Federal officers “gassed” Portland police officers and fired pepper balls at one local officer outside the U.S. Immigration and Enforcement building in the city in the past month.
When Portland police later confronted federal law enforcement for aiming at and striking their officer with pepper balls, federal officials responded, “help or get out of the way,” according to police.
Portland police supervisors are expected to testify about the encounter in a trial that gets underway Wednesday as the state of Oregon, city of Portland and state of California continue to challenge President Donald Trump’s Sept. 27 mobilization and attempted deployment of National Guard troops to Portland.
Portland police also are expected to testify that the increased presence of federal officers outside the ICE building since Sept. 27 has “caused the situation to deteriorate,” with federal officers responding with “needless” and sometimes “arbitrary” firing of tear gas, pepper balls and smoke canisters.
The federal government created “the very emergency they propose to resolve with the National Guard,” lawyers for the two states and city wrote in a trial memorandum filed in federal court Monday.
Lawyers for Oregon, California and Portland will urge U.S. District Judge Karin J. Immergut to issue a permanent injunction barring Trump from sending any National Guard members to Oregon to protect Portland’s U.S. Immigration and Customs Enforcement.
Federal officials counter that local police have been “unhelpful” and “hostile” at times and they can’t rely on Portland police to protect the property or officers working in the South Waterfront building as nightly protests have continued since June.
The Police Bureau has not directed its officers to move protesters who block the ICE facility’s driveway and prevent ICE vehicles going in and out.
“The record is replete with evidence of the PPB failing to provide assistance when federal officials have requested it,” federal lawyers countered in their own trial memorandum.
The Police Bureau’s policy against assisting with immigration enforcement goes “far beyond any ordinary” understanding of enforcement, the U.S. Department of Justice lawyers argued.
Oregon, Portland and California submitted more than 1,200 exhibits for trial, including Trump’s social media posts, video of protests and Portland police and Federal Protective Service incident reports.
TIMELINE: Follow the flurry of court action in challenge of National Guard deployment to Portland
As lawyers prepare for trial, they’re also awaiting a decision by the 9th U.S. Circuit Court of Appeals on whether its 29 active judges are going to vote to rehear a ruling by a three-judge panel that sided with the Trump administration last week and put a hold on Immergut’s Oct. 4 temporary order barring federal control of Oregon National Guard members in Portland.
Federal lawyers argue that the court must give a “great deal of deference” to the president and his determination that he’s met at least two of the criteria required before he can federalize National Guard members under federal code’s Title 10, Sec. 12406: that there was a danger of a rebellion against U.S. government authority, and “regular officers” have been unable to execute federal law.
They cite damage to the ICE building since June, spraypainting of violent threats on its exterior, protesters’ blockading of the gated vehicle entrance, protesters throwing rocks and fireworks, doxxing of officers online and attempts to follow officers’ cars home or to hotels and the resulting closure of the building for three weeks during the summer.
On June 12, for example, they contend that 450 protesters barricaded federal employees inside the ICE building and ignited fires, leading to the three-week closure. In late July, the federal government said protesters threw titanium screws in front of the driveway to damage tires of federal vehicles. Federal officers say they’ve had to use “non-lethal” force to clear people out of the driveway in order to allow vehicles in and out, according to the U.S. Justice Department’s trial memorandum.
The federal government also contends the Federal Protective Service agency, responsible for security of federal property, is stretched thin and not staffed to provide around-the-clock protection. But even with the help of extra ICE and U.S. Customs and Border Protection officers, the coverage is unsustainable, federal lawyers wrote.
Lawyers for the states and the city of Portland counter that the Trump administration has not met any of the required criteria to deploy Guard members. They argue there’s no evidence of a rebellion or the threat of one in the city, and federal officers in Portland have not shown they were unable to carry out federal law without the help of National Guard troops in the weeks or even months leading up to Trump’s Sept. 27 authorization of Oregon National Guard members.
Federalizing National Guard troops is an “extraordinary” measure that should be allowed only as a “last resort” and definitely should not be based on Trump’s “obviously absurd” and “brash” assessment of the conditions in Portland, their lawyers wrote in a trial memorandum.
While the president is due deference and law enforcement has “faced challenges” outside the ICE facility in the South Waterfront neighborhood since June, only one riot was declared, on June 14, and after that protests quickly dwindled, with sporadic demonstrations that warranted “targeted responses,” the lawyers for the two states and Portland noted.
Only after Trump’s Sept. 27 post on Truth Social authorizing federal control of Oregon National Guard members, including his “incendiary rhetoric” that Portland was “War ravaged” and the ICE building was “under siege,” did the protests once again become larger and more tense, the states’ and city’s lawyers wrote.
