Chicago Caught In The Trump Administration's Crosshairs

Summary

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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.

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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.

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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]

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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]

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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.

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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.

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Transcript

[A]

Foreign It's Tuesday, September 2nd. I'm Josie Duffy Rice in for Jane Coaston. And this is what a day. The show congratulating Naomi Osaka on her US Open win on Monday. On today's show, guess who's back? Congress back in session. Yay. And people across the US Celebrate Labor Day by turning up to protest the Trump administration's love affair with billionaires. But let's start with federal law enforcement being deployed to major cities. The Trump administration is preparing a major Immigration and Customs Enforcement operation in Chicago, and it may come as soon as this week. Here's Kristi Noem on Face the Nation on Sunday.

[B]

We've already had ongoing operations with ICE in Chicago and throughout Illinois and other states making sure that we're upholding our laws. But we do intend to add more regions resources to those operations. I won't disclose the details.

[A]

So the administration is staying somewhat mum about its plans, but the operation would likely significantly increase the number of ICE and Border Patrol agents in the city. In fact, according to border czar Tom Homan, the White House is even considering taking over a naval base north of Chicago to hold the quote, 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 I say unsurprisingly because one of Trump's favorite things to do is fear monger about Chicago because it has a Democratic mayor and a popular Democratic governor and its majority people of color, all things he notably does not like. Trump has said he may deploy the National Guard to the city or even send an active military, which I cannot emphasize enough would be an incredibly alarming escalation. Mayor Brandon Johnson has vocally rejected the Trump administration's potential actions, a marked difference from D.C. mayor Muriel Bowser. And on Saturday, Johnson signed an executive order instructing local police not to cooperate with troops or federal agents. If Trump's threats come to fruition, we.

[C]

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. Our people have not asked for this. But nevertheless, we find ourselves having to respond to this.

[A]

Trump does not have the same level of authority to interfere with local policing there as he does in the District of Columbia because as we know, D.C. is under federal control in a way that other cities are not. However, rules as a concept have not really stopped this guy before. Meanwhile, in D.C. the deployment of Federal officers has led to an increase in arrests and prosecutions, which could have a long term impact. Here to talk to us about that impact is Jessica Brand, a lawyer and executive director of Wren Collective, a nonprofit focused on criminal justice reform and prosecutorial power. Jessica Brand, welcome to what a Day.

[D]

Thanks for having me. Josie, good to see you.

[A]

Good to see you, too. President Trump sent the national guard into D.C. a few weeks ago now, and they have ratcheted up arrests, but at least twice prosecutors have been unable to even secure indictments in some high profile cases. So, for example, after a former DOJ employee allegedly threw a sandwich at an officer, prosecutors tried to charge him with multiple felonies, but the grand jury refused to indict. Not a ton of failure to indict, but at least a couple notable ones. What does that tell us about the DOJ prosecutors right now and their priorities?

[D]

Well, you know, they're taking orders from a pie, and the orders are charge things as harshly as you can. And that's not normally how it works. Right. Normally you take a case, you look at the evidence and you decide, okay, what's the appropriate charge that I can actually prove? Right. That makes a lot of sense. That's not what's happening right now. It's okay. This could possibly meet some really harsh, terrible standard, and so we're going to charge it as such, but you actually have to have evidence of proof that they're not making it and juries are rejecting it. So I think it tells you they're overcharging a lot of these cases.

[A]

So given the presence of the National Guard and this ongoing presence of ICE and this increase in, like, federal police presence, how is that affecting D.C. residents? And like, what, what is the long term impact of an increase in law enforcement like this?

[D]

Well, I think it's huge, and I'll put it in a couple of buckets. One is just the long term impact of people who are living on there, right? So you can see that businesses are really being impacted because who wants to go out to dinner and go to the monuments when there's armed guards all of a sudden in your street? Right. That's not what anybody wants. And you can see there's the stories about reservations going down. There's also the story about people not wanting to go to work. Right. Immigrants not wanting to be Uber drivers or not wanting to do their jobs and bring food delivery service. Right. It's just shutting that whole damn thing down because people are terrorized. And it's not, of course, improving the places where there's actually crime that's not, you know, the National Guard is out, like, you know, putting mulch on the Mall. They're not actually policing places where there are high crime hotspots. And for good reason. They actually don't know how to do that. That's not what they do for a living. They wouldn't be very good at that. So there's sort of aspect number one is people are not really living their lives in the same way. And then there's sort of aspect number two, which is what's happening in the court system. But it's actually bringing the court system to a standstill because it's not like all of a sudden police and the National Guard and the FBI are solving a bunch of unsolved murder cases or really serious crimes. What's coming in is their misdemeanors. Right? And often they're misdemeanors that are happening because there's increased interaction with the new law enforcement on the ground. So there are like a whole bunch of misdemeanors that wouldn't exist but for the presence of new law enforcement there. But then you need lawyers, you need judges, and it's. You need grand juries if they're being charged federally. These cases are almost never charged federally. Now suddenly they are. And so it's sort of bringing the legal system to a standstill and straining it beyond all comprehension and all resources that exist in Washington, D.C. so life is going poorly for a lot of people who live there. And then the legal system is really at a breaking point.

