Chicago Caught In The Trump Administration's Crosshairs | Crooked Media
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September 01, 2025
What A Day
Chicago Caught In The Trump Administration's Crosshairs

In This Episode

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:

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TRANSCRIPT

 

Josie Duffy Rice: 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 U.S. Open win on Monday. [music break] 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. 

 

[clip of Kristi Noem] Well 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 resources to those operations. I won’t disclose the details. 

 

Josie Duffy Rice: 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 in 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. 

 

[clip of Chicago mayor Brandon Johnson] 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. Our people have not asked for this, but nevertheless we find ourselves having to respond to this. 

 

Josie Duffy Rice: 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, DC 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 DC, 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. 

 

Jessica Brand: Thanks for having me, Josie. Good to see you. 

 

Josie Duffy Rice: 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 DOJ prosecutors right now and their priorities? 

 

Jessica Brand: Well, you know, they’re taking orders from up high 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 gonna charge it as such, but you actually have to have evidence of proof. They’re not making it and juries are rejecting it. So I think it tells you they’re overcharging a lot these cases. 

 

Josie Duffy Rice: 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 DC residents? And like what what is the long-term impact of an increase in law enforcement like this? 

 

Jessica Brand: 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 the 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 sudden in your street, right. That’s not what anybody wants. So 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 down thing down because people are terrorized. And it’s not, of course, improving the places where there’s actually a crime. That’s not you know, the National Guard is out like um, you know, putting mulch on the mall. They’re not actually policing places where there are high crime parts. But some for good reason, they actually don’t know how to do that. That’s now 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’s system to a standstill. Um. Because there 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. The what’s coming in is they’re misdemeanors, right? And often they’re misdemeanors that are happening because there’s increased interaction with the new law enforcement on the ground. So they’re like a whole bunch of misddemeanors 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 that they’re being charged federally and 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. 

 

Josie Duffy Rice: We keep hearing that ICE officers have been working in tandem with DC 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 DC residents and what does it means for all of us to have ICE kind of working with local police like this? 

 

Jessica Brand: 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. 

 

Josie Duffy Rice: Right. 

 

Jessica Brand: 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 department also cooperate with ICE in making arrests, but not on this scale. I mean what does that mean? 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–

 

Josie Duffy Rice: Right. 

 

Jessica Brand: –separated from their families and put into immigration custody. And so 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 are an under-documented person and you were 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 gonna 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. 

 

Josie Duffy Rice: Right. 

 

Jessica Brand: Um. With this cooperation. 

 

Josie Duffy Rice: 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, um uh 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? 

 

Jessica Brand: I mean, he has a lot more control over what happens in D.C. because D. C.’s, 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 know we saw him do it in LA. 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 DC, right? It’s gonna happen in other cities. And um 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. 

 

Josie Duffy Rice: 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? 

 

Jessica Brand: 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 a lot communities it’s stagnant, right? You know, you may see a reduction in car jackings, 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, right? You would have hospital-based programs that treat trauma. You would have 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 DC 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–

 

Josie Duffy Rice: Right. 

 

Jessica Brand: 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 relied on these programs and their lives depend on them. 

 

Josie Duffy Rice: Jessica Brand, thank you so much for joining us. 

 

Jessica Brand: Thank you, Josie Duffy Rice. 

 

Josie Duffy Rice: 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. [music break]

 

[AD BREAK]

 

Josie Duffy Rice: Here’s what else we’re following today. 

 

[sung] Headlines. 

 

[clip of protesters chanting] Hey hey ho ho, billionaires have got to go! Hey hey ho ho, billionaires have got to go.

 

Josie Duffy Rice: 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 U.S. 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. 

 

[clip of House Speaker Mike Johnson] This is not your father’s Democratic Party. They’ve gone full Marxist, socialist. 

 

Josie Duffy Rice: Actually, House Speaker Mike Johnson, this is not your father’s Republican party, but go on. 

 

[clip of House Speaker Mike Johnson] 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. 

 

Josie Duffy Rice: Congress is back in session, and Mike Johnson is back on Fox News. Lawmakers returned 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’s support to pass the short-term spending measure before federal funding runs out on September 30th. 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 asks them to do. It’s gonna 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 DC judge, who by the way, has one of the greatest judge names of all time, Sparkle L. Sooknanan, 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.” 

 

[clip of Arianna Podesta] We can indeed confirm that there was GPS jamming um but the plane landed safely in Bulgaria. 

 

Josie Duffy Rice: 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? 

 

[clip of Arianna Podesta] 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 regular uh that are a regular component of Russia’s hostile behavior. 

 

Josie Duffy Rice: 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 and 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 news. [music break]

 

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Josie Duffy Rice: 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 at Burning Man, like me, What a Day is also a nightly newsletter. So check it out and subscribe at crooked.com/subscribe. I’m Josie Duffy Rice. And this truly sounds like a true crime podcast in the making. [music break] What a Day is a production of Crooked Media. It’s recorded and mixed by Desmond Taylor. Our associate producer is Emily Fohr. Our video editor is Joseph Dutra. Our video producer is Johanna Case. We had production help today from Greg Walters, Matt Berg, Shawn Allee, Gina Pollack, and Laura Newcomb. Our senior producer is Erica Morrison, and our senior vice president of news and politics is Adriene 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 East. 

 

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