How Portland Became a Nightmare for Democrats



For Donald Trump, cities are crime-ridden, infested with rioters and looters, and overseen by liberal mayors who are either absent or complicit—or often both. But among the cities about which the president has railed though this summer of unprecedented protests, Portland has stood out as his personal punching bag. He has called it a “ mess ” (and “has been for many years,” apparently) and dispatched unmarked federal agents to the city. Just this week, Trump’s Justice Department singled out Portland as an “ anarchist jurisdiction ,” one in which city leaders have “permitted violence and destruction of property” and from which the White House is now threatening to withhold federal funding if the city doesn’t change course.
Trump has misleadingly blamed the city’s agitation solely on the far left, conveniently ignoring the role armed, far-right groups play in fomenting the violence. But when Trump says that Portland has “been burning for many years,” as he recently told Fox News’s Laura Ingraham, he’s not necessarily wrong.
The fact that Portland has presented the kinds of domestic unrest America hasn’t seen in decades—downtown protests surrounding the federal courthouse recently passed the hundred-day mark , and the city just saw its deadliest month since the 1980s—is not surprising to those who know its history. Just three years ago, during Trump’s first summer in office, POLITICO dubbed Portland “America’s most politically violent city” after left-wing anarchists rioted in the months after Trump’s election and a right-wing white supremacist verbally abused two minority women on a train and stabbed to death two men who intervened.
But with only six weeks remaining until the election, the current conflict has reached new levels of violence, and anyone paying attention can see that things are getting worse. That roiling unrest is presenting an unprecedented challenge for local officials who are struggling to contain the violence—as well as for national Democratic leadership that is struggling to figure out an effective response to an intensely local crisis that has broader political implications, all while the president hectors them as weak and incapable.
“Looking at what’s on the ground right now, I think Portland in a lot of respects represents a worst-case scenario, in terms not of how bad it could possibly get, but how bad it is now,” Mark Pitcavage, who researches domestic political extremism with the Anti-Defamation League, told POLITICO. “It’s hard to be optimistic in the near- or medium-term for Portland.”
Portland’s homegrown clash of extremists on both sides has become so entrenched it is creating a gravitational pull on others from around the country. Left-wing forces, including antifa and others, insist that “Riots and looting” are “a legitimate and profound form of protest,” as a post on one of the popular far-left regional Facebook pages encouraging violence recently read. Meanwhile, the pro-Trump group Patriot Prayer, headquartered north of the city, are eager to confront the opposition. “They go there to provoke physical confrontation, to try to bait people into street fighting,” Daryl Johnson, a former Department of Homeland Security official focused on domestic extremism, said. “Now people are transiting the country, learning from people in Portland. People may have traveled to Portland to get some battle experience, so to speak.”
And that expansion has led to escalation, especially when it comes to the weapons now being used. “We’re starting to see the beginnings of this violence escalating from throwing objects ... to them now pointing guns at each other,” Johnson said. Late last month, an antifa supporter named Michael Reinoehl shot and killed Aaron Danielson, a prominent Patriot Prayer member. A video captured Danielson’s final moments—the footage of which has already spread far and wide.
“People are going to watch that video over and over and over until they get to the point they’re on the brink of pulling the trigger on someone else. That video is a radicalization tool,” Johnson said, pointing to similar footage out of places like Kenosha , Wisconsin, and Albuquerque , New Mexico. “Just like a foreign fighter would go to Syria or Ukraine—it’s the same experience. You’re on the ground, seeing the deterioration of civil order, and it reinforces your little wet dream of an apocalyptic outcome.”
As head of the Oath Keepers, America’s largest militia, said after the Portland shooting, “Civil war is here, right now.”

