Portland Mayor Ted Wheeler, with a history of four winning state and local elections, four years leading the city and a financial edge over his opponents, was nevertheless forced into a runoff last week by a narrow margin.
Political observers say his overly optimistic promises to solve homelessness, his tepid campaign compared to challenger Sarah Iannarone’s more active one and his failure to quash repeated violent protests at the heart of the city help explain his vulnerability after he trounced a similarly crowded field when he first ran for the job of Portland’s top elected official in 2016.
Wheeler came within 1,540 votes out of roughly 218,000 cast of reclaiming the office outright in the primary election.
But Iannarone, an urban policy consultant in her second race for mayor ran an aggressive campaign, captured nearly one out of every four votes cast and could continue to gain momentum as Wheeler’s sole contender with the expected higher voter turnout come November, pundits say.
“The progressive politics that Sarah projects, it’s clear there’s an appetite for that in the city,” said John Horvick, political director at Portland-based polling firm DHM Research. “At this point, it’s hard to see her gaining the majority in the general election. But let’s be realistic, Wheeler’s the incumbent and more than half of voters voted for somebody else. That says a lot about how Portlanders see him right now.”
Wheeler is the first Portland mayor to seek reelection since Vera Katz was re-elected to a third term in May 2000.
In his first run, Wheeler won 55% of the vote. Former Multnomah County Commissioner Jules Bailey finished second with 17% and Iannarone received third-most with 12%.
Horvick said prior to this year, seven of the 34 incumbents who’ve run for re-election to the Portland City Council since 1980 failed to get the needed 50% to avoid a runoff. Wheeler and Commissioner Chloe Eudaly, who was forced into a runoff by political newcomer Mingus Mapps, have now brought that number to nine.
Five of the seven who competed in runoff elections went on to lose their council seats, including Steve Novick against Eudaly in 2016.
Wheeler captured 49% of the vote in this year’s primary. Iannarone received 24% and the next three finishers, community organizer Teressa Raiford, TriMet board member Ozzie Gonzalez and entrepreneur Bruce Broussard, received 19% of the vote combined.
In 2016, Wheeler campaigned largely on a platform to better address affordable housing and homelessness in Oregon’s largest city. Among his campaign promises was to secure shelter space for everyone who needed it by 2019, his second year as mayor.
There were roughly 600 shelter beds in Multnomah County when Wheeler took office, and work by the city and county has doubled that number since then. Still, that’s nowhere near the number advocates say is adequate given the lack of affordable housing and treatment for addiction and mental health needs.
Wheeler told The Oregonian/OregonLive a week before the primary that in hindsight, he initially took the wrong approach to solving the city’s huge unhoused population.
“I wish I had known at a more fundamental level that the answer to the problem isn’t just shelter,” he said. “It’s part of the emergency response, but the way we can actually address homelessness is to connect people on the streets with whatever services they need to get off and stay off the streets.”
He said his term has seen “wins and losses” in addressing homelessness, housing, economic development, policing and making government more responsive. But he said he feels he’s laid a foundation of leadership and coalition-building among city, county and state colleagues that can be built on over the next four years.
Among the first-term successes Wheeler noted are working to build more affordable housing units, increasing protections for renters and helping the city pass restrictions aimed at addressing climate change. He also said the city is more focused on equity and inclusion initiatives.
He said with at least two new commissioners on the Portland City Council come January, the city needs steady leadership to oversee the city’s COVID-19 response as well as ongoing projects and proposals to add new housing citywide and improve some neighborhoods
“When opponents say we’re not there yet, I don’t disagree,” Wheeler said. “But it doesn’t mean we’re not on the right path and that doesn’t mean we’re not moving forward because we most certainly are.”
Iannarone is seeking to be the fifth new mayor elected by Portland voters in five election cycles.
A week before the election she told The Oregonian/OregonLive that lessons she learned from her first run as well as the city’s new public campaign finance program made her a stronger candidate this time around.
She noted that in 2016, she entered the mayor’s race in January and wasn’t able to raise enough money to clear the threshold to be allowed to participate in some debates or forums. Her latest bid began in July 2019 and she was the first candidate in this election cycle to qualify for the city’s public campaign funding, which provides a 6-to-1 match on donations up to $50. Enrolled candidates can only receive up to $250 from each donor.
She’s received $333,262 from the program thus far, city records show, the most of the 16 candidates who were enrolled in the program. She was the only mayoral candidate in the program. Public funding made up the vast majority of the roughly $386,000 she has reported to state campaign finance officials that her campaign raised as of Election Day.
Wheeler, who did not take part in public financing and could accept large donations as a result, reported receiving $443,000 since 2018, according to state records.
Iannarone said she believes the program helped broaden her base of support noting she had to gain contributions from 500 individual Portlanders just to qualify. She said being empowered to seek small donations helped build her campaign into “a grassroots powerhouse” with a sense of inclusion among more Portlanders.
“This campaign is powered by people with a vested interest, some who’ve maybe never been engaged in politics before,” Iannarone said May 14. “Being able to engage people in fundraising and for them to know even $5 goes a long way is a powerful thing.”
Among Iannarone’s priorities are to ramp up the city’s response to climate change by transitioning to entirely clean energy by 2030, advocate for TriMet to expand access to public transportation including eliminating fares and create supervised injection sites for people struggling with drug addiction. She also supports launching a gun buyback program to lessen gun violence, removing all armed police officers from Portland schools and requiring future Portland police officers live in the city as a prerequisite for being hired.
