jefferson smith
Image: Daniel Root

Jefferson Smith at David Douglas High School

The Outlook


“There was no obvious funding for the streetcar or, for that matter, Pioneer Courthouse Square.”

If Hales becomes mayor, what’s the next “big, bold thing”? “We’ll find it,” he says—and how to pay for it. His own possibilities include transforming a defunct rail line along the Columbia into a cycling path to Astoria, and an idea seldom discussed since his days in City Hall: burying the east-bank freeway(That project was once penciled out at as much as $5.8 billion in 2003 dollars). Hales also cites unpaved roads, the many “five-acre blackberry patches” that could become East Portland parks, and making every neighborhood “a complete community” through classically Portland planning and development.

Hales scored a political coup by landing the endorsement of Vera Katz, the enduringly popular ex-mayor under whom he served. Otherwise, his campaign, so far, has a low-key feel. Hales shows up at the pool solo (his two chief rivals are escorted to their photo shoots by a campaign staffer), shortly after finishing the annual Worst Day of the Year bike ride, and leaves for a small coffee date with potential supporters.

Hales’s style leaves him open to criticisms that he’s fighting the last war. The build-it-and-they-will-come approach of the ’90s and early ’00s—when Portland developed huge chunks of the central city around the rail and streetcar projects Hales supported—may not fit the tight budgets and ever-more-complex economic and social issues of the ’10s.

In his council days, Hales could be sprightly, combative, and rarely shy about seeming the smartest guy in the room. These days, he exudes a more mellow energy: the wise uncle who’s seen a few things, but wants to see a few more. In a race that might, in the end, last more than a year start-to-finish, knowing a few local political war stories by heart could come in handy. Hales obviously thinks so.

“There’s no learning curve for this job. You become mayor right away when you’re sworn in.”




“I’m new to the political scene, and I don’t know how to talk in sound bites.”

The specifics of Brady’s policy proposals—and she can wonk with the best of them—seem to matter less, for now, than her larger message: that she could unleash Portland’s ambitions to be simultaneously sustainable, lively, and prosperous. And despite her yen for PowerPoint-speak, Brady is the candidate closest to catching fire. She leads the few early polls. She’s racked up a rangy list of endorsements that somehow spans the downtown-centric Portland Business Alliance, Portland General Electric, and the local Green Party, along with several usually apolitical tech executives like venture capitalist Nitin Khanna and Urban Airship founder Scott Kveton.

To get to this early lead, she spent a lot of money by the standards of Portland politics: over $400,000 at press time. According to campaign staff, her rookie status required expensive new mailing lists and other infrastructure for an “aggressive” push. “She started with about 80 donors and her personal e-mail list,” campaign director Jon Isaacs says. “We needed to introduce her to voters.”

A high burn-rate (to borrow a term from, yes, the entrepreneurial world) may indeed be working for a candidate who wants to jump straight from political obscurity to the city’s executive suite. Brady does seem to be assembling an alliance—big business, small business, green activists—not quite seen before in Portland politics. If she succeeds, the real test begins. The other denizens of City Hall might make her nostalgic for Zenger’s chicken coop. Meanwhile, Portlanders have seen two promising mayors—Tom Potter and Sam Adams—vow transformational leadership, only to limp away after a single term.

To Brady, it’s all about building new coalitions. “Zenger was once one of those cool little ideas that could be big, but it was just a piece of land until we found the right team of supporters,” she says.

“New Seasons succeeded because we pulled together conservative farmers and urbanites who think going to yoga is the same as going to church.”

“It’s all about finding things that unite us.”




“I had never considered running for a city office.”

Generally viewed as the race’s wild card—the upstart who might burn brightly or just flame out—the 38-year-old Smith is a full generation younger than rivals Hales and Brady. Observers tend to credit his palpable smarts—but also warily describe him as “frenetic.” He’s copped to an ADHD diagnosis (now under control, he says) and an “atrocious” driving record. His dog has a Twitter account.

For Smith, the outer east side—which, he points out, would be Oregon’s second largest city—is both a home base and a metaphor for those Portlanders who have not joined Portland’s rise to coveted livability and cultural quirk.

“I realized that if we have another 10 years of underinvestment in neighborhoods that lack political connections, it will be too late to act,” he says. “We’ll lose a chance to create a Portland that works for everyone.”

Smith aims to be the race’s truth-to-power progressive outsider; hence, in part, his choice of David Douglas. “People around here tend to be less avid members of the chattering classes,” he notes. In mid-February, Smith landed the endorsement of an influential pro-cycling and transit group. He’s the candidate most forthrightly critical of the proposed massive (and, some feel, massively flawed) Columbia River Crossing bridge project.

A candidate trying to win the mayoralty by talking up Portland’s least connected neighborhoods will certainly need insurgent strength. Perhaps conveniently, Smith debuted in local politics by founding the Bus Project, a youth-oriented voter turnout initiative that’s become a finishing school for earnest progressives. Whether Smith’s get-out-the-vote expertise (and connections to potential foot soldiers) can shift the relatively small electorate likely to turn out for the city primary remains to be seen. But as he strides the asphalt at David Douglas, Smith seems determined to be a different kind of candidate.

“We need one of the most robust grassroots campaigns in the city’s history.”