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Home Politics

Lessons from Trump’s “war” on Chicago

December 13, 2025
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Lessons from Trump’s “war” on Chicago
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Border Patrol chief Greg Bovino and agents gather for a photo at Millennium Park and the Cloud Gate after the winter storm overnight in Chicago on November 10, 2025.Colin Boyle/Block Club Chicago

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Chicago has been one of the latest stops on the Trump administration’s deportation tour. “Operation Midway Blitz” started in September and, for months, Immigration and Customs Enforcement and Border Patrol agents have been roaming the streets and detaining hundreds of people.

This week on Reveal, host Al Letson and producer Ashley Cleek visit Chicago to see “Operation Midway Blitz” in action, and find out what it’s been like for those targeted by it. Letson and Cleek found citizens detained, Chicago police officers pepper-sprayed, and communities terrified. Most Chicagoans arrested by federal agents in the operation had no criminal record, not even a traffic ticket.

Letson and Cleek also see how communities are mobilizing to protect each other, and how some of the tensions over immigration raids stretch back to decisions made by the city back in 2022. They also learn from 404 Media’s Joseph Cox about face-scanning apps used by federal agents in Chicago—and how the use of this kind of surveillance points to a broader shift in the US government’s deployment of its technologies against people inside the country.



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