As protests and riots over George Floyd’s murder rocked cities across the country in the summer of 2020, President Trump sent federal law enforcement officers to Portland, Ore., to quell large nightly demonstrations at the city’s federal courthouse.
Now, five years later, the chaotic and sometimes violent upheaval in Portland and the subsequent clashes between protesters and the federal authorities that followed the deployment in 2020 have become an unflattering part of Portland’s public image, one that many residents are eager to erase.
But for Mr. Trump, those weeks appear to have provided a playbook, which he is now following as he moves to send National Guard forces to cities that he argues are out of control. And for many people who lived through that trying time in Portland, the fraught days of 2020 offer a cautionary tale, as demonstrators gather in the city once again, this time to protest the treatment of immigrants.
In interviews, police officers, federal agents, protesters and city officials described missteps in 2020 that made a tense situation worse and are already being repeated in other cities by police forces and protesters alike.
Some of those veterans of 2020 expressed hope that the experiences of five years ago would inform what happens in the weeks and months ahead. Others worried that the combination of Mr. Trump’s penchant for provocation and the presence of a small cadre of protesters and counterprotesters bent on sowing chaos would once again make the city a tinderbox.
“It’s hard for me to give you lessons,” said Aaron Schmautz, a Portland police sergeant and head of the city officers’ union. “All I can really remember is how tired and traumatized we all were.”
Luis-Enrique Marquez, a frequent demonstrator in Portland, had this warning: “The biggest lesson, to me, is that this is going to get bad.”
A sudden escalation
The Black Lives Matter demonstrations in Portland began with thousands of people decrying injustice; a few also took part in setting fires to vehicles and buildings, hurling objects at the police and clashing with law enforcement officers. But those protests were down to a few hundred people a night by the time the Department of Homeland Security began “Operation Diligent Valor” on June 26, 2020, to protect the federal courthouse in downtown Portland.
The arrival of federal officers from Immigration and Customs Enforcement, the Border Patrol and other federal agencies prompted tens of thousands of people to take to the streets around the courthouse and the justice center.
“All those people coming out each night gave the feds justification for doing whatever they wanted,” Mr. Marquez said.
Local police departments generally have more experience with crowd control, compared with federal agencies whose daily duties revolve around immigration enforcement. Even National Guard troops who have some training in coping with protests are usually not as well-versed or well-equipped for crowd management as municipal and county officers are.
“Taking people whose job is being a border patrol agent at the southern border or a National Guardsman on a peacekeeping mission overseas and asking them to do urban crowd control, that’s just not going to succeed,” Sergeant Schmautz said.
Two recent shootings in the Chicago area seem to point up that concern. In September, an ICE officer shot and killed a man who tried to speed away from a traffic stop. The incident proved fatal in part because of the way the ICE officers pulled the man over. Then federal agents shot and injured a protester on Saturday morning after they said she had boxed them in with her car.
The presence of troops or federal law enforcement agents at protest sites also tends to attract counterprotesters hoping to show support for Mr. Trump. In 2020, fights broke out in Portland between right-wing and left-wing demonstrators.
“People who come to express their First Amendment rights need to be aware of the dynamic,” said Chris Dobson, an assistant chief with the Portland Police Bureau who was the incident commander for many of the 2020 protests. “In 2020, what we saw was that in the daytime, we had these large, often beautiful, marches,” he said. “But when the sun went down, the dynamic changed.”
Extremists in the crowd
People who participated in the 2020 demonstrations bristle at suggestions that the protesters in general behaved in ways that justified the use of force by law enforcement officers.
But most nights, a small but persistent group, often black-clad anarchists, would appear and throw rocks, frozen water bottles or small incendiary devices at federal agents who were guarding downtown buildings. These protesters broke windows, damaged parked cars and, at least twice, tried to set government buildings on fire. Mr. Trump’s Department of Homeland Security would then ratchet up its tactics in response.
“Embedded in that crowd were people — not many, but still, people who were willing to set a building on fire with people in it,” said Renn Cannon, who in 2020 was the F.B.I.’s special agent in charge for the state of Oregon. “From a law enforcement perspective, that is where I have to focus my attention.”
Mr. Schmautz, the union leader, said that when they demonstrate this year, protesters should police themselves.
“Some people in the crowd would see violence and go, ‘OK, time for me to go home,’” he said. “I’d hope more people will do that, if this all happens again.”
