In early October, Keith Wilson, the mayor of Portland, Oregon, visited 4310 South Macadam Avenue, an address that has thrust his city back into the national spotlight—and into the crosshairs of President Donald Trump. Since June, this site, the local headquarters for U.S. Immigration and Customs Enforcement (ICE), had been the focus of daily protests, with activists rallying against the Trump Administration’s immigration policies, often clashing with MAGA counter-protesters. Although the demonstrations were colorful—a carnivalesque atmosphere, with people wearing inflatable frog suits and other costumes—the ICE facility itself, a former data-processing center for a regional bank, with boarded-up windows, was about as incognito as the masked, armed federal officers who guarded it from the rooftop.

To the public, what was going on inside the building largely remained a mystery. No media, beyond Trump-friendly right-wing influencers, had been allowed in. But Wilson was “summoned” to the building, in his words, to meet with Kristi Noem, the Secretary of Homeland Security, who came to town after Trump announced, on Truth Social, that he was authorizing “all necessary Troops to protect War ravaged Portland.” Wilson hoped to persuade Noem that there was no need for federal intervention—that the city had its protests under control. But, after visiting the building, he reached the conclusion that ICE itself lacked any discipline or control. “It’s dishevelled,” he told me, of the conditions inside. “It’s unkempt. It’s disorganized.”

It was a warm day, around eighty degrees, and the first thing Wilson noticed when he entered the facility was how hot it was inside. “The H.V.A.C. system was broken,” he said. During his visit, he saw overflowing dumpsters. He saw tired, agitated officers. In otherwise empty offices, he saw crowd-control munitions and body armor strewn about. “You can just see they’re making it up as they go,” Wilson, a former C.E.O. of a trucking company, said. “There’s no plan. And, if there’s no plan, you don’t know the objective. Without an objective, you’re just wasting time and money—and they’re wasting time and money.”

Noem’s visit to Portland didn’t quite go as planned. The apparent purpose of the trip was to bolster the Administration’s case that the city was overrun by left-wing insurrectionists, but, during a rooftop photo op, Noem surveyed the site of the daily protests, presumably the most war-torn part of the city, only to find the street below empty. The Portland police, in accordance with its policy when dignitaries visit the city, had cordoned off the area. A smattering of demonstrators stood on the periphery, including a man in a chicken costume. Another protester blasted the theme from “The Benny Hill Show,” mocking Noem’s visit. In a video circulating online, Noem is expressionless—this probably wasn’t the war zone she’d come to capture. When she met with Wilson, he further shattered the plot, asking her to reconsider sending in troops. “She took issue with that,” he told me. “They’re trying to create a narrative. It’s a falsehood. It’s got no legs.”

I’d seen this split screen before. When I covered the last wave of high-profile protests in Portland, back in 2020, I discovered that the Trump Administration’s characterization of the situation didn’t always match what was happening on the ground. This time, the contrast appeared even sharper. I arrived in Portland last Monday—the same day that a three-judge panel of the Ninth Circuit Court of Appeals ruled that the White House can federalize the Oregon National Guard to deploy in the city. Residents seemed on edge, the mayor included. Was there a sense of anxiety about potential troops on the streets, I asked Wilson. “Every day,” he said.

Trump has been preoccupied with Portland since at least 2018, when he publicly scolded then Mayor Ted Wheeler for allowing “an angry mob of violent people” to confront federal agents. In 2020, in the wake of George Floyd’s murder, Trump referred to Black Lives Matter protesters as “radical anarchists” and deployed seven hundred and fifty-five D.H.S. officers to Portland to protect the city’s federal buildings, intensifying nightly clashes between protesters and law enforcement.

In recent weeks, Trump has reignited his fight with the largest city in Oregon. “I don’t know what could be worse than Portland,” he said in October, during a White House roundtable on the supposed dominance of Antifa in America. “You don’t even have stores anymore.” (There are more than three thousand retail businesses in the city.) “When a store owner rebuilds a store,” he said at a news conference, “they build it out of plywood.” (In four days of driving around the city, I was unable to spot a store constructed of plywood.) “Portland is burning to the ground,” he claimed, on multiple occasions. (I couldn’t find any fires, either.)

