drop out of college, McDuffie says he half-assed an earlier attempt at UDC, withdrawing from one class and failing another. But the second time around, he says he had a purpose, which, corny as it sounds, he says was to give back to his community.

After college came a stint in Del. Eleanor Holmes Norton’s office before law school at the University of Maryland. McDuffie, who says that in his youth he was occasionally harassed by police for being a young black man out late at night, says he initially “wanted to be the next Johnnie Cochran” but instead found himself drawn to the enforcement side of the law. After graduating law school in 2006, McDuffie worked as a prosecutor for the Prince George’s County State’s Attorney’s Office and in the Civil Rights division of the Department of Justice. He ran for the Ward 5 seat in 2010 and came in third behind Thomas and Delano Hunter, who he beat this month.

McDuffie says he left a good job at the Justice Department to make the long-shot run at Thomas because he was frustrated with what he felt was a lack of leadership. McDuffie hadn’t had much luck in city politics before that race: He lost a bid to be an ANC commissioner in 2002. After getting walloped in 2010, McDuffie worked as a policy advisor for Paul Quander, Gray’s deputy mayor for public safety.

McDuffie’s tour of his new constituency ended with a look at the spiffy brick alleyways near his house in Stronghold. He says he joined the local civic group in his 20s and played a key role in getting the bricks installed. At the end of one alley is a garage where several generation of neighbors have etched their name in brick. “Kenyan” is there, along with the names of McDuffie’s father, brothers, and other relatives.

“Boone, that’s my best friend’s dad,” says McDuffie, who lives with his wife and two young girls in the house where both he and his dad grew up.

As he reads, LL can’t help but think of the similarities between McDuffie’s and Thomas’ upbringing, and how they’re both products of tightknit, middle class Northeast D.C. neighborhoods.

For Thomas, getting into politics was a given: Both parents were in the game, and his father was a three-term Ward 5 councilmember. But McDuffie, who says his parents were never political, may turn out to be more of the natural pol. He surprised everyone with his lopsided victory in the special election to fill Thomas’ seat, which he won by forming a diverse, broad coalition and infusing it with something that’s been lacking in other recent city campaigns: genuine enthusiasm. Voters were drawn to the fresh face who promised ethical leadership.

Says Justin Fairfax, an attorney who grew up with McDuffie, “I think this was the thing he was born to do.”

We’ll know soon enough whether that’s true.

Photo by Darrow Montgomery

Got a tip for LL? Send suggestions to lips@washingtoncitypaper.com. Or call (202) 650-6951.