[A]

We keep hearing that ICE officers have been working in tandem with D.C. police, as well as federal officers like the National Guard. And we've seen immigration officers at car checkpoints, for example. What does it mean for D.C. residents? And what does it mean for all of us to have ICE kind of working with local police?

[D]

Like, I think the scale is for sure new. I mean, you know this, Josie. ICE for a really long time has worked very closely with sheriff's departments, which in a lot of the country, especially the south, is a big part of traditional law enforcement. The sheriff handles a lot of arrests and stops. And like in Texas, we have a law where there has to be cooperation, at least in the jail. But a lot of sheriff's departments also cooperate with ICE in making arrests, but not on this scale. I mean, what does that mean? Well, one, you presumably want your police department really focused on solving street crime, right? Solving murders, which traditionally go unsolved in this country, solving sexual assaults. Right. They're not doing that. They're just pulling over people now willy nilly and making arrests and putting them into ICE custody. So they're not actually doing the investigative work that police departments are supposed to do. So that is actually a public safety issue. But the second thing is, look, people, especially in cities, they don't like these policies. They don't like what's happening with ICE right now. They don't like that their daycare providers and their nurses and their teachers are getting separated from their families and put into immigration custody. When you see that actually that's what your police department is doing, that'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 that they're supposed to represent. And so that is just a tremendous problem. And I'd say the third thing is if you want 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 to protect you because you know they are cooperating with ICE and so you know that you're going to end up in ICE custody. So if you were robbed or you were harmed or anything bad happens to you, you have no recourse at all right now with this cooperation.

[A]

Right. So let's talk about what's happening outside of D.C. so the president has talked about sending National Guard troops to all these other places, including Chicago. He's been talking about purportedly cracking down on crimes in Chicago. Do you predict that we will see what we're seeing in D.C. happen in Chicago and other places?

[D]

I mean, he has a lot more control over what happens in D.C. because D.C. is, you know, it has home rule, but home rule is really limited. So obviously he has way more autonomy over what happens in the District of Columbia than if he does and he goes into, for example, Chicago. But you always saw him do it in L. A. And obviously I'm not a crystal ball reader for this president, but I think if you assume, as I do, that this is not about public safety, but about taking over black and brown cities and places that don't vote for the President and creating a climate of fear and desensitizing people to military force so you can grab power, then it can't stop with Washington D.C. right. It's going to happen in other cities. And it's also a president who actually does like to follow through on a lot of his threats. And so I think we should expect the worst.

[A]

Yeah. Something you just said is what I was going to kind of talk about next, which is how much of this do you think is actually an attempt to address the problem and how much of it is politics?

[D]

Yeah, I mean, I think it's really important to start with the premise that crime is real and serious in a lot of communities. And you know, there's a. John Rich is a doctor who has studied trauma in black and brown communities and violence. And in his book Wrong Place, Wrong Time, he says, you know, the problem with people saying like, crime is up, crime is down, crime trends is in a lot of communities it's stagnant. Right. You know, you may see a reduction in carjackings and that's wonderful. But there's still too much violence in certain communities. And I think we all need to accept that and then think like rational people and figure out how to stop that instead of making those communities political volleyballs, which is what they really are. And if you wanted to actually address what is a very real problem, we know what would you would do because there's like a lot of research on this. You would have hospital based programs that treat trauma. You would put credible messengers, but also just doctors and healthcare providers and trauma counselors and with really high risk kids and high risk communities to help them so that you don't end up with the serious violence that often explodes from untreated trauma. And yes, you would also have better schools and sort of the like, bigger picture things, but there are immediate interventions that you could do. Right now he's cut all the funding for it. Right. It's gone. The D.C. budget is gone. The DOJ grants are gone. The substance use treatment money is gone. It's all gone. We know what you would do and he's not doing it at all. He's actually making it incredibly worse. And that is a really, you know, it's a scary thing for all of us because it means a power grab, but it's also really sad because there's people who really rely on those programs in their lives depend on them.

[A]

Jessica Brand, thank you so much for joining us.

[D]

Thank you, Jazzy Duffy Rice.

[A]

That was my conversation with Jessica Brand, a lawyer and executive director of Wren Collective. We will get to more news in a moment, but if you like the show, make sure to subscribe. Leave a five star review on Apple Podcasts. Watch us on YouTube and share with your friends. More to come after some ads.

[E]

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[A]

Here's what else we're following today. Head of Lines.

[D]

Hey hey ho ho.

