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Jules Bailey went silent.
The Multnomah County commissioner trailed off midsentence as activist Sara Long approached him at the speakers' table at a mayoral candidate forum. A video recording of the April 7 confrontation shows Long—who had been spending her days occupying a Southwest Portland cedar tree as an act of protest—grabbing Bailey's name card from the table, then ripping it up.
It was not an isolated incident.
Since Bailey, 36, entered the mayor's race in January, his opportunity has been to present himself as the progressive alternative to Oregon Treasurer Ted Wheeler. In most Portland City Council races, the more liberal candidate typically wins, and many observers expected Bailey, a generation younger than Wheeler and the product of a middle-class, eastside upbringing, to make hay with his wealthy opponent's coziness with the city's business elite.
Instead, it is Bailey rather than Wheeler who has become the whipping boy for Portland's hard-left activists—who think he's insufficiently radical in the face of economic inequality and skyrocketing rents. In response to protests, Bailey has seemed dazed and robotic.
Bailey has so far squandered the chance to run hard to Wheeler's left and harness the anger of an electorate mobilized by housing prices and homelessness.
"If there was going to be a contrast, it would have to come from the left," says Portland pollster John Horvick.
Limited polling in the mayor's race shows Bailey badly trailing Wheeler, despite Wheeler's West Hills background and reported admission he'd rather be running for governor. Bailey's performance is doubly surprising, because in three terms in the Oregon Legislature, he established himself as an excellent lawmaker, skilled at wringing results from Salem's partisan battles.
Interviews with more than a dozen people who've worked closely with Bailey suggest his struggle in the mayor's race is the logical result of his pragmatic approach to politics—one that has always valued consensus and process over telling people what they want to hear.
"There are certain elements that can sometimes hope for a silver bullet," Bailey says. "There are rarely, rarely silver bullets."
Bailey grew up in the Hawthorne District and, after graduating from Lewis & Clark College and Princeton University, was voted into the Oregon Legislature to represent his old neighborhood. House District 42 in inner Southeast Portland is arguably one of the bluest districts in the state.
In Salem, Bailey was a quick study. He earned the highest score among rookie lawmakers in WW's 2009 survey of Portland-area legislators, "The Good, the Bad and the Awful." He quickly established a reputation as someone who would work with Republicans or fellow Democrats to pass complicated legislation. "The guy did an amazing amount of work, figuring out where there was resistance and making sure to address those concerns," says former state Rep. Tim Freeman (R-Roseburg).
Bailey's first initiatives included a bill that compelled power companies to allow homeowners to pay back energy retrofit loans on their utility bills. Rep. Brent Barton (D-Oregon City) worked with Bailey on the legislation, which provided the legal framework for what was then called Clean Energy Works. Barton credits Bailey for bringing opposing groups together to pass the bill nearly unanimously.
"Energy work is volatile," Barton says. "It has lots of competing interests, but he had a gift for moving progressive legislation."
Seven years later, the program is still running, and Bailey boasts it has improved the environment and created jobs. A 2014 report criticized the program for costing more than other retrofit programs by several measures, but Bailey maintains the analysis missed the point by not counting its impact on economic development.
If Portlanders in his district saw him as progressive, colleagues in Salem tended to think of him more as a workhorse.
Also in his freshman session, for example, Bailey helped craft a sunset provision for tax credits that otherwise needed a three-fifths majority vote to overturn. "He's one of those people who can take a problem, worry about it for a while, then come up with a solution," says Rep. Phil Barnhart (D-Eugene).
Later, Bailey led efforts to rein in Oregon's controversial Business Energy Tax Credit, an achievement that former Rep. Vicki Berger (R-Salem) likened to "changing an airplane engine in the middle of a flight."
Bailey prides himself on such measures. "I tended to take on a lot of technical issues that were hard but important," he says.
But Bailey also addressed other, perhaps symbolic efforts that kept him in step with his constituents' interests.
