New book chronicles Mayor Lori Lightfoot's rise and fall in Chicago politics: 'Raised hell and left'

Chicago Tribune reporter Gregory Pratt covered Mayor Lori Lightfoot throughout her short political career in Chicago. He’s chronicled Lightfoot’s rise and fall in a new book, "The City is Up for Grabs: How Chicago Mayor Lori Lightfoot Led and Lost a City in Crisis."

He talked with Fox 32 Chicago on the day of the book’s release.

This conversation has been lightly edited for clarity.

Interviewer: This book that you wrote starts with an interesting anecdote about the "mini mayor" - a young child here in Chicago who went viral for a Halloween costume, dressed in oversized clothing which matched Mayor Lightfoot's penchant for wearing clothes that were just a little bit too big for her. Tell me how that story began and ended and how it reflects Lightfoot's relationship with the city of Chicago.

Pratt: When Lightfoot was a young mayor in 2019, this child had dressed up like her, and it went viral. The mayor's office caught on, brought the kid in for some pizza, and they had a nice little meeting. It was very sweet and very appreciated. By the end of her term, when she had lost reelection, she was at her last City Council meeting. Mayor Lightfoot was not happy with the city and the city was not as happy with her. They just rejected her by 85% of the vote.

So, the mother had brought the child to come see her one last time, and the mayor didn't make time to take the flowers that they brought. And for me, what that symbolizes was just the way that she came in with all this hope and promise and inspiration. And she left sulking her way out of City Hall. And it was really unfortunate.

Interviewer: One criticism from the end of her tenure that I remember, which was very clarifying, was that she went into this mayorship thinking that she was going to be able to either reform the machine or work around it, and really, the machine in Chicago doesn't really change a whole lot. Is that a pretty accurate description of the difficulties that she ran into? Because she came in here as a reform candidate to a large degree.

Pratt: Sure. The reason Mayor Lightfoot won her election in the first place was because Ed Burke got pinched by the feds, and it became a referendum on who is he connected to and who is connected to the machine. As an outsider and as a former federal prosecutor, she was able to ride that wave. Once she took office, she abandoned some of those efforts.

That aldermanic prerogative in particular; partly because aldermen, including friends of hers and allies of hers, didn't want to give up their power for them. It's a great thing that they get to control zoning in their ward. They say, ‘We know our community, we know the city. We know our neighborhood. We are in the best position to do this,’ which there's some truth to. But the aldermen… there's almost 40 of them that have gone to prison in the last 40 years. And most of them found themselves in prison because of this. Mayor Lightfoot lost her focus on that issue and wasn't going to win that fight unless she expended a lot of resources. So, she eventually just dropped it.

Interviewer: And the book gives a couple of examples. Right at the beginning of her tenure, she was naked about saying one thing on the campaign trail and just flat-out denying that she was going to pursue any of these goals.

Pratt: Well, one of the interesting little moments is as I take the reader into her meeting with Mayor Emanuel after she had won the election, and she comes into City Hall to meet with Rahm to talk about transition stuff. And he's worked up about how he wants her to know that an elected school board is bad from his perspective, and she had campaigned on an elected school board. Mayor Emanuel talks to her about this, and at the end she says, 'Oh no, I'm not for that.' And Rahm and his people are flabbergasted because they don't trust her. They don't trust her because they had appointed her to the police board. She had told Mayor Emanuel she wasn't going to run for mayor. And then she ran for mayor.

They think her team are jerks, and she thinks that they're a bunch of jerks as well. They don't like each other. They don't trust each other. And for them they thought, that's a good thing that she's abandoning this crazy school board idea, but also you can't trust her. And they went around telling people that story. That was one of the biggest examples because that wasn't just like a campaign promise. She put it on her commercials. For her to switch, which was one of many ways that she campaigned on one thing and then did something else and on core issues as well.

Interviewer: When I was refamiliarizing myself with the 2019 race, I'd forgotten about how much of a landslide Lightfoot's win was. Do you think she would have seen that same level of success against any of the other candidates, like Mendoza and Daley, or was Preckwinkle a special sort of weak candidate?

