Exclusive: L.A., D.C. Leaders Brief Chicago Counterparts on Coming Trump Crackdown

An inside look at the preparations.

Federal agents stand around after arresting an individual outside the Hellmann’s mayonnaise factory in Chicago’s Little Village neighborhood on September 9, 2025. (Photo by Joshua Lott/Washington Post via Getty Images)

EVEN BEFORE DONALD TRUMP DECLARED WAR on Chicago via a reposted, AI-generated meme, activists and organizers from Los Angeles, New York, Washington, D.C., and elsewhere were quietly meeting with Windy City officials to prepare them for the possibility of the president sending in the National Guard.

An August 26 call organized by Cristina Jiménez, veteran activist and director of the Shared Future immigration campaign, brought together more than five hundred activists from across the country. According to multiple attendees and organizers, the call involved representatives of the Coalition for Humane Immigrant Rights (CHIRLA) in Los Angeles, California Calls, Free DC, and the New York Immigration Coalition, among others. Stacy Gates, president of the Chicago Teachers Union, was also involved.

The purpose of the call was for activists from the cities that have already experienced Trump’s military overreach to share best practices. They also discussed what they wished they had done differently when federal agents, mostly from branches of the Department of Homeland Security, descended on their neighborhoods, snatching immigrant workers, provoking local populations into larger protests and showdowns, and building a pretext for the president to send in the National Guard.

Now more savvy to the government’s tactics, one Chicago organizer who works to connect immigration groups and local government employees stressed the importance of maintaining a nonviolent approach.

“The big push is to be calm and peaceful,” said the local organizer, who asked for anonymity to provide details of internal conversations. “The peaceful component is what the ACLU and on-the-ground organizers have been pushing due to the desire from the federal government to have some kind of altercation to excuse federal violence against organizers and citizens.”

The call, which has not been previously reported, underscores just how heightened the tensions have become in Chicago, as the White House issues repeated threats to send federal forces into the nation’s third-largest city.

So far, the National Guard has not been dispatched. But the administration is sounding the horn on what it’s calling its “Midway Blitz”—a significant new deployment of ICE agents to Chicago. Local community groups are using social media to make residents aware of ICE sightings. I was sent one such “community alert,” which was illustrated with a melting ICE cube and gave the cross streets where “3 unmasked ICE agents with green ‘POLICE’ vests” had been spotted in a Nissan Titan and a white Grand Cherokee.

Preparations for ICE descending on Chicago had begun before the call was convened. But the presence on the line of Gates, the Chicago Teachers Union president, was still encouraging to city teachers, who had received guidance from the union and the school district on protocols to help protect students during potential ICE visits. Educators in the city have painted a troubling picture of what might be ahead for teachers, parents, and children.

A Chicago teacher who asked for anonymity to protect her students and school told me that schools in the city had recently instituted safety committees called “sanctuary teams.” Their purpose is to figure out how to provide for children’s safety and prevent fear from setting in during activities where there is a risk of federal interference. Examples include special arrangements for conducting morning entry if there is an ICE presence nearby, or for letting students out for lunch and recess. Students, the teacher stressed, “need to live their lives,” while teachers need to refuse “to spread mass fear.”

The sanctuary teams’ guidelines call for every school district employee outside a school building to be equipped with a walkie-talkie. Willing parents are being recruited to help as well.

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“We’re asking if you are willing to carpool an immigrant family who lives nearby or help a parent looking to get a ride because they otherwise take public transportation,” the teacher said. “Are you willing to be a community-safety person and walk them to the Blue Line or the bus?”

Meanwhile, the Chicago organizer working with immigration groups similarly said their organization is connecting nonprofit partners and small business owners with ancillary legal services. The goal is to provide workshops on short-term guardianship, for people to take with their kids, helping business owners create succession plans in case they are apprehended, and educating people on what could happen if the ICE surge becomes an extended operation in the city.

A representative for CHIRLA, the influential immigrant-rights group, also shared on the call that the organization had resurrected part of its COVID program to help immigrant families by dropping off groceries and necessary items ranging “from toilet paper to water, pampers and formula.” The hope is that these supplies will see them through until the immediate danger posed by the increased ICE presence has passed.

Resorting to techniques from the height of the pandemic makes sense, as feelings of anxiety and panic are starting to shape people’s lives in Chicago today as they did back then. One Chicagoan I interviewed, Virginia Barbosa, a 27-year-old marketing and communications professional, told me of the eerie sense of a return to the old COVID mood in her community, where “people are living in fear, not coming out of their houses, and young people have to get groceries for their aunts who know they’re being targeted.”

“It’s really incredibly scary, and if this president is using his power like that, it makes us think: What else is he capable of doing to our communities?” she said.

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THE PAINFUL REALITY that people are investing all this time and energy in preparing for a possible confrontation with their own government has not been lost on those involved. Chicago residents, politicians, organizers, and teachers who spoke to me described feeling stunned and saddened by the cruelty, and appalled to know that the president of the United States was choosing to use the power of our massive military to threaten a U.S. city, with the goal seeming to be taunting, bullying, and oppressing a large black and brown population into submission.

The unity so far from Democratic leaders in Chicago—from Governor JB Pritzker to Mayor Brandon Johnson on down—has heartened residents. Pritzker has exhorted Chicagoans to know their rights and to record video if they see ICE agents grabbing people in their neighborhoods. For his part, Johnson signed an executive order last week making clear that Chicago police would not be working hand-in-hand with ICE agents. His order also requires Chicago police to wear uniforms and not wear masks, measures intended to “clearly distinguish them from federal agents,” as the Associated Press reported.

“Any rational person who has spent even the most minimal amount of time studying human history has to ask themselves . . . one important question,” Pritzker said last week. “Once they get the citizens of this nation comfortable with the current atrocities committed under the color of law, what comes next?”

Local and state leadership’s unified front against Trump’s federal incursions into Chicago was a source of encouragement in the eyes of Los Angeles–area activists on the call. Some of them relayed their frustrations with some of the LAPD’s early actions against protesters in that city, arguing that the heavy-handedness of these actions helped accelerate the federal crackdown that followed.

Angelica Salas, the executive director of CHIRLA, told me one thing she tried to convey to her counterparts in Chicago is an understanding that the old approach to immigration enforcement was over. It was once relatively common to see one factory being raided; this would be done to provide past administrations with a big, showy operation they could then hold up as proof of their seriousness about addressing the issue of illegal immigration, or maybe as an implicit warning to other companies.

But now agents are fanning out, intent on meeting harsh quotas set by the White House by apprehending as many people as they can find, often those working in open-air industries like carwashes, construction, gardening, or farmwork. What’s more, the Chicago ramp-up is coming after the Supreme Court ruled Monday that ICE’s reliance on textbook racial profiling to detain anyone Latino could continue—a ruling that engendered a scathing dissent from Justice Sonia Sotomayor.

“People in those industries are easily accessible and vulnerable to the massive level of racial profiling the government has set up not just for noncitizens, but also for citizens,” Salas said.

“We wanted them to understand it’s a new reality in terms of enforcement: It’s aggressive, it’s violent, and there’s a green-lighting of what you can do to catch people. And if you make a mistake—oh well, oops.”