Will Portland Reelect Ted Wheeler?

The city’s mayor is already facing calls to resign. His main opponent sides with the protesters. Right-wing groups keep coming to the city.

Ted Wheeler swings his arm.
Mayor Ted Wheeler reacts after being exposed to tear gas while attending a protest on July 22 in Portland, Oregon. Nathan Howard/Getty Images

On the night of Aug. 29, Portland, Oregon, resident Aaron “Jay” Danielson was killed after several hours of violent clashes between left-wing demonstrators supporting the Black Lives Matter movement and Trump-supporting members of various alt-right groups who’d gathered for a rally and car parade. Danielson was a supporter of the far-right Patriot Prayer group and was wearing a hat with its insignia at the time of his killing. Suspect Michael Forest Reinoehl, who was later killed by police as they allegedly attempted to arrest him, had aligned himself with antifa, the decentralized faction of anti-fascist activists behind many of the more aggressive protest tactics seen in Portland and elsewhere.

For national media outlets that had been observing increasing violence in Portland from afar for months, there was a rush to figure out what had gone wrong. It had seemed clear, when federal forces invaded Portland against the will of city and state elected officials this summer, that these outsiders were to blame for the escalating brutality against protesters. Portland’s mayor, Ted Wheeler, a Democrat, was out in the crowds, choking on tear gas and decrying the federal law enforcement agencies as an “occupying force,” using the same language as demonstrators. But after Danielson’s killing, which occurred a month after federal forces withdrew, it’s become less obvious where the fault lies, and what could have been done to prevent his death.

Back in August, the president blamed Wheeler, echoing the line he’d taken for months on the unrest. The day after the shooting, he called Wheeler a “Do Nothing Democrat Mayor” who has “watched great death and destruction of his City during his tenure.” In a strange alliance, left-leaning activists agreed with Trump. Some Black Lives Matter activists had previously demanded that Wheeler resign, back when federal agents were still running rampant in Portland. That demand gained momentum the day after Danielson’s killing, when several progressive advocacy groups called for Wheeler’s resignation in a statement that accused the mayor of exacerbating tensions and violence in the city. The previous night’s killing “was inevitable given Mayor Wheeler’s repeated failures,” the statement said.

The ask for resignation may seem premature—the mayor is up for reelection in November. Nothing is guaranteed for Wheeler, who received just under 50 percent of the vote in a sprawling open primary in May, triggering a Nov. 3 runoff election in which he faces Sarah Iannarone, an activist and former university staffer. Iannarone calls herself an “everyday anti-fascist” and has been slamming Wheeler on every front: his gentle handling of the Portland Police Bureau, or the PPB (“a rogue police force with sympathies for white nationalists,” according to Iannarone); his relationship with business interests (“a neoliberal grounded in finance”); and his leadership style (“a failure to listen to the people whose opinions and expertise matter most”). Iannarone only received 23.8 percent of the vote in the primary, falling far short of Wheeler’s 49.4 percent, but a lot has happened since May. A June poll found Portland voters evenly split between Wheeler, Iannarone, and “not sure.” In a September poll of Portland voters, nearly two-thirds of respondents rated the mayor unfavorably. He switched campaign managers last week.

Bobbin Singh, executive director of the Oregon Justice Resource Center, one of the groups demanding that Wheeler resign, said he and his fellow advocates hadn’t been planning on making that ask, since voters will be able to decide the mayor’s fate in less than two months. But Danielson’s killing proved to them that Wheeler’s leadership, or lack thereof, was putting the city’s residents at urgent risk in a volatile political climate that will only intensify as the election approaches. For years, Singh said, he and his colleagues have been warning Wheeler that the conditions in Portland—impassioned protests for racial justice, incursions from white supremacist vigilante groups, an out-of-control police bureau with a history of brutalizing protesters—would likely lead to loss of life.

“We were scared that a protester would be killed by law enforcement,” Singh said, noting that OJRC represents a protester who sustained a skull fracture from a police-fired aerial munition that penetrated the helmet he was wearing. “We were scared someone would take out their frustrations or anger on law enforcement. And we were scared of conflicts between far-right groups and protesters.”

On Aug. 29, those fears were borne out. At a video press conference about the groups’ demand that Wheeler resign, Olivia Katbi Smith, co-chair of the Portland chapter of the Democratic Socialists of America, called Danielson’s killing “the logical conclusion” of “the environment that Ted Wheeler has created in this city.”

