No endorsement decision for the November ballot generated more debate here at WW than the choice between the incumbent mayor, Ted Wheeler, and challenger Sarah Iannarone.
Wheeler came in first in the May primary, but because he did not win more than half the votes, he was forced into a runoff this November with Iannarone. In the past five months, his political fortunes have resembled a blob of Silly Putty sliding down a wall, at an accelerating pace.
Most of his problem: a wildly inconsistent response to the nightly protests touched off by the Minneapolis police killing of George Floyd on May 25.
Wheeler, 58, who is also the police commissioner, has been reactive, isolated and indecisive. As a consequence, he has been closely linked to the Portland Police Bureau's riot cops, who have been caught on video ambushing and battering protesters (and the press). Meanwhile, he's incurred the wrath of downtown business owners who think he's acted too timidly—both in finding a way to end the protests and stemming the expansion of homeless camps.
That's why, having beaten Iannarone by 25 points in the primary, Wheeler now faces the very real prospect of losing to her.
Iannarone, 47, an urban policy wonk and former small business owner who ran against Wheeler in 2016 and finished third, has made the most of Wheeler's struggles, pummeling him on social media and running a vigorous campaign that has tapped into the discontent many Portlanders feel.
Their respective résumés could hardly be more different. Wheeler, a graduate of Stanford, Columbia and Harvard, is the heir to a multigenerational timber fortune who served as Multnomah County chair for four years, followed by six years as state treasurer. Iannarone, who has a bachelor's degree from Portland State University, served on the Mt. Scott-Arleta Neighborhood Association, led an effort to fix up a surplus city property there, and for a decade worked at First Stop Portland, a nonprofit that marketed the region's planning and transportation achievements. She's never held office or led an organization of any size, let alone one comparable to the city of Portland, which has a $5.6 billion all-funds budget and 7,500 employees. Earlier in this decade, she and her then-restaurateur husband didn't pay state income taxes for four years.
But campaigns are not run on paper. Iannarone is razor sharp, a good communicator, and adept at contrasting her scrappy, community-oriented style to Wheeler's awkward demeanor.
Iannarone has sketched out a sweeping vision of City Hall in which every citizen gets a say—in budgeting, policy and process—and she'd immediately hand over responsibility for the city's largest general fund bureau, the police, to Commissioner Jo Ann Hardesty.
Teressa Raiford, the founder of Don't Shoot Portland and a longtime Black Lives Matter activist, finished third in May. But some activists are running a write-in campaign for Raiford, 50, arguing she best represents the energy of the protest movement and can directly advocate for people of color. Raiford's critique of the Police Bureau is necessary, but she has not demonstrated the expertise required for this job.
Wheeler has the technocratic soul of a city manager rather than the empathic knack of a skilled retail politician and has at times engaged in self-pity.
At the same time, Wheeler has also demonstrated a deep understanding of the ways in which this complicated city functions, and his term in office has generated real progress. He fixed structural problems with the Portland Clean Energy Fund and ushered across the finish line the residential infill project, an ambitious and controversial plan to place fourplexes amid single-family homes and, in so doing, increase housing density and affordability. He's also hired two Black police chiefs and built a mostly solid alliance with Hardesty, at least until he refused to cede oversight of the Police Bureau to her. He's bird-dogged the city's spending on affordable housing and structured a complex, innovative deal to redevelop a large swath of downtown surrounding the former post office.
Wheeler's shortcoming—and it's a big one—has been his inability to find the right response to the protests. Some of us on WW's editorial board believe Wheeler abandoned ship in a fog of tear gas—a failing that's more severe because he pledged four years ago to make police reform a top priority. Like many politicians in 2020, he was presented with the crisis he was least personally equipped to handle, with predictably dire results.
While we understand the desire to toss out the incumbent, we're not ready to do that. For one thing, Iannarone leaves us with serious doubts. She has repeatedly inflated her academic credentials in the Voters' Pamphlet. And her combative social media presence displays both hostility and a lack of discipline.
Leaders govern in the same way they campaign. And for much of four years, Iannarone has pilloried anyone who disagrees with her. She has too often sought the applause of her fans by excoriating and embarrassing potential allies.
That matters because if Iannarone wins, she would have to negotiate with people she has dismissed: business owners frustrated by looting and homeless camps; police officers who want more job security, not less; and the vast majority of Portlanders, who aren't on Twitter and don't go to protests.
