A Look into 2026 Chicago Politics

I'm Dana Carvey. I'm David Spade. Flying the Wall's back for another season now on audio and video every Monday and Thursday. So many incredible guests will be joining us. Follow and listen to Fly on the Wall everywhere you get your podcasts. To Good Be True. 2025 began with the inauguration of Donald Trump for his second non-consecutive term as president, and it ended with a city budget agreement that passed over the objections and without the signature of Mayor Brandon Johnson. This year is an election year. It will largely be a referendum on what's happening in Washington, but it will also test the political power of J.B. Pritzker, who has his eye on the White House two years from now. I'm Rob Hart. We set up the year in politics and talk about the year that was with political editor Jeff Buckhulls this week on At Issue. My, I'm going to stick to this despite assertions to the contrary that my predecessor, the great Craig Delamore, saw this coming and said, nope, I'm out and decided to retire leaving me with my first budget cycle being this one. And boy, it was something. The mayor in October told Alderman about his $16.6 billion spending plan, which included a number of. progressive planks, which speaks to sort of his background and his philosophy. And the biggest and most controversial of those, well, not the biggest, but the most controversial one was the thing that he called the community safety surcharge and literally everybody else called the head tax. This was the per worker charge that would have been collected on the top, the biggest employers in the city of Chicago. That was the thing that emboldened a group of aldermen to come up with a different proposal. This upended decades of tradition at City Hall. Typically how this works is the mayor proposes a budget, the alderman go through it and go, I don't like this, I don't like that. If I could get this, I can do this, whatever, mayor goes back, makes some changes, comes back, alderman approve it. We all saw this in their rich daily years, the 48 to 2, 49 to 1, 50 to nothing budgets. This head tax was a bridge too far for these alders. So they worked with their own experts, which they have not yet identified, by the way, and the information that they got from the city, and remember that the mayor has his own budget-making arm with, like, lots of people and analysts and that kind of thing. The alders kind of have each other. They're at the mercy of what the city provides them in terms of information. So they work with their own experts to come up with their own spending plan, which took the head tax out and replaced it with some other things, legalizing video gambling terminals across the city, which has been a pet wish list item for Anthony Beale, the longtime alderman from the far south side. And a few other things, collecting debt.

owed to the city of Chicago for things like red light camera tickets and parking tickets and that kind of thing. It's like a billion dollars of money outstanding owed to the city on this kind of thing. So the idea is that they could sell that off. And then some other novel revenue producing ideas, selling naming rights to the bridge towers downtown, selling ads on city vehicles, that kind of thing. And the fight. between the mayor's team and his surrogates outside of city government, and I think we're going to talk about that in a minute, and the alternate alders got, and their supporters outside of city hall, got fairly ugly for city council in city council history. And yet somehow... 39 or 30 aldermen, 30 aldermen for one, 29 for another, voted for this alternate budget plan, even though the mayor's office initially said he was out of whack by about $160 million. And then later they came back and said, oh, no. We've made some tweaks. It's balanced. The idea here was that this budget, the alternate budget, would not deal a hit to the city's biggest employers at a time when economic growth is still kind of shaky. And it would also restore a full advanced pension payment, which needed to happen to avoid a credit downgrade for the city, which a lot of aldermen are talking about. and also insured more sustainable revenue. The mayor didn't like it at all, but apparently realized he didn't have the votes to stop it and might lose a veto override. And remember that all this is happening, this was all happening on the 19th and 20th of December. And the city needed to get a budget passed by the end of the year to avoid a shutdown, which has never happened in the modern history of the city of Chicago. So after the vote, the mayor then did a splashy, very campaign-like appearance with supporters, including his longtime supporter and friend, Stacey Davis Bill Gates, the head of the Chicago Teachers Union, outside of his city office on the fifth floor. and said, I'm not signing this budget, but I'm not vetoing it. So it's going to go into effect without my signature. But I'm signing two executive orders to deal with things that I think are issues with this budget. And whether those, what authority those have is something that remains to be seen. But it's the first time anybody can remember. And I remember asking Craig and our colleague and friend Mike Flannery about this. We don't remember a time when a budget has been allowed to be enacted in the city without the signature of the mayor. These are unprecedented times that we're in. And the alders who were part of this alternate slate.