A generous read is that Trump is conflating images from 2020 with the state of Portland today. At the height of the pandemic, much of downtown was indeed shuttered, owing to COVID-19 restrictions, and many retail windows were covered with plywood. Footage from the Black Lives Matter protests—of federal officers marching through clouds of pepper spray, and masked demonstrators taunting them and then fleeing the sometimes bloody barrages of nonlethal munitions—played on cable news, seemingly on a loop. A recurring shot was of a burning American flag wrapped around the head of a George Washington statue. On September 4th of this year, Fox News, in a report on the current ICE protests, ran clips from the 2020 protests, without distinguishing between the two. (Fox later added an editor’s note acknowledging that the report included footage from both 2020 and 2025.)

“The characterization of ‘the city is on fire’ or ‘a war zone’ is not accurate,” Bob Day, Portland’s police chief, who had joined Wilson during his meeting with Noem, told me recently. His exasperation was palpable. Day retired from the department in 2019, a year before it became the subject of national attention. He returned in 2023, as police chief. “I get asked almost every day why I came out of retirement for this job,” he told reporters, after the meeting with Noem. “And I will tell you this is one of those days where I ask myself the same thing.”

Day, who is fifty-seven years old, grew up in Portland. And to grow up in Portland is to grow up in a city existing on the edge of political extremes. In the nineteen-eighties and early nineties, Portland had one of the country’s most active neo-Nazi scenes; a group of them killed an Ethiopian student in 1988. The murder helped galvanize anti-racist and antifascist groups to push the neo-Nazis out of the city, and those anti-racist and antifascist networks remain active in the city to this day, Joseph Lowndes, a political-science professor at Hunter College, at the City University of New York, who has studied extremism in the Pacific Northwest for more than twenty years, told me. Lowndes said that he believes the White House is now looking for the same kind of cinematic conflict it had with protesters in 2020. “What better way then to conjure up antifa,” Lowndes has written, “than to try to bait Portland into the mother of all antifascist confrontations.”

This is precisely the kind of conflict that Day is trying to avoid. Before entering the force in 1990, he had considered a career as a pastor. He still evinces the avuncular regard for the community that one associates with the cloth. “The Portland Police Bureau has a responsibility to all Portlanders,” he told me. This included both the workers at the ICE facility and the protesters facing off with them and with one another.

But, he said of D.H.S. and ICE, “I don’t know that we have shared priorities in regard to the specifics around safety.” He added, “That’s a work in progress that we’re trying to determine.” Day pointed to the bureau’s compliance with a state law that prohibits local law enforcement from assisting federal agencies in immigration matters. He also brought up the bureau’s renewed commitment to protecting free speech.

Most of all, Day wanted to make sure I understood the geography. The area in question in 2025, he reminded me, is a single block in a city that stretches a hundred and forty-five square miles. So, only with a lens focussed tightly enough, at just the right moment, and on just the right stretch of one specific city block, can you make the case that there is chaos in Portland.

At the ICE facility last week, three D.H.S. officers squeezed through a second-story window and camped out on a low roof. Fully masked, and dressed in camouflage, they held rifle-like launchers, presumably to fire pepper balls at the crowd below should it become unruly. It was the end of the workday in Portland, rush hour, and that afternoon the Ninth Circuit had ruled in the White House’s favor, bringing the National Guard that much closer to occupying the city. (This past Wednesday, it was revealed that some National Guard troops had already been in the ICE facility on October 4th, three days before Noem’s visit and hours after a judge had issued a temporary restraining order against their presence.) As commuters entered the intersection, they honked and shoved their middle fingers out their windows, flipping off the D.H.S. officers.

The man in the chicken costume, the same one who’d made a mockery of Noem’s visit, stood just outside the gate of the ICE facility, behind a blue line on the sidewalk labelled “U.S. Government Property.” A group of protesters, fluctuating in number between about thirty and fifty as the night unfolded, knew that crossing the blue line might mean tear gas, a beatdown, arrest, or all three. In addition to the chicken, there was the regular retinue of inflatable costumes, including frogs, a unicorn, an alien. A guy dressed as a butterfly picked cigarette butts off the asphalt.

On opposite ends of the street, a couple of groups of Trump supporters had gathered. One group keeps vigil with a banner, facing the officers on the roof, that reads “We are so proud of you.” Another group was farther down the street, and seemingly led by a man who had a court-mandated order to stay two hundred feet away from the facility, after he’d previously assaulted a protester. Now he shouted insults at the anti-ICE demonstrators from afar, through a megaphone.

