Portland, Oregon, Mayor Ted Wheeler was all but sure of a second term in office when he won nearly half the votes in a crowded Democratic primary in May. But he fell just short of the 50 percent plus one vote needed to secure his seat, which forced him into a November runoff against his closest challenger, Sarah Iannarone, a progressive urban policy consultant who had earned less than half his votes. Then, days after the primary, a Minneapolis police officer killed George Floyd, kneeling on his neck for eight minutes. Floyd’s killing set off a historic wave of protests against racism and police violence that rocked the nation for weeks — perhaps nowhere more than in Portland, where nightly protests continued uninterrupted for more than 100 days, reconfiguring the mayoral race and putting Wheeler’s once-solid reelection prospects at risk.

Since the protests started, hundreds of Portland residents have been arrested, including many who were protesting peacefully. Two people were killed in connection with the protests: a man who joined a rally by far-right supporters of President Donald Trump, and a self-declared anti-fascist and the prime suspect in the first man’s killing, who was gunned down by police days later. Residents are now bracing for more violence as a rally by the far-right group Proud Boys is planned for Saturday.

As Portland became a symbol and battleground for the divisions enflaming the country, Trump deployed federal agents there, aggressively peddling the narrative that Democratic leaders like Wheeler had allowed U.S. cities to descend into chaos. The mayor, in turn, seized on the federal deployment to brand himself as a leader willing to stand up against the abuses of the president — calling the federal agents an “occupying force” and at one point getting teargassed by them. That episode catapulted Wheeler into the national spotlight, but few in Portland were impressed with the show of solidarity with protesters.

“Local law enforcement had been engaged in very similar if not the exact same type of behavior against the residents of Portland,” said Bobbin Singh, executive director of civil rights group Oregon Justice Resource Center, who has called for Wheeler’s resignation. “The very same things federal law enforcement was doing, local law enforcement had done and has continued to do since federal law enforcement left.”

Ted Wheeler reacts after being exposed to tear gas fired by federal officers.

Mayor Ted Wheeler reacts after being exposed to tear gas fired by federal officers while attending a protest against police brutality and racial injustice in Portland, Ore., on July 22, 2020.

Photo: Nathan Howard/Getty Images

Over the last four months, those actions have included officers from a number of law enforcement agencies regularly firing tear gas, sometimes deep into residential neighborhoods, and even flash-bang grenades. Police have arrested journalists and legal observers, and have defied the new district attorney’s policy against prosecuting nonviolent protest-related crimes. Officers have slashed the tires of protesters’ cars and threatened residents just outside their own homes.

Protesters have filed lawsuits against both the federal government and local police, while images and videos of officers beating bloodied protesters have gone viral. In June, Portland’s independent police oversight body reported more complaints of excessive force than in the three previous months combined.

Earlier this month, Wheeler finally banned the use of CS gas, the type of tear gas most frequently deployed at protests — but he allowed the continued use of OC gas, which is fired with impact munitions that have seriously injured protesters. Police have publicly criticized him on the partial ban. By then, calls for Wheeler’s resignation had multiplied. As the protests dragged on, the mayor first slipped and then sank in the polls, which earlier this summer projected him in a head-to-head runoff with Iannarone and by September put his favorability rating at a dismal 26 percent.

How much the events of the last few months will determine the race remains to be seen: Wheeler swapped campaign managers earlier this month, a move many saw as recognition that his reelection bid is flailing. And Iannarone is campaigning hard on the incumbent’s failed response to the protests. But her prospects, too, are complicated by the write-in campaign of Teressa Raiford, a local activist and founder of the racial justice group Don’t Shoot Portland, who finished third in the May primary and is a favorite among some protesters.

In an interview with The Intercept, Wheeler defended his record on police reform and public safety issues, but acknowledged that he and other officials in the state share responsibility for the violence and two deaths that have occurred in connection with the protests. “All of us who hold positions of power or influence or authority in this community who could have done more to stop the violence, to end the violence, to denounce the violence, are culpable,” he said.

“I clearly was able to differentiate on the first day of the demonstrations between nonviolent demonstrators who were taking to the streets by the tens of thousands in support of racial justice, and equity, and common sense police reform on the one hand, and other people who were just showing up to throw Molotov cocktails, injure people, and break stuff,” he said, arguing that many of his colleagues did not. “If I could do anything differently, I would go back, and I would build that consensus against violence early, and make it clear that violence has no role to play, regardless of whether the violence is coming from the public or whether it’s coming from the police.”