which include, by the way, the mayor's hand-picked finance chairman, Pat Dowell from Bronsville, all are saying that they intend to stick together over the next year and take more of a leadership role in budgeting in the city of Chicago. And the larger issue, too, and this was something you heard along the way during the negotiating process, is that... They agreed on what, 98 or 99% of the issues, and this head tax, it was more or less replacing COVID-era money that was rolling off the books. It was nowhere near as dramatic as what we saw with the CTA, but at the same time, the city needed to find extra sources of revenue to make some of these policies stick that were being funded with the COVID money. And that was the real sticking point here, and that leads us to the air war. that we saw as this budget negotiation process dragged out. You were seeing issue ads on TV about the city budget. I remember watching the Bears Packers game at the end of December on 32, and all of a sudden you're seeing commercials about the budget. I thought, I've never seen this before. Yeah, and this is part of the sort of new reality around City Hall. Mayor Johnson was elected with the great support of the Chicago Teachers Unit and other labor groups. And indeed, his history is as a community organizer and an activist. This is what he knows. So it's not a surprise necessarily that his supporters would sort of go to that well to try to sway public opinion. To the frustration of a lot of alders, many of whom are progressive, including Andrei Vasquez, who's the co-chair of the Progressive Caucus, who said, look, I have no problem. asking rich people to pay more. But this ad suggesting that I'm a puppet of Elon Musk and Donald Trump is insulting and offensive on its face. And appears to have swayed a number of alders who may not have been inclined to support the alternate budget plan to get on board or signal to the mayor's office in the days following its passage that they would have voted to override any veto. So it remains to be seen, particularly it's not too far down the road where we're going to be voting on alderman and the mayor. We got another 13 months or so. That dynamic is going to be an interesting one, and you're going to see this pop up a lot in the months to come as the city charts a course forward. Let's talk about campaign 2027, and that is. There was a report out this week that suggested Mayor Brandon Johnson's war chest was somewhat meager, $15,000. And in a day and age when there are so many...

PACs and other organizations that can pour money into a campaign. Your own individual war chest doesn't necessarily matter. But at a time and in a year in 2026, we're going to see probably a number of people jumping into next year's elections. What kind of message does that send? So, yeah, the report in kudos to... Craig Wall from Channel 7, who reported that this week. The mayor has raised $15,000 in donation since the end of September. His war chest is about $930,000. It's still okay. But he hasn't raised, a lot of people would suggest he hasn't raised a lot of money. The one declared candidate so far is Joe Holberg. He's a teacher-turned entrepreneur. We interviewed him back when he got in the race over the summer. He's raised a half a million dollars. Mike Quigley, who has told other broadcast outlets in town that he does intend to run for mayor, which we had long suspected, has raised a hundred and... $100,000 plus already for this new thing. And yes, you're right. A lot of other people are going to get into the race. Maria Pappas, the venerable Cook County clerk and baton twirling enthusiast. Calendar model, too. Yes, told me several weeks ago she's going to get in. So there's a lot of Alexei Janullius has raised $5 million. He's got a $5 million war chest. on a race for Secretary of State where he is not opposed in the primary and faces pretty unknown and token Republican opposition. So he's clearly raising money for something. The mayor, when asked about it, and we asked him this week, said, look, my focus is on, you know, my priorities, my administration's priorities. Our audience has heard chapter inverse of the mayor talking about, you know, building the safest most. affordable big city in america is is the line um and then he said and if we're really talking about money i was out spent three to one And I'm the mayor of Chicago. So he is suggesting that maybe fundraising isn't the isn't to his mind anyway or into his supporters mind maybe isn't the biggest metric because Paul Vela spent a lot of money on that race to come in second. But you're right. The CTO and other labor organizations will probably. contribute not only money because money is important in a big city like chicago where ads cost a lot of money but also and critically in chicago the ground game where you have hundreds of volunteers who will go out and knock doors and get the word out about your candidate so that's that kind of contribution's hard to quantify but