Portland authorities, who didn’t respond to POLITICO’s questions, have proved themselves unwilling over the past few months to confront those causing the ongoing damage downtown and those who are promoting deadlier conflicts. Efforts at enforcing curfews have fallen flat, and Portland police—who have their own history of brutality and abuse of power —are hardly a trusted force among protesters. Portland Police Bureau Chief Chuck Lovell admitted last month that the time may come for authorities to call in the full weight of the Oregon National Guard. “I don’t have any hesitancy one way or the other,” Lovell revealed. Gov. Kate Brown, however, has proved reluctant to call in the Oregon National Guard, noting that they’re not trained as law enforcement. (The DOJ’s statement this week designating Portland an “anarchist jurisdiction” specifically called out Portland Mayor Ted Wheeler for “expressly rejecting the Administration’s offer of federal law enforcement to stop the violent protests.”)
It’s unclear, though, how other cities are going to handle the escalatory tactics we’ve already seen unfold in Portland. After the eruption in Kenosha , after the storming of state capitols in Michigan and Idaho , after massive Second Amendment rallies in Richmond earlier this year—even after the deadly encounter in Charlottesville in 2017, in which America’s far-right militia movement came out as private security for the white supremacists—local authorities have shown themselves to be flat-footed when it comes to handling the volatile combination of far right and far left.
Nor are local leaders, already battling everything from a rampaging pandemic to a swelling recession, willing to talk about any tactics to combat potential political violence in the coming weeks. Requests to discuss strategies with leaders of cities in key electoral states—Milwaukee, Pittsburgh, Houston and Miami—were either ignored or turned down. “One of the things that’s become clear not just in the past couple months, but the past few years ... is that local law enforcement and local leaders by and large don’t have a good approach to this,” Chelsea Parsons, who helps run the Gun Violence Prevention program at the Center for American Progress (CAP), told POLITICO.
At CAP, the leading Democratic think tank, Parsons and her team have compiled a white paper, due to be released later this month, to disseminate to mayors and governors outlining potential means of mitigating the political violence looming. Parsons’ unfortunate conclusion: There’s no silver bullet, no switch to flip in order to defuse the extremism rankling the street fighters and armed militias ranging freely in Portland.
The solution, such as it is, rests largely on being proactive, rather than simply reacting to the latest convoy of would-be Minutemen facing off with masked antifa crowds. “In the absence of leadership federally, it is incumbent on state and local leaders to get in front of it and at least start educating the community,” Parsons said.
Part of that solution stems not from new policies, necessarily, but from local leaders familiarizing themselves with the laws as they exist—especially those laws that prohibit armed crowds massing near polling places, or that limit open-carry rights. There are still “widespread misunderstandings of the scope of the Second Amendment, and the scope of the abilities to openly carry firearms in the community, and where lines are around the ability to do this,” Parsons said. Or as Justice Antonin Scalia wrote in the Supreme Court’s 2008 Heller decision expanding the rights of private citizens to wield firearms, the “Second Amendment right is not unlimited.”
Such recommendations have been echoed elsewhere. “Law enforcement and local officials have to get way out in front of it,” said one person involved in a recent bipartisan exercise gaming out potential election outcomes, which ranged from a Joe Biden landslide to the potential break-up of the U.S. (This person requested anonymity because of threats the bipartisan group has already received from right-wing voices.) “You can’t wait for there to be right-wing militia roadblocks . They need to be getting out the communications however they can to say, ‘We have laws, we have courts, we have police, and vigilante activity is not acceptable—and violence on the left or the right is not acceptable.’” That goes doubly for Democrats trying to dodge Trump’s increasingly illiberal threats and trying to reframe the picture Trump has painted in places like Portland: “Democratic leaders both local and national need to be … continuing to repeat that there is no role for violence in this country, that First Amendment free speech is a cherished American value, that there is never a role for violence, and that violence always breeds more violence.”
To be sure, Biden, and his running mate, Kamala Harris, have thus far done precisely that. After the Portland shooting, the former vice president called the violence “unacceptable,” adding that he “condemn[s] this violence unequivocally.”
But the thousand-pound elephant remains the federal government. Trump has already proved willing to use Portland as a Petri dish for his police state tactics, with DHS agents memorably hauling protesters into unmarked vans earlier this summer. “The way [the federal response] was done forcibly only served as reinforcing the far-left perception of a militarized police, of social injustice, all this stuff,” Johnson said. “It just seemed like a police state, and it just reinforces that anti-capitalist view of the police—that they’re the Gestapo.”
Not that Trump minded; as acting DHS head Chad Wolf recently said, “all options are [still] on the table” for Portland—including, apparently, a reprise of unmarked vehicles and unmarked agents sweeping protesters off the streets. And when asked about the death of antifa suspect Reinoehl at the hands of U.S. Marshals, Trump appeared to endorse extrajudicial killings. “I'll tell you something—that's the way it has to be,” Trump said . “There has to be retribution.”
“If ever there was a moment for the president of the U.S. to be saying, ‘Calm the fuck down everybody, the U.S. is fine, no vigilante activity is acceptable on any side of the political spectrum, nobody should be going out and buying ammunition, that’s crazy shit,’ it’s now,” as the person involved in the bipartisan war games told POLITICO. “But obviously, at a moment when the president should be saying that, he’s saying the precise opposite.”

Meanwhile, back in Portland, the far-left and far-right contingents continue to gather and collide. After the killing of one of their own, Patriot Prayer gunmen launched a convoy just south of Portland, gathering at a Trump rally at the Oregon state capitol in Salem, with baseball bats and pipes and guns in tow. As The Oregonian reported, social media clips showed Patriot Prayer members “charg[ing] counterprotesters, leaving several injured.”
“They splintered off in Salem and pretty severely beat BLM protesters, like something from Mississippi in 1964,” said Randy Blazak, a former Portland State University professor who’s currently helping lead a steering committee charged with implementing Oregon’s new bias crime law. Tweeted Seth Cotlar, an American history professor at local Willamette University, the Salem rally “felt like a terror campaign.” (“I can definitely foresee someone from Patriot Prayer or other groups doing some kind of terrorist act,” Johnson added.)
More concerningly, one of the far-right figures arrested revealed he’d driven in from Colorado—the latest evidence of Patriot Prayer’s sprawling influence. Around the same time, the national leader of the Proud Boys, another pro-Trump organization, announced his group would be joining the melee in Portland, organizing a rally later this month in the middle of the city. “It’s the long hot summer winding down, and we’re about to get a sizzling autumn of discontent,” said Blazak. (A recent poll showed that a significant majority of Portlanders disapproved of the ongoing protests downtown.)
If there’s a silver living in all this, it’s that the ingredients that propelled Portland to the center of Trump-era political violence—the region’s fraught racial history, the localization of groups like Patriot Prayer, the incapacity and inability of civil authorities—aren’t necessarily all factors found simultaneously in other metro areas.
While killings in Kenosha, as well as police slaying of Black Americans, illustrate just how much tinder remains across America, Portland still remains a city apart—for the time being, at least. But within that reality, there’s also an opportunity. “The thing that’s been happening in the country, the political division over race, has been happening here—we’re kind of one step ahead in that conversation. But that’s exciting too, because the reform that can happen here can happen elsewhere,” Blazak said. “Portland is positioned to lead that conversation ... I think Portland can help guide the way.”
In order to get there, though, the city and the region need to get through the next few months first. Confrontations—and escalation—will almost certainly continue in Portland and its environs, from the steps of the Oregon capitol to the Confederate memorial just a few miles north of the city . “I thought some of the recent killings might cause some people to pause for a moment, take a breath,” Pitcavage said. “But that doesn’t seem to have happened, and I don’t see any reason for it to go away in the conceivable future.”
“We’re in for a long six to eight months,” Johnson said, “and maybe even longer than that.”

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