Wheeler also noted that while the scale of the protests was unprecedented even for a city well accustomed to demonstrations like Portland, “in retrospect, I think we all see what was different was that it wasn’t two different groups coming into this community to battle it out with each other, what happened here was the protest was against the police themselves.”

“There were definitely times when I believe police could have had a less obvious presence, or they could have de-escalated situations more quickly or better than they did,” he added.

But on and off the streets, many of Wheeler’s constituents have placed blame for the violence of the last four months largely on the mayor himself, who in Portland’s commission government system also oversees the police bureau.

“The past hundred days have crystallized more clearly the vacuum of leadership that exists,” said Singh. “As we head into the November election, the idea is how do we, as a city, begin to navigate this. And the mayor unfortunately hasn’t been able to demonstrate a strong track record of collaborating or the ability to bring parties together.”

Sarah Iannarone, Wheeler’s opponent, told The Intercept that the mayor “has lost the trust of the public by virtue of failing to address the violence and the police brutality and the racial injustice in Portland’s police state.”

“It’s pretty easy to pick fights with Donald Trump; he’s a bully,” she added. “What that doesn’t do is address the fact that the protests here, night after night, are about Mayor Wheeler.”

Both protesters and observers watching from the sidelines have singled Wheeler out for what they see as his unwillingness or inability to control a police force many say has gone rogue.

“At what point, as a leader, do you say, ‘Listen, this is obviously not working, we’re going to come at it from a different angle,’” said Rachel Myles, who was arrested three times while peacefully protesting. “Instead they just keep coming in with violence, violence, violence. And it’s absurd, because that is the very thing that we are protesting.”

Graffiti on the walls of the Justice Center in Portland, Oregon.

Graffiti on the walls of the Justice Center in Portland, Ore., on July 20, 2020.

Photo: Justin Katigbak/SIPA/AP

Raising the Stakes

In an effort to distract from his record on the coronavirus pandemic, Trump has seized on the protests that have gripped the country over the summer to pitch himself as the pro-law enforcement candidate and stoke fears about chaos he claims is enabled by Democratic leaders. Earlier this month, Trump declared Portland, as well as New York City and Seattle, “anarchist jurisdictions” and threatened to withhold federal funding.

But if that narrative might benefit the president politically, it has also offered a boost to local leaders eager to style themselves as part of the resistance to Trump, and hoping in the process to deflect scrutiny from their own leadership shortcomings. “What you see across the country is democratic mayors and governors using President Trump and the federal government as a way to distinguish themselves, and as a talking point,” said Singh. “But locally, advocates and the community have been very focused on what local law enforcement has been doing.”

In fact, Democratic mayors, including a number who have billed themselves as progressives, have been a primary target of protests over the conduct of the police departments that they, and not the president, control. And even when they have embraced progressive positions on a variety of issues, most local leaders have been hesitant to take on police reform in any meaningful way.

“Some of our most violent police forces in America are in major cities and major cities are almost all governed by Democrats and mostly progressive Democrats,” said Gregory McKelvey, a Portland activist and Iannarone’s campaign manager. “So we obviously have a situation where you can call yourself a progressive yet still be willing to utilize police brutality or at least not be willing to rein it in.”

Despite Trump’s attacks on him, Wheeler is hardly a progressive. Once a registered Republican, he ran a moderate Democratic campaign for mayor in 2016. “I would draw a distinction between true progressives and more corporatized neo-liberal democrats,” Iannarone told The Intercept, noting that she is the first publicly financed candidate in Portland’s election history. “I can actually stay true to progressive values because I don’t have to take large donations from interest groups, unlike mayors like [New York’s Bill] De Blasio, [Seattle’s Jenny] Durkan, and even Wheeler.”

When he first ran, Wheeler did promise to take on police and criminal justice reform, and his platform at that time listed a 10-point program that included promises like the one to “actively demilitarize the police force and encourage a culture of community engagement and problem solving.” In August, three months into the protests, the mayor released a new plan to address racial injustice in the city, including by redirecting funding from police to communities of color and supporting non-police public safety response teams. Wheeler told The Intercept that 12 of the 19 steps outlined in the plan have already been achieved or are in substantial progress. On his re-election campaign website, Wheeler also touted “progress” made under his administration, mentioning efforts like de-escalation and bias training for officers, but he steered clear of specific pledges, promising instead “public safety system reform that reflects our community’s values and is responsive to calls for transformational change.”