Every half hour or so, the gate would open and a phalanx of D.H.S. officers would march into the street to clear the way for vehicles exiting the facility. The crowd and the officers traded taunts. “You’re a bunch of fucking losers,” one protester shouted. “I’m sorry daddy didn’t love you enough.” A D.H.S. officer apparently called a female protester fat. She replied, “I’d rather be fat than a motherfucking Nazi.”

One night, outside the facility, I met a man named Vincent Hawkins. He had set up speakers just outside the blue line, from which he blasted Mexican ballads, and he occasionally spoke to the officers on the roof, telling them that, eventually, they would go to jail for their unconstitutional behavior. Hawkins, an emergency-room nurse and a former National Guard medic, had a scar on his face: back in June, during a No Kings rally, he had been struck by a tear-gas cannister. “Hit me in the left eye,” he said. “Hit the lens of my glasses, and then that dug into my eyebrow ridge” and “almost ruptured the eyeball.” Hawkins, who is of Mexican heritage, told me that his main beef with ICE, aside from his scarred brow, was its interference with health care and the undocumented community. “The way that they operate has made people feel like they can’t come to the emergency room safely,” he said, speaking from experience in the E.R.

I also met Pamela Hemphill, a seventy-two-year-old woman from Boise, Idaho. Hemphill had been among the insurrectionists on January 6th; she pleaded guilty to parading in a Capitol building, and spent sixty days in prison. Now she was wearing a black sweatshirt that read “Call me Antifa,” and was outside the facility protesting against Trump. Speaking into a microphone, she told her fellow anti-ICE demonstrators that Trump and his supporters had lied to her, not only about the 2020 election but about the rest of America. “They told me the Democrats wanted to make this a communist country,” she said.

Hemphill and I spoke after she finished her speech. She asked if she could sit while we talked—she’s a cancer patient, and recent chemotherapy treatments had caused pain in her legs. That still hadn’t stopped her from making the six-and-a-half-hour drive from Boise to Portland, multiple times in the past few months, to protest ICE. I asked what she thought of the possibility of the National Guard entering the city. “We respect the military,” she said. “But it’s unnecessary. What are they going to do, pick up trash?” she asked, in reference to reports that troops deployed in D.C. had been relegated to litter duty. “We already pick up our own trash,” she said, gesturing to a protest zone that was relatively clear of litter.

On another night, I met Daniel DiMatteo, a Portland police sergeant and a part of the department’s “dialogue liaison” team, members of which are trained to reach out to activists to de-escalate tense situations. Day, the police chief, had mentioned DiMatteo’s division as a positive step the bureau had taken. But I was already aware of DiMatteo. A Trump-friendly X account had posted a video captioned “Portland PD gives ‘ANTIFA terrorists’ advice on how to keep federal troops out of the city.” (In the clip, DiMatteo is heard asking protesters to stay out of the street to avoid getting run over, because it could give the courts further reason to say that Portland needs federal help.)

DiMatteo said that his goal was to “facilitate the right to free speech.” In the current conflict between protesters and counter-protesters, each side had tried to persuade him to detain their opponents, he said. He hadn’t done that, insisting that an arrest would happen only if there was violence or property damage. (Portland police says it has made sixty arrests in the area since June. In early October, the Oregon District of the U.S. Attorney’s office said it had charged twenty-eight defendants for federal crimes at the ICE facility, including for “assaulting federal officers, failure to comply, and depredation of government property.”)

I joined DiMatteo and another liaison officer as they patrolled the block. There wasn’t much to de-escalate. They seemed like two beat cops shooting the shit with locals. They joked with protesters about their costumes. They took a break for dinner and returned about an hour later. When the biggest moment of the night finally arrived, it came with a soundtrack.

At around 6:20 P.M., roughly twenty people rushed onto the street corner across from the ICE facility. Salsa music emanated from a speaker that someone had carted in on a hand wagon. The new arrivals twirled and dipped and swung one another around. A group of protesters wearing frog costumes joined in; so did a guy dressed as the painter Bob Ross. This went on for an hour. And then another hour. A conga line formed. Some activists engaged in a dance-off. More people showed up. They swayed to reggaetón. They danced to Bad Bunny. All the while, the masked Feds on the roof stood watch, their pepper launchers at the ready. ♦