Chicago Mayor Declares War on ICE as City Defies Trump’s Orders

Paul Riverbank, 2/2/2026Chicago and Portland openly challenge Trump’s ICE, intensifying the national immigration enforcement standoff.

Monday in Chicago, Mayor Brandon Johnson made headlines with a surprise move: a freshly inked executive order that sent the police department into new territory. Officers were instructed not just to keep an eye on federal immigration agents, but to actively investigate them for potential wrongdoing—a sharp pivot from standard operating procedure. The directive, known in city hall as Executive Order 2026-01, calls for any suspicion of serious misconduct by federal agents to be referred straight to Cook County State’s Attorney.

Johnson’s words at the signing felt freighted with both history and present-day anxiety: “Nobody is above the law. There is no such thing as ‘absolute immunity’ in America,” he proclaimed, as camera shutters snapped. “The lawlessness of Trump’s militarized immigration agents puts the lives and well-being of every Chicagoan in immediate danger.” With rhetoric like “putting ICE on notice,” he made it clear that, for now at least, Chicago’s patience had run thin.

The response at the State’s Attorney’s office? Less ceremony, more confusion. Eileen O’Neill Burke, who holds the job, told reporters her office was in the dark up until Johnson’s announcement hit the news cycle. That bit of bureaucratic disconnect hints at how quickly the political ground is shifting.

Of course, these latest steps come amid ongoing federal efforts—described by officials as an effort to root out “criminal illegal aliens”—which many in Chicago, and nationally, view as overly harsh. Community advocates who remember previous sweeps point to the way trust can fray when local and federal priorities collide.

Travel two time zones west, and the plot thickens. In Portland, Oregon, the scene outside a federal immigration facility last weekend turned uncommonly tense. Protesters crowded around the ICE building, and reports swept through social media of rubber bullets, tear gas, and pepper balls. Mayor Keith Wilson, never one to shy away from a microphone, responded with a call that was both raw and resolute: “Resign,” he told ICE agents operating in his city. “And to those controlling this facility,” his message was plain, “Leave.”

Wilson didn’t shrink from describing the chaos. “Parents frantically trying to tend to little children in strollers,” he recounted, “people using motorized carts trying to navigate as the rest of us staggered in retreat, unsure of how to get to safety.” There was even mention of “two guys with rocket launchers” firing gas into a crowd—a detail that sounds cinematic until you realize it left families gasping and scrambling in the dark.

If you’re wondering about the police response, you wouldn’t be alone. No arrests made. Portland officers said they didn’t use force, but the Fire Bureau dispatched medics to treat injured demonstrators. It’s a snapshot of a city where the lines between protest, policing, and federal action have grown impossibly tangled.

Wilson’s plan now? He pledged to document every act by federal agents—savvy lawyers will see the signals—and promised to slap a new fee on any detention centers using tear gas in Portland going forward.

Up the chain, Oregon’s Governor Tina Kotek and Attorney General Dan Rayfield joined the chorus of condemnation. “Trump’s ICE has no place in Oregon,” the governor declared, her statement circulating before noon. The Attorney General called the agents’ tactics “a horrific abuse of authority,” the kind that, in his view, tears at the fabric of public safety.

Anger over the Portland protest echoes a recent string of demonstrations across U.S. cities, some sparked by shootings involving federal agents. Minneapolis, among others, has become shorthand for how quickly outrage can spill from city streets to national headlines.

Into this volatile mix came former OregonLive journalist Erin Hoover Barnett, who attended the protest herself. Her written account lingers on “parents frantically trying to tend to little children in strollers, people using motorized carts trying to navigate as the rest of us staggered in retreat”—a reporter’s eye for the human cost.

Naturally, President Donald Trump weighed in online, blending warning and support for his field agents. Local police, he contended, should handle protests—but he would not pull back federal forces. “Please be aware that I have instructed ICE and/or Border Patrol to be very forceful in this protection of Federal Government Property,” he wrote. “There will be no spitting in the faces of our Officers... If there is, those people will suffer an equal, or more, consequence.”

None of this suggests tensions will cool soon. What it does show is that local leaders—especially in cities like Chicago and Portland—are increasingly willing to draw sharp lines, even if it means challenging the White House directly. Supporters say these stands are about defending neighborhoods and upholding civil liberties; detractors worry about confusion, escalation, or worse, violence.

Yet amid the back-and-forth, one fact is hard to ignore: the debate over who polices immigration, and how, isn’t going anywhere. And for now, the only certainty is that the nation’s big cities intend to make their resistance visible, loud, and difficult to ignore.