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Police wearing anti-riot gear march towards protesters through tear gas smoke during the 100th day and night of protests against racism and police brutality in Portland, Ore., on Sept. 5, 2020.

Photo: Allison Dinner/AFP/Getty Images

“He’s basically saying he wants to listen to the community, but he’s been in office for several years, and the community is very active, pushing him on policy changes around policing, and moving away from police, and finding alternatives to deal with our social problems, and people from so many different groups have gone to the council and testified on these issues,” said Crystal Maloney, a Portland lawyer and activist.

Maloney contrasted Wheeler’s vague pledge with his opponent’s public safety plan, a detailed, multi-element proposal several pages long, which Iannarone released late last year before updating it in light of the recent protests. “She took every single thing the community has been saying and said, ‘I’m listening to you’ and put it on her platform,” said Maloney, noting that Iannarone’s plan also promises metrics for evaluation and success, “building into her policy platform accountability, which we just didn’t see at all with Wheeler.”

Wheeler pushed back against the criticism, and argued that while the city’s charter gives him control over the police bureau, over a period of decades different city administrations have ceded authority to police through labor contracts, while state elected officials have “tied the hands” of city leaders through legislation that favors police.

“When people say I haven’t heard or I haven’t responded, the reality is, I’ve done more than any prior mayor in the history of the city,” Wheeler said. “I’m moving quickly. But I also acknowledge that there are others who are frustrated that we can’t move faster.”

“At the end of the day, we are trying to completely restructure and reimagine policing in our community,” he added. “And none of those things can happen within weeks. That is going to take the hard work of governance, of finding that elusive middle ground on issues where our community is divided, and being able to overcome substantial collective bargaining and state law requirements which make immediate change difficult; that’s just the reality of governance.”

Advocates have given the mayor credit for some of the positions he has recently taken on policing issues, like his support for an overhaul of the city’s police oversight system and his belated partial ban on tear gas. But they suggested the mayor only embraced such reforms as a result of sustained pressure. “His banning of tear gas was responsive to this moment, but it was the bare minimum he could do,” said Maloney. “This is something that’s been happening in Portland for years, he’s been gassing protesters multiple times since he’s been elected.”

With the tear gas ban and other measures, the mayor appears to have caved to demands for reform rather than lead them, critics noted. Even then, the reforms have been mild. In June, early in the protests, Portland’s Chief of Police Jami Resch stepped down, about six months into the job and after having selected her own replacement, current chief Chuck Lovell, with no public oversight process. Critics slammed the move to replace Resch with Lovell, who is Black, as “superficial.” (Wheeler, for his part, has touted the appointment of an earlier chief, Danielle Outlaw, the first Black woman to run the bureau, among his police reform successes.)

Then, as the protests and pressure on elected officials mounted over the summer, the Portland City Council voted to shut down a controversial gun violence reduction team, and to remove armed officers from public schools and transit. The council also cut about $15 million from the Portland Police Bureau: a six percent budget reduction. But those cuts came after enormous public pressure, including some 70,000 emails sent to one of the five members of the City Council and the public testimony of hundreds of residents, many of whom were demanding $50 million in cuts to the police budget.

“From the perspective of people pushing for these reforms, it felt like very little was done in terms of defunding the police; these are incremental changes at a time when people were demanding transformation,” said Elliott Young, a co-chair of the Portland Committee on Community-Engaged Policing. “The problem is that the mayor seems intent on ending the protests rather than solving the longer-term issues.”

Instead, the protests have raised the stakes and made the public’s demands for change more pressing and ambitious.

“The situation has drastically changed. We had the primary just prior to the murder of George Floyd and the conditions not only in this country but in this city were different,” said Singh, of the Oregon Justice Resource Center. “And what we demand of elected leaders has also changed.”

What Wheeler and elected officials across the country are now facing is a growing movement demanding not so much piecemeal fixes as a more fundamental reckoning with white supremacy and its manifestations in law enforcement violence, Singh added. “The biggest issue is having leadership that actually is very comfortable with the uncomfortable conversation of racial justice,” he said. “And I think it’s just not that simple or clear for Mayor Wheeler, that’s not his value system.”

