Chicago Caught In The Trump Administration's Crosshairs
What A Day2 Sep 2025

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.

Show Notes:

Episoder(1579)

MAGA Meltdown Over Trump’s War

MAGA Meltdown Over Trump’s War

Joe Kent – someone you’ve probably never heard of – made huge news on Tuesday. He was the director of the National Counterterrorism Center – until he posted a resignation letter on Twitter. In it, Ken...

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Meet Trump's Pick To Lead DHS

Meet Trump's Pick To Lead DHS

This week, the Senate will hold a confirmation hearing for Oklahoma Republican Senator Markwayne Mullin, President Donald Trump's pick to replace Kristi Noem as Department of Homeland Security Secreta...

17 Mar 23min

Can Big Oil Grease The Courts?

Can Big Oil Grease The Courts?

The war in Iran has essentially closed the Strait of Hormuz, the world's most important oil transfer point, sending oil prices over $100 a barrel with the potential to go even higher. And yet, the odd...

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Why Trump Abandoned America First

Why Trump Abandoned America First

The war with Iran has already killed more than a thousand Iranians, including 175 people killed at an elementary school on February 28th. Remember America First? That swath of the MAGA movement that p...

13 Mar 22min

The Cost Of War Is More Than Oil

The Cost Of War Is More Than Oil

The war with Iran has already killed more than a thousand Iranians, including 175 people killed at an elementary school on February 28th. According to multiple news outlets, a preliminary report from ...

12 Mar 24min

Trump, Iran And A Brewing Economic Crisis

Trump, Iran And A Brewing Economic Crisis

In case you haven’t noticed, the American economy isn't doing so well right now. Oil prices have been on an absolute rollercoaster since the Iran war began — but that’s not all. On Friday, the Bureau ...

11 Mar 28min

The War With Iran Has No Exit Plan

The War With Iran Has No Exit Plan

The Iran war is a little over a week old and the Trump administration has supplied more than a dozen explanations about why, exactly, it began. Confused? Well, now we’re getting wildly conflicting mes...

10 Mar 23min

Can States Stop Trump’s Election Meddling?

Can States Stop Trump’s Election Meddling?

President Donald Trump wants to dramatically change how Americans vote, and to make that happen he’s holding all other legislation hostage until Congress passes the SAVE America Act. The bill would re...

9 Mar 20min

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