[A]

Billionaires have got to go. Hey hey oh Billionaires have got to go. Protesters in Chicago gathered as part of the workers over Billionaires Day of Action joining demonstrations in more than 800 cities and small towns across the US on Monday. The mobilization effort was led by America's largest federation of unions, AFL CIO, along with dozens of other workers rights organizations. Organizers say they planned the multi city event to protest the billionaire takeover of the government, the Trump administration's embrace of corporate influence and the president's authoritarian policies. They added that it was important to hold protests not only in blue cities, but also in small towns, especially those that Trump won in 2024. Participants also protested against deportation policies that target immigrant workers. More than 1.2 million immigrants disappeared from the labor force from January to July, according to preliminary census data.

[B]

This is not your father's Democratic Party. They've gone full Marxist, socialist.

[A]

Actually, House Speaker Mike Johnson this is not your father's Republican Party, but go on.

[B]

So look, I'm for bipartisanship when we can do it. We want to bring common sense Democrats along with us to solve these problems. But if they're not willing to come along, we have to do it ourselves.

[A]

Congress is back in session and Mike Johnson is back on FOX News. Lawmakers return after a month long August recess which started sooner than expected after Johnson sent everyone home early to prevent them from holding a vote that could have forced the release of the Epstein files. And he's currently giving us zero confidence that his party will be reaching across the aisle anytime soon, or any confidence that he knows what the words Marxist or socialist mean. The dictionary is right there, Mike Johnson. Or it should be. But if they don't find a way to work with Democrats, we could find ourselves looking at another government shutdown. Republicans will need Democrat support to pass the short term spending measure before federal funding runs out on September. So what else should you expect this season? More fighting in the Senate over Trump's nominees? Potential tariffs on Russian exports? Health and Human Services Secretary Robert F. Kennedy Jr. Asking for more money. And while we can't technically see into the future, we bet the Republicans will basically say yes to anything that Trump asked them to do. It's going to be great. Or something. A federal judge issued an urgent temporary restraining order early Sunday morning blocking the Trump administration from deporting hundreds of unaccompanied minors back to Guatemala. The early morning hearing occurred after the judge learned that the administration had taken children from shelters in the middle of the night and loaded them onto planes at several Texas airports. The planes were immediately grounded and the children were returned to the custody of the Office of Refugee Resettlement. One flight was already in the air, but turned around when the order was made. The federal D.C. judge, who by the way has one of the greatest judge names of all time, Sparkle L. Sukhnen, said during the hearing, quote, I have the government attempting to remove minor children from the country in the wee hours of the morning on a holiday weekend. That's surprising. Unaccompanied minors are supposed to go through full immigration proceedings before deportations happen.

[G]

We can indeed confirm that there was GPS jamming, but the plane landed safely in Bulgaria.

[A]

The GPS connection on a flight carrying European Commission President Ursula von der Leyen was disrupted, Commission spokesperson Arianna Podesta said on Monday. As for the suspect behind the operation.

[G]

We have received information from the Bulgarian authorities that they suspect that this was due to blatant interference by Russia. We are of course aware and used to somehow to the threats and intimidations that are a regular component of Russia's hostile behavior.

[A]

Podesta said the jamming reinforces the European Commission's commitments to, quote, ramp up defense capabilities and support for Ukraine. Von der Leyen's plane landed safely in central Bulgaria. Von der Leyen is known to be critical of Russian President Vladimir Putin in Moscow's war against Ukraine. And this incident is just the latest in a series involving suspected Russian electronic interference with GPS satellite navigation. And that is the before we go Money Murder, Betrayal, Revenge. This is the unbelievable true story of United Mine Workers of America and the son who took on a dangerous union boss to avenge his family's murder. In the newest season of Shadow Kingdom, Coal survivor host Nicolo Manoni digs into the rise and fall of the United Mineworkers of America under Tony Boyle, once the most powerful and corrupt labor leader in the country at the height of America's Cold wars. It's a political thriller wrapped in a courtroom drama, and every detail is real. Catch the latest episode on the Shadow Kingdom feed wherever you get your podcasts. Or better yet, Friends of the Pod. Subscribers can listen to the full season of Shadow Kingdom right now. Join friendsofthepod.com Friends, that's all for today. If you like the show, make sure you subscribe, leave a review, read about the terrifying and bizarre recent events at Burning man and tell your friends to listen. And if you are into reading and not just about the open homicide investigation, or the woman who didn't know she was pregnant spontaneously giving birth, or the orgy tent getting blown over by a windstorm, or Burning man like me, what a Day is also a nightly newsletter, so check it out and [e-mail] subscribe I'm Josie Duffy Rice and this truly sounds like a true crime podcast in the making. What a Day is a production of Crooked Media. It's recorded and mixed by Desmond Taylor. Our associate producer is Emily Foer. Our video editor is Joseph Dutra. Our video producer is Johanna Case. We had production help today from Greg Walters, Matt Berg, Sean Ali, Jaina Pollack and Laura Newcomb. Our senior producer is Erica Morrison and our Senior Vice President of News and Politics is Adrienne Hill. Our theme music is by Colin Gilliard and Kashaka. We had help from the Associated Press. Our production staff is proudly unionized with the Writers Guild of America.

[D]

East.

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