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.)
