Since Portland Mayor Ted Wheeler first announced his run for re-election, his bid has been framed as history-making.
Related: OPB’s 2020 election coverage, ballot guide and results
For the first time in two decades, a mayor would be seeking a second term, offering a city starved for stability someone who could enter office with his sea legs already under him. In a city so difficult to govern that mayors are applauded for trying it twice, Wheeler’s announcement was a big deal.
But months of protests have opened the door to another historical outcome: for the first time in three decades, it is distinctly possible that a Portland mayor could be unpopular enough to lose reelection.
For months, Wheeler has been lambasted for a mishandled protest response from all sides. His nickname includes a chemical weapon. The section on his Wikipedia page devoted to his mayoral tenure is now primarily about his protest response. The entry is not particularly flattering.
The mayor emerged from the May primary with the support of half of Portland’s voters. Polling conducted last month showed two-thirds of Portlanders viewed Wheeler unfavorably.
“I see that and I would be shocked if he won,” said Steve Novick, a former Portland city commissioner who not so long ago saw his own lukewarm approval ratings foreshadow voters booting him from office in favor of an insurgent bookstore owner, Chloe Eudaly.
In the lead up to the primary, it was Sarah Iannarone, the wonkish, untested community activist opposing Wheeler, who local politicos painted as the clear longshot. Running against an incumbent is hard. In the midst of a crisis, say a global pandemic, it’s harder. If you are running with no elected experience of your own to tote, well …
After a brutal summer for the mayor, the certainty with which some predicted Wheeler clinching victory has vanished. Grim favorability numbers have translated into low polling numbers. And the city’s mayoral race now appears to be a toss up between a candidate far to the left with no experience holding political office and an incumbent whose record as a moderate has earned the ire of Portlanders on both sides of the political spectrum.
A rocky first term
Late last month, David Kahn, former president of the Minnesota Timberwolves and friend of Wheeler, sent out a note to his friends, family and other contacts, urging them to vote for his friend Ted.
“Yes, that Ted Wheeler,” the letter read. “This will not be your typical pitch.”
It was not. The note urged voters to stand with the mayor they knew rather than cast a protest vote for an untested candidate without experience in government. But it also sought to acknowledge what Kahn seemed to assume most of his neighbors were thinking anyway: “Ted’s first four years in office were fair-to-middling.”
Four years ago, Wheeler’s bold progressive promises and a formidable resume fueled an easy victory against former Multnomah County Commissioner Jules Bailey and Iannarone, who was making her initial bid for mayor. With a decade of elected experience as the Multnomah County chair and Oregon state treasurer and degrees from Harvard, Columbia and Stanford, The Oregonian crowned Wheeler’s CV “one of the most impressive resumes of anyone running for Portland mayor in a generation.” Wheeler pledged to harness this experience as an executive to enact transformational change: improving the community’s strained relationship with its police force, demilitarizing officers and — in perhaps the biggest lift of all — providing everyone sleeping outside with the option of a shelter bed.
It was an ambitious, progressive platform. These are not the adjectives people generally use to describe the term that followed.
While the administration has overseen an increase in the number of shelter beds and homeless services, homelessness remains an intractable problem for the city. The mayor himself is signaling that, after four years, the city needs to change its approach. Months of protests have unraveled the frayed relationship between Portlanders and police to the point that his colleague Commissioner Jo Ann Hardesty has considered trying to create a Truth and Reconciliation Commission modeled after what was done in South Africa post-apartheid.
Granted, these were massive, messy problems, and the mayor’s supporters point to many reasons he struggled to deliver. The city’s unique form of government, in which commissioners have almost as much power as the mayor, gave Wheeler little space to push big agenda-setting ideas forward. He was hamstrung in the early days by a staff that didn’t always appear up to the job. It’s hard to solve nearly insoluble problems when you’re constantly beset by crises.
But some simply blame a leadership deficit in City Hall.
“I’ve worked with Ted over the last four years and he’s a nice guy, and he’s a smart guy, but he’s not a leader,” said Milwaukie Mayor Mark Gamba, who added he’s grown frustrated with Wheeler’s lack of urgency on his signature issue of climate change and supports Iannarone. “He’s not somebody that’s going to get out in front of something and cause significant change.”
