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I'm Charlie Sykes. Welcome to the to the Contrary podcast. And we're going to be a little bit contrarian today now that everybody else is talking about what's going on in the Middle east. The jubilant scenes out of Israel where the 20 living hostages have been released, the signing of the the Ceasefire deal. Not a complete peace deal, but a rather extraordinary day in world diplomacy. I'm gonna talk about that obviously coming up on podcast with Matt Lewis and Tom Nichols and Tim o' Brien from Bloomberg. But today I wanted to try something different. I thought that today would be A good day. While the eyes of the world are fixed on conflicts in the Middle east, to shine the spotlight on the conflicts in the Midwest and in this country. And so I have called upon my old friend, my old colleague Rob Hart, who is the midday anchor for Chicago's WBBM Radio, to tell us what's going on in war torn Chicago. So first of all, Rob, welcome to the podcast. Good to talk with you again.
D
Yeah, Charlie, it's great to talk to you too. It's been far too long. And once again, you know, as someone who was once a midday anchor on your show, I'll be out by six past the hour on the dot, just so you're back into programming.
B
See, you know, this is something every once in a while we'll mention to people that if you've been into broadcast, you have a different view of time than anybody else. Right. So, you know, if somebody says, hey, we're going to do this at 6 o', clock, that means 6 o', clock, not 6:01. Right. And everything. And six minutes is a long time. I give you six minutes and you can give me the world. Right, Something like that.
D
Exactly. More or less. It was three and a half with commercials and traffic and the TV meteorologist. If it was a nice sunny day, it was a 90 second forecast and if there was a blizzard, it was a 92 second forecast. So you were operating inside a lot of time restraints. But the joy and pleasure of broadcasting, of operating inside those restraints and creating great art inside those restraints, that's part of the fun and the challenge of the business.
B
It is because, you know, concision is an art form and, you know, brevity is an art form. And this is something that I learned on the radio. Of course, I got to go on at great length. I got to, you know, do the whole blowhard thing because that's what we did as talk shows. And by the way, for people who aren't familiar, Rob and I actually worked together in Milwaukee at WTMJ Radio for many, many years. And I think, you know, there is, there's, I like going along, I like writing books, I like writing, you know, detailed analyses. But there is that discipline of mind. To boil it down and say, what is the nub of the issue? What is the heart of the issue? And to be able to get to that, it's, I think it was one of the more valuable skills that I learned. So it is good to be with you. Okay. And for people who wonder whether I'm going to troll you about the Milwaukee Brewer Chicago Cubs Series. America's team in the National League Championship Series. America's team, of course, being the Milwaukee Brewers. But you're a former Milwaukee guy, so what do you still have the Brewer paraphernalia? You haven't gone completely Chicago on me flat.
D
Well, I mean, I. I grew up on the south side, so I. I'm a White Sox fan first and foremost, so I'll be very diplomatic about the Cubs. But my. I still remember I actually ran the board during brewers games. That was one of my first jobs at TMJ. And to this day, 20 years later, I have not run a Brewers game since about 2001. But every now and then when I would listen to euchre. Cause 620 comes into Chicago. Every now and then when I listen to Euchre and he'd call for an id, my finger would start to shake. I was just instinctively reaching for the board to fire the station ID at the top of the hour. And on Saturday night when they won, I managed to find a WTMJ Radio 62 Harvey's Wall Bangers bumper sticker. And I was sending that to everybody.
B
That's good.
D
It's great to see the brewers move on. Especially, I mean, when I was there, when. When we were there.
B
Frustration.
D
It was the middle of that they had hit a winning season since 1992. They were wondering if the ballpark was even worth the expense, just given the fact that the team was doing so poorly. And then the whole thing changed in a dime. And it's a great ballpark, it's a great team, and it's a fantastic story for Milwaukee. It.
B
All of those things are true. Okay, so let's move on from the sports talk to get to what's going on in your city, Chicago. I mean, I mean, wow. As I said before, I wanted to do something contrarian. Everybody else is focused on the Middle East. You know, peace in the Middle east or ceasefire in the Middle East. And yet we have the ongoing, I don't know, invasion violence in Chicago. And of course, last week, ICE enforcement in Chicago escalated rather dramatically under Operation Midway Blitz, the deployment of National Guard troops to the Broadview ICE facility. It was temporarily blocked by a federal judge. We now have National Guardsmen from Texas and Illinois who have been federalized. Major pushback from the Governor of Illinois, J.B. pritzker, the mayor of Chicago, Brandon Johnson. So I'm just going to ask you this question. So what is it like in Chicago right now? What should the rest of the world know about what it's like in the hellscape of war torn Chicago at the moment.
