Editor’s Note: On April 5, 2024, The Cliff Dwellers its latest presentation of “Journalism: Today’s Story.” In the event, Laura Washington, Chicago Tribune contributing columnist and political commentator for ABC-7 interviewed Chicago Tribune reporter Gregory Royal Pratt about his new book, The City Is Up for Grabs: How Chicago Mayor Lori Lightfoot Led and Lost a City in Crisis.

Pratt offers the first comprehensive behind-the-scenes look at the tumultuous single term of Mayor Lightfoot and the chaos that roiled the city and City Hall as she fought to live up to her promises to change the city’s culture of corruption and villainy, reform its long-troubled police department, and make Chicago the safest big city in America.

A groundbreaking figure—the first Black, gay woman to be elected mayor of a major city and only the second female mayor of Chicago—Lori Lightfoot knew the city was at a critical turning point when she took office in 2019. But the once-in-a-lifetime challenges she ended up facing were beyond anything she or anyone else saw coming.

On February 28, 2023, Brandon Johnson and Paul Vallas advanced to an April runoff election to be Chicago’s mayor. Neither had received more than 50 percent of the vote. They were the top-two vote-getters among the field of nine candidates, with Vallas receiving 33.8 percent and Johnson receiving 20.3 percent. Mayor Lori Lightfoot, first elected in 2019, finished third with 17.1 percent of the vote.

In her interview with Gregory Pratt, Laura Washington probes the underlying reasons Mayor Lightfoot was the first Chicago Mayor to be defeated for a second term since Mayor Jane Bryne was defeated in 1983 when Harold Washington was elected Chicago’s first Black mayor.

The interview discusses the following:

• Pratt’s reasons for writing the book and his experience covering Lightfoot’s term.
• Lightfoot’s challenges as mayor, including her relationship with the Chicago Teachers Union and her handling of the COVID-19 pandemic.
• Pratt’s attempt to interview Lightfoot for the book and her refusal.
• Lightfoot’s decision to keep David Brown as police superintendent despite criticism.

Here are some key takeaways:

• Pratt believes Lightfoot never adapted to the role of mayor and lacked a clear vision for many institutions.
• Lightfoot’s inability to build relationships and her unwillingness to admit mistakes were recurring problems.
• The book offers a critical perspective on Lightfoot’s mayoral tenure.

Transcript of Laura Washington’s Interview of Gregory Platt

    Eve Moran for The Cliff Dwellers (EM): Thank you. Welcome to The Cliff Dwellers. We’re a warm community of artists and art lovers. A community that values good and rich conversation. So, during the noon hour, we frequently gather at the Members’ Table. This specially designated table at the club, we eat lunch, tell stories, exchange ideas on a wide range of topics. Our recently established journalist series aims to bring about a similar experience during the evenings. We gather to hear stories. Very timely, interesting and important stories.

The differences, they’ll come to us through a gifted moderator engaging with today’s news maker. In honor of Hamlin Garland, the novelist and founder of our club, who was very shortly going to be inducted into the Chicago Literary Hall of Fame. John McDermott, a past club president and founder of the Chicago Reporter, and our distinguished late member and Pulitzer Prize winner, Roger Ebert, a brilliant journalist and critic on cinema.

These programs celebrate the art of journalism under the banner of today’s story. For today’s story, we’re thrilled to spotlight Laura Washington, a maker of deep and compelling conversation. Washington is a Chicago Tribune contributing columnist and political analyst for ABC 7 Chicago. Of course, we all know Laura. She brings more than two decades of experience as a multimedia journalist who covers local and national politics, race and social justice. All important things.

Here tonight, Washington will engage in conversation with Gregory Royal Pratt. He is an investigative reporter for the Chicago Tribune and the author of an interesting new book titled, and I quote, “The City is Up for Grabs: How Chicago Mayor Lori Lightfoot Led and Lost a City in Crisis.” Pratt’s book, for those of you who haven’t gotten it yet, will still be available for purchase after the program, and I’m sure Greg will graciously autograph our copies. So there’s not a minute to waste. Please help me to warmly welcome Laura Washington and Gregory Pratt.

