On September 28, 2025, Portland, Oregon, found itself thrust once again into the national spotlight as hundreds of demonstrators gathered outside the U.S. Immigration and Customs Enforcement (ICE) building. Their cause: to protest the Trump administration’s deployment of National Guard troops to the city, a move that has reignited longstanding tensions between local leaders and federal authorities, and drawn sharp lines between political factions both within and outside of Oregon.
The demonstration, which began on a sunny Sunday afternoon and continued well into the evening, was marked by a diverse crowd. As reported by OPB, families with children on bicycles mingled alongside seasoned activists clad in the now-familiar "black bloc" attire. The air was alive with chants, the steady beat of bucket drumming, and an unmistakable sense of urgency. Federal agents, some armed with long-barrel firearms, watched from nearby rooftops, while an armed escort of about two dozen agents periodically moved through the crowd to allow vehicles access to the ICE facility.
Despite the heavy presence of law enforcement, the protest remained largely peaceful during the day. Portland police, who monitored both the ICE protest and a separate downtown march, reported that their main role was directing traffic. But as night fell, tensions simmered. According to KOIN 6, minor physical altercations broke out between opposing protesters. At approximately 9:30 p.m., a 17-year-old was arrested for fourth-degree assault, followed shortly by the arrest of a 38-year-old man for third-degree assault. Police emphasized that no force was used during either arrest, and outside of these incidents, the demonstrations continued peacefully.
The backdrop to Sunday’s events was President Trump’s declaration a day earlier that he had authorized the use of federal forces to "protect war-ravaged" Portland. The president’s characterization of the city drew swift condemnation—and not a little sarcasm—from state and local officials, as well as confusion and frustration from residents. "The version of Portland described by the president is simply not, as anyone here can see, reality," Mayor Keith Wilson stated, as quoted by The Oregonian. He pointed to a city enjoying the outdoors, attending sporting events, and shopping—hardly the war zone painted by Trump.
The president’s announcement, amplified by administration officials and echoed by Labor Secretary Lori Chavez-DeRemer, who described Portland as a "crime-ridden war zone," quickly became a flashpoint for political debate. Prominent Republicans in Oregon, including House minority leader Christine Drazan, welcomed the decision, calling Democratic leaders’ reassurances "tone-deaf." In stark contrast, Governor Tina Kotek and Attorney General Rayfield, both Democrats, denounced the deployment. On Sunday, they announced that President Trump had invoked Title 10, and, in a dramatic escalation, filed a federal lawsuit seeking to block the use of Oregon National Guard troops against demonstrators.
The legal memorandum, signed by Secretary of Defense Pete Hegseth, called 200 members of the Oregon National Guard into federal service for up to 60 days, as part of a broader deployment to cities across the country. The stated purpose: to "protect U.S. Immigration and Customs Enforcement and other U.S. Government personnel" carrying out the administration’s policies. Governor Kotek, however, had refused to mobilize the Guard for crowd control herself, insisting that local law enforcement was more than capable of handling the situation, and warning that federal intervention would only heighten tensions.
For many Portlanders, the federal show of force felt like déjà vu. The city’s history of political protest is well documented, with the 2020 racial justice demonstrations—sparked by the murder of George Floyd—still fresh in collective memory. During that summer, federal agents deployed tear gas, rubber bullets, and other crowd control measures, drawing national scrutiny and fueling political campaigns. This time, city leaders, perhaps wary of repeating past mistakes, urged calm. "Let’s not take the bait," Governor Kotek advised residents, a sentiment echoed by Mayor Wilson and others.
Yet, not all protesters agreed with this approach. Dina, a protest organizer and the wife of a veteran, told OPB that Trump’s deployment of the Guard was a "moral injury" to her husband. "We are not going to stand for people following illegal orders," she said, explaining that many demonstrators felt the call for calm "perpetuates the Trump administration’s posturing about how we are dangerous protesters." Dina was adamant: "We are average, everyday citizens who are tired of the illegal actions of this administration and we are out here protesting well within our constitutional rights."
As the evening wore on, the mood shifted. According to OPB, several protesters were struck by pepper balls fired by ICE agents as they attempted to escort a vehicle into the building. The presence of more than a dozen counterprotesters—an uptick from previous nights—led to heated verbal exchanges, though major violence was avoided. The protest also shut down bus service through the area, underscoring its impact on the city’s daily rhythms.
Federal officials justified their increased presence by citing "weeks of violent riots at ICE facilities" and threats posed by domestic terrorists—claims that local leaders and journalists have repeatedly disputed. In fact, The Oregonian reported that arrests outside the ICE building had actually declined in the three months preceding the deployment, and that gun violence and other violent crimes in Portland were down in 2025 compared to previous years. The protests, the lawsuit argued, were "contained to a small area near Portland’s ICE facility" and "successfully managed by local law enforcement," posing no rebellion or imminent threat.
Still, the deployment and the president’s rhetoric have rekindled old divisions. Some see Portland as a symbol of resistance to federal overreach, and a test case for the limits of home rule and local autonomy. Others, particularly among the city’s more conservative circles, view the protests as evidence of lawlessness and failed leadership. As Senator Ron Wyden mused, "Why us? That’s something I ask myself a lot." The answer, perhaps, lies in Portland’s reputation as a bastion of progressive activism—a city with a long memory and little patience for outside interference.
Throughout the weekend, city and state leaders urged residents to stay calm and not play into the hands of those seeking confrontation. But as the crowd outside the ICE facility made clear, many in Portland are determined to defend their rights and challenge what they see as federal overreach. The legal battle now unfolding in federal court will determine not only the immediate fate of the National Guard deployment, but also set a precedent for the balance of power between Washington and America’s cities.
In the end, while the streets of Portland may have echoed with chants and the occasional clash, the city’s resolve—and its contradictions—were on full display. The world, once again, was watching.