A summer of protests have churned the general disenchantment with Wheeler’s approach to the job into palpable rage. Furious over his inability to reign in the force used by his police department, protesters dubbed him “Tear Gas Ted,” learned his address and made a habit of storming the lobby of his Pearl District condo. After a self-proclaimed antifa supporter fatally shot a far-right rally participant, a group of progressive organizations blamed Wheeler’s hands-off leadership and called for him to resign. And after months of graffiti and smashed windows in downtown Portland, some business owners and conservatives feel the city’s top elected has given protesters a free pass on lawlessness.
To some of these factions, Wheeler has seemed paralyzed by indecision on who to support and what to do. The mayor argues that’s not a fair reading.
“People believe if you don’t pick a side, you’re not leading,” he said. “My style of leadership has always been the same: I have constituents throughout the community who represent a diversity of needs and opinions, and I seek compromise. I don’t think compromise is a dirty word, and I seek the elusive center — that’s what most successful mayors do.”
In an interview with OPB, Wheeler said if reelected he’d enter his next term on sturdier footing, with his first term serving as something of a crash course in governing during crises.
This promise of a steady hand has earned the mayor support from labor and business groups that have established relationships with Wheeler over his term. UFCW Local 555, SEIU and the Northwest Labor Council are all listed as endorsing Wheeler under his headshot in the voter pamphlet.
Voters will not, however, find the name of Commissioner Jo Ann Hardesty. She pulled her endorsement of Wheeler this summer, citing his handling of the police as a key reason. Days after she announced she wouldn’t endorse anyone in the race, Commissioner Amanda Fritz threw her support behind Wheeler.
“He’s really concerned about fiscal responsibility and spending taxpayers' money wisely. ... He’s had the experience of leading many of the bureaus personally himself and also having worked in City Hall for these four years,” said Fritz, who is leaving the council at the end of this year. “It’s not a time that we have the luxury or time for a new person to start understanding how that works."
Supporters such as Fritz point to the mayor’s plan to use tax dollars to pay for bonds for deteriorating infrastructure as an example of his financial acumen. As an example of his ability to skillfully lead, supporters point to his successful push to convince Gov. Kate Brown to issue a stay-at-home order at the onset of the coronavirus pandemic in Oregon. Other highlights of the mayor’s tenure include overseeing the final stages of the residential infill project, a mammoth zoning code update to increase density the city passed this summer; tackling a $75 million COVID-caused hole in the budget; and successfully managing the implementation of the affordable housing bond voters passed in 2016.
Some supporters say that while these changes were important, Wheeler didn’t knock it out of the park.
“I don’t think Ted’s record is such that somebody would say, ‘Oh my Lord, these last four years have been out of this world,’” said Kahn, the former Timberwolves owner and Wheeler supporter. “To use a sports analogy, I think he’s hit a lot of singles and a couple of doubles.”
But Kahn said he believes Wheeler’s first-term difficulties are behind him and “a page has been turned.” Plus, he contended in a call with OPB, just as he did in his letter to his friends and family, Portland is not ready for the alternative.
“I’m very concerned that Portland would make a mistake of colossal proportions that could set back this city by decades if people were to elect his opponent,” he said. “Because I don’t think that she is a consensus builder or has any demonstrated experience or competence to manage a $5.6 billion budget or fight for more assistance from Salem or D.C., which we’ll sorely need.”
"I’m very concerned about having a mayor who walks into meetings and people say, ‘You’re that antifa mayor, aren’t you?’”
A challenge from the left
Sarah Iannarone calls herself an everyday anti-fascist.
“What she means by that is we fought the Nazis in World War II,” said Mark Lakeman, a friend of Iannarone’s and co-founder of nonprofit City Repair Project. “You’re supposed to be tiptoeing around that identity because antifa is being vilified, and she knows that’s not true.”
Iannarone has said she wants to clear up the discourse around the ideology whose uniting principal is opposition to fascism. Misinformation swirls around the far-left activists the president has sought to link to violence and destruction. Her willingness to double down on a statement that’s bound to turn off some portion of voters and likely confuse a whole lot more emphasizes what is likely obvious to anyone watching this campaign cycle: Iannarone is not a typical Portland mayoral candidate.
