Dispatches from Portland have appeared here and in Reason and other publications since 2020. A semi-full list appears at the end of this piece, which is part of an ongoing project.
If I could chart how the young people of Portland found themselves on the offensive in the summer of 2020, I had a harder time understanding why politicians and the press were so ready to give them an assist. I would live-stream activists bashing in the face of the federal building with a fire extinguisher and be told, variously, that they were defending themselves, that the police did worse, or that I’d staged the attack in a studio. Most media outlets seemed of the opinion that to distinguish protester from rioter risked shining a bad light on the entire protest movement, and they were unwilling or institutionally discouraged from reporting from more than one vantage point. (Reason, on the other hand, never asked that I report from any particular position.) Those witnessing or participating in the destruction would make sure to capture and stream images of the activists on defense-only. When I filmed things that countered the narrative of activists/heroes, police/evil, activists would cover my camera with their hands, shout “PHOTOGRAPHY EQUALS DEATH!" and, one time, steal my phone. I should mention that a girl in black bloc washed teargas out of my eyes in the park across from the federal building. So, at a different event, did a Proud Boy.
With the exception of a blubbery young man who yelled from a curb across from Justice Center, "I'll shave your shit right off your fucking [head]" and later swung a metal rod at me, most protesters were both relatively friendly one-on-one and ill-equipped for confrontation, college-age girls fumbling to master umbrellas and homemade shields, and boys who as often as not appeared frail, uncoordinated, splay-footed, or fat. This was not an elite fighting force, and why Portlanders tolerated shouts of 'WHOSE STREETS? OUR STREETS!" night after night had less to do, at least at first, with intimidation than wanting to see themselves on what seemed the ineluctable right side of history. Were news anchors not warning, as they did every four years, that the 2020 elections were the most important our lives? And, regarding Portland in particular, invoking variations on "Trump goons!" around the clock, arousing and validating anxieties and also, a sense that the things worth fighting for - abolishing of racism, carceral reform, and taking power from those who'd historically abused power - were on the line. And Portland? Portland would hold that line.
This put local politicians in an unwinnable position. The constituency, or that part of it that was getting used to being listened to, demanded city leaders denounce the forces occupying the federal building. (Not a heavy lift: the federal rollout had been messy and included agents hauling people into unmarked vans.) And while the violence roiling the city every night had its downsides, it also acted as a pressure release valve for anyone driven to distraction by the Trump administration, and of these there were plenty. And so local officials squinted hard enough to make the continued destruction look, first, like freedom fighting, then like free speech, then as a thing to be tolerated in order to rebalance the scales of justice. With the city showing no stomach to go hard on those engaging in violence, there was little reason to not, for instance, set fires in front of Ted Wheeler’s condo on his birthday and demand he move out. He moved out.
That the chaos went largely unchallenged by the ostensible adults in the room would turn out to be less “Greetings, fellow kids!” than, “The enemy of my enemy is my friend.” And everyone in Portland knew who the enemy was.
"You probably remember there was massive rioting in [Portland's] Pearl District the day after Donald Trump was elected. Millions of dollars of damage were inflicted," a Portland colleague told me in late 2020. "How many people in the Pearl District voted for Donald Trump? It's probably not even one percent. Who on earth are these people who declare war on a place where nobody voted for Donald Trump? That's not how people in a democratic society are supposed to behave. You don't go trash neighborhoods with the opposing political party in a healthy democracy, but they didn't even do that. They declared war on the city as a whole."
This colleague chose to move out of the city. So did a half-dozen other Portlanders I knew. They saw the nightly violence and lack of accountability as eroding the social compact and, when they spoke up about it, faced pushback and public shaming. Neighbors got in screaming matches, jobs were on the line. People told me privately they were not in favor, or were no longer in favor, of the protests but kept quiet about it, lest they face reprisal. Did you want to chance squads of people in gasmasks shining lights into the windows of your house at night? It did not feel safe to appear anything other than full-tilt ally, and it did not feel safe because it was not safe.