In the early 2000s, Jefferson Smith grew a reputation in progressive grassroots political circles as the hulking 6' 3" strawberry-blond force of nature behind Oregon's The Bus Project, a non-profit merry band of allies named for a 1978 touring coach bought on eBay, which busied itself , training scores of young people in the mechanics of democracy, signing up tens of thousands of new voters, and selling t-shirts emblazoned with the slogan "Vote, F*cker." In 2008, Smith won election to the Oregon House of Representatives, where he memorably convinced colleagues on both sides of the aisle to Rickroll the chamber, one word at a time. A well-styled and widely-circulated TED talk last summer on the structural opportunities of politics in the public interest added to his mainstream credibility as a big thinker. In some liberal circles, Smith, now 38, is the embodiment of the promise of netroots-generation politics: the idea that, as the Bus Project puts it, "democracy works best when more people do it"– even when throwing your mind, body, and soul into the process might look a little unhinged. Smith admits that friends think of him even now as "a golden retriever who is constantly picking up a bone, bringing it back, and not wanting to stop bringing it back." What Smith is up to now that might count as the most curious turn of his curious career: He goes into today's crowded non-partisan primary in a surprisingly good position to be the next mayor of Portland.

"Jefferson's brand of politics," says Colorado congressman Jared Polis, a Smith friend, "is about getting people involved." As an organizer, Smith's been deeply involved in bringing more people into the political process for more than a decade. "It's something we all talk about during campaigns now," says Polis. "But it can be incredibly difficult to enact while in office." Look no further than the Harvard Law School graduate, like Smith, now occupying the White House, and his struggles to apply the community organizing principles of his campaign to his presidency. But if anyone can really engage a wide swath of the public in running their government, says Polis, Smith is the one to do it. For the last nine months, Smith's been working hard at convincing the people of Portland of the same thing.

For a long while, it wasn't much working. "If someone was picking a presumptive favorite," a yawning, fidgety Smith says in a New York City café near City Hall on a January morning, "they wouldn't pick me." He'd gotten to the state legislature, sure, but he'd never held city-wide office like his opponent, former city commissioner Charlie Hales has. He'd run The Bus Project, but he didn't have private-sector business experience, like Eileen Brady, the long-time favorite in the race and a strong fundraiser. With his poll numbers barely breaking the single digits, he couldn't shake the aura of someone for whom a mayoral bid was just the latest in a string of civic experiments. As The Oregonian later put it in endorsing Hales, "on the stump and in interviews, Smith often seems more activist than executive."

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The night before we meet, Smith's campaign had thrown a fundraiser at Legends, a sports bar in Midtown Manhattan. It was a chance for Smith to reconnect with some old East Coast friends, raise a little money, and spread the word. It was also a reminder that, for some, Smith remains a national figure, no matter how local his ambitions might now be. Among the 70 or so people gathered in the bar's basement was a healthy helping of the better known figures of the liberal blogosphere and local grassroots politics, like Living Liberally's Justin Krebs, Democrats.com's Bob Fertik, and Matt Stoller, who made his name blogging on MyDD and Open Left. After Smith delivered his stump speech over the thumping tones of Gym Class Heroes, he opened up the floor to questions. One came from Stoller. Did Smith think, asked Stoller, that recent history suggests that the United States is at risk of turning into an authoritarian country?

Kinda, answered Smith. But his full response suggests that one thing he's learned on the trail is how to use the opening he creates by being "activist,"-per The Oregonian, to sell himself as plausibly executive. "We're going to have to figure out how to have a more robust middle class," said Smith to Stoller, "or we're going to have to figure out how to be more like Singapore." In other words, the growing gap between rich and poor is helping to foster friction, resentment, even violence. "If you have that, the only way to make sure that folks don't rob folks blind is to have more armed police." In a way, it's a strange answer. One imagines that the question implied worries about police crackdowns on Occupy Wall Street more than, say, concerns about neighbors stealing one another's stuff. But as the response of an activist-mayor, it makes a ton of sense, bridging existential political worries and the nuts and bolts of running a city. No mayor of Portland, Oregon is going to ever completely answer such fraught questions, admitted Smith. "But when I say, 'a commitment to democracy,' what I mean is a commitment to citizen rule."

"There has to be a town in this county where the people rule."