D
Well, Charlie, things were so bad yesterday, tens of thousands of people were running through the streets. Now, some people will tell you the fake news media will tell you it was called the Chicago Marathon. But some people know better. But I don't want to make light of a very real situation that's happening in the city that that changes almost by the day as far as the National Guard is concerned. On Saturday, the appellate court did uphold the federal judges ruling on Thursday that said that the National Guard could not be deployed in Illinois. But they can't go back either. They can't go back to Texas. So they can stay in their base. They can stay at their base. They're in Elwood, Illinois, which is just southwest of Chicago, about an hour outside of Chicago. And so we're still waiting to see where because obviously the National Guard ruling is going to move up the food chain. So we'll see what happens with that. There have been numerous videos going around on social media, I think we've all seen them of various ICE enforcement operations. There was an operation that took place over the weekend in the Albany park neighborhood on Chicago's northwest side where it looked like ICE agents were using tear gas to disperse a crowd that had gathered. And that was in the face of another federal judges ruling that said the federal agents had to give two warnings before using crowd dispersal techniques such as tear gas and pepper balls and the like. According to the video and according to people who are on the scene, those warnings were not given. So that was the big story today. Governor J.B. pritzker has talked about how potentially the state of Illinois could investigate ICE operations in Chicago. And the enforcement operations go on. 12 ride share drivers taken at O' Hare over the weekend as part of Operation Midway Blitz. The Chicago Tribune reporting today a man named Reuben Antonio Cruz was in the Rogers park neighborhood on the north side when ICE pulled up and he asked him if he had his immigration papers on him. He did not. This is a guy in his 60s and they left him with a $130 citation. So that's the extent of the immigration enforcement, which, which is ongoing.
B
Could I just mention that Cruz story was very interesting to me because apparently there is a law in the books that no one has ever enforced until yesterday that if you are a foreigner in this country, you have to carry around your papers all the time, right? So that if you do, if you don't have them on your, you know, on your person, you are in technical violation. No other administration has ever enforced that. So it was literally a show me your papers arrest and charge, wasn't it?
D
And even then, there have been other stories in which people carry their passports as proof of American citizenship. And in some instances, that's not good enough.
B
Okay, how would that not be good enough?
D
That's just the way it. This is just ramping. It's ramping up pressure. This is something that Governor Pritzker talked about in an interview today in discussing that a lot of this that's been going on is in some ways about generating content as much as it is about law enforcement to demonstrate that you're being very tough on. Being very tough on illegal immigrants and sending everyone back, and that this is all, in many ways, what happens is later turned around into highly produced videos that are posted to various social media channels.
B
This is a really interesting aspect of this. And obviously we're seeing this playing out in Chicago, kind of the Instagram enforcement. The most dramatic example, of course, was that assault on the five story apartment building on the South Shore where you had the helicopters having the ICE agents rappel down and could. Kristi Noem made that into a hell of a sizzle reel, didn't she? I mean, with music and everything.
D
I mean, there's a long history of this, of once you grasp a new communications technology, you can master that. I mean, this is going back everyone likes to talk about. And since this took place in Chicago, the Nixon Kennedy debate, which took place at WBBM TV in 1960, and the takeaway from that was that, you know, Kennedy looked better on TV and that's why he won the election. However, by 1968, Richard Nixon was a master of the medium. He knew. And Roger Ailes knew how to create compelling television where they controlled the programming from start to finish. And it was used very effectively. It was the rolling out of a playbook that served Richard Nixon and subsequent Republican presidents very well for a very long time. So at this point, it seems like the Trump administration and DHS is just filled with digital natives who know how to use social media effectively and they are telling their own story as this immigration enforcement goes on.
B
Now, this raises an interesting point, though. I mean, you're absolutely right that they are doing that. But of course, social media is also flooded with the. With the videos of the brutality of the ICE agents. So you have these dueling video narratives, don't you, on social media?
D
You know, yeah, that is something the governor said today, that because people are using their own phones to shoot video of these ICE enforcement operations, it's, it's not only generating content, but when they go to court, it's generating a lot of evidence as well.
