What A Day: "Chicago Caught In The Trump Administration's Crosshairs"

Date: September 2, 2025
Host: Josie Duffy Rice (in for Jane Coaston), Crooked Media
Featured Guest: Jessica Brand, executive director of Wren Collective
Episode Theme:
A deep dive into the Trump administration’s planned federal law enforcement surge in Chicago, paralleled with recent crackdowns in D.C., and the broad implications for immigration enforcement, local policing, civic trust, and democracy.

Episode Overview

The episode examines the Trump administration’s escalating federal law enforcement actions, with a looming ICE operation in Chicago as its focal point. Host Josie Duffy Rice explores the implications for Chicago, the comparison to D.C.'s current experience under a heavy federal police and National Guard presence, and broader concerns about democracy, public safety, the risks posed to immigrant communities, and the overt politicization of law enforcement. The segment features an in-depth conversation with criminal justice reform advocate Jessica Brand.

Key Discussion Points & Insights

1. Trump Administration's Planned ICE Surge in Chicago

[00:00–02:14]

• Announcement: The Trump administration is preparing a major ICE operation in Chicago, possibly expanding to a military installation to house agents (per border czar Tom Homan).
• Kristi Noem (Trump ally) on Face the Nation:

  “We've already had ongoing operations with ICE in Chicago and throughout Illinois… We do intend to add more resources… I won't disclose the details.” [00:48]

• Context: Chicago is often targeted in Trump’s rhetoric due to its Democratic leadership and diverse population.
• Mayor Brandon Johnson’s Response:
  Johnson signed an executive order instructing local police not to cooperate with any federal deployments, signaling opposition to the operation.

“Trump has said he may deploy the National Guard to the city or even send in active military, which I cannot emphasize enough would be an incredibly alarming escalation.” — Josie Duffy Rice [01:14]

2. The D.C. Precedent: Legal and Civic Fallout

[02:14–06:30]

• Authority Distinction: Trump has more direct control in D.C. than in other cities due to federal jurisdiction.
• Militarized Enforcement & Civilian Impact:
  • Jessica Brand explains the damaging impact of constant armed federal presence:

    “You can see that businesses are really being impacted... people not wanting to go to work. Immigrants not wanting to be Uber drivers... people are terrorized.” [04:00]

  • Increase in federal arrests focuses almost entirely on misdemeanors manufactured through new federal presence, overwhelming the local legal system.

    “It’s sort of bringing the legal system to a standstill and straining it beyond all comprehension... life is going poorly for a lot of people who live there.” — Jessica Brand [06:10]

• Police–ICE Collaboration:
  • ICE working directly with local law enforcement escalates fears, breaks trust, and creates chilling effects on crime reporting:

    “If you are an undocumented person and you are a victim of a crime, you are now a sitting duck because you cannot call the police department... you know you’re going to end up in ICE custody.” — Jessica Brand [08:14]

3. Will D.C.'s Experience Be Repeated in Chicago?

[08:34–09:52]

• Legal Limits & Political Motive:
  • Trump has less formal authority to intervene in Chicago.
  • Brand warns the pattern is likely to spread as part of a political strategy rather than a sincere public safety effort:

  “If you assume… this is not about public safety, but about taking over black and brown cities…and creating a climate of fear… then it can’t stop with Washington D.C., right?” — Jessica Brand [09:19]

4. Core Insight: Public Safety vs. Power Grab

[09:52–11:30]

• Community Trauma and Real Solutions:
  • Brand acknowledges that violence and trauma are real in many communities, requires investment in proven, community-based interventions.
  • Under Trump, funding for such programs has been cut, while high-profile deployments ramp up:

  “If you wanted to actually address what is a very real problem… there are immediate interventions you could do. Right now he’s cut all the funding for it… he’s actually making it incredibly worse.” — Jessica Brand [11:12]

Notable Quotes & Memorable Moments

• On Federal Overreach & Rhetoric:

  "One of Trump's favorite things to do is fear monger about Chicago because it has a Democratic mayor, and…its majority people of color, all things he notably does not like." — Josie Duffy Rice [01:08]

• On Militarized Policing:

  "We may see militarized immigration enforcement. We may also see National Guard troops. We may even see active duty military and armed vehicles in our streets. We have not called for this…But nevertheless, we find ourselves having to respond to this." — Mayor Brandon Johnson [02:14]

• On Overcharging by DOJ:

  "They're taking orders from up high, and the orders are: charge things as harshly as you can…But you actually have to have evidence of proof and they're not making it and juries are rejecting it. So…they're overcharging." — Jessica Brand [03:50]

• On Systemic Disruption:

  "It’s sort of bringing the legal system to a standstill and straining it beyond all comprehension." — Jessica Brand [06:25] "It's a huge breach of trust between a department that's supposed to work on behalf of you and keep you safe and the community they're supposed to represent." — Jessica Brand [07:32]

• On Victims’ Fears:

  “If you are an undocumented person and you are a victim of a crime, you are now a sitting duck…you have no recourse at all right now with this cooperation.” — Jessica Brand [08:15]

• On Politics and Power:

  “If you assume…this is…about taking over black and brown cities…and desensitizing people to military force so you can grab power, then it can’t stop with Washington D.C.” — Jessica Brand [09:19]

• On Proven Criminal Justice Solutions:

  “We know what you would do…it's gone. The D.C. budget is gone. The DOJ grants are gone. The substance use treatment money is gone…he's actually making it incredibly worse.” — Jessica Brand [11:12]

Secondary Stories: Headlines Recap

Labor Day Protests

[14:37–15:36]

• Protests in 800 cities/towns nationwide, coordinated by AFL–CIO, targeting billionaires and protest against Trump’s authoritarian and anti-immigrant policies.
• 1.2 million immigrants disappeared from the workforce Jan–July 2025.

Congress Returns: Partisan Gridlock & Shutdown Threat

[15:38–16:49]

• Speaker Mike Johnson returns to Fox News, signaling little potential for bipartisanship.
• Looming government shutdown if spending isn’t approved by September deadline.
• Ongoing drama over Trump's nominees and foreign policy (e.g., tariffs on Russia).

Emergency Legal Ruling on Deportation of Minors

[16:50–18:00]

• Judge Sparkle L. Sukhnen issues restraining order stopping deportation of minors “in the wee hours of the morning on a holiday weekend.”
• Federal government had begun removing children from shelters and putting them on planes—actions reversed by the order.

GPS Jamming Incident

[18:00–18:45]

• GPS jamming on flight carrying EC President Ursula von der Leyen, attributed to Russian interference; plane lands safely.

Conclusion

This episode spotlights the accelerating federal enforcement push under the Trump administration—a development with profound consequences for local autonomy, immigrant rights, democratic norms, and everyday life in targeted cities like D.C. and Chicago. Through expert analysis and attention to lived experiences, the episode emphasizes how these federal interventions are about power and political spectacle, not public safety—offering a sharp warning about the erosion of civic trust and democratic checks and balances.