Pratt: She would have beaten any of those candidates handily. Susana Mendoza at the time was connected to Burke. That was going to be a problem for her. Bill Daley just looked like he didn't want to be there. You know, Bill was a terrible candidate. I’m not saying he's a bad person, he’s just a terrible candidate who ran a terrible race. 

Interviewer: You have a brief anecdote about her rejecting the idea of working with Wilson on his reparations concept.

Pratt: She said she didn't want to deal with some Willie Wilson BS. Willie was working with some black aldermen on some sort of reparations ordinance. I think at the time Evanston had just done its own version of reparations, where they were giving housing assistance to Black families and people were kicking the idea around. She didn't want to do it because she thought it was a waste of time. She thought it was polarizing, and she didn't want to give energy to Willie, who by this point she didn't have much use for.

She was resistant to a lot of new ideas, even some things she ended up doing, like the universal basic income pilot that she put in for a while. She was fighting with Alderman Gil Villegas about that. He was pushing it. He's a moderate guy, but he's pushing this more progressive ordinance. And she said, "I'd rather have people work." Eventually, she came around on that one, too. But she was a centrist. She was middle of the road. She was very reluctant to push a lot of change, which is also consistent with being a corporate lawyer.

Interviewer: I always got the impression from her, especially as we were reacting to the summer of 2020, that she wanted to be a little bit more pro law-and-order, more so than a lot of other progressive mayors that would have been in her same position. It just felt like she was a little hamstrung by the left-leaning nature of City Council or the media that was watching her. Do you get that? Is that a fair assumption that in a different environment, she might have been a little bit more pro-law-and-order?

Pratt: No doubt about it. You know, she was a prosecutor. She's very pro-police. I mean, there's an anecdote where after there was the riot at the Columbus statue, she calls a conservative alderman, Matt O'Shea and says, "These animals attacked our police," which is pretty strong language. I was with her while she was campaigning on the far southwest side of Beverly and Mount Greenwood during the South Side Irish Parade in 2019. And she was in a room full of cops. Mancow was there wearing some ridiculous cow costume. It's a fun time. And she comes up to some cops and she says, "I'm going to be good to you. I'm going to take care of you." She's having these conversations.

At the same time, she's in other parts of the city talking about police accountability, talking about reforms, talking about racism. She never found a lane. So, one minute she's out there saying to people, "These animals attacked our police." The other minute, during the Floyd protests, if you recall, there was an officer who flipped off some protesters, and it got caught in a photo, and she gets asked about this at a news conference, and she very heatedly says that that person should be fired. These are very hard things to keep together. The middle finger, that's an overreaction. When Mayor Lightfoot talks about the difficulty of police reform, we'll talk about John Burge, the police torture commander – he kept his pension after going to prison.

So, these are complicated themes. But her inability to pick a lane, be clearer, and pick her fights better. You did not have to pick the fight with the officer. They flipped off some protesters. Okay.

Interviewer: You have an interesting anecdote about a conversation she had with Eddie Johnson about trust, which also informs this idea of not being able to pick a lane. What happened during that conversation about trust and how it reflected not just her hot and cold relationship with Johnson, but her relationship with police reform in general.

Pratt: One of the first things that she says in a meeting with Superintendent Eddie Johnson is: "Do you know who I trust in CPD?" He says, "Who?" She says, "You." And that's it. She would drop hints about sources she had in the department, and she's hearing certain things. And it really created a tense environment. Johnson said there's 10,000 people that work for this department. You got to be able to trust more than just one of them.

One of the first things she was adamant about was she didn't want to be protected by a Chicago police commander. She wanted to bring in Jim Smith from the U.S. Marshals, and that was seen as widely disrespectful. Superintendent Johnson tried to talk her out of it. She said that's my guy. He said okay, because he wanted to pick his battles. But that was a moment of her not being comfortable trusting the officers and that showed.