Laura Washington (LW): Thank you, Eve. Thanks so much. It’s always nice to be back at The Cliff Dwellers again. Eve, you mentioned that we have timely conversations here, and I can’t imagine anything that’s more timely than this one because Greg, your book is just hot off the presses, what, two days ago? That’s right. yes, so we’re among the first audiences to not only be able to get a copy of it, but to hear it from the guy who did it, and I’m really thrilled to welcome my colleague, area’s team colleague here tonight, and I’m just going to introduce Greg briefly, and then we’re going to get right into it. Gregory Royal Pratt is the Chicago Tribune reporter who covered every day of Mayor Lori Lightfoot’s term, and he was deeply sourced in City Hall, as well as in offices in other local, state, and national politics that shaped the mayor’s administration. Greg grew up in Chicago’s Little Village neighborhood, and he’s won several awards for his political reporting, national awards. He’s also a regular commentator on local and national media, including CNN and NPR. His investigative reporting has spurred reforms in local government and helped exonerate two men. Welcome.

GP: Thank you all for having me. I’m really excited to be here with you tonight and repeat some of Lori Lightfoot’s bad words. yes, we talked about this a little bit over dinner about, how do you all feel about bad words?

LW: Go for it. Not too queasy about it, because if you know Lori Lightfoot and he knows her better than just about anybody, there’s going to be some bad words shared if you want to talk about her tenure. So let’s go for it. I just wanted to say that this book is just so tremendous. I mean, there’s, I can’t come up with one word for it, but I’ll come up with two words. Juicy, very juicy, and educational. I can’t tell you, I learned a lot from this book, and I thought I knew a lot about Lori Lightfoot. I followed her career even before she became a known player in Chicago.

Actually, I’m pretty good friends with her, one of her ex-girlfriends, and knew a lot about her from that. But I knew nothing like what I read in Greg’s book. I learned so much from that book, and so thank you for doing it. Thank you. It’s a real treasure and a real gift to the city. So I want to just kick it off by asking you to just, if you would just summarize briefly what your main message and conclusion is from the book.

GP: So from a big picture perspective for the City of Chicago, the city is up for grabs. It’s about a city that is in a state of flux and transition, which it was at the time that she was running in 2018 when Rahm Emanuel steps down and Eric and Ed Burke is castrated by the federal government. And those are two extremely powerful people who had shaped the city for decades, who are no longer in position. And so you have a power vacuum there that she ends up coming to fill. And when she ends up losing to a new mayor in the new paradigm with enormous influence from factions that had not had power, the city still remains up for grabs.

The title is also a reference to a text message she sent during the riots of 2020, where she was complaining to an older person that the city is up for grabs. A city should not be up for grabs. And so it is a really remarkable period of time. As far as big picture leadership, I like to talk about one of the issues for Mayor Lightfoot is that she never adapted. And leadership, whether it’s at a club, a museum, a mayor’s office, a police department is about adaptation. And that’s not about pandering. That’s not about changing your style.

But Mayor Lightfoot was a prosecutor, and she saw everything as a prosecutor. And you have to adapt that because every problem is not a prosecutor problem. You might be dealing with somebody that you don’t like or you have to work with, and it doesn’t mean they’re a criminal that you’re going to put in jail. You mentioned that she herself said that the city was up for grabs, and this was in the middle of a major crisis. And she’s the mayor. What does that say about her that she would express that opinion?

I think, and you saw this with Mayor Lightfoot and you see this with Brandon Johnson, that you have two mayors who were not executives, who did not have that executive experience at that time. So they were learning and growing on that job. One thing they have in common is that they would both get very mad to have me describe them as learning and growing on the job because they think of themselves as we’re big boy executives from day one. And that’s not the case. And there’s nothing wrong with that. They didn’t have executive experience when they became mayor, and they have to learn that. And for Mayor Lightfoot, she never adapted that style.