Political consultant Paige Richardson, who has guided many campaigns in Portland and Oregon, said Wheeler’s responses to the winter storm at the very start of his term in early 2017, years of violent protests, community mistrust in policing and the city’s homeless and housing challenges combined with a lack of a clear vision and goals didn’t inspire much public confidence.
His administration stumbled in particular in addressing homelessness, Horvick agreed.
It became “so central to every political conversation in the state and it was under his leadership where that really became intense for voters even though it obviously started before him,” Horvick said. “It’s become especially intense during the last four years.”
But Richardson said Wheeler’s recent handing of the COVID-19 crisis has been his “finest hour” as mayor. He led the city’s effort to apply pressure on the governor to issue a stay-home order sooner than later and helped lead the Portland-area response, including in city efforts to issue funds to small businesses and low-income families, she noted.
“If he can hold on to that and let that part of himself lead, I think Portlanders will be happy to reelect him and he may be able to accomplish more in the next four years,” Richardson said.
Before becoming mayor, Wheeler served two terms as Oregon state treasurer, first being appointed to complete the term of the late Ben Westlund in 2010 and then winning elections that same year and in 2012. He was also elected as Multnomah County chair in 2006.
Wheeler’s mayoral campaign leading up to the primary was lackluster, however, and he didn’t make a strong enough case to voters that it’s in their best interest for him to stay at the helm, Richardson said. Part of it was due to the demands of leading Portland’s pandemic response, she said, but another aspect could be that campaigning is not Wheeler’s forte.
Wheeler is a natural introvert, she said, noting his penchant to gravitate toward individual sports like Ironman triathlons and mountaineering. It also appeared the Wheeler campaign underestimated his primary opponents, particularly Iannarone and her ability to keep a grassroots movement going amid a pandemic, Richardson said.
Several political observers told The Oregonian/OregonLive they received several mailers, texts and phone calls from Iannarone’s campaign and a single mailer from Wheeler’s campaign, if they received any at all.
Iannarone likened a potential win over Wheeler to Bud Clark’s win over then-incumbent mayor Frank Ivancie in November 1984. It was the last time an incumbent Portland mayor lost to a challenger.
She described Clark and herself as “small neighborhood personalities with a lot of hutzpah, a lot of heart and some really great ideas about the future.”
“I think it may be a shock to the establishment, but I don’t think it’ll be a shock to the people who are in the streets that I talk with because they are very excited about the possibility of having a mayor like me,” Iannarone said.
In recent weeks, Iannarone took part in a lawsuit against Wheeler seeking to stop him from using contributions more than the $500 limit that Portland voters overwhelmingly approved in 2018. Courts ruled that limit did not apply until recently, as it has been ruled unconstitutional. Once the limits took effect, Wheeler said he would limit his contributions to $500.
Wheeler was however twice ruled to be in violation of election rules this year, once for not properly disclosing his top donors and later for identifying them in print deemed too small. A campaign finance reform advocate, not Iannarone, filed those complaints.
Wheeler, a week before the election, called the suit and campaign finance complaints made against him “distractions meant to take me off my strategy.”
“When your opponent is spending all of her time talking about your campaign, that’s a sign that she doesn’t want to fight me on the issues confronting our city anymore,” Wheeler said. “So she has changed tactics and has decided to hire an attorney and sue me instead.”
“Holding someone accountable for what 87.4% of Portland voters have said they want, which is campaign finance limits, isn’t a distraction, it’s the basis of a healthy democracy,” Iannarone said.
Wheeler told The Oregonian/OregonLive before the election that he felt his campaign got off to a good start with some canvasing before COVID-19, but once the state’s response started ramping up in March, campaigning wasn’t his focus.
Christopher Shortell, political science professor at Portland State University, said all candidates experienced challenges during a pandemic due to most alternatives being less effective than knocking on doors and holding events to meet voters in person.
“This was a really tough electoral environment for all of the candidates, and I think we have to cut them all a little bit of slack,” he said. “It’s hard to evaluate them by the same criteria that we would use in a normal election.”
The mayor’s post has been a contentious position to hold in recent years, Shortell said, and he believes the primary election vote reinforced that.
“There’s a lot of demands placed on the office and significantly less actual powers and control that the office holds versus what the public expects of that individual who holds the title,” he said. “And that means it’s hard to retain that support into a second term.”
He noted that it’s unclear who the tens of thousands of people who voted for a candidate other than Wheeler and Iannarone in the primary will back in the general election.
Horvick said Iannarone’s making the runoff was a credit to her campaign.
Iannarone’s strengths are her clarity in what she wants to bring to the city and that her campaign has proven her to be “an excellent community organizer,” Horvick said.
“The campaign she’s ran was well-organized, she has enthusiastic people, tons of small donors and she was active in spaces where she does well, like social media,” he said. “She did what she needed to do to get that core group of voters to get into the runoff. I don’t think the average voter could tell you much about the messaging of the Wheeler campaign.”
The question, Richardson said, is whether Iannarone can convince enough voters by November that she would be a better mayor amid a pandemic.
“I think this crisis has made people feel better about Wheeler’s leadership in ways, but clearly not enough to give him a free pass,” Richardson said. “He’s going to have to make his case by November and she will have to as well.”