The arrest of Nicholas Sortor, a 27-year-old right-wing influencer from Washington, D.C., was quiet and quick.
A bike patrol officer from the Portland Police Bureau handcuffed Sortor shortly after 11 p.m. Thursday, about 200 feet away from most protesters outside the city’s U.S. Immigration and Customs Enforcement facility. Officers arrested two others, booking all three on disorderly conduct charges.
The fallout after Sortor’s arrest was loud and dramatic.
Right-wing influencers and top federal government officials accused Portland police of siding with “antifa,” an umbrella description for far-left-leaning militant groups, and discriminating against conservatives. In reaction, the Trump administration promised a “surge” in federal agents, similar to what’s happened in Chicago.
That may still happen, but the president won’t be able to send in the National Guard as he originally planned. A federal judge on Saturday granted a temporary restraining order blocking Trump’s effort to deploy 200 Oregon National Guard troops to Portland.
The president said the city was “war ravaged,” but District Court Judge Karin Immergut found “The President’s determination was simply untethered to the facts.” Her order will stand for 14 days, pending more court hearings.
The pressure is rising in the Rose City. A little over a week after Trump first announced the planned deployment, Portlanders are now facing the familiar sensation of watching their city be constantly maligned by the president, and in reaction, seeing formerly tame protests reignite.
Just this Saturday, federal agents sprayed tear gas into a crowd of about 400 protesters and arrested at least three people.
The consequences of the days and weeks ahead could be even worse than in 2020, the last time Trump set his sights on Portland, said 26-year-old protester Jack Dickinson on Thursday night.
“My biggest fear is we will never fix this,” Dickinson said, “and this country slides further and further into something we couldn’t have ever imagined.”
How did Portland get here?
For an area claimed by Trump to be under siege by terrorists, South Portland at nightfall has been conspicuously quaint in recent days.
About three blocks north of Portland’s ICE facility, customers lounged outside a brewpub and sipped their last dregs of beer shortly before 9 p.m. Thursday.
Across the street, a couple strolled their dog through the amber glow spilling from a wine bar. There, the loudest sound was the wind rustling leaves of trees lining each sidewalk, their trunks bright with strands of twinkling lights.
Given the relative calm, Trump’s National Guard announcement, made through a post on Truth Social in late September, caught many Portlanders by surprise.
For some, however, it was only the latest jab in a nearly decadelong feud between the president and their famously weird city, known for its leafy neighborhoods, indie stores, artisanal doughnuts and penchant for protesting.
Trump has long maligned these protesters as “antifa,” something he claims is a domestic terrorist organization in Democrat-led cities bent on violently opposing his administration. Its stronghold, he believes, is in Portland, where at least one group of activists, Rose City Antifa, has reportedly been using the label to identify itself since 2007.
In a statement Tuesday defending its decision to send the National Guard to Portland, the White House used the word “antifa” 16 times and described protesters as “terrorists” six times, listing incidents in Portland dating back to 2016.
Antifa, as an official organization, does not exist.
The word, a contraction of “anti-fascist,” is an umbrella term often used to label activists who share similar — sometimes aggressive — protest tactics, and generally oppose white supremacy, authoritarianism, racism, xenophobia and homophobia.
There is no group leader or centralized structure. Protesters often organize in secret, covering their faces and communicating via encrypted messaging apps such as Signal.
Among Portland protesters, a small number have been alleged to spray paint city property, block exits to government buildings, throw rocks at police and get into skirmishes with officers. Seattle protesters have faced similar allegations, including throwing fireworks at officers, kicking them and shining lights in their eyes.
In both cities, police clad in riot gear have responded, sometimes using pepper spray, striking demonstrators with their shields or batons or firing munitions they deem less lethal," like blast balls or tear gas, into large crowds of protesters.
Such clashes were most intense and visible during the summer of 2020, when thousands of protesters faced off against law enforcement officers in downtown Portland after the murder of George Floyd, a Black man, by a Minneapolis police officer.
Trump sent Federal Protective Services officers to guard the city's federal courthouse in July 2020. A month later, he wrote on social media that National Guard troops could quell the protests, but he never tried to follow through with that threat.
City and state leaders say that Trump’s perception of Portland now may be influenced by outdated footage of 2020 Portland protests that are recirculating online and on TV.
Recent protests at Portland’s ICE facility, which have been held nearly daily since June in reaction to immigration raids in Southern California, have never gotten close in size or intensity to those of 2020. They had mostly petered out in recent weeks, with crowds rarely exceeding 25 protesters.
Portland police and federal officers had arrested a total of about 60 people outside the city's ICE facility from June to this Saturday, according to The Oregonian. In contrast, local law enforcement agencies arrested nearly 1,000 people within the first five months of Portland's protests in 2020.
And Portland is not the same city it was five years ago, according to officials' open letter last week. Tourism there is at a post-pandemic high, and gun violence and homicides have plummeted in recent years.
The city still faces real issues around housing, infrastructure, schools and behavioral health, Mayor Keith Wilson wrote in an open letter published Thursday by Time magazine. But instead of addressing those, Trump has promised to use "full force" on a "situation that does not exist, with murky, unknown, and potentially deadly rules."