The larger protests instigated by the president’s rhetoric and actions gave Trump the optics of “smoke, flashes of fire and explosions” that he sought, which were broadcast on national TV, the states’ and city’s brief says.
Federal agents use chemical crowd control munitions during a protest at the Portland ICE facility on Saturday, Oct. 4, 2025.Allison Barr/The Oregonian
Portland police will testify that the demonstrations outside the ICE building have not been “organized,” but have largely been unstructured and decreased in volume and intensity since they declared a riot on June 14.
The protests presented “ordinary challenges,” including sporadic crime amid First Amendment-protected protests, according to local police.
“Plaintiffs seek to protect their sovereignty, retain control over their own National Guard, law enforcement and public safety, and prevent unnecessary disruption to Oregon’s largest city,” their lawyers wrote. “Plaintiffs have filed this suit to protect the basic structure of American federalism from an alarming intrusion that was, until the events in Los Angeles just months ago, unprecedented. In contrast, the federal government faces no harm from an injunction.”
Federal officers in Portland can continue to enforce federal law, including immigration enforcement, even if the National Guard is barred from deploying to the city, they wrote.
Lawyers for the city and state urge the court to consider that there have been three phases to the protests outside the ICE building: The first two weeks of June, which involved some “disruptive and unlawful” actions, including minor fires, use of fireworks, paintballs and lasers, harassment and assault on a public safety officer and damage to the ICE building. Windows and doors were broken, a driveway entry card reader was destroyed and graffiti threats were scrawled on the exterior. Portland police said they made arrests “as appropriate,” until declaring a riot on June 14, when “many” in the 300-person crowd engaged in violence and disorderly conduct, according to the states’ and city’s brief.
In phase two, Portland police after June 14 adapted their stance to enforce not just felony person and property crimes, but other misdemeanor crimes. They made no arrests at the protests in late June, July, August and early September. Protests in the rest of June after the riot was declared were largely “low energy,” the states’ and the city’s lawyers said.
Federal Protective Service officers never moved more than 31 officers from other regions to Portland at any one time and the agency has “untapped” capacity to protect the building if needed, lawyers for the two states and city argued.
Oregon State Police Capt. Cameron Bailey and Portland police Assistant Chief Craig Dobson, Central Precinct Cmdr. Brian Hughes and Specialized Resources Division Cmdr. Franz Schoening are expected to be called as witnesses by lawyers for the state and city of Portland.Court Document
The federal government never exhausted its “non-military options,” with more than 80,000 law enforcement officers under the Department of Homeland Security, more than 4,500 other Homeland Security staff cross-designated to fulfill Federal Protective Service duties, or asked the FBI, DEA or U.S. Marshal’s Service to help if needed.
Phase three has been the period since Trump announced he was sending troops to Portland. This has seen larger protests again and has been largely non-violent, with few arrests, the states’ and the city’s lawyers say.
Federal lawyers point to the Oct. 20 ruling by a three-judge 9th Circuit panel that sided with the Trump administration, finding that his deployment of 200 Oregon National Guard members was measured. They also noted a different three-judge panel of the 9th Circuit put a hold on an injunction issued by a federal judge in California intended to block National Guard troop deployment there. They ask Immergut to consider anti-ICE actions in other states, such as the shooting outside an ICE field office in Dallas last month and alleged targeted bounties placed by Mexico-based criminals of up to $50,000 for the kidnapping, assault or assassination of Homeland Security personnel in Chicago.
Major General Timothy L. Rieger, acting vice chief of the National Guard Bureau; Cammilla H. Wamsley, the Seattle-based field office director for U.S. Immigration and Customs Enforcement’s Enforcement and Removal Operations; Robert Cantu, deputy director of the Federal Protective Service Region 10; and William Turner, of the U.S. Department of Defense, are on the federal government’s witness list.Court Document
They argued that the Oregon National Guard members would serve in a “purely protective capacity” at the Portland ICE building and that their deployment for a limited period of time would not harm the state. In fact, the federal lawyers contend, the Guards presence would “provide the presence needed to counter persistent violence and threats in Portland.”
“It is simply common sense that federal agents would be able to engage in greater enforcement of the immigration laws if they were not operating under the threat of assaults and obstruction, and that they are currently bearing unacceptable risks to their safety while doing their jobs,” the federal Justice Department lawyers wrote.
Even if the decision by the 9th Circuit’s three-judge panel –- placing a hold on Immergut’s first temporary restraining order barring federal control of Oregon National Guard troops in Portland – stands, Oregon, California and Portland said they still expect to succeed at trial “because the factual record will be “more complete” than the limited record on which the panel’s stay decision was based, their lawyers wrote.
Whichever side prevails at trial, the result undoubtedly will be appealed.
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