On October 4, 2025, a federal judge in Oregon delivered a significant blow to the Trump administration’s efforts to deploy the National Guard into Portland, issuing a temporary restraining order that blocked any such move for at least two weeks. The ruling, which could be extended for another 14 days, comes amid intensifying clashes between federal authorities and local leaders in several Democratic-led cities, with Chicago also emerging as a flashpoint in the ongoing struggle over immigration enforcement and federal intervention.
District Judge Karin Immergut, who was appointed by President Trump, found that both Oregon and the city of Portland were “likely to succeed on their claim that the President exceeded his constitutional authority and violated the Tenth Amendment.” In her opinion, Immergut wrote, “Recent incidents cited by the Trump administration of protesters clashing with federal officers are inexcusable, but they are nowhere near the type of incidents that cannot be handled by regular law enforcement forces.” She further warned that the administration’s arguments risked “blurring the line between civil and military federal power—to the detriment of this nation.”
The Trump administration had called for the federalization of 200 members of Oregon’s National Guard, but as of the evening of October 3, those troops were still in training and had not yet been deployed to Portland. The White House has repeatedly pointed to weeks of unrest outside the city’s Immigration and Customs Enforcement (ICE) facility, characterizing the demonstrations as “violent riots” and linking them to so-called “Antifa domestic terrorists.” Local officials, however, have vigorously disputed this depiction. In a joint lawsuit, Oregon and Portland leaders described the president’s portrayal of the city as “wildly hyperbolic.”
Caroline Turco, an attorney for the city of Portland, pushed back against the administration’s narrative, saying, “The president’s perception is it’s World War II out here. The reality is, it’s a beautiful city and a sophisticated police force that can handle the situation.” According to Oregon state attorneys, the president’s power to call up state troops for federal action is strictly limited to circumstances like “rebellion” or invasion by a foreign nation, and federal law requires such action to be coordinated through state governors. Oregon Governor Tina Kotek has been adamant in her opposition to the deployment.
The legal wrangling comes after a summer marked by the closure of Portland’s ICE facility for three weeks due to violence, according to the Trump administration. On October 3, protests outside the facility led to the arrest of a conservative influencer, who was released hours later without bond, as well as two other individuals—one of whom was allegedly carrying a can of chemical spray and a collapsible metal coil baton. The Portland Police Bureau stated, “Just because arrests are not made at the scene, when tensions are high, that does not mean that people are not being charged with crimes later.”
This latest confrontation in Portland is part of a broader pattern. The Trump administration has made similar attempts to deploy federal forces in other Democratic strongholds, including Washington, DC, Los Angeles, and Memphis, often citing the need to protect federal property or enforce immigration laws. These moves have sparked fierce opposition from local and state officials, who argue they are politically motivated and lack proper justification. In September, a federal judge in California ruled that the Trump administration had broken the law by sending thousands of federalized National Guard soldiers and hundreds of Marines to suppress protests in Los Angeles—a decision the White House is now appealing.
Meanwhile, Chicago has found itself at the center of escalating tensions. On October 4, President Trump authorized the federalization of 300 members of the Illinois National Guard to “protect federal officers and assets” in the city following protests at an ICE facility in Broadview, Illinois, which resulted in at least 18 arrests the previous day. Among those arrested, five faced charges of aggravated battery to a police officer and resisting and obstruction. The Department of Homeland Security (DHS) reported 13 additional arrests that evening.
Illinois Governor J.B. Pritzker has publicly refused to call up the National Guard, despite a request from the Department of Defense. In a statement, he declared, “This morning, the Trump Administration’s Department of War gave me an ultimatum: call up your troops, or we will. It is absolutely outrageous and un-American to demand a Governor send military troops within our own borders and against our will.” He continued, “There is no need for military troops on the ground in the State of Illinois. State, county, and local law enforcement have been working together and coordinating to ensure public safety around the Broadview ICE facility, and to protect people’s ability to peacefully exercise their constitutional rights.”
Tensions in Chicago escalated further on October 4, when law enforcement officers were rammed by vehicles and opened fire on an armed US citizen who allegedly tried to run them over. The woman, accused of “doxing law enforcement officers online,” drove herself to the hospital after being wounded, according to DHS. The Chicago Police Department said it initially responded to the scene but was not involved in the investigation. The FBI is now handling the case.
Protests in the Chicago area have surged in recent weeks, fueled by word of a “large-scale enforcement campaign” by federal authorities. DHS has reported more than 1,000 arrests as part of the Trump administration’s immigration enforcement agenda. The White House has accused local leaders, including Governor Pritzker, of failing to quell “ongoing violent riots and lawlessness.”
Chicago’s local officials have also found themselves in direct confrontation with federal agents. On October 3, Alderperson Jessie Fuentes was briefly handcuffed by agents at a hospital after questioning ICE officers about their authority to detain a man who had injured his leg while fleeing law enforcement. Fuentes recounted, “Not only do they refuse to respond, but they respond with violence by shoving me in the emergency room, and then I continue to ask if they have a signed judicial warrant, and then they handcuff me … and they threaten arrest because I’m exercising my constitutional right to ask a question.”
Mayor Brandon Johnson has also weighed in, defending the right of elected officials to document ICE actions and inform their constituents. “Any attempt to block this work is a direct attack on democratic accountability and an assault on the rights of the people of Chicago,” he stated.
Governor Pritzker has been especially vocal in his criticism of the administration’s tactics. In response to a recent overnight raid that resulted in the arrest of 37 undocumented immigrants, he said, “Federal agents reporting to Secretary Noem have spent weeks snatching up families, scaring law-abiding residents, violating due process rights, and even detaining U.S. citizens. They fail to focus on violent criminals and instead create panic in our communities.” Mayor Johnson added, “Masked men going into people’s homes in the middle of the night, pointing long guns in the faces of Black and brown and working people and poor people is unconstitutional, reprehensible and, in the city of Chicago, we’re gonna fight back.”
Underlying these high-profile standoffs is a broader strategy by the Trump administration to withhold federal funds from Democratic-led cities as part of what critics call the Project 2-025 blueprint. Local leaders say these moves are designed to punish political opponents and undermine the autonomy of states and cities—allegations that the White House denies. As the legal and political battles play out, the nation watches closely, aware that the outcome may shape the boundaries of federal power and civil liberties for years to come.