Certainly based on the amount of money raised, it's easy to look at that and go, well, maybe the mayor needs to do a better, probably the mayor needs to do a better job raising money. And his argument is, look, I'm focused on doing the city's work, plus I beat a guy who had more money than me. You're listening to At Issue on WBBM News Radio. I'm Rob Hart. We're talking about 2026 and potentially 2027, the year in politics with WBBM political editor Jeff Buckhulls. Let's move to the elections taking place this year. We do have people in Illinois will vote for their members of Congress. They will have the chance to vote for a new senator to replace Dick Durbin, who is retiring after 30 years. Well, let's begin with the fight over redistricting in Illinois. You're starting to see some mid-cycle redistricting moves. We saw it in California. Sometimes it feels like the news is full of things that have never happened before. And that is not exactly true. In fact, it may have happened this very week, hundreds or thousands of years ago. I'm Sally Helm, host of the podcast History This Week from the History Channel. Trade embargoes, Thomas Jefferson tried them. Rent too high? We've been arguing about that for a while. Each episode is proof. The past isn't that far away. Listen to History this week, available now on Apple, Spotify, or wherever you get your podcasts. And in Texas, other states were thinking about it. Indiana famously pulled back from it. There was some talk about redrawing congressional seats in or congressional districts in Illinois to shore up Democrats' chances in a state that's already tilted pretty substantially in the Democrats' favor. Where did we leave that in 2025? On the back burner. Not on the back burner. I'm sorry. In the fridge. It's not going anywhere this year. And I think that the final nail in that one was the failure of the Indiana legislature to approve any kind of a redraw of their maps. And remember, we're talking about two states that are already pretty well in hand for a particular party. I mean, in Indiana, there are... two congressional districts that are Democratic, and both of them are kind of in the northwest part of Indiana. In Illinois, there are three congressional districts that are Republican, and they are largely central in Southern Illinois, or have been divided in that way. But with the failure of the measure in Indiana, I think that took that completely off the table. And that's a conversation that doesn't benefit J.B. Pritzker, by the way, or any of the legislative leaders in Springfield at all.

You have two races in this state that will test the power of J.B. Pritzker. The first one, obviously, his reelection campaign, he is running for a third term. Not since Jim Thompson, have we seen a governor of Illinois successfully run for a third term. And also you have a Senate race that features his lieutenant governor, Giuliana Stratton. And... It will test the power of his political apparatus to push her over the line in a very crowded field that includes the well-funded Congressman Roger Krishna-Morthe. Indeed, the congressman of the 8th District has brought in a lot of money from his supporters in the northwestern suburbs, and he has been all over the place, not just on television a lot. You talk about TV ads. The guy's been on TV. for weeks now. And also has been all over the place most recently talking about the end of Affordable Care Act subsidies. He did a couple of appearances at Cook County Health Facilities with Board President Tony Preckwinkle, who's also the head of the Cook County Democratic Party, by the way. I asked her, she says it's not an endorsement. But indeed, Juliana Stratton, the lieutenant governor, has a hill decline here. A, I don't know that a lot of people know who she is, even though she's been the lieutenant governor of Illinois now for two terms. And B, she has to overcome a massive fundraising deficit vis-a-vis Congressman Krishnamorthy. Now, the question is whether J.B. Pritzker, who certainly has the money, will make a contribution to her campaign to help boost her numbers there and help her get on the air. I imagine that that will probably happen. Of course, let's not forget completely that there is another sitting congressperson in this race, and that would be Robin Kelly of the second district representing the south side and south suburbs, who is in any other cycle would be a formidable candidate for U.S. Senate and has staked out a position of being anti-gun. That was the thing that got her. got her into power following the departure of Jesse Jackson Jr. from that seat. And she's extremely well-spoken and has a history of beating heavily favored candidates. There are seven other Democrats in that race. By the way, we talk about crowded. A lot of these races are crowded. But indeed, the top two there seem to be Congressman Krishnamorthy and Lieutenant Governor Stratt. I'm getting flashbacks to 20 years ago in 2006 when people would ask then Senator Obama, are you running for president in 2008? And he would defer and say, no, I'm still a first term senator. I have, I'm not going to talk about that right now. And the next thing you know, it's a very cold day in February of 2007, and everybody is gathered at the old state capital and Springfield for that presidential announcement. Now, J.B. Pritzker is heads into the 2026 campaign as the favorite over whoever the Republican nominee will be. At the same time, though, it seems like...