What environment, exactly? The perception, among those calling for Wheeler’s resignation, is that the mayor has hidden behind the “free speech” mantle to avoid taking a stronger stance against the right-wingers who regularly travel to Portland for demonstrations, even as the police force he commands cracks down on leftist demonstrators. In 2017, Wheeler held a private City Hall meeting with Patriot Prayer leader Joey Gibson in advance of a scheduled protest mere days after a white supremacist murdered two people on a local light-rail train. Wheeler had asked the federal government to revoke the permit for the right-wing protest, which was to be held on federal property, to no avail.

A few months after the stabbing and Patriot Prayer protest, the Unite the Right rally happened in Charlottesville, Virginia. Alt-right demonstrators injured counterprotesters and killed Heather Heyer. In response, a Georgetown Law clinic used laws prohibiting private paramilitary activity to get court orders banning certain groups and people from returning to the town. The clinic has since used the same tactic to support efforts in other localities to keep rogue militia groups out. Singh said this approach appealed to OJRC as a model for Portland. “When far-right groups were coming into Portland, we showed [Wheeler’s office] the playbook from Charlottesville,” Singh said. “We even reached out to law firms to help with it. We reached out to the Georgetown clinic. Nothing happened from that. “

Two years later, the PPB protected members of Patriot Prayer and the Proud Boys as they staged a dramatic march across a Portland bridge. “It was a striking scene,” HuffPost reported, “the same group of out-of-town fascists that have terrorized people here for years, given free rein over a city bridge, on their way back from an unpermitted rally in a public park, after weeks of threatening to harm and kill local anti-fascists.”

Activists also have long-standing problems with the way Wheeler has led the PPB: They say he has been neither clear enough in his denouncements of police brutality nor stringent enough in his directives to curb officers’ worst behaviors; and when he does order the bureau to do something, he allows officers and bureau leaders to ignore his instructions. The fact that the previous police chief, Jami Resch, was able to choose her own replacement soon after the 2020 protests began, with no civilian or community oversight, is a testament to the lack of accountability the PPB enjoys, Singh said.

The short tenure of Danielle Outlaw, the chief Wheeler appointed a few months after winning his 2016 campaign on a platform of police reform, offers another example. Outlaw immediately began cracking down on protesters in the city, pushing to give police more leeway to corral demonstrators, authorizing the use of flash-bang grenades, and bragging that she “kicked [protesters’] butt” after police responded to protests with violence in 2018. Wheeler and Outlaw worked together on some attempts to curtain protest activity, including an ordinance that would have allowed Wheeler to dictate the time and place of planned protests in an effort to reduce violence between opposing groups (the ordinance failed). At other times, Outlaw blatantly ignored Wheeler’s orders, as when he told the PPB to stop towing stolen vehicles (a measure meant to serve low-income victims of theft) and to avoid clashes with an Occupy encampment. When Patriot Prayer staged a demonstration in Portland in 2018, police found members on the roof of a parking garage with a cache of weapons. The officers temporarily seized the guns, then returned them, and then neglected to tell the mayor about the incident for months.

Teressa Raiford, an organizer who founded Don’t Shoot Portland in 2014, has been critical of Wheeler’s leadership of the PPB for some time. She is currently running a write-in campaign for mayor after placing a distant third in the primary. Her desire to replace Wheeler stems in part from an early glimpse at how he would handle a sustained protest movement, the likes of which has been roiling Portland for months. About a month after Wheeler took office in 2017, Raiford organized a “Not My Presidents’ Day” protest against Trump in front of a federal building downtown. “I sent a public plea to Ted, because I’d supported his campaign, and asked him not to show up with violence, not to allow police to be violent toward us,” she said. Nevertheless, police officers arrived in riot gear, pushed protesters off the streets and onto the ground, and pepper-sprayed at least one restrained demonstrator in the face at close range. Citing the protest’s lack of a permit, officers arrested more than a dozen protesters when they refused to vacate the streets and sidewalks. “I was like, ‘This is incredible,’ because [Wheeler] ran on this very progressive platform and this was his first month as mayor,” Raiford said. “You want to protect Portlanders and their right to free speech? You don’t go out and attack them.”

More recently, these lingering frustrations with Wheeler’s leadership have exploded. In response to the Portland uprising, which began after George Floyd’s killing in Minneapolis in May and still continues with nightly demonstrations more than three months later, Wheeler and the Portland City Council have made a few changes to city policy. The council cut the PPB budget by $15 million. (Activists had asked for $50 million, about one-fifth of the total police budget of about $245 million.) They ended armed police presence in public schools and on public transportation, and allocated nearly $5 million to a forthcoming program that will enlist unarmed first responders to deal with calls involving people experiencing homelessness or mental health crises.

