The scene outside Portland’s U.S. Immigration and Customs Enforcement (ICE) compound Monday evening was calm — a brief pause in what has become a turbulent national spotlight for the city. Protesters in inflatable costumes milled about peacefully, federal officers stayed mostly back, and even the usual livestreamers called it an early night.
But behind that quiet exterior, the situation surrounding the ICE facility — and the broader National Guard deployment controversy — remains deeply unsettled, as Oregon officials and the Trump administration continue to clash in court.
Right-Wing Influencers Granted Exclusive Access
Controversy erupted earlier this month when U.S. Secretary of Homeland Security Kristi Noem made an unannounced visit to Portland’s ICE facility on October 7. Unlike standard protocol, local media outlets — including The Oregonian/OregonLive — received no notice, itinerary, or access to Noem’s meetings.
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Instead, a handful of right-wing social media influencers were given what appeared to be VIP treatment. Videos later posted online showed them riding in Noem’s motorcade, entering the ICE compound, and filming interactions with detained individuals. Several clips featured Noem addressing the camera from the roof of the facility, flanked by armed officers.
Experts say the selective access raises troubling ethical questions.
“This is propaganda by invitation,” said one Portland State University media scholar. “When federal officials shut out independent journalists and only allow partisan influencers to document their actions, the public loses its right to unbiased information.”
Federal officials have repeatedly declined interview requests from major Portland outlets since June, continuing what local reporters describe as a pattern of restricted access.
‘Daily Show’ Films Naked Bike Protest
While government officials were controlling media narratives, late-night satire found its own way into the story.
Jordan Klepper, the Daily Show correspondent known for his political field segments, was spotted in Portland Sunday night during the city’s “emergency” World Naked Bike Ride — a rain-soaked protest against the National Guard deployment.
Witnesses described Klepper pedaling shirtless in a bulletproof vest labeled “PRESS”, conducting interviews with riders mid-route. Social media posts showed him joking with participants and remarking on the city’s unique protest culture.
Although The Daily Show is currently on hiatus until October 23, fans can expect the segment to air later this month, highlighting Portland’s blend of humor, defiance, and civic performance.
Federal Officers Threatened EMTs, Union Says
Meanwhile, new reports detail a disturbing confrontation at the same ICE facility earlier this month. On October 5, federal agents allegedly threatened to shoot an ambulance driver who was attempting to transport an injured protester, according to the American Medical Response (AMR) union and records reviewed by Willamette Week.
The protester had suffered a broken collarbone, and medics said federal personnel delayed their efforts by insisting on riding in the ambulance — a violation of medical protocol. One officer allegedly told a medic he would “shoot and arrest” them if they disobeyed. The patient was eventually taken to a hospital for treatment.
Calm Returns to ICE Facility — For Now
By Monday night, the tense scenes had given way to a subdued atmosphere. Protesters dressed as inflatable animals danced to portable speakers but kept clear of driveways. Officers avoided confrontations, and Portland police made no arrests. Even popular protest streamer Tommyboi signed off early, saying simply, “I’m bored.”
Legal Battle Over National Guard Deployment
In the courts, however, the fight is far from over. Lawyers for the state of Oregon and city of Portland have urged U.S. District Judge Karin Immergut to hold an emergency conference this week to determine the next steps in their lawsuit against the Trump administration’s plan to deploy the National Guard to Portland.
The administration has asked the 9th U.S. Circuit Court of Appeals to pause Immergut’s temporary restraining order, which currently blocks the deployment. That order expires Friday.
Federal lawyers argue Immergut lacks jurisdiction to extend or hold hearings while the appeal is pending. Oregon officials, however, insist the case can and should move forward immediately.
As of Monday night, the timeline for any future hearings — and for a possible National Guard arrival — remains uncertain.
For now, Portland’s protests continue to blend the serious and the surreal — a place where federal standoffs, viral satire, and inflatable animal costumes coexist on the same rainy streets.