For her, it was a white knuckle bluster situation where one of the reasons I like the pose in the cover, which is from the day she fired the police superintendent, Eddie Johnson, and she’s very not happy in the photo. And she is holding onto the podium for dear life. And that’s really her white knuckling her way through her four years in office. And she tried to bluster her way through, but never had the control of really any of the institutions that she had the control of. So I do think that Up For Grabs epitomizes that too.

LW: Now, you say she didn’t have control of the institutions. Well, some of the institutions in the city were then and still are in trouble. And so it would have been a challenge for any new mayor. How much did that have to do with her inability to be successful? That, you know, that you, I mean, she came in as a reform mayor and we have a lot of corruption in city hall. We still do, you know, the pandemic, you know, tore everything apart in the city. So how much did that have to do with it?

GP: Let’s take the schools as a good example of this, where, you know, the Chicago public school system has been losing students for a long time, had been losing students for years. So that’s, that’s, of course, an unhealthy institution from that perspective. You have a ascendant teacher’s union that had gone to war with Rahm Emanuel and in some ways lost in 2012, when they go on strike in 2012, Rahm wants a longer school day, Rahm wants a longer school year. They get some stuff in their contract, but they don’t reverse that. The school, now we, Rahm used to brag about how long his school year was at the end of his term and is now compared to what it used to be. It used to be pretty bad.

And Mayor Lightfoot did not have a clear vision for the schools. She had, she campaigned on an elected school board and that was as close to a clear vision. And she didn’t actually believe in an elected school board. She abandoned the idea almost immediately. So she didn’t have a clear vision for the schools. And that meant that the Chicago teacher’s union ate her lunch. Because if you’re competing with someone, whether it’s in business or in government or in politics or in sports or whatever it may be, if you don’t have a clear idea and your opponent does, you know, you’re already lost, right? You’re starting at a disadvantage.

And you know, Mayor Lightfoot’s a really intelligent person, but she doesn’t have clear ideas about that issue. If Paul Vallas were here, he would talk about charter schools and school choice. If Brandon Johnson were here, he would talk about fully funding different schools and getting rid of the per pupil formula. He would talk about the formula. He has a theory of that. Mayor Lightfoot did not have a theory of that beyond happy schools, happy students, which is great. Everybody would like happy schools and happy students, but how do you get there? And that’s where the teacher’s union, which disagreed with her on all these issues, didn’t like her politically, didn’t agree with her on the issues, more or less ate her lunch.

LW: Well, what’s the difference between her and Rahm Emanuel? They hated his guts as well.

GP: On the substance of schools, probably not a lot, which is part of why they disliked her so much, is because Mayor Lightfoot ran on a platform of I’m not like Rahm Emanuel and governed similarly to Rahm Emanuel, certainly when it came to the schools. And that was, except that, you know, I mean Rahm, I remember, and I used to poke Rahm Emanuel about this when I would see him because every time you saw him, you’d say, “Good morning.” He’d be like, “Hey, good morning. I had some bacon today and I’m thinking about universal pre-K.” And he would just bring up universal pre-K in every single conversation he had, because that was his, and that’s a good thing, by the way, universal pre-K, but he had a talking point that he wanted to bring up every single day.     Mayor Lightfoot didn’t have that. And so that was one of the differences. She didn’t have an organizing counter offensive to the CTU. When they were negotiating, she gave them a big raise on the front end before they went on strike. They said, “Thank you. We’re still going on strike.” And she didn’t have a clear argument to the contrary of, “Okay, well, you know, if we’re going to do that, then we’re going to need an extra hour on the school day.” And I’m making this up, put an extra hour on the school day for pre-K, for extra after school activity, whatever it may be.