B
So on balance, it's too early. We don't know who's got the edge there. It is interesting and there are larger themes here, which is the ICE agents are largely masked when they go out. I mean, they don't want the accountability. And yet you have these videos and they are rather dramatic. You got a WGN television producer thrown to the ground, captured on video. I think everybody's probably seen that. What is it? It was but a bike messenger who flipped off some of the agents and.
D
They, they chased him.
B
I mean, so, yeah, I mean, so this is, this is the first time the, the revolution slash enforcement is all televised every, every single moment. And this is going to continue. It's happening in Portland, it's happening in Chicago, and it's going to continue to be this, the kind of, the new, the new medium of what's happening.
D
Well, what's interesting is that regardless of what's going on with the National Guard and what's going on with ICE and the ramped up immigration enforcement, 2025 is shaping up to be one of the safest years in Chicago in a very long time. The homicide numbers that we're seeing this year are just simply staggering compared to where we were just a few years ago. Someone compiled a list of the number of days in Chicago. This is 1991 to this year, through the middle of October, the number of days without a homicide. 2011 led the pack. 104 days without a homicide. 2025, 101. And then 2014 was 100. So this is one of the safest years of the 21st century. And yet, because we live in this world of social media content, anytime someone posts a video of a fight breaking out at a baggage claim at o', Hare, it colors the perception of safety in this city. I mean, when I moved from, from Milwaukee to Chicago 20 years ago to work at WGN AM, one of the big stories then was the, the fact that homicide numbers had fallen through the floor and that in the mid-2000s, it was the safest stretch of years in the city since the 1960s. And everybody was celebrating that. In fact, one of my first news series that I did for GN was how did this happen? And talked to the police and talked to various people who were all pulling together to pull off this remarkable feat in making Chicago considerably safer. And we're talking about these same numbers 20 years later. And instead of celebrating Them because there's just so much social media content out there. Some people believe it's time to bring in the National Guard.
B
Yeah, no, so let's, let's, let's step back because I think this is important to put this into some context, because I'm sitting up here in Milwaukee, you're down there in Chicago. We all know that there were those weekends where you would wake up on Monday morning and there would be a horrific number of shootings and killings in Chicago. And it became a theme in the media all over the, the, all over the country. You know, it was, was one of those hot takes that anytime there was a mass shooting someplace or where there was a debate about gun control, people would say, well, what about Chicago? So Chicago did at various times objectively have a very serious gang problem.
D
True.
B
And it was a violent gang problem.
D
This, this is absolutely true.
B
Okay.
D
Because so 20 years ago when they had, when, when we were celebrating the, the drop in crime, one of the reasons driving that drop 20 years ago was that the feds went after the large street gangs that controlled vast swaths of territory that, that made a lot of money, that even had their own headquarters that people could go to and talk to their leadership. And they were scattered to the four winds. And what happened in the intervening 20 years. And I talked to somebody who was, was in a street gang not too long ago on one of our interview programs and she said, in the 90s you had, they were these big enterprises and then once they went away, they were replaced by these smaller entities that may have been two or three people and they controlled just several city blocks. And everybody got in on the heroin trade. And just because Chicago is centrally located, it's really easy to bring illegal guns into the city. And then you had a great deal of violence that was driven by social media. Online beefs became very real violent events as a result of just people feuding online. And that drove a lot of the violence that took place in 2020 and 2021.
B
And this is one of the reasons why I think Chicago was targeted because I think there was that muscle memory of Chicago being a gang ridden place where you'd have these violent weekends. Tell me about, though, also the, let's talk about the politics a little bit. Your mayor, new mayor Brandon Johnson, is a progressive and he is deeply unpopular. So I'm trying to think of these sort of reverse engineer. Why does Trump want to go into Chicago? Because a lot of his constituents, he is based, remembers that Chicago used to be extremely violent. He's picking A political foe who is very politically weak. Why was, before all this started, why was Brandon Johnson so unpopular? And the number that sticks in my mind, tell me if I'm right about this. Was it at one point, he had a 16% approval rating.
D
It was less than that. It was in the single digits, less than that. And this was literally.
B
That's almost inconceivable. Okay, so what was going on there?
D
Well, you have to remember he got in with a little over 50% of the 30% who voted. So there were a lot of Chicagoans in 2023 who stayed home. And then he made all the same mistakes that new mayors make in trying to figure out how to turn the levers of power and building coalitions and relationships with the city Council. And he stepped on a lot of rakes along the way. He may have found his footing with the White House, turning its ire on the city, but for him, it may be too late, because there are a lot of people who are thinking about jumping in and running in 2027.