Portland protestor holds sign that states " your taxes pay an avg. of $400k/yr for police misconduct".

Protesters demonstrate outside the Portland Police Association building in Portland, Ore., on July 13, 2020.

Photo: Alex Milan Tracy/SIPA/AP

Brokering the Peace

As much as the protests have reconfigured the mayoral race in a way that was unthinkable in May, the election won’t be a referendum on the handling of the protests alone, several people said. Instead, the protests shone a light on problems that advocates have denounced for years, and they have put Wheeler’s entire record on public safety issues under scrutiny.

“To be honest, Portland as a city has not focused on policing or criminal justice reform until very recently and I think a lot of it has to do with the fact that policing tends to affect Black Portlanders and people suffering mental health crises and homeless people, so the average white citizen is not so concerned,” said Young, of the Portland Committee on Community-Engaged Policing. “It’s only as a result of the protests that this has become an issue that no resident of Portland can avoid and certainly no politician can avoid.”

The PCCEP itself was appointed by Wheeler to comply with a 2012 federal settlement between Portland and the Justice Department, which had found that city police had routinely used excessive force in their interactions with people with mental disabilities. It replaced an earlier body for community engagement, the Community Oversight Advisory Board, which had disintegrated amid infighting. At least one member of the PCCEP has met with the mayor throughout his tenure, pointing to data that showed the disproportionate impact of policing on Black residents and the homeless. Wheeler told The Intercept he established the committee because the community had demanded more direct involvement in policing matters, but Young noted that several of the committee’s recommendations, as well as its more recent condemnations of the use of tear gas and of violence against protesters, went unheeded. “PCCEP has also held town halls pointing to the data on disproportionate policing, but there has been no response or plan from the mayor to address this situation,” said Young. “Since the end of May PCCEP has made five recommendations and one statement that the mayor has not responded to in spite of the fact that they are mandated to respond to our recommendations within 60 days.”

Tackling homelessness, in particular, was a key promise of Wheeler’s 2016 campaign, and the mayor has claimed a series of achievements on that front, like the doubling of shelter capacity and strengthening of transitional housing offers. But police targeting of the homeless has worsened during the mayor’s tenure, said Young, who noted that in 2017 more than half of all arrests in the city were of homeless people. “He has not been effective,” he said. “And what he’s campaigning on is, ‘Give me another four years to solve a problem I haven’t been able to solve in the last four years.’”

Wheeler’s opponent, for her part, said that the mayor’s failure to address policing issues motivated her to run long before the most recent wave of protests. “George Floyd’s tragic murder brought to light for many people who are not on the receiving end of police brutality and racialized policing that things in Portland are not going well for everyone,” she said. “But I ran against the incumbent because he ran on police accountability in 2016 and broke his promise to address this situation long before now.”

Iannarone added that it was “not a coincidence” that her campaign manager was a prominent local Black Lives Matter activist, and she reiterated her pledge, if elected, to put City Commissioner Jo Ann Hardesty in charge of the police bureau on her very first day in office. Hardesty, the first Black woman to be elected to Portland City Council and a well-known police reform advocate, has publicly asked Mayor Wheeler to transfer responsibility for the police bureau to her, but he has refused and kept the role for himself. Wheeler told The Intercept that he is already working with Hardesty on a number of police-related initiatives. “The only difference if I gave her the police bureau now is that she would be making decisions about mass demonstrations,” he said. “I have told Commissioner Hardesty that come January, when we know who our other colleagues will be on the Portland City Council, all the bureaus are up for consideration.” Hardesty did not respond to a request for comment.

Iannarone has also promised to take on the next police contract negotiations to ensure they are “much stronger from a community perspective,” she said. She plans to introduce policies requiring officers to live in the city and to carry liability insurance. And she wants to curb wasteful spending by police. “We know that $20,000, $40,000 worth of tear gas purchases is not keeping anyone safe,” she said. She has pledged to make every decision about police policy the product of a community-involved process.

“What we see clearly is that over 75 percent of Portlanders believe that Black Lives Matter and that policing needs to be transformed,” Iannarone said, citing a recent poll. “I don’t believe that until you actually bring people to the table to broker the peace that you will have peace.”