In addition, it's worth considering the coming makeup of the Portland City Council. It will consist of Hardesty, elected in 2018; Commissioner Dan Ryan, elected in August; Carmen Rubio, who takes office in January; and, very likely, according to polls, newcomer Mingus Mapps.
It could be one of the most inexperienced council lineups in Portland history, at a time when the city will face extraordinary management challenges. Placing an untested council in the hands of a mayor with Iannarone's limited track record is an enormous risk.
Wheeler has relationships with business and labor—pillars of this city that will need all the help they can get digging out of Great Depression-sized job losses. A mayor needs such relationships. Iannarone hasn't shown much ability—or inclination—to build them.
The next mayor faces a daunting challenge. Not since 1957, when Robert F. Kennedy grilled Portland mobsters about corruption, has this city suffered such damaging blows to its reputation as it has in 2020. Its downtown storefronts are shuttered. Its police force has disgraced itself. The president and his fascist fanboys have picked our streets for showdowns. Citizens who are not furious are weary and despondent.
The candidate whom voters choose as mayor in three weeks must summon Portland's historic virtues—creativity, pluck and cooperation—to rebuild the city. We think Wheeler is more likely to do that.
Wheeler's most awkward moment on Zoom: He got caught playing the ukulele—badly—on a staff call. "I thought I was muted," he says.
Portland City Council, Position 4
When Chloe Eudaly defeated incumbent Commissioner Steve Novick in 2016, it was an extraordinary upset. She ushered out a longtime political insider on a platform that promised to shift power from landlords to tenants in the middle of a rash of rent hikes and residential evictions.
Stylistically, Eudaly, 50, has mirrored her predecessor. Like Novick, she can be insular, thin-skinned and uninterested in sitting down with those who disagree with her.
But Eudaly, a former independent bookstore owner, has earned our endorsement because she has accomplished quite a bit in four years, most of which we agree with, by focusing city policies on aiding those who can't afford to buy a home and who are more likely to clean offices in the city than sit in their boardrooms.
She forced landlords to pay tenants they evict without cause, ended discriminatory renter screening practices, and pushed through street improvements that will speed up buses.
For a novice with little management experience, Eudaly proved adept at surrounding herself with capable staff. She successfully oversaw two of the city's key bureaus, the Portland Bureau of Transportation and the Bureau of Development Services, finding new leadership for each.
She had less success with a smaller bureau, the Office of Community & Civic Life. Mayor Ted Wheeler had asked her to fix the broken bureau and the city's relationship with its 95 neighborhood associations.
But her efforts resulted in an avalanche of complaints from current and former bureau employees and a revolt by the neighborhood associations, which felt Eudaly wanted to get rid of them. The reaction was so strong it both stopped her reforms cold and ushered an opponent into the race: Mingus Mapps, a former employee of the bureau.
Mapps, 52, earned a Ph.D. in political science from Cornell and taught at the university level for a decade before going to work for the city. He is making his first run for office. His campaign is short on specifics: Until a week before ballots were mailed out, much of his platform still hadn't made it onto his website. His views are clearest on the current form of city government: He thinks it should be scrapped and replaced by a larger City Council, elected by district, that would delegate bureau management to a professional city manager.
Mapps' position on policing is less clear: He took the endorsement and $15,000 from the Portland Police Association in the May primary, yet says he doesn't agree with the police union on much of anything. His basic position is to increase civil discourse, even with his opponents.
Mapps is a good talker and, unlike Eudaly, an extrovert eager to meet with people, whatever their outlook. That's a plus—and unlike some of the Police Bureau's critics, we don't think his willingness to talk to the cops union is disqualifying,
Where Mapps comes up short is his lack of a burning desire to make specific changes. That's where Eudaly has shined.
When she ran in 2016, Eudaly made it very clear if elected she'd push hard for changes that would ease renters' pain. She has. Her relocation ordinance compensates tenants when evicted; another ordinance she passed makes it more difficult for landlords to exclude prospective tenants based on their prior history; and she worked at the state level to make rent control a reality. Eudaly delivered on her promises, held true to her principles and, as transportation commissioner, advanced her agenda to create better transit for Portlanders who take the bus—pushing through the Rose Lane Project to dedicate bus-only lanes across the city to lower commute times.
Eudaly is often her own worst enemy (that's why she is seriously behind in this race), but we've never had any question about where she stands. She's often right, never in doubt, and gets stuff done. Vote for Chloe.
Eudaly's most awkward moments on Zoom: Trying to tend to her son and hold meetings simultaneously.