Activists say these nods to demonstrators’ demands do not meet the urgency of this moment of racial reckoning. In previous years, advocates fought hard for such incremental reforms, because that was “the paradigm that we had to exist under,” Singh said. “We had to create these wins to push toward culture change.” Now, they feel the culture has changed. At a time when Black Portlanders and civil rights activists are demanding dramatic policy changes to match the new mood, they feel betrayed and abandoned by Wheeler’s lack of focus in his joint roles as mayor and police commissioner, a setup that distinguishes Portland among major U.S. cities. Instead of concentrating on issues of police brutality and racial injustice during this time, activists say, he’s given private briefings to business owners and made sure, in his public addresses, to decry the property damage that has resulted from some demonstrations.

Jo Ann Hardesty, a member of the Portland City Council, is pushing to establish a new independent oversight board for the PPB, has laid out a plan for a reimagined PPB, and told police Chief Chuck Lovell exactly what she’d change about the PPB’s protest response if she were given control of the agency. At the height of the protests, as federal agents and PPB officers teamed up to crack down on demonstrators, she asked Wheeler to let her take over as police commissioner. Wheeler refused. Allowing Hardesty to take the wheel “would actually be a strong signal to suggest that [Wheeler] recognizes where his limitations are,” Singh said. Raiford agrees: “I believe he feels that he doesn’t know what to do. He should show leadership by saying, I can’t handle this.”

Wheeler appears caught between a set of factions whose opposing interests seem impossible to reconcile: the business community, whose leaders are angry that Wheeler hasn’t done more to stop the destruction of property in downtown Portland; the majority of Portland metro voters who disapprove of the nightly protests, including a majority of voters of color who believe they’re not helping race relations, in spite of broad citywide agreement on the fact that racist police brutality is an urgent problem; and the demonstrators themselves, who are determined to keep at it until they see radical changes in city policy. Had Wheeler taken immediate action to meet more of the protesters’ demands, other Portlanders might have thought he’d gone too far. But he might have also successfully deescalated the protests before some of these other voters turned against them—and, more importantly, before anyone was killed.

Now, it’s difficult for activists to imagine how Wheeler might recover his credibility after he tried to stake an untenable middle ground between supporting and condemning police brutality against protesters, journalists, and medics. Wheeler told the PPB to stop beating and arresting journalists covering the protests, but they continued to do so. It took more than a week for an officer filmed punching a protester on the ground to be taken off the streets and placed on administrative duty. It took seven weeks from the time Wheeler himself was tear-gassed by federal agents—an experience he said made him “think long and hard about whether this is really a viable tool”—to ban the PPB’s use of tear gas on protesters. Wheeler has allowed PPB officers to cover their name badges, contributing to an appearance of impunity among local law enforcement agents, even as he decried federal agents who abducted demonstrators in unmarked vans. When a Rolling Stone writer asked Wheeler about the violent tactics the PPB has used during the demonstrations, Wheeler equivocated, saying he “would not cop to saying that I support those or if they’ve been OK with me,” then mentioned a recent dumpster fire outside a police precinct and said, “There are times when the Police Bureau has a duty to protect lives and safety.”

In the weeks since the Aug. 29 killing, Portland-area media outlets have reported on several ways in which the PPB failed in its response to the alt-right demonstration. The city’s preparation for the rally and car parade, even in the wake of months of protests and police violence, was minimal compared with the precautions taken before previous incursions of armed right-wing groups. And the PPB failed to keep Trump supporters’ caravan on the interstate, which police Chief Lovell claims the bureau tried to do. In his public statements and addresses, Wheeler doesn’t have much to offer. “It’s hard for me to stand here, with a human being dead, and say that we did everything we possibly could,” he said at a press conference the day after the August killing. “I can’t make that statement. It would be preposterous of me to do so.” At the same event, when asked how the PPB could have prevented the previous night’s violence, he admitted, “I don’t know how, operationally, you prevent this.” Right-wing groups are planning another demonstration on Saturday; Wheeler has directed PPB to plan ahead.

Unless there is a drastic shift in the Portland political climate over the next few weeks, it seems unlikely that Wheeler will resign before the election. With no experience in elected office and the confrontational posture of an activist, Iannarone is a dark horse whose aggressive agenda may veer too far left for some Portlanders. (Right-wing media outlets are already having a lot of fun with her “I am Antifa” tweet from last year.) On the other hand, as Nigel Jaquiss wrote in Willamette Week, “If Portlanders are fed up with Wheeler, Iannarone has a simple pitch for them: She hated Ted before it was cool.” She already knows what she’ll do as PPB commissioner if she’s elected: hand the reins to Hardesty.