She was raised in the rust belt factory town of Fulton, New York, not far from the Erie Canal. Her father worked as an electrician in the town’s Nestle factory and her mother taught special education. Voter records show Iannarone registering as Republican at the age of 18, but she said it must have been a mistake or maybe a joke. She said she’s always been liberal.
She started a catering business in Fulton as a teenager and refined her craft at Johnson & Wales University in Rhode Island. She didn’t graduate and left Providence to cook in kitchens across the country — Charleston, South Carolina; New Orleans; Branson, Missouri. She moved to Portland in 1998 with her then-husband, Nick Iannarone, and landed a job as a pastry chef at the now-closed Lucy’s Table on Northwest 21st Avenue.
“She’s still just the same. In the work atmosphere, very meticulous, very particular about how she does things,” said Peter Kost, who owned Lucy’s Table at the time and now runs Carina Lounge on the same strip. “She pushed me really, really hard to get [health] insurance for the staff. And it’s expensive now. But it was obviously expensive then, and she pushed me for the whole time she was there”
He eventually agreed. But at that point Iannarone had moved on. She took a few years away from the industry after her daughter was born in 1999 and then started a restaurant with her then-husband in their neighborhood; the Arleta Library Café was known for its baked goods. It closed due to financial struggles early in the COVID-19 pandemic.
She completed her undergraduate degree at Portland State University in 2005, and went into the Ph.D. program in urban studies and planning. She hasn’t yet defended her dissertation, a fact that made headlines after Jules Bailey, an opponent in her first run for office, filed an election complaint saying it was misleading to put Ph.D. (ABD) — the latter acronym standing for all but dissertation — on her voter pamphlet statement. Iannarone stands by the listing.
In 2008, she helped start up Portland State University’s First Stop Portland, a program that organized tours for foreign delegations on Portland’s sustainability infrastructure. Iannarone has said her decade spent at First Stop and experience as a neighborhood activist gave her a sense of what worked in Portland and what the city needed. It’s influenced extensive policy proposals — on the environment, public safety, housing, governance, the economy and COVID — each thousands of words long with accompanying podcasts.
If elected, she wants to end homeless camp sweeps, implement a residency requirement for new Portland police, decriminalize sex work, and see the city become carbon neutral by 2030, to name a few of the many progressive planks in her platform. She has earned the support of progressives including activist Cameron Whitten, State Rep. Karin Power and Oregon Justice Resource Center executive director Bobbin Singh. Former Portland Commissioner Steve Novick threw his support behind her candidacy this month after coming across a line in her environmental platform on banning natural gas in new homes, an idea he, too, was fond of but did not foresee happening under Wheeler’s leadership.
But how adept Iannarone will be at turning these progressive policy proposals into reality if elected is an open question. Parsing her resume, voters will not find any experience in elected office or overseeing a large organization. Voters are deciding who they want to manage a $5.6 billion budget, oversee thousands of employees and steer the city through a remarkably turbulent time.
Iannarone said she doesn’t think this should disqualify her. There’s precedent: In 1984, Portland picked tavern owner Bud Clark for mayor.
“Ideally, I would have prior elective experience, but I don’t,” she said. “I just have what I bring, which is this good sense of what’s going on in the neighborhoods, across the city and across the region, around the world and a good vision for how we need to move forward from here. So prior elected experience is a luxury I don’t have, but I also think that we can move forward without it.”
Lack of elected experience isn’t the only factor that has given some pause.
On a widely-watched interview on KGW-TV’s “Straight Talk,” Iannarone declined multiple times to condemn the property destruction connected to ongoing protests in the city, which has fueled concerns that she wouldn’t do enough to protect businesses as mayor. She later followed up with a statement to the network, saying “Criminal activity is illegal, and of course I don’t condone it.”
Others have pointed to her failure to pay personal income taxes from 2010-2013. She said she wasn’t sure how she should be filing during her divorce and paid it off when she discovered the lapse.
Iannarone’s active Twitter feed has also received increasing scrutiny as Election Day nears. Supporters say they appreciate the unvarnished channel into her thoughts. Others worry she’s too quick to the draw for an elected official, publicly rebuking people and groups she disagrees with. They say this may not bode well for a position that puts a premium on collaboration, requiring the vote of at least two colleagues to get anything passed.