She just didn’t have that, whereas Ram did. Does she care? Oh, yes. She cares very deeply about schools and police and all of these institutions. She just didn’t have a clear vision for most of them. And that was perhaps because of her lack of experience and never having been in a governing position before. And you mentioned the elected school board issue, which you have an interesting anecdote about that, about how much she really was committed to the elected school board issue. So just to back up a tiny bit. So when every school district in Illinois, except for one, has an elected school board, and the one is Chicago. And that’s because Mayor Daley convinced the state legislature that it’s a bad idea and that the mayor should control it. There’s arguments for and against it. And mayor, in the late 2010s, it became a popular, after Rahm Emanuel closes all the schools on the south and west sides, and after there’s all these controversies, there becomes an argument that they wouldn’t do these unpopular things if the board was elected.

So let’s get an elected school board, let’s get some democracy, let’s get some more representation. And it became a very popular idea, it became so popular that most of the candidates in 2019, and there was 14 of them, so it was a freak show, most of the candidates were campaigning in favor of an elected school board, including Lori Lightfoot, who didn’t want to have a difference with Tony Preckwinkle on that issue.

So when Lori wins on April 2, I think it is, she has a meeting on April 3 with Rahm Emanuel to talk about transition for him to show her where the bathrooms are and to discuss where the bodies are buried and all of these issues. And he has really worked up because he understands from his perspective that the teachers union is a threat. And he wants to explain to her that an elected school board is bad. So he goes on a little spiel to her about we don’t need more politics in schools. And at the end of a spiel, she looks at him and says, oh, I don’t want that. And tells the state legislature don’t pass an elected school board, which at the time the state senate president was willing to do, John Cullerton before he retired. And that was it. And for the Rahm people, they were like, they were happy with the outcome. But they’re like, see, we told you, you can’t trust her.

So like a day after she gets elected, she’s like backing off on a key campaign platform. Immediately. And incidentally, the, and one of the chapters in the book is called Adults in the Room. And it’s about when she loses the elected school board and the state legislature votes to take it away from the mayor of Chicago, they vote to take it away from her. And her aides, her advisors, wanted her to go out and acknowledge that she had changed her mind. And just go out there and argue that a hybrid board is better because the mayor needs to retain some control and too much democracy would be bad, which is there is an there is an articulatable argument to be made about that.

But she did not want to acknowledge that she had changed her mind. So they couldn’t get her to go out and speak on this. She was paralyzed by indecision and the CTU ate her lunch. And that’s how she lost that fight because she wouldn’t acknowledge the change. So she couldn’t fight them on their terms. It was a really remarkable moment. And it’s one of my favorite chapters in the book because it is a substantive issue.

LW: Now, as I said, you you’ve covered life from the very beginning. When and how did you decide to do this book? And how did you how did you go about I mean, you were based on what I can see, you were reporting this book while you were reporting that you didn’t wake up one morning and decide, oh, I’m gonna write a book about Lori Lightfoot. Tell us about that.

GP: So, you know, I I’ve thought about Lori Lightfoot for the last four years more than I’ve thought about my girlfriend, my mother, my cat, my dogs, my friends, my enemies. You know, it is it is unhealthy. You know, I am a very sick person. And and I take my job very seriously. My job for the Tribune was to cover City Hall and we have stiff competition. So I wanted to know the good, the bad, the ugly. I wanted to understand why is this happening? Why is this not happening? What are the problems here? And so I always threw myself into it of being thorough.

And I knew in 2019, when I became the number one guy on our team, that I wanted to write a book about Mayor Lightfoot, who was our first first black female gay mayor of Chicago. And that is remarkable in and of itself. I think that every four years of a Chicago mayor probably could merit a book if you wanted to do that. And I was determined to make that interesting. But then, of course, in the year 2020, that tranquil year that nobody remembers, the gates of hell opened up.