A cause quickly forgotten
The Portland protests of 2020 may have begun as rallies for racial justice and against police violence, but whatever messages had initially motivated protesters became muddled once Mr. Trump sent federal forces to downtown Portland and the crowds there grew to the thousands.
The demonstrations devolved into protests against federal agents.
“A lot of the work we’d done to dismantle white supremacy got sold out,” said Teressa Raiford, the founder of a nonprofit that works on racial issues and civilian oversight of the police in Portland. “The priority was, ‘We’ve got to get rid of Trump.’”
Ms. Raiford and other activists who were part of the Portland protests still feel frustrated, five years later, by how quickly they believe their cause was forgotten in 2020. Portlanders have made some big changes in their city since 2020, including voting to create a new police oversight system. But the City Council later rolled back some efforts to expand civilian oversight of the police.
“I hear people say, ‘They left in 2020, so we won,’” said Anita Randolph, an assistant professor at the University of Minnesota Medical School who organized mental health care for demonstrators in 2020, referring to the withdrawal of federal agents. “It’s hard for me to say that we won when I look up and we’ve got this president threatening to do the exact same thing again.”
Mr. Marquez said he anticipated a repeat of 2020, as protests over the treatment of immigrants at ICE facilities morph into opposition to a perceived overreach of presidential power. As it was in 2020, the president’s stated justification for mobilizing federal forces now is the protection of federal buildings — the courthouse last time, the ICE facility this time.
The president’s bully pulpit
Civic leaders in Oregon are putting one lesson that was learned in 2020 into practice now: They are pushing back against the president’s assertion that Portland is “war-ravaged.”
The demonstrations that drew international attention in 2020 were largely confined to about a six-block area in the center of the city. Yet Randy Blazak, a sociologist and activist, recalled getting regular calls from his Fox News-watching father in Georgia, asking, “‘Are you OK? It looks like Antifa is burning down your house.’”
“You can roll your eyes all you want,” Mr. Blazak said, “but perception matters.”
This time, Oregon leaders have recruited business owners to provide legal briefs objecting to federal activation of National Guard soldiers because of the negative economic impact that they feared mass demonstrations could have. The leaders have held media briefings on the Willamette River waterfront as tourists sauntered by.
“This president knows how to craft a narrative aimed at people’s fear,” said Candace Avalos, a member of the Portland City Council. “You have to be able to counter that.”
An ‘isolated’ police force
Chief Bob Day of the Portland police looks back on 2020 and sees a series of missed opportunities for his agency, almost all of them lost through a lack of communication.
Portland’s elected leaders barred his officers from coordinating with federal law enforcement agencies. That meant the city police could not assist federal agents in quelling protests, nor could they offer the federal authorities advice that might have prevented violence. And while his officers had regular conversations with counterprotesters on the right in 2020 to understand where and when they planned to rally, he said the police had few solid connections with demonstrators on the left.
That gap made it harder to separate the few agitators who were causing trouble from the majority of peaceful protesters.
“We were just very isolated in many ways,” Chief Day said of the Portland police, “from our City Council, from our state government, from the people out protesting.”
In Chicago, the consequences of the city’s prohibition against local cooperation with ICE agents have already been felt, notably on Saturday when Chicago police officers appeared at the scene of a shooting of a protester and wound up being tear-gassed. Mayor Brandon Johnson of Chicago has demanded an investigation.
His police chief, Larry Snelling, said in August that he hoped that with better communication, local and federal forces could “find some type of balance” and avoid “an adversarial environment.”
Since 2020, Portland’s police department has revamped its approach to crowd control. New “dialogue officers” now serve as liaisons between the police and protest organizers, with a goal of de-escalating demonstrations rather than shutting them down. At the ICE building in Portland, city police officers have been wearing white uniform tops rather than the standard dark blue, and simple bulletproof vests rather than full riot gear.
Mr. Blazak, a scholar of political extremism, has worked with the city police to set up conversations between officers and demonstrators, and between demonstrators and neighbors of the ICE building.
Back-channel communication was what defused the 2020 crisis in Portland. The governor at the time — Kate Brown, a Democrat — negotiated directly with Vice President Mike Pence, whom she had known since he was governor of Indiana. A month into “Operation Diligent Valor,” they reached a deal to replace the federal forces downtown with officers of the Oregon State Police. The largest demonstrations ended.
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