And that town, Smith has argued throughout his campaign, has to be Portland. After all, it's history is as a city where the public interest had real political pull. The turn of the 20th century saw the invention of "The Oregon System"-a blend of referenda, ballot initiatives, and other direct democracy measures like letting citizens suggest legislation. People-centric politics, the argument goes, held back corruption and created an environment for governing experiments that have turned out pretty well: the direct election of U.S. senators, land-use planning, voting by mail, public beaches, Labor Day. "At multiple intervals in American history, we've been willing to answer history's questions with a different set of responses," Smith said on the stump. What he is warning against is mistaking what has made Portland Portland as expendable quirks. "There are some powerful forces that would like Portland to be more like Phoenix with rainier weather," cautions Smith.

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Rather than ignoring what makes Portland different, he argues, the city's next mayor should double down on it.

The geography of the city has provided Smith with a powerful case in point. "They don't film a lot of episodes in my part of town," says Smith of IFC's Portlandia. Other candidates talk about the city's failed promise to East Portland, a once largely rural and suburban area mostly annexed in the '80s and '90s that lacks central Portland's public-transportation infrastructure, including bike lanes and bus routes. Smith, his wife, and their dog actually live there. "I need an East Portlandia," he says. As he sees it, as goes the relative racially, ethnically, and economically diverse East Portland, so goes Portland, eventually. "We've got to get the full city to make a commitment that this city has to work for everyone." Smith can be a rapid-fire policy wonk: ask him about "economic gardening," an approach to home-growing small businesses that came out of Littleton, Colorado. But in the end, his argument for mayor is basic: Democracy works best when there are more people on the bus. And at the moment, the bus isn't stopping in East Portland.

His all-aboard philosophy can get Smith in trouble. When he gained the endorsements of the city's police and fire unions, questions arose about how willing he might be in the future to keep up his detailed critiques of law enforcement. But the knock against Smith that seems hardest to shake is more personal. For one thing, he's young, a decade more so than either Hales or Brady. But his youth seems to serve to emphasize another trait: He can be disorganized. He's neglected to pay bar dues over the years. His driving record is less than stellar. "I would never hire Jefferson to be an administrative assistant," says Matt Singer, the executive director of The Bus Federation, a four-state umbrella organization that grew out of The Bus Project, who counts himself as a friend and strong supporter. "I just never thought that the job of mayor was to be an administrative assistant." Smith bristles at the notion that his story thus far is one of sloppiness and loose ends. He's run a major organization, he says. Hammered out policy. Passed legislation. Organized local programs.

"If they want to talk details, let's talk details." He pauses for a long time. "We have a real comfort with details."

Spend time around Smith, and it seems that when he describes his vision of Portland, he could easily be talking about himself-weird, maybe, but in a way that's a strength. His exuberance, his need to keep going back and getting that bone time and time again, the occasionally messy energy that flows from him, the actual cartwheels that he's willing to do to attract small-dollar donors-that's all part of the package. "Friends from school who are trying to change the world as investment bankers, for good or for ill, they put in a lot of hours," he says. "If we're going to change the world for the public interest, we're going to have to work really hard. It's not going to happen with seven hour days." His insistence upon working overtime seems to be paying off; polls last week put him, somewhat improbably, tied for first place in the mayor's race. Absent a majority, the top two vote-getters will go on to the general election in November.

If things go well for Smith, that will be the point at which he'll really begin to answer Polis's question about engaging people into the political process once you're actually in office. Smith talks about budget transparency, and of introducing to Portland the sort of non-emergency 311 system that can connect people directly to the parts of government most relevant to them. But from day one, Smith would have an organizer's challenge even closer at hand. Portland is distinct among big U.S. cities in having a city-commission style municipal government. The city council divvies up the portfolio of managing the city and the mayor is, really, first among equals. Getting anything done "just takes three votes," says Stacey Dycus, Smith's campaign director. A Mayor Jefferson Smith would find his strength in convincing other members of the city council to go along with him. It's organizer's task that, Smith argues, he's uniquely qualified to pull off.

As we finish up at that New York City café, I ask Smith what's next for him should he fall short in convincing Portlanders of the merits of having an activist-mayor. "I'll buy a flock of sheep," he jokes, "and tend to them."