B
Wasn't he one of the people who got caught up in the defund the police movement as well? So, in many ways, he became kind of the perfect foil for Trump and for maga. Didn't he have a track record of that kind of rhetoric and kind of an. As a. I'm sorry to use the term, woke progressive. He comes in with a lot of, you know, trailing a lot of that. A lot of that baggage, which apparently he thought he had a mandate to implement when he narrowly won that election.
D
Well, I think that that was part of it, was there was a lot of stuff that people said in 2020 that got them a great deal of attention in 2020. And then that tide went out to sea. And so all of a sudden, you have to answer for these things that you said a couple of years ago. But the larger thing about Brandon Johnson is that, first off, his. He can brag about the crime numbers because they happened on his watch. I mean, obviously, I think that the best hire that he made was Larry Snelling as the Chicago Police superintendent, who people want to work for him. He has done a very good job of improving morale on the police department. So that is one of Brandon Johnson's absolute wins. A lot of his issues stem with. From relationships with the school board. And there are going to be a lot of very unpopular budget choices coming down the road in terms of balancing the books for next year. Do you have a property tax increase? All those things are on the table. So even though he can rail against Donald Trump. And he gets a lot of press for that and a lot of national news attention for that. But there's some unfortunate political and unfortunate budget realities facing him at City Council.
B
Okay, so let's talk about J.B. pritzker, because J.B. pritzker is one of those people who nationally certainly looks like he's just stepped into the, into the spotlight in terms, you know, Democrats have been looking for somebody who is going to fight, you know, JB Pritzker is a billionaire who is going to, I guess run for reelection next year. Obviously has presidential ambitions. So give me your sense of how J.B. pritzker is navigating this and what this might mean for him. How does it play locally?
D
Well, this will, I mean, obviously it'll certainly burnish his national profile. It's interesting how it's going to play for him locally because he's well, he does well in the Chicago area. That's his base of power. And if he is going to run for reelection next year, how he does in the Chicago area will really determine how he does statewide. And we talk about, you know, joking about how Chicago is a hellscape. And he was on Jimmy Kimmel Live last week.
B
I saw that.
D
But the thing though is I used to work on Saturday and Sunday mornings. And so you talk about those days in which there were the weekend homicide numbers were staggering and they were very hard to get your head around. So we can talk about war torn Chicago. But there was a lot of heartbreak in those numbers and a lot of lives shattered and lives taken. So Governor Pritzker living in the content era in which we all have to operate, that's good social media video. But at the same time, if you're joking about how dangerous the street dangerous thing, how dangerous the streets of Chicago are and then something like that happens where 20 where there's a shooting involving 14 people outside of a nightclub and, and you're making light of that situation that could potentially come back to haunt him.
B
Was there blowback to that? I mean, I thought he handled it pretty well. He was joking about the, you know, the brewers invading, you know, it was blood hot dog. He was very well done. But so has there been some blowback, some, some blowback locally to that?
D
There really wasn't any blowback locally. That was just my impression from watching it was that maybe eventually this could be used against him if something awful were to happen in the city, something very tragic. That's why you gotta walk a very fine line about you can make fun of the overheated rhetoric. But at the same time, I mean, there's a very real human toll.
B
This is, I think the kind of, the danger is that, and especially, you know, in this social media world that also has these information bubbles that people begin to think, well, okay, I mean, obviously when Trump describes Chicago as a hellscape, he is exaggerating, he is exploiting it, he's looking for a pretext. Same thing with Portland, Oregon. On the other hand, don't buy into the counter narrative that somehow there was no violence in Portland or that there was no gang violence in Chicago because that just makes you look like you are completely tone deaf and have no idea what's going on. So, you know, keep those two thoughts in your head at the same time. Okay, can we talk about some of the specific incidents that I think have really stuck in people's minds? I mentioned the videotaped assault on the apartment building, the shooting of a local minister in the head with a pepper ball. This would be the Reverend David Black, who is, I guess a well known activist in your town. They were protesting outside the ICE facility in Broadview. Correct me if I'm wrong about any of this. And these heavily masked ICE agents on the roof, it certainly looks from the video that, you know, he's waving his arms, he claims he was praying, they shoot him in the head with the pepper ball. So tell me about that incident. What we need to understand about that incident and whether we've learned anything since those images have gone out across the world.
