Chicago: Scenes from a city under siege

Federal agents point a weapon at protestors in Chicago

For many Chicagoans, life is now “filled with uncertainty and confrontation”

(Image credit: Jim Vondruska / Reuters)

published 27 October 2025

“President Trump has had Chicago in his crosshairs for a long time,” said Geraldo Cadava in The New Yorker. But since launching his immigration crackdown early last month, he has subjected this city to what feels “like a full-on assault.” Masked federal agents have grabbed people from the street, outside churches, and inside hospitals, and bundled them into unmarked cars. Passersby who try to film these detentions have been threatened at gunpoint, and journalists, protesters, and legal observers have been blasted with rubber bullets and pepper balls and violently thrown to the ground. U.S. citizens are routinely detained without cause: Maria Greeley was on her way home from work when she was stopped and zip-tied by agents; one called her passport “fake” because the 44-year-old Latina didn’t “look like” a Greeley. Last week, agents rammed an SUV during a chase through residential streets. When angry residents came out to protest, the agents lobbed tear gas and smoke grenades at them before dragging away a 15-year-old U.S. citizen.

For many Chicagoans, life is now “filled with uncertainty and confrontation,” said Adrian Carrasquillo in The Bulwark. No one wants to be the next Silverio Villegas-Gonzalez, the Mexican immigrant shot dead by ICE “moments after dropping off his 3-year-old at day care.” Homeland Security officials said Villegas-Gonzalez “seriously injured” an officer while trying to drive away from a stop; in bodycam footage, that agent describes his injury as “nothing major.” Some Black residents initially welcomed the crackdown, said Vic Mensa in The New York Times. They thought it would target only newcomers from Latin America who compete with them for subsidized housing. But the reality of being Black in America “means that the oppression of anyone invariably affects us.” Black Chicagoans have had their doors kicked down and been dragged from their homes in nighttime raids. In a recent viral video, agents hold a young Black man in a choke hold while another shouts in disbelief, “Y’all supposed to be choking Mexicans.”

Chicagoans have found “creative ways to resist,” said Patricia Lopez in Bloomberg. Residents in some Latino neighborhoods now carry whistles to warn of ICE activity. Small businesses are blocking agents from using their bathrooms. White parents are volunteering to walk Latino children home from school. But how sustainable are these efforts when President Trump just wants to escalate? The scenes of brutality will stop only when Americans in red and blue states denounce “Trump’s authoritarian flex” and recognize that after Chicago, their hometown could be next.