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

Episode Date: September 2, 2025

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:Learn more about The Wren CollectiveCall Congress – 202-224-3121Subscribe to the What A Day Newsletter – https://tinyurl.com/3kk4nyz8What A Day – YouTube – https://www.youtube.com/@whatadaypodcastFollow us on Instagram – https://www.instagram.com/crookedmedia/For a transcript of this episode, please visit crooked.com/whataday

It's Tuesday, September 2nd. I'm Josie Duffy Rice in for Jane Koston, and this is What a Day. The show congratulating Naomi Osaka on her U.S. Open win on Monday. On today's show, guess who's back? Congress, back in session. Yay? And people across the U.S. celebrate Labor Day by turning up to protest the Trump administration. 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 Christy Noam on Face the Nation on Sunday. 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. 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 Borders Tsar, 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 city. as part of his so-called crackdown on crime.

And I say unsurprisingly, because one of Trump's favorite things to do is fearmonger 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 voted locally 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 may see militarize 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. 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. Thanks for having me, Jesse. Good to see you. 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 out 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? 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? 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. They're not making it, and juries are

rejecting it. So I think it tells you they're overcharging a lot of these cases. 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 a long-term impact of an increase in law enforcement like this? 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 any B-Wat. 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 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, you know, putting mulch on the mall. They're not actually policing places where there are high crime heart spots. 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 are really serious crimes. 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 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 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, So life is going poorly for a lot of people who live there, and then the legal system is really at a breaking point. 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 like this? I think the scale is for sure new. I mean, you know this, Josie Ice for a really long time has worked very close. 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 and making arrests, but not on this scale. I mean, what does it 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 they're daycare providers and they're not. nurses and their teachers are getting separated from their families and 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 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. 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?

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 rule is really limited. So obviously, he has way more autonomy over what happens than the District of Columbia than if he does and he goes into, for example, Chicago. But, you know, we 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. 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? 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 that'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, right? You would have hospital-based programs that treat trauma. You would have, you would put credible messengers, but also just doctors and health care 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 God. 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 relied on those programs and their lives depend on them. Jessica Brand, thank you so much for joining us. Thank you, 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. What a day is brought to you by Ollie. My dog has big paws, big ears, and a big heart. And he absolutely loves Ollie. Ollie delivers clean, fresh nutrition in five drool-worthy flavors, even for the pickiest eaters. Made in U.S. kitchens with highest quality human-grade ingredients, Ollie's food contains no fillers, no preservatives, just real food.

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joining demonstrations in more than 800 cities in small towns across the U.S. on Monday. The mobilization effort was led by America's largest Federation of Union's AFL-CIO, along with dozens of other workers' rights organizations. Organizers say they plan 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. This is not your father's Democratic Party. They've gone full Marxist, socialist.

Actually, House Speaker, Mike Johnson, this is not your father's Republican Party. But go on. 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. 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 this 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 Democrats' support to pass the short-term spending measure before federal funding runs out on September 30th. So what else should you expect this season? Or 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. Suknanan, 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. And a company minors are supposed to go through full immigration proceedings before deportations happen. We can indeed confirm that there was GPS jamming, but the plane landed safely in Bulgaria.

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

of Russia's hostile behavior. Podesta said the jamming reinforces the European Commission's commitments to, quote, ramp up defense capabilities and support for Ukraine. Vonderland's plane landed safely in central Bulgaria. Vonderland 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.

Before we go, money, murder, murder, betrayal, revenge. This is the unbelievable true story of the United Mind 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 Niccolo Manoni digs into the rise and fall of the United Mine Workers of America under Tony Boyle, once the most powerful and corrupt labor leader in the country. At the height of America's coal 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 podcast, or better yet, friends of the pod subscribers can listen to the full season of Shadow Kingdom right now. Join Friends of

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I'm Josie Deffie Rice, and this truly sounds like a true crime podcast in the making. What a Day is a production of Cricket Media. It's recorded and mixed by Desmond Taylor, our associate producer, is Emily 4. Our video editor is Joseph Dutra. Our video producer is Johanna Case. We had production help today from Greg Walters, Matt Berg, Sean Ali, Janea Pollock, and Laura Newcomb. Our senior producer is Erica Morrison and our senior vice president of news and politics is

Adrian 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 at East. I don't know. I don't know. Thank you.