D
Well, I mean, that is continued too. There was another effort by a local Catholic parish to administer the Eucharist to people who were in ICE custody in Broadview and they were turned away. You can only go off of anecdote here, but in my own conversations with people who aren't very politically engaged, but they follow what's going on and it's, it's not, it's making people uncomfortable. And that, that's the takeaway that I get from just talking to people is that they, they see these, they, they see these videos, they, they have stories in their own life about people who have been taken into ICE custody. And they think whatever is going, you know, you know, I, I, I believe that we need to enforce the borders, but whatever is going, whatever is going on here is, is simply unacceptable. Now, is this going to pull them away from potentially voting for the Republican ticket in 2028? We don't know yet. Is this going to turn them into very passionate supporters of JB Pritzker next year? We Also don't know that. But this, what's going on right here, people are talking about it and a lot of people say it makes them uncomfortable.
B
Well, I mean, I'm gonna stick with David Black for a moment because, you know, those are feel like iconic pictures. You know, there's the picture of him being shot in the, with the pepper ball. There's the picture of him looks like he's being, you know, sprayed in the face with, with, with, with, with. With Mace. And you know, all eras have their, Their, their iconic, their iconic pictures. Now he is. I mean, is there anything more to this story in terms of the context? I mean, ice. I mean, we all saw. We saw. And yet ICE and Homeland Security are defending this. You know, suggesting that somehow they were. It looks to me like it was a peaceful protest, but they're saying that entrance or the exit sty. That they were doing something. I mean, what, what is the, what's the story on the ground about what was going on there?
D
Well, that's the other frustrating thing about following this is that the stories about this, this is what one particular person was doing, they fall apart under scrutiny. Video tells a counter narrative. And then there's just so many videos floating around on social media and so many different stories and so many different accounts. Trying to get to the center of what's going on is very difficult, especially as a reporter, when your job is to find out what really happened. And by the time you find out what really happened, the discourse and the cycle has. It's three or four stops down the road. So that's kind of where we are in this particular situation, is that he's okay, he's recovering, and I would imagine he's going to court before too long to seek some sort of recourse. But. And that's where we're at right now because once again, we've moved on to two or three different things.
B
Boy, do. I mean, this is really an important point, actually. And it is more and more difficult to figure out, to sort out, because I do know that there are bad actors who will push narratives that turn out not to be true. And then we have seen a number of incidents in Chicago where the ICE agents have taken an action and they claim, they make certain claims about it at the time. And yet later we find out that the video, the, you know, the body cam or whatever do not support that. I'm thinking specifically of the. That a woman was shot, was shot by ICE agents. She survived, but initially they were saying that she had rammed her car, was blocking the ICE agents pointed an automatic weapon at them. And as far as I can tell, now that we find out more about it, it turns out that a lot of the claims by the ICE agents do not hold up under scrutiny, which, by the way, is extremely disturbing. If you have these guys, these masked agents who are acting as if they are above the law, and then we find out that they are very unreliable narrators, to put it in a very, very polite way, about what they are doing and what's happening. So what can you tell me about that incident or the other shooting incidents?
D
Well, there was the one shooting incident that took place in Franklin park several weeks ago where the video came out and the one person said he was okay under the circumstances. And once again, this just goes back. This goes to show you how frustrating this whole situation is where you're trying to figure out what's going on, because they're very quick to put out what happened, their narrative of what happened. And then you're trying to go through different social pieces of video from social media and trying to figure out what's going on here. So there's just a great deal a fog of confusion that really struck me when I was trying to put together everything that happened before I came on with you today because there's just so much going on. There are so many incidents. There's so much video that is just out there of different things that are happening. For example, in Broadview, there were a number of people were arrested outside of the ICE facility on Saturday, and it was so disruptive that the mayor of Broadview came out today and said, we're shrinking the area in which protesters can gather partially in response to what happened on Saturday. But also, 25th Avenue in Broadview is a pretty busy street. And she said we need to shrink the protest zone before somebody walks into the street and gets hurt.
B
So tell me you made a list there of some of the things that have been happening. Bring us up to date on what is actually happening on the ground in Chicago today, this weekend.