Interviewer: What do you think that she got right about police reform during her tenure here? It looked like her appointing Charlie Beck as the interim superintendent was positively productive. You made the mention that he took his name out of the running for the top job so that he had the space to make the tough changes. How would you grade her response to police reform during her four years as mayor?

Pratt: Police reform is one of the big, missed opportunities from her administration. It was a failure. She had been a very thoughtful critic of the police department. Perhaps she had been tougher on it as head of the Police Accountability Task Force and that was prudent. But maybe she wasn't tough enough where it matters. But she was a very thoughtful critic of issues in the department. Let’s be clear about the fact that the Chicago Police Department has a lot of issues, and it has a lot of brave men and women working every single day. But the department also has a lot of problems in terms of training, in terms of safety standards for officers and for civilians and even for suspects. As a city, we lag behind New York and Los Angeles.

So, Johnson has to go. She makes a change. She was going to fire him no matter what. Then, he has this incident with drinking at Ceres and she brings in Charlie Beck. She didn't bring in Charlie because they were necessarily aligned on vision. He’s a legend in the policing board, and he does a lot of very smart things. He takes away what's called merit promotions, which were perceived as just giving a promotion to your buddy, whether that's fair or not. And he made other changes that more or less got thrown out by his successor, David Brown. That's another example where she wasn't picking a lane, she was just reacting. So, they said, 'Hey, we got this guy. He's great. Can we bring him in?' And she said, sure. Charlie Beck is a very impressive guy. But they ended up not following through with a lot of his plans, and it was a real mess.

Interviewer: We haven't talked a whole lot about Covid yet, and we could spend the entire amount of time that we've been here already talking about her response to Covid. How would you rank her overall response to the pandemic? And do you think that was more of a deciding factor in her reelection loss than the crime and police accountability?

Pratt: Covid was, in a lot of ways, one of the things she had going for her in Chicago. What her campaign would say is that she polled well on Covid. Gov. Pritzker got reelected on Covid. Which was funny because she was not for a lot of the stuff that they did with the shutdowns. She ended up wearing the jacket for them because she was the mayor, but she didn't want to close schools. She didn't want to close businesses. She was concerned that they were overreacting. She and her team would refer to one of Governor Pritzker's outside doctors as "Doctor Doom."

The only big shutdown she did was the lakefront. And that was, in retrospect, a mistake. They had kept it closed for much longer than expected.

She wanted to run on Covid, but they told her that she was being hit hard on crime. We need to defend you on crime. We need to have you out there saying that you have a plan. The problem with that was she hadn't taken steps to make changes. I personally think that if she had fired the police superintendent, she probably would have got reelected because she would have had something to talk about.

Interviewer: One of the things I noticed going through your book is that I didn't see a lot of repeated mentions of names in terms of confidants, people that she could rely on as advisors throughout her entire career. You don't even really talk about her wife very much, at least in the first half of the book. Was she a woman alone in a lot of respects in her career? And do you think that informed her combative defensive management style?

Pratt: It's remarkable how she had some falling out with people that she was close to, that her first chief of staff was chief of staff for two years. They don't talk anymore. She had a falling out with her lawyer, Mark Flessner, who had been a close ally, and they stopped talking. She had a falling out with the deputy mayor for public safety, Susan Lee. She had a falling out. I could go on and on – the mayor couldn't separate personal from work and get good advice from people working with her. She really struggled with that idea, even with some of her aldermanic allies. She would not always make the time to talk to her fellow members of the City Council.

I think that's an astute observation - she didn't have a lot of confidence because she was blowing through people. She liked my work when I was tough on Tony Preckwinkle because I used to cover the county. I wasn't tough on Toni Preckwinkle because I don't like Toni Preckwinkle, and I want to help someone else. That's not what journalism is. I was tough on talking about Lori because I’m tough on whoever I cover. If you became an elected official that I'm covering, I'm going to be tough on you. It just is what it is. And when I applied the same standards to Mayor Lightfoot, she took it personal, which, of course, it never was. I mean, I actually on a personal level, I like Lori Lightfoot. She's funny. She’s very smart. She just lacks some political skills.