In 2009, he sponsored what became known as the Honest Pint Act to crack down on pubs that sold pints that were in fact less than 16 ounces—so-called "cheater pints." During the course of a normal health and safety inspection, a pub could volunteer to have its glasses tested. If its pints were in fact "honest," it would get a sticker to advertise. (It passed the House but languished in the Senate.)
"That was a good consumer-protection bill," says former state Rep. Nick Kahl (D-Portland), "even if it seems inconsequential."
Bailey also championed a bill pushed by the Bicycle Transportation Alliance known as the Idaho Stop bill. The measure would have allowed bicycles to make rolling stops at stop signs. But it failed in the face of lawmaker opposition. "We hadn't done the outreach," Bailey recalls, "and there was a lot of misconception that it was going to allow bicyclists to blow through stop signs at high speed."
Yet he fell out of favor with some in the cycling community, largely because he supported the failed Columbia River Crossing after initially opposing it.
As a Multnomah County commissioner, Bailey's work has similarly divided his attention between high-profile policies and behind-the-scenes work. County Chairwoman Deborah Kafoury tasked Bailey with helping to craft programs to address homelessness and the lack of affordable housing. But she also asked him to help area drainage districts re-certify their levees.
"Nobody's going to write news articles about the levee work," Kafoury says. "It's not going to get you on TV, and you're not going to be able to put it in the Voters' Pamphlet. Some people wouldn't do it, and he did."
When Bailey announced Jan. 9 he would challenge Wheeler to become Portland's next mayor, it was widely assumed he would stake out the liberal turf that helped Tom Potter defeat Jim Francesconi in 2004 and Sam Adams defeat Sho Dozono in 2008.
"I'm a dyed-in-the-wool progressive," says Bailey, who capped individual campaign contributions at $250.
On the campaign trail, however, Bailey and Wheeler have marched in lockstep on most issues.
"I've been to most of the candidate forums and they have not really been able to distinguish themselves from each other very much," says Chloe Eudaly, a candidate for the Portland City Council running against Commissioner Steve Novick.
Meanwhile, hard-line left-wing activists—and several of the 13 additional candidates seeking to replace Mayor Charlie Hales—have focused their criticism almost exclusively on Bailey.
"If you really gave a crap about homelessness or affordable housing," activist and candidate Jessie Sponberg shouted at Bailey at an April 8 forum, "you wouldn't be throwing away your position at the county for a mayor's seat when you're only polling at 8 percent!"
Bailey shrugs off the criticism, saying it's to be expected when you're probably in second place and others are trying to make it into a two-way November runoff with Wheeler. (His camp says the poll that put Bailey at just 8 percent is inaccurate.)
But Bailey also fundamentally disagrees with the activists' specific calls for reform, saying they are unrealistic and perhaps illegal.
"People were frustrated with me that I wouldn't push the county commission to enact immediate rent control, but I don't believe it's legal to do that," he says. "I don't believe it's something we have the tools to do. And while I think we should have that debate locally, I think it's still a debate about whether that's the most effective way to deal with the housing crisis."
Bailey's chances of advancing past the May 17 primary depend on finding like-minded voters who are progressive but also pragmatic. He says they're out there, and on a recent walk through Southwest Portland's leafy Maplewood neighborhood he unexpectedly proved it.
Trudging down the steep hill of Southwest 51st Place, campaign leaflets shielded from a light drizzle under his Army green jacket, Bailey approached a $600,000 house. Dave Drescher, a U.S. Fish and Wildlife employee on the verge of retirement, stood next to his garage sorting items to go to Goodwill.
"Hi, I'm Multnomah County Commissioner Jules Bailey and I'm running for Portland mayor," the candidate told Drescher.
Like a lot of voters, Drescher told Bailey he's concerned about homelessness and housing affordability. He bought his house in 1995. Today, he says, he couldn't afford it. But he was mostly at a loss for how to address the twin problems.
"There are no silver bullets," Drescher said, bringing a smile to Bailey's face.
"I was just saying that," Bailey replied.
Willamette Week