And we had all of these remarkable things that changed the trajectory of the City of Chicago, that changed the way the city functions in a lot of ways, and that changed the way we all live our lives outside of politics, outside of that. So I thought, yes, I’m definitely going to write a book about this.

LW: And so what was your, what was your, I mean, you didn’t, you did a lot of reporting, obviously day to day reporting, but then at some point when you decided to really plunge into the book, how did, how did you proceed on that? Did you have to go back and do a lot of other interviews? How did you structure your approach to the book?

GP: I went back and I begged people, please talk to me. And for the most part, they were pretty receptive because I’m a very thorough reporter. I’m a very, and I don’t, I don’t BS people. If it’s a negative story, I will tell you, hey, look, there’s this thing, I’m trying to understand it, you know, surely you can’t be this stupid. Surely you can’t, why did you do this wrong? And people will be like, surely I am not this stupid. Let me explain it to you. I think that we have a, you know, so there was a lot of re-reporting, you know,

I didn’t rely on my old Tribune stuff. I went back and I talked to people, but over the course of four years, I built a lot of relationships and a lot of knowledge and a lot of a lot of things like that. And unfortunately for me, I have a pretty good memory for, for things. So I will, I mean, it’s fortunate and it’s unfortunate, but you know, if somebody told me, you know, something three years ago and, and it’s stuck and it’s like, well, you know, part of it is, is storytelling and you, you know, this from your work in politics and in media, you know, that, you know, there, there are, there are only a certain number of things that really matter, right?

There’s, there’s your day and you go through your day and much of it is, doesn’t matter in 20 years, but there’s things that will matter. There are things you will remember. And when, when I, when somebody said, well, you know, a little, a little story, I mean, there’s an older woman, Rosanna Rodriguez Sanchez, who is a socialist and she goes to meet with Lori Lightfoot for the first time. And her closest friend and ally is a socialist, all the men named Carlos Ramirez Rosa, who Lori Lightfoot hates. And Lori sits down with Rosanna and she says, I have some, may I give you some advice? And Rosanna says, sure. And Lori says, people say that you are a puppet of Carlos Ramirez Rosa and you do whatever he tells you to do. I would like to help you develop your voice as a woman of color in politics. And Rosanna was not impressed by that approach because Rosanna said, she said, well, for, from Rosanna’s perspective, she said, Oh, you are his puppet and I want you to be my puppet, which is really what Lori Lightfoot said to her in actual meaning.

And so Rosanna told me about that, like four years ago. And I’m like, yes, that’s going in the book. Because that’s a, that’s one of those things where, where you just hurt yourself, right? You’re for no reason. And so the building of the book is just remembering things that matter and, and building around them and doing the narrative and understanding where the pressure points are.

LW: And of course, since your subject was Lori Lightfoot, it probably would have been nice to be able to talk to Lori Lightfoot about the book. How’d that work out?

GP: You know, not well. There, first of all, there was a famous email she sent her staff in 2020. She was mad at me because my reporting caused her to fire her head of security. And, and she was really pissed off about that. And I tell the story in the book. And she had to fire her head of security. She wasn’t happy about my reporting about that. And so we had, and then she sent out an email, everybody saying, you will not talk to Greg Pratt unless you absolutely have to. And you will not talk to him except for as brief as possible. And, you know, they’re all sitting there. They’re like, wow. And he’s the main reporter for the biggest paper in town and you want us to not share your story with him. We’re just hurting ourselves. But she went along with that.

We made peace for a little while after that. And then she got mad at me again, wouldn’t talk to me. And then by the end, she wouldn’t talk to the Sun times or WTTW or NBC five or channel two. I think I could probably continue.

The thing about it though, is that she really liked me for about three years and we would talk a lot. And that’s in the book as well. And she liked me because I was tough on Tony Preckwinkle, which I used to cover Tony Preckwinkle and the County board. And I was tough on Tony Preckwinkle because my job is to be tough on the people I cover, whoever it is. If Laura became mayor tomorrow, you know, I, we might, we might do well for ourselves. And I like Laura a lot. Laura has been a mentor to me in some ways. And, and, you know, even when she was a competitor at the Sun Times, she was always very good to me, but I would annoy the hell out of you if you became mayor.