You don’t often see big city mayors take on federal agencies with the sort of directness that played out this week in Chicago and Portland. Yet, as a fresh round of immigration enforcement sweeps unfolded, both cities planted their flags firmly in opposition—with little regard for tiptoeing around Washington’s agenda.Monday in Chicago, Mayor Brandon Johnson made headlines with a surprise move: a freshly inked executive order that sent the police department into new territory. Officers were instructed not just to keep an eye on federal immigration agents, but to actively investigate them for potential wrongdoing—a sharp pivot from standard operating procedure. The directive, known in city hall as Executive Order 2026-01, calls for any suspicion of serious misconduct by federal agents to be referred straight to Cook County State’s Attorney.Johnson’s words at the signing felt freighted with both history and present-day anxiety: “Nobody is above the law. There is no such thing as ‘absolute immunity’ in America,” he proclaimed, as camera shutters snapped. “The lawlessness of Trump’s militarized immigration agents puts the lives and well-being of every Chicagoan in immediate danger.” With rhetoric like “putting ICE on notice,” he made it clear that, for now at least, Chicago’s patience had run thin.The response at the State’s Attorney’s office? Less ceremony, more confusion. Eileen O’Neill Burke, who holds the job, told reporters her office was in the dark up until Johnson’s announcement hit the news cycle. That bit of bureaucratic disconnect hints at how quickly the political ground is shifting.Of course, these latest steps come amid ongoing federal efforts—described by officials as an effort to root out “criminal illegal aliens”—which many in Chicago, and nationally, view as overly harsh. Community advocates who remember previous sweeps point to the way trust can fray when local and federal priorities collide.Travel two time zones west, and the plot thickens. In Portland, Oregon, the scene outside a federal immigration facility last weekend turned uncommonly tense. Protesters crowded around the ICE building, and reports swept through social media of rubber bullets, tear gas, and pepper balls. Mayor Keith Wilson, never one to shy away from a microphone, responded with a call that was both raw and resolute: “Resign,” he told ICE agents operating in his city. “And to those controlling this facility,” his message was plain, “Leave.”Wilson didn’t shrink from describing the chaos. “Parents frantically trying to tend to little children in strollers,” he recounted, “people using motorized carts trying to navigate as the rest of us staggered in retreat, unsure of how to get to safety.” There was even mention of “two guys with rocket launchers” firing gas into a crowd—a detail that sounds cinematic until you realize it left families gasping and scrambling in the dark.If you’re wondering about the police response, you wouldn’t be alone. No arrests made. Portland officers said they didn’t use force, but the Fire Bureau dispatched medics to treat injured demonstrators. It’s a snapshot of a city where the lines between protest, policing, and federal action have grown impossibly tangled.Wilson’s plan now? He pledged to document every act by federal agents—savvy lawyers will see the signals—and promised to slap a new fee on any detention centers using tear gas in Portland going forward.Up the chain, Oregon’s Governor Tina Kotek and Attorney General Dan Rayfield joined the chorus of condemnation. “Trump’s ICE has no place in Oregon,” the governor declared, her statement circulating before noon. The Attorney General called the agents’ tactics “a horrific abuse of authority,” the kind that, in his view, tears at the fabric of public safety.Anger over the Portland protest echoes a recent string of demonstrations across U.S. cities, some sparked by shootings involving federal agents. Minneapolis, among others, has become shorthand for how quickly outrage can spill from city streets to national headlines.Into this volatile mix came former OregonLive journalist Erin Hoover Barnett, who attended the protest herself. Her written account lingers on “parents frantically trying to tend to little children in strollers, people using motorized carts trying to navigate as the rest of us staggered in retreat”—a reporter’s eye for the human cost.Naturally, President Donald Trump weighed in online, blending warning and support for his field agents. Local police, he contended, should handle protests—but he would not pull back federal forces. “Please be aware that I have instructed ICE and/or Border Patrol to be very forceful in this protection of Federal Government Property,” he wrote. “There will be no spitting in the faces of our Officers... If there is, those people will suffer an equal, or more, consequence.”None of this suggests tensions will cool soon. What it does show is that local leaders—especially in cities like Chicago and Portland—are increasingly willing to draw sharp lines, even if it means challenging the White House directly. Supporters say these stands are about defending neighborhoods and upholding civil liberties; detractors worry about confusion, escalation, or worse, violence.Yet amid the back-and-forth, one fact is hard to ignore: the debate over who polices immigration, and how, isn’t going anywhere. And for now, the only certainty is that the nation’s big cities intend to make their resistance visible, loud, and difficult to ignore.