"Is the safety of our people less important than fleeting political optics?" Wilson wrote in his letter. "Should I tell our hospitals and morgues to prepare for the unthinkable?"
"Why are we the scapegoat?"
Protest crowds swelled almost immediately after Trump’s Truth Social post Sept. 27, with over 100 people showing up outside the ICE facility some nights.
Some were longtime protesters, including Jack Dickinson, who always wears a chicken suit with an American flag draped around his neck.
They want to be able to have the riot that they have been saying has been going on for years as an excuse for them to crack down on antifa, or whatever they label as the anti-fascist,” Dickinson said.
Many of the new faces belonged to what Portland police and protesters call “agitators,” or counterprotesters who rile up the crowd. About 20 of them squabbled with protesters Thursday night, with people on either side hurling insults and filming each other on their phones. They taunted each other over the sounds of a low-flying military plane and a boombox blasting Rage Against the Machine.
Occasionally, their fights turned physical.
As tensions ratcheted up, Portland police officers — who for months had stayed largely out of the way — started emerging from the sidelines. Shortly after 11 p.m. Thursday, officers arrested three people for disorderly conduct after seeing them allegedly getting into fights earlier that night.
Among them was Nicholas Sortor.
By Friday morning, footage of Sortor’s arrest had rocketed across right-wing social media circles. Their outrage reverberated up to the White House, where top officials accused Portland police of discriminating against conservatives while letting antifa criminals roam free.
“The irony here is we were condemned in 2020 for our approach toward the left,” Portland police Chief Bob Day said at a Friday news conference. “Now we're being condemned in 2025 for our approach to the right.”
Seeing Portland constantly maligned by the president and on TV is exhausting, said 39-year-old Hannah Wallner on Thursday night, standing across the street from Portland’s ICE facility.
For days, Wallner’s friends in Los Angeles messaged to ask whether Trump’s comments about Portland were true, and whether the city was really at war. She said it was difficult to tell what was going on based on short clips of the protests shown by local TV stations.
On Thursday, Wallner and her partner drove to the protest from their home in a suburb just east of Portland to “see what was really happening.” There was clearly hostility between the anti-ICE protesters and the conservative protesters gathered there, she said, but nothing about the intersection outside of the ICE building resembled war.
For the couple, this realization only launched more questions, Wallner said: Why do federal officers seem to police protesters in Portland more aggressively than in other U.S. cities? Why is the city so often portrayed inaccurately on TV? And why is the president not seeing what they see?
“Why are we the scapegoat?” Wallner asked. “The train wreck?”
“This is our home”
At about 9 p.m. Thursday, a fresh round of cat-and-mouse began.
After a loudspeaker announcement commanding protesters to get off federal property, the facility’s driveway gate opened. About 30 armed federal officers, most with their faces covered, marched out wearing helmets and gas masks.
Several dozen protesters shouted insults and filmed the officers. One protester dressed as a giant frog wiggled in front of them. A smaller group of counterprotesters, some wearing MAGA gear, also filmed with their cellphones, cheered and thanked the officers.
A tense hum of anticipation built after a car exited the facility’s garage, traveled down the driveway and past a group of officers.
“Get back!” One officer shouted as a protester walked off the sidewalk, precariously close to the row of police. The protester spun around and walked back.
In a sudden scuffle of activity, officers tackled another protester. It was not clear why. Other protesters screamed as the counterprotesters jeered. Four officers lifted the protester, who seemed to be unconscious, and carried them up the driveway and into the facility.
After about a minute, the remaining officers began marching backward up the driveway and behind the gates.
The protesters returned to their posts, many standing in clusters on the sidewalk and shouting at the officers now gathered on the building’s roof. Some socialized or smoked cigarettes. One person used a bubble machine.
The cycle of tension, a sudden arrest, anger and then waiting would repeat itself for about four hours, as it had several nights that week, protesters said.
Finnegan Greene, 20, said he was standing with his girlfriend that night about a foot back from the officers’ “shield line” when one officer told them to move. They stepped back, but continued yelling.
As the officers started marching backward up the driveway, one of the officers pepper-sprayed Greene and his girlfriend. Protest medics rushed forward to help flush their eyes and mouth. His eyes were still bloodshot about an hour later.
The pain, he said, motivated him to keep protesting.
“Families are being torn apart by these facilities and these people,” Greene said. “I feel pretty pissed off. I want to come down even more now.”
Norm Kalbfleisch, 72, observed the scene from down the block. The retired emergency medicine professor lives about five blocks away and said he visits the protests several times a week to see what’s happening.
By and large, he said the protesters, many of whom are students and older adults, have “acted really well.” But he worries the city and its activists are becoming so vilified that something like Kent State — when Ohio National Guard members killed four and injured nine anti-Vietnam War protesters in 1970 — could happen in Portland.
“I’m frightened for people who don’t want to do anything other than to protest what’s happening to their city,” he said. “This is our home. It’s an imperfect place, but it’s not dangerous. It’s not under anarchy. The people who are protesting are not bad people.”
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