His margin of victory will tell the tale about his ability to wage and possibly win a nomination campaign in 28. Yeah, that's true. And over the last year, you've seen J.B. Pritzker making more appearances in national media. I know he's been on Stephen Colbert. I think he's been on Kimmel a couple of times. He's been on The View. He's doing what he can to introduce himself to a national audience. And not that very, not very many months ago, I was watching the CBS Evening News and they were doing, or maybe it was the CBS Mornings, and they were doing a story about some program in Illinois, helping people who've been incarcerated. And one of the speakers in that piece, M.K. J.B. Pritzker, the governor's wife. So. They are clearly, the J.B. Pritzker's together are working to introduce themselves to a national audience. I think it's a pretty safe bet here that J.B. Pritzker will seek the nomination in 28. And you're right. The margin, how much he beats the Republican opponent by will tell the tale in terms of what his viability is for that. campaign the republican field right now is is there's I can't remember now, five or six candidates. The one with the highest profile is the guy J.B. Pritzker beat four years ago in former state senator Darren Bailey, who now is a running mate, has Aaron Delmar, the former co-chair of the state Republican Party. They've made some news this week with a proposal to create a Doge department for Illinois if they're elected. That's certainly getting some attention. And indeed, J.B. Pritzker's campaign operation put out a press release this week, bashing Darren Bailey. So clearly, J.B. Pritzker thinks Bailey's the frontrunner in a field that also includes Ted Debrowski, the founder of Wirepoints, and James Mendrick, the sheriff of DuPage County. It remains to be soon who he'll face. He beat... Bailey by 10 points in 2022, I think, 55 to 45. If it's more than that, that's probably the win he's looking for. Yeah, you have to look at it in terms of what is the national environment because J.B. Pritzker's margin of victory over Bruce Router in 2018 was largely in line with the blue wave environment. And... Maybe you can make the argument that his victory over Darren Bailey was muted somewhat by the slightly more Republican environment in 22. So now this is turning into 538. I don't want that to happen, Jeff. But you have to look at fundamentals. And if J.B. Pritzker overperforms the fundamentals come November, people will be more bullish on his presidential campaign. What's J.B. Pritzker's win over replacement? That's proprietary, good sir.

And if you know that joke, you listen to this show regularly. Let's talk about some of the other issues that are taking place and could become very big issues in Illinois and in the Chicago area especially. Let's talk about property taxes where a number of people, after those long-delayed property tax, and second installment bills came out. opened their envelope and nearly passed out from the sticker shock from some of those figures that were quoted towards them. You always hear about tax revolts. all over the country that that peter out once something else comes along but does this have the potential to stick uh the people just uh people who are really walloped by their property taxes just because of an assessment system that push the burden off of downtown and into the neighborhoods and into the suburbs yeah i think it can um and a lot of people this is something a lot of people are talking about um When Maria Pappas, the treasurer, and I talked about this a few months ago, she spelled out the extent of the increases here. I mean, some neighborhoods saw more than 100% increase in their assessments. And as you point out, a lot of the reason for that is, A, because... The number of people working downtown has decreased because people are successfully working from home. Exactly. You guys talk about that on the noon business hour all the time. As a result, buildings downtown aren't worth as much as they used to be. And the people who own those buildings can afford to hire very good attorneys who can go to the Board of Review and get the property taxes negotiated down. And as the city... increases its spending. I think Ms. Pappas told me the city's spending went up like $600 million or something in the last few years. the corporate fund spending, the money's got to come from somewhere. So the burden, indeed, gets pushed onto homeowners who don't have access to expensive attorneys and often don't understand what the appeals process is. If you ask people in Cook County what the issue is, of course, everyone's going to point the fingers at everybody else. Maria Pappas says it's because the city's spending too much money and also... The appeals process is ridiculous. Maria Pappas is also going to be a candidate for Chicago mayor, so you have to keep that in mind. The assessor's office, Fritzkege, the assessor says, hey, don't blame us. It's the Board of Review. And in the meantime, a lot of people are stuck trying to figure out how to pay these bills. And unfortunately, a lot of the increases have come in neighborhoods where people historically...