D
Well, this weekend we did have the I think I talked about this before. The federal agents who were trying to take a man into custody on the Northwest side in the Albany park neighborhood. That's the one where the older woman there, Rosanna Rodriguez Sanchez, mentioned that tear gas had been used. We did have the federal court ruling. We did have the protest borders in Broadview that were restricted today. Emmanuel Chris Welch, the speaker of the Illinois House, once again was calling on Immigrations and Customs Enforcement to tear down the fence that was outside of the ICE facility because they were. That was a judge ruled for the fencing to come down by this week. And we talked about the immigration arrests at o'. Hare. And then also there is stepped up immigration enforcement in Lake county, in Waukegan and North Chicago where officials there say at least 20 people have been arrested. So this is ongoing and things. There's new information almost hourly going on about what's going on here.
B
I'm looking here at an account of arrests outside of Westside Elementary School where officers forcibly removed adults from vehicles reportedly without presenting a warrant. So what moms on the pickup line are being arrested? Because what, I mean, do you have any sense of how they're targeting people? I mean, do they actually have a list of, you know, wanted criminals? Or are they, does it look like they're just hanging out at places where Hispanic looking people might show up that we don't know about the pattern?
D
Yeah, that really is the big question here is, I mean, there have been a number of arrests at Home Depot because people, you know, day labor is looking for work. But if there's a pattern, if they're going off of a list, we don't know that just yet. But it does seem in many ways that it's almost like a force of nature. It just happens and then, and then the video shows up on social media within seconds.
B
So my wife and I are probably going to come to Chicago for an event next month in downtown Chicago. What are we going going to see if I come into Chicago this week, next week, next month? What am I actually going to see? These guys? Will I see the presence? Or is this something you have to go look for them? I mean, what actually feel like? Because on social media they're everywhere and they're doing everything. There are helicopters overhead, there are people in tanks. There are people in it. But what will I see when I drive down Michigan Avenue?
D
Well, this really depends on whether the federal, the appellate court or eventually the Supreme Court, whether they give the green light to deploy the National Guard in the streets of Chicago. Because then you could see National Guard personnel walking up and down Michigan Avenue. But I can tell you right now, as somebody who works on Michigan Avenue, that you will see a long line outside of the Nutella restaurant and you better get reservations for Wild Berry in the Prudential building because for brunch it fills up quickly. But outside of that, it looks like a typical day in downtown Chicago. It's still kind of light in the morning because a lot of people are still working from home or Working later, but it's still very busy in the afternoon. You're ducking and dodging tourists all the time. So it's just a lot of people are downtown. I mean, not only that, it's not just the central business district anymore. 100,000 people call downtown home. This is one of the fastest growing neighborhoods in the city. So if, when you come here a month from now, I mean, depending on what the courts say, you'll just. You'll just see a lot of people. And if you're coming in early to mid, if coming in mid November, you know, Saturday night in just before Thanksgiving is the Magnificent Mile Lights Festival. Stay as far away from that as possible because just traffic is a nightmare. But outside of that, it just looks like a typical day.
B
Yeah, I don't want to make. I do not want to make light of the problems here, including what we don't see. And what we don't see is the fear and the anxiety of people who are probably staying inside, who are afraid to come out because they don't know what's going to happen, because they don't know whether their papers will be demanded. They don't know whether a loved one will be snatched. I was really struck by the letters that were presented to Pope, the Pope, Pope Leo, the first American pope, from American migrants who talked about the fear, how they wouldn't leave the house, they were afraid to go to the store and everything. And so, you know, again, I don't want to come off as, as, as belittling, you know, what's actually happening. Sure. People are going about their lives. They're going about. They're going to brunch, they're going to restaurants. But there are probably thousands of people, including children, who right now are looking over their shoulder, who don't feel safe, who don't know what will happen to them, who do wonder whether or not a loved one will be taken away and renditioned, put on a plane somewhere, or put into these facilities. And we are getting the reports of how horrific the conditions in these facilities are. And this is something, again, circling back to something you mentioned before. It does seem as if the Catholic Church, which is a major presence in Chicago, is now, with the support of the Pope, ramping up its resistance to all of this. Are you seeing this? I mean, what role will the Catholic Church play in what's unfolding in Chicago?
