Portland’s uneasy relationship with law enforcement and federal agencies ignited once again Saturday night, and if it feels like déjà vu — that’s because it is.
What began as a nationwide protest dubbed “No Kings Day” quickly devolved into outright violence outside the U.S. Immigration and Customs Enforcement (ICE) facility in South Portland. By nightfall, police declared a full-blown riot. Protesters hurled fireworks, smoke grenades, and rocks at officers. A mob shattered glass, breached the building’s entrance, and injured four federal agents.
Activists throwing smoke bombs at police officers at the ICE detention facility in Portland, Oregon. Other things were exploding but I have no idea what. Possibly just very powerful fireworks. I saw a few dozen officers in riot gear nearby and things started escalating so I left pic.twitter.com/6CXs9bgzlx
— Kevin Dahlgren 🥾 🥾 (@kevinvdahlgren) June 15, 2025
Sound familiar?
This wasn't a peaceful protest gone sideways — this was a calculated escalation. And it’s starting to look a lot like the riots that rocked Portland during the summer of 2020. Only this time, the fuse seems shorter, and the playbook hasn’t changed: gather en masse, provoke confrontation, and set the stage for late-night destruction.
Anti-Trump 'No Kings Day' protesters demonstrate in Portland, Oregon pic.twitter.com/ePM10Kzqsl
— Molly Ploofkins (@Mollyploofkins) June 15, 2025
Federal agents deployed tear gas to disperse the crowd. Portland Police made targeted arrests. At least three people were taken into custody for charges including criminal mischief, assaulting a public safety officer, harassment, and theft. One protester was arrested for picking up traffic control devices and throwing them into his truck. Another used pepper spray on officers.
This wasn’t “civil disobedience.” This was chaos.
The Portland Police Bureau made it clear: “The arrests were strictly focused on criminal actions, and not constitutionally protected free speech.” DHS echoed the sentiment, calling the violent offenders “cowards” and vowing full prosecution for assaults on law enforcement.
"This is what democracy looks like" being chanted at the Portland No Kings protest, as the flags of an authoritarian regime wave overhead pic.twitter.com/QJ0uH3cEIr
— ghost Tara Faul (@tarafaul503) June 15, 2025
Despite the clear pattern of violence, many in the city’s leadership have remained conspicuously silent — a response we’ve seen before when Portland makes national headlines for all the wrong reasons.
This week alone, Portland saw multiple confrontations at the ICE facility, with arrests nearly every night. Protesters attempted to start fires, block entrances, and antagonize federal officers. On Saturday, police were forced to declare a riot after rocks and fireworks rained down on law enforcement. At one point, a federal officer was injured inside the building.
Portland, Oregon
— MəanL¡LMə♡₩ (@MeanLILMeoW) June 15, 2025
No Kings Protest | ANTI-I.C.E. Riot
Last night, Portlands federal Ice Facility,Were attacked freely with little to no repercussions as Police were no not engaging the crowd we mostly on bike unprotected (not riot gear prepared) there were some officers firing… pic.twitter.com/lipnLmkCJM
In other words, it’s not just a “bad night” — it’s a troubling pattern.
What’s even more disturbing is the dissonance: large peaceful marches during the day, followed by violent riots at night — a trend that became all too familiar during the BLM protests years ago. And here we are again.
The “No Kings” protest started with a message against authoritarianism. But somewhere between South Moody Avenue and South Bancroft, it morphed into something else entirely: another black eye for a city that still hasn’t recovered from the last round of street-level anarchy.
Portland, Oregon
— MəanL¡LMə♡₩ (@MeanLILMeoW) June 15, 2025
No Kings Protest | ANTI-I.C.E. Riot
Last night, Portlands federal Ice Facility,Were attacked freely with little to no repercussions as Police were no not engaging the crowd we mostly on bike unprotected (not riot gear prepared) there were some officers firing… pic.twitter.com/lipnLmkCJM
In response to the chaos, Portland Mayor Keith Wilson issued a statement Sunday acknowledging both the scale of the peaceful daytime protests and the violent outbreak that followed. “An estimated 50,000 Portlanders marched together in solidarity and protest yesterday,” he said, commending those who “peacefully and powerfully raised their voices against Federal overreach.”
However, Wilson made a point to distance the violence from the earlier march, stating that the riot at the ICE facility occurred “miles from the planned demonstration.” He drew a clear line between the lawful protesters and the smaller, more volatile group that targeted federal property. Wilson confirmed that fireworks and other materials were used to damage the facility and that three federal officers suffered minor injuries.
He emphasized that Portland remains a sanctuary city but warned that “violence, destruction, and obstruction carry consequences.” While reaffirming that Portland police will not serve as agents of ICE, he stated they will “intervene when criminal acts occur,” and noted that even when arrests aren’t made on the spot, “follow-up investigations and prosecutions will continue.” Wilson also condemned the federal deployment of the National Guard to cities like Los Angeles, stating that Portland neither needs nor welcomes military intervention.
How many more riots will Portland tolerate before leaders take a harder stance on violent extremism masquerading as protest?
The fact is, most Portlanders support free speech. What they don’t support is being held hostage by the same small group of agitators who treat every weekend like open season on law and order.
And while the smoke clears once again over the ICE facility, one question remains unanswered: Will anything change this time?