have a harder time paying those bills. South, Southwest, West sides are crazy. And in particular in Woodlawn, where I think that I'm trying to remember now the specific percentage of property tax increases. I mean, they're up, you know, 70-some percent, I think. And remember, Woodlawn's about to get the Obama Presidential Center, which is going to open this year. And already there's been lots of speculation in that neighborhood. So, yeah, I do think it has a real potential to be something. We'll see how. Voters respond to that in the Cook County elections, which are coming up this year. Tony Preckwinkle, the county board president, who has been the county board president now for years, is facing a well-funded challenge from Brendan Riley, the downtown alderman. So we'll see if outrage about property taxes triggers a change there. And then public safety, you know, the ongoing issue in the Chicago area. And it's it's it's it's a national issue. Chicago finished 2025 with 416 homicides. That's the lowest number since 1965. Now, at the same time, you know, the argument, and it's a very good argument, that any number over zero is entirely too high. But at the same time, when we talk about where things were in 2020 and 2021 or 2019, this represents substantial progress. And this is something that Mayor Brandon Johnson can absolutely run on. in 2027. What were some of the factors driving the drop last year and are they sustainable? So part of what's happening here is a national trend. Okay. The crime went up pretty much across the country 2020, 2021, do an extent 22. There was a pandemic. We were upset, sort of generally. Just people were mad. Just a lot of anti-social behavior. Yes, exactly. We all kind of forgot how to be around other people. And so a lot of what... What's fueling the decrease are sort of national factors. The mayor's office will say that a lot of it in Chicago specifically has to do with the department, the police department's partnership with other groups. Community violence intervention specialists, youth jobs. I hate the term youth. It's so broadcasty. Jobs for young people.

and other investments in organizations in neighborhoods that historically haven't had a lot of investment on the south and west side, which tend to see greater pockets of crime than in north side neighborhoods. And the part of the mayor's budget, which was largely left untouched by the alternate alders, by the way, preserves a lot of that funding. So the mayor believes clearly that that's the way to go. And the mayor claims that the city's drop in violent crime is in fact ahead of the national average, is more than the national average. Let's... Let's remember, too, that the reason crime in Chicago is a national story is because the president of the United States has made it one, because he frequently uses Chicago as a target for frustration over the city's immigrant sanctuary policies and other factors. A lot of people can speculate on that. I'm not going to. When the president of the United States puts your city on blast, on social media, every single act of violence takes on outsized importance or outsized, gets an outsized profile. To that point, in November, the burning of a passenger on the CTA blue line. Horrible story, women still trying to recover from critical burns. The gentleman who's now facing charges in that case had been in and out of courts for years and was only put on electronic monitoring because a judge refused the prosecutor's request to lock them up before this incident. Because... the president and others got a hold of that. It became a national story. It might have been otherwise, but, and not to say that it isn't terrible. And I remember we asked J.B. Pritzker about this. And he's like, look, every incident of violence is bad. And everyone deserves attention. And we're doing what we can to bring that number down. But when, uh, when the president picks that out for his own agenda. It takes on a whole other life. And we'll have to leave it there. Thanks, Jeff, for joining us on At Issue this week. If you want to hear the program again, you can do so at WBBM Newsradio.com, the Odyssey app and the IHeartRadio at-issue. Join us next week for another edition of At Issue. Until then, I'm Rob Hart. News Radio 105.9 WBBM. Hey, it's Jen Hatmaker. Here's what I've learned in midlife. Joy isn't the reward you earn after all the work is done. Joy is the work. That's what this new series on For the Love is all about. The sacred yes. It's choosing delight, rest, and pleasure on purpose. Because saying yes to yourself, that's the thing that finally lets you fill your table with everybody else. Come find your sacred yes with me. Follow and listen to For the Love wherever you get your podcasts.