Jefferson Smith wants to loom large in the mayor’s race, and not just because he’s the tallest candidate so far (6 feet 4 inches), but because he sees himself as an alternative to former City Commissioner Charlie Hales and businesswoman Eileen Brady. 

Smith, 38, grew up in California and Portland, graduating from Grant High School and the University of Oregon before earning a law degree from Harvard. He’s now in his second term in the Oregon House representing Southeast Portland (he lives in the Hazelwood neighborhood).

He didn’t last long working for law firms, preferring politics instead. He’s best known as founder of the Bus Project, a get-out-the-vote organization launched in 2002 that seeks to involve young people in politics. (Full disclosure: Smith and the Bus Project work with WW on the “Candidates Gone Wild” election-year showcases. )

Smith’s experience as a political organizer and potential favorite of labor unions (and their money and supporters’ help) could allow him to triangulate in a race against Hales and Brady. He also trumps them in one area of the city they’ve been playing to: east Portland, where he’s already shown he can win.

Smith also entered the race late and is famous for his frenetic, verbose style that leaves many associates wondering how effective a mayor he would be. Smith has publicly acknowledged he has attention deficit hyperactivity disorder—he blamed his condition in part for his failure to pay his bar dues.

In a two-hour interview, we asked Smith about his past accomplishments and top issues, the economy, the Police Bureau, engaging citizens in civic debate and how his ADHD does and doesn’t matter. We also talked about his performance as a legislator, his political history in high school, and why he’s like the giant Soviet boxer in Rocky IV.

WW: You say you quit your first job out of law school, with New York City law firm Wachtell, Lipton, Rosen & Katz, because you didn’t like the firm’s representation of tobacco companies. Is that the one industry that created ethical problems for you?

Jefferson Smith: Yeah.

If it had been Exxon, you would have been fine?

Yeah, probably. I was briefly at [Portland law firm] Stoel Rives and I gave a speech at a Labor Day picnic, where I criticized Enron and Capital Consultants in a speech. And then afterwards I realized, wait a minute, those are both clients of the firm.

You stayed about a year at Stoel Rives.

About the same time I started there, I started the Bus [Project]. I was thinking it would be a sort of avocation. Ended up doing, trying to do both things for a year, a little better. And went to half time for a little bit. You know, ended up getting probably a C in one, a D-minus in the other.

Did they ask you to leave? 

I had lousy billable hours, but I—both because I was trying, essentially, two very full-time jobs. I think the phrase that was used [was] “a mutual parting of ways.”

You probably spent $150,000 going to law school. As we’ve learned, you weren’t a terribly active voter in those days. What made you throw away a comfortable living for a nonprofit in an area that you didn’t appear to have a burning interest in?

The thing that helped motivate the Bus were a series of conversations with people of my generation. And we were looking at ourselves like, you know what, maybe we’re lazy bastards. Or if not lazy, selfish. The [Harvard] Kennedy School of Government in the ’70s, the ’80s sent three-quarters of its graduates to public service. And in my graduating year, I think they sent one-third.

What would you say is the single greatest accomplishment of the Bus Project?

In 2004, Oregon had one of the biggest gaps between older voter turnout and younger voter turnout in the country. In 2008, Oregon had one of the five smallest gaps and the biggest growth in youth vote share in the country. It was the Obama year, which certainly played a role, but Obama was running in every state of the union. And there weren’t yet buses in other places.

The [second] most significant contribution will, in 10 years, be the easiest to tell a story about—the people who came through and the leaders that were developed.

How about biggest failing?

I think we would have had some impact on voter registration, which, in 2010, Oregon saw a dip. I think the Bus bears—that I bear—some responsibility for that. I think had I put my energies into it and the Bus’s energies into it, we would have passed voter-owned elections in Portland in 2010.

When we met you five years ago, it was clear you were running for office someday. When did that first occur to you? 

I think any kid who is precocious and verbose without being entirely obnoxious gets, “Oh, you’re going to run for office one day.” I think the first time I was told I was going to be president, I was 14 and I was running for, you know, high-school student council and we were doing a car wash.

What was your slogan?

I think it was “fresh start.”

Did you win?

No, I didn’t win my first election. I think I was appointed.