Before the spotlight shifted to Los Angeles, the city of Portland, Oregon, took center stage in the national conversation about civil unrest.
During a tumultuous stretch of over 170 days in 2020, thousands of residents of Portland converged to express their dissatisfaction with police brutality. They didn’t just gather in typical protest fashion; they lay down peacefully on the city’s renowned Burnside Bridge and marched alongside local NBA star Damian Lillard. However, the protests also took a chaotic turn, with acts of vandalism and looting peppered throughout the demonstrations. Law enforcement responded with tear gas, while President Donald Trump’s administration sent 750 federal agents to the city without any local approval, leading to nighttime arrests of protesters in unmarked vehicles.
As anti-Trump demonstrations swell once again, with major rallies planned nationwide this Saturday, officials in Portland are understandably apprehensive about a repeat of the previous year’s events.
“The way the Portland Police and federal forces reacted back then only fueled more outrage and brought people out to protest,” remarked Ali King, a seasoned community organizer who had ties to now-retired Rep. Earl Blumenauer (D-Ore.) during that period. “Seeing the recent events in LA brought back memories. I felt a wave of PTSD.”
The repercussions of the 2020 protests were profound, prompting a complete overhaul of Portland’s governmental framework. The county appointed a more hardline district attorney, while the police department restructured its approach to handling protests.
Fast forward five years and 1,000 miles away, and we find President Trump once again dispatching federal officers into a city grappling with protests, much to the dismay of local and state authorities. The recent unrest in Los Angeles has reignited concerns in Portland. While this week’s protests in the Rose City have mostly remained peaceful, city officials are hoping that proactive policy changes will stave off a recurrence of the violence witnessed in 2020 and deter federal intervention.
“We’ve made significant strides since 2020,” stated Mayor Keith Wilson, a political outsider and trucking company owner who campaigned in 2024 on a progressive agenda focused on addressing homelessness and public safety. “However, the threat of federal overreach remains a significant concern, and we are ready to take legal action if necessary.”
An independent review conducted post-2020 protests identified numerous shortcomings within the city and its police force, including poor communication with the community, inadequate training in de-escalation techniques, and unclear protocols regarding the use of force. These deficiencies contributed to a breakdown of trust between the public and police and exacerbated tensions rather than alleviating them.
In response to the review and subsequent lawsuits against the police department for actions taken during the 2020 protests, significant revisions have been made to the city’s policing policies. Both Wilson and Portland Police Chief Bob Day emphasized to POLITICO that these revisions include limiting the use of tear gas and military-style gear, revamping the rapid response team, and appointing liaison officers to foster relationships with community organizations. Officers have also undergone training in Cincinnati and London, focusing on de-escalation and crowd management strategies.
“Our approach to large-scale events has evolved considerably,” noted Day, who was brought out of retirement in 2023 to serve as interim chief after previously holding the position of deputy chief. “From a public safety perspective, the goal is to avoid adding fuel to the fire.”
While most protests since the implementation of these changes have been peaceful, Sergeant Aaron Schmautz, president of Portland’s police union, expressed concern that the city has yet to face a situation reminiscent of the tumultuous events of 2020 that would truly test these new strategies.
“There’s a palpable sense of anxiety right now,” he admitted.
Portland is not navigating these tensions in isolation. Nearby cities like Seattle and Spokane are also experiencing unrest against ICE and the federal response to protests in Los Angeles. Seattle Police Chief Shon Barnes stated on Tuesday that he would do everything possible to protect Seattle residents “from anyone who comes to the city with the intention to harm them or infringe upon their First Amendment rights,” even if it means risking arrest. However, just a day later, at least eight demonstrators were arrested in Seattle after a dumpster fire was reported. Meanwhile, Spokane’s Democratic Mayor Lisa Brown imposed a curfew after over 30 arrests, including that of a former city council president, during protests.
King noted that Portland protesters are prepared to physically intervene to obstruct ICE actions, whether that means blocking agents’ paths or diverting their attention. However, she also acknowledged that trust between protesters and the Portland Police Bureau remains tenuous. Despite this, there have been ongoing community discussions focused on promoting nonviolent resistance and de-escalation strategies within protest circles.
Terrence Hayes, a community activist with a history of incarceration and a member of the city’s criminal justice commission, remarked on the shift in sentiment since 2020. The chaotic scenes of violence, gas, looting, and federal arrests are not experiences Portland residents wish to relive.
“We’re not looking to reignite that conflict,” Hayes stated. “If ICE attempts to push boundaries, people will certainly protest, but I don’t anticipate a repeat of the destructive behavior seen in the past.”
King added that “if someone is abducting an innocent person off the streets … we might need to step in physically.”
Over the past week, protests have erupted across Portland, including outside local ICE offices. While the majority have remained peaceful, Schmautz confirmed that there have been isolated incidents of violence and property destruction, such as arson, leading to around 13 arrests. For a city previously dubbed “Little Beirut” — a nickname that was once a badge of honor for local activists — the recent week has been surprisingly subdued.
Day asserted that this week’s calm reflects the efficacy of the newly implemented policies aimed at de-escalation. However, the landscape of 2025 differs significantly from that of 2020: back then, Portlanders were directing their ire towards their own police force, whereas now, the focus has shifted to the federal immigration system. While the police will not assist ICE, they still face the challenge of maintaining order without escalating tensions. Day described this balancing act as “a very complex, nuanced challenge.”
He provided two examples: Earlier this week, Portland Police removed protest debris obstructing ICE contractors from accessing a parking lot, a move that drew criticism from city residents. At that moment, the police believed the contractors were not engaged in enforcement actions and that clearing the debris would help ease tensions. Conversely, on another occasion, officers chose to observe passively rather than assist federal agents in navigating a similar blockade to allow a transport van for detained immigrants to pass.
Day explained that under normal circumstances, they would clear a blocked street. However, with ICE, they “are not going to actively enforce some of these laws” that impede ICE operations, but he stressed that “we can’t allow the ICE facility to become a free-for-all where any actions can be taken against it.”
The unpredictable element in these scenarios is the small faction of individuals who appear to incite conflict and encourage unlawful behavior. Nearly everyone interviewed for this article mentioned the presence of groups, both on the right and left, that infiltrate peaceful protests to provoke violence.
“Law enforcement may need to step in to address criminal behavior that exists on the fringes of free speech events, which complicates matters,” Schmautz noted.
At the heart of this ongoing struggle lies Portland’s enduring identity as a city that is unafraid to resist. Chief Day emphasized Portland’s long-standing protest culture, while Schmautz reiterated that free speech demonstrations are integral to the city’s values. King expressed concern that she and her fellow protesters may soon find themselves the target of the Trump administration’s scrutiny once again.
Yet Hayes aptly summarized the sentiment: “If you push, Portland pushes back,” he said. “If they come to Portland stirring trouble, you can bet Portland will respond in kind to that LA energy.”
