Episode September 2, 2025 20 min 38s

Chicago Caught In The Trump Administration's Crosshairs

The Trump administration is preparing a major Immigration and Customs Enforcement operation in Chicago, and it may come as soon as this week. The details have been few and far between, but it would likely increase the number of ICE and Border Patrol agents in the city significantly. According to “border czar” Tom Homan, the White House is even considering taking over a Naval base north of Chicago to hold the “large contingent” of federal agents. Chicago, unsurprisingly, has long been in the crosshairs of President Donald Trump’s threats to federally invade cities as part of his so-called crackdown on crime. And Chicago Mayor Brandon Johnson is not having it. On Saturday, he signed an executive order instructing local police not to cooperate with troops or federal agents if the President’s threats come to fruition. For more on the impact that federal arrests have on federal courts, we spoke with Jessica Brand, a lawyer and Executive Director of Wren Collective, a non-profit aimed at criminal justice reform and prosecutorial power.

And in headlines: Congress is back in session, a federal judge blocks the Trump administration from deporting hundreds of migrant children to Guatemala, and more than 800 demonstrations take place across the country on Labor Day to protest billionaires taking over the government.

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