Interviewer: Did your access to her change over her tenure? She was a candidate who did not rely on identity a whole lot during her campaign. Didn't really reference it a whole lot. But that whole moment on the back half of her tenure – the interviews where she was only going to take questions from Black journalists. What was your reaction to her becoming a little more combative with the press, especially with that racialized edict?

Pratt: She famously sent out an email to her staff in 2020. She was mad at me, and she said, "I don't want you guys helping him with anything. If he's got a question, you answer it as briefly as possible. But I don't want you proactively helping him with anything." She got angry about some stories and decided to banish me, and she ends up having an embarrassment over Anjanette young, where she attacked me at a press conference. And she was wrong. She was wrong on the facts, and she was wrong on the way she handled it. She apologized publicly and privately.

We started talking a little bit better, you know, and then when she did the Black and brown journalist edict of like, "I will not talk to white journalists for this day. You know, I want to draw attention to the lack of diversity." I canceled my interview with her because I'm a Latino, and I canceled my interview. And she was mad about that because she felt that I had shown her up. It was a mistake, you know, it was alienating to a lot of reporters. It was very controversial with a lot of people. Mayors and governors need a filter of somebody to say, yeah, you know, the idea of that is interesting, but it doesn't work. And don't do it. It's just it's offensive, it's bad. She didn't always have that. On that one there were people egging her on, which was incredible because it was a PR disaster from a mile away.

She ended up even doing an interview with The Tribe, which is a Black Chicago website where they asked her where she goes to eat on the South and West Side, and she couldn't name a restaurant.

Interviewer: Do you think that lacking a famous political last name like Daley or not coming from certain expected elite circles like Rahm; do you think as a one-term mayor, Lightfoot runs the risk of not really having much of a legacy that as we just continue electing more mayors, she drifts into obscurity. Or do you think there's enough there because she was such a national lightning rod for criticism that we'll be talking about her many mayors later?

Pratt: We will always remember Lori Lightfoot for the good and the bad and for some of it, there were positive things there. She was a fighter for Chicago. She would advocate for the city. She cared about equity. That was laudable, that that's a good thing. This is a city with a lot of segregation and a lot of problems. She got dealt a tough hand and did the very best she could to be strong and reassuring to the city. She wasn't perfect, obviously. You can't sugarcoat the fact that 85% of the voters rejected her, but we will always remember because when you and I are old and dying, we're going to remember Covid, and we're going to remember the riots, and we're going to remember the time Mayor Lightfoot said this crazy thing about the Italians. It’s just the way that she led, and we will remember some of that positivity.

I mean, sometimes people today, right now, they're like, oh, Brandon Johnson is terrible. There were a lot of people who were closer to her ideology but didn't realize it. Or she couldn’t convey that. Now they miss her. It’s complex, but she is a personality fitting very much with every other great Chicago mayor like Jane Byrne or Harold Washington. She didn't have the success of Rahm Emanuel. She didn't have the success that some of them did. But she is very much a part of Chicago. And this iconic person that came in, raised hell and left. People didn't think she was doing a good job at the time. So, they switched directions. People will have positive memories. They'll also remember the bad stuff, but they'll, they will have positive memories.

Interviewer: You can say pass to this last question because it involves a little bit of mind reading, but how do you think as an outside observer, she is perceiving the Johnson administration, especially considering that his polling numbers now match where she was towards the end of her mayorship?

Pratt: Well, you don't have to guess because she has made a couple comments in a couple settings. People come up to her all the time and say, we miss you. So, you know, she enjoys that schadenfreude. Everyone who has been in a leadership position in Chicago cares about the city, Rahm cares about the city. Daley probably is still watching and thinking about things that are happening.

I'm sure that she's concerned because she's opposed to a lot of the things that Mayor Johnson does. But I know that Lori is just like all those other people who would like the city to succeed. And that means that Mayor Johnson succeeds at the same time. She absolutely makes a comment of "be careful what you wish for, because you didn't want me."

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