D
It's a lot more assertive, especially on issues, and probably because Pope Leo is not only from America, but he's also from the Chicago area. And of course, went to college in Philadelphia. And that probably maybe in his mind, makes him feel that he can be more assertive about what's happening in America. But Cardinal Blaze Cupich also is being very forceful about his beliefs about what's going on. And it's all about building maybe a network, perhaps of just people who feel empowered and that they're not alone and that they do have friends in the community. And you're seeing this here and there. There was a story today in the Tribune about how several local aldermen are up building, getting community volunteers to look out for immigration agents and warning people or standing outside of schools to talk about, you know, talk about that pickup line situation. And that's just part of alleviating some of that anxiety that people may have that they're not 100% alone and that the church is behind them and that their neighbors are here to help them as well.
B
Yeah. I probably should have mentioned this a little bit earlier, because it was a couple of weeks ago that the President of the United States, who has complete control over the Department of Justice, actually called for the arrest of Illinois Governor Pritzker and the mayor of Chicago. How did that play locally? Does everybody think that's kind of a joke, that he's just. Oh, that's just Trump on social media again. What's the reaction to the President of the United States suggesting that your mayor and your governor may be arrested because they are resisting some of these ICE enforcement efforts?
D
Well, that was our lead story that day. It did make everybody stop and think for a second, because these are now words that can be backed up by actions.
B
Yeah. Don't assume he's bluffing.
D
And this is after, you know, James Comey was indicted, and now we have Letitia James indicted, and then potentially John Bolton is next, reportedly. So this, this isn't a joke anymore. And, and that could very well potentially happen. But Governor Pritzker and Mayor Johnson both said, you know, go ahead and do it if you want to.
B
So people are taking that seriously.
D
Yeah, Yeah. I think it's, it's, it's, it's. It's no longer. It's no longer social media snark. They. They followed through on things, and that's changed the equation.
B
And this is Chicago, Illinois. Rob Hart, thank you so much for joining me. I appreciate it. Rob is the midday anchor for WBBM Radio, the all news station. You are still old news, right?
D
We are still all news. Yes. All day and all night.
B
All day and all night. Longtime colleague. Rob, thank you for giving me some perspective because it's one of those things where there's so much going on nationally and around the world that, that every once in a while I want to take a deep breath and just focus on like, do we understand what's happening here? By the way, do people in Chicago kind of feel that they're at the epicenter of all of this that's going on, that you may be the epicenter of a conflict between the President of the United States and the American Pope, that all of this is playing out in your city? I mean, do people have that sense?
D
You know, I don't know if they really grasp the full enormity of what's going on. It's certainly just part of individual conversations that people are having. But it's probably no different than what was happening in Los Angeles earlier this year or what's happening in Portland right now, or what's currently going on in Washington, D.C. it's just, it's it. There was a new poll out today that had 69% of respondents saying they don't want the National Guard.
B
Chicago is a poll of Chicago poll.
D
Of Chicagoans saying they don't want the National Guard performing crime fighting duties. That's not their job. We have a police department. Let the cops do it.
B
Rob Hart, thank you so much for joining me. I appreciate it very much.
D
Well, Charlie, great to talk to you. It is.
B
Thank you all for joining us for watching this episode of to the Contrary podcast. I'm Charlie Sykes. You know why we continue to do this, why we're going to do this for the duration? Because we continually have to remind ourselves that we are not the crazy ones.
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To The Contrary with Charlie Sykes
Host: Charlie Sykes
Guest: Rob Hart (Midday Anchor, WBBM Radio, Chicago)
Date: October 14, 2025
In this episode, Charlie Sykes turns attention from international turmoil to the escalating domestic situation in Chicago, marked by intensified immigration enforcement, legal standoffs over National Guard deployment, and a city wrestling with its fearsome reputation. Veteran Chicago reporter Rob Hart joins to provide a ground-level look at life in Chicago amidst "Operation Midway Blitz" and the political and civic fallout for local leaders. The conversation also navigates the complexities of media narratives, the real experiences of residents, and the unique role Chicago now plays as a focal point of national conflict.
On Media and Narrative:
On Actual Safety:
On Local Politics:
On Enforcement Tactics:
On Information Fog:
On Community Anxiety:
On National Guard:
The episode illuminates the volatile intersection of enforcement, politics, media, and lived experience in Chicago. While the city copes with reduced crime levels, an extraordinary federal crackdown, and national political theatrics, it becomes clear how perception, narrative, and policy collide. For many, life goes on almost as normal, yet for thousands, fear and uncertainty dominate. At the heart is a city now serving as a battleground for national power, media, and morality.