“What I’m trying to envision is Carmen Rubio, Dan Ryan, Jo Ann Hardesty, working with Sarah,” said Portland Public Schools board member Michelle DePass, who said she’s been an acquaintance of Iannarone’s for two decades. They were enrolled in several programs together at Portland State University and their kids attended preschool and grade school together. DePass appeared in a mailer supporting Iannarone’s campaign, but then asked not to be put on additional material because she said Iannarone didn’t have her express permission to use her image.
"I understand Twitter is snarky by its very nature, but I’m just having a hard time envisioning how she’ll work with her colleagues, said DePass, who said she has worked for the city on-and-off for the better part of three decades. “And I can’t envision what will happen if her colleagues disagree with her approach.”
But Iannarone said the public, overall, seems to appreciate the access they have to her through her Twitter feed, where she keeps something like office hours. Whether people like what they hear or not, at least they know where she stands.
“I’ve always tried to maintain a pretty even keel that this is my real thoughts, for better, or for worse,” she said. “Sometimes it’s not always what people want to hear.”
Up in the air
Iannarone knows a summer of fury directed at Wheeler has increased her chances of making it to City Hall.
“We didn’t have anyone saying, you know, ‘Fuck Ted Wheeler,’ in the streets when we embarked on this,” she said of the downturn in the mayor’s public support.
But she’s not the only one whose support has risen as Wheeler’s has plummeted. Advocates of Teressa Raiford, the founder of Don’t Shoot PDX and a distant third-place finisher in the May mayoral primary, have launched a write in candidacy for her.
“Teressa’s platform has always been about police violence and police accountability. These were things that were on our platform way before they were in the national news,” said supporter Token Rose, who volunteered for Raiford during the primary. “People in Portland were not ready for these conversations — until they were ready.”
Raiford has said she’s not campaigning.
But she has watched as a new wave of Portlanders learn her name and past accomplishments pushing for police accountability and advocating for victims of gun violence and their families. This summer, the group sued the city to get police to stop using tear gas and organized Moms United for Black Lives.
“I will be writing myself in along with anyone else,” Raiford said. “I wouldn’t vote for either one of the other ones on the ballot.”
Raiford describes the write-in campaign that has sprung up to support her as radical, anti-racist, and “filled with love.” The platform posted by the write-in campaign pledges that as mayor, Raiford will commit to cutting the Portland Police Bureau’s budget in half, work with the state to begin reparations, and “invest in alternatives to calling the PPB.”
Raiford has earned the support from organizations like the voter mobilization group Next Up, and has the support of about 6% of Portland voters, according to a recent poll conducted for OPB.
These are voters that Iannarone, who is running to Wheeler’s political left, could certainly use.
The campaign gets rougher
Last month, some political consultants believed Wheeler had a path to victory, but it was one he seemed reluctant to take. He would have to campaign hard against Iannarone.
“You can’t say, ‘We’re a shining city on the hill and vote to keep Portland Portland.’ That’s not the message. It’s got to be, ‘I’ve got both the skills and the ability, and I’ve got some track record that I want to explain to you,’” said Len Bergstein, head of the consultancy firm Northwest Strategies. “'And I can do this, certainly, better than the challenger who professes to be in favor of more chaos.'”
Wheeler seems to have picked that path. After putting $150,000 of his own money into the race, his campaign sent out mailers reminding Portlanders that Iannarone had tweeted about being part of antifa and calling her “just too divisive.” Iannarone has accused the mayor of emitting a clear dog whistle and of baiting right-wing attacks on anti-fascists. Meanwhile, a coalition of labor, business and environmental groups has coalesced under the name United For Portland to form an independent expenditure campaign on Wheeler’s behalf. It released an attack ad against Iannarone this month.
But this could backfire. Bergstein notes Iannarone has been able to counterpunch when Wheeler draws attention to his track record, pointing to her own experience working in the community as just as important as his prestigious degrees.
Novick said he’s standing by his initial belief: people are angry with the mayor, and Iannarone will be the ultimate beneficiary — as long as she makes sure the election is a referendum on him.
Novick’s political strategy for Iannarone? Wait it out.
“If I were advising her, I’d tell her to go hide in a basement,” he said.
