Last month, Jim Middaugh was camped out in his dining room—which doubled as a command center—coordinating volunteers who were fanned out across Portland, collecting $5 contributions and signatures for his bid for public campaign financing. Defying expectations, Middaugh turned in 1,623 valid contributions in just two weeks, following City Commissioner Erik Sten's sudden announcement that he was leaving office later this spring.

This month, Middaugh's found a campaign office on NE Sandy, ordered lawn signs, and is planning both a neighborhood canvass for March 1 and a party at the Green Dragon Bistro & Brewpub for March 2 "to talk about how we'll run a winning grassroots campaign." Middaugh and his opponents have little more than two months before voters start receiving their ballots in the mail.

His main opponent Nick Fish had only $5,290 in the bank as we went to press on February 26—compared to Middaugh's expected $140,535 check from the city now that he's qualified for public funds. However, Fish has name recognition from two previous council runs.

Not so for Middaugh, who has spent most of his career working behind the scenes in environmental organizations and government, segueing between advocacy and public affairs. After picking up a journalism degree from the University of Oregon, he worked for two congressmen—Jim Weaver, then Peter DeFazio—before heading to the Environmental Defense Fund in Washington, DC, to be the press director. Back in Oregon, Middaugh worked for groups like the Oregon Natural Resources Council, and the Northwest Power and Conservation Council.

Along the way, he met Sten at a house party for the commissioner's first campaign in 1996. "I wrote him a $100 check," Middaugh says, explaining that it was the biggest political contribution he'd "ever written." He helped Sten get elected, and eventually landed in one of Sten's bureaus, as the city's endangered species program manager. These days, he's Sten's chief of staff.

It was Sten who urged him to run for the vacated seat. While grabbing lunch one afternoon in mid-January, Middaugh mentioned that a few people had "surprised" him by suggesting he run, even pledging financial support. Sten agreed that he should go for it—adding, "You've got to go voter-owned," according to Middaugh. But he'd watched other candidates take months to collect the required 1,000 contributions—and Middaugh had just over two weeks. "I was really honored, but freaked out."

After a weekend of calling people in his network, however—"We know a lot of people," Middaugh says of himself and his wife Anna, citing their work on political campaigns, in their kids' schools, and in the community—he had enough pledges from people willing to collect $5 contributions.

Middaugh hopes to pick up where Sten left off on his signature issues of homelessness and affordable housing, while also focusing on schools, the environment, and Portland's livability.

On affordable housing, he'd like to explore bringing "another housing opportunity bond," to the ballot. "Let's make some investments."

And on the homelessness front, he supports Sten's 10-year plan to end homelessness, with its housing-first model. But going a step further than Sten, Middaugh is outspoken on the criminalization of homelessness, calling it "absolutely wrong and inappropriate." He wants to revisit the city's camping and sit-lie ordinances, and thinks private security downtown is unfairly targeting the homeless—a stance that puts him out in front on the issue.

"I'm an organizer, rabble-rouser, activist type," he says, adding that he's eager to employ his "what do I have to do today to get things done" philosophy on the city council.