And so it was never personal with Preckwinkle, just like it wasn’t personal with Lori, but she took it that way. And so I, I knew how she thought, cause I talked to her a lot for three years. And then I would get a lot of her text messages and her emails through public records law, which show a lot of how and what she was doing and thinking in her own words, in real time.

LW: So, but you did request an interview with her and what, what happened with that?

GP: You know, they danced around it and, and then they said no. And then, you know, I wanted to make sure that, that I could, I could, if she walked in that door right now and said, you didn’t give me a chance to explain this or this or this, and you’re an asshole, which is what she would say. I can say, here is, here is the email I sent you. It’s like a thousand-word email with, I know you don’t want to talk to me, but here are a variety of, of different anecdotes and issues that I would like to talk to you about that I would like to give you notice for. So, you know, I didn’t blindside her because that’s not, that’s not fair.

You know, if I was writing a book about you and you know, you’re, and you don’t want to talk to me, I’m still going to try to find a way to get you something of like, you know, do you remember when you killed that guy and, and what really happened when you killed that guy? And you’ll say, yes, I don’t talk about Fred. So what is the one, I mean, there you had, I saw the list of questions that you, that you sent her or sent her people that she refused to answer.

LW: What’s the one question you would have, you were dying to ask her?

GP: I would really like to talk to her about the police superintendent, David Brown, who she brought in from the city of Dallas. And there’s a story in, and, you know, basically nobody thinks that Superintendent Brown did a good job. There are some people who think he was a nice enough guy, but nobody thinks that he did a great job. And David was an interesting choice. It could have worked out. It didn’t. But he, in his first like three weeks here, Mayor Lightfoot criticized him in the media. And he was very upset about this.

And he, the Cook County States Attorney, Kim Fox, called him to check on him after she criticized him in the media. And he said, and this is in the book, I’ve never been talked to like that in my life. If she does that again, I’m going back to Dallas. She needs me more than I need her, which by the way is true in that situation, because you can’t lose your police superintendent two months in. And she kept Brown for the next three years. And he wasn’t fitting in.

He was, you know, Mayor Lightfoot lost her chief of staff, her deputy mayor for public safety and other key advisors and a bunch of relationships over him. It’s like, and it’s kind of like, you know, have any, has anybody here ever had a friend with a bad boyfriend or a bad girlfriend? And you tell him, hey, you steal your money. And they say, well, shame on you. I’m happy. And who do they get mad at? They get mad at you. They don’t get mad at the significant other. And that was Lori Lightfoot with David Brown.

And I would really like to, I would love to do a heart to heart with her about how that relationship unfolded and how she saw it. And, you know, she would, it was a really, it was, it was a mistake. She would probably still be mayor if she had got rid of David Brown. And you would, you would ask her this, but do you have any theories as to why she didn’t? She couldn’t admit she made a mistake. Oh, and that was, that was a trend or threat that, that followed her throughout her, her mayoral career. yes. And you know, there’s, there’s a, in the world of logic, they call it the sunk cost fallacy, right? And that is Mayor Lightfoot to a tee of, I don’t want to admit I made a mistake.

And of course, there are ways to fire someone without acknowledging you made a mistake. You know, he can have a family matter. Spending more time with the family. Spending more time with the family. What are the other euphemisms that they use? Taking a break. I want to go, I want to take a sabbatical. I want to, you know, refresh my life, whatever. Family works. Now, one of the things that was, was, and this is not Lori Lightfoot per se, but maybe relates is that many people felt that he really was never really committed to Chicago. He was never really here in the way that he needed to be as, as a police leader. I think that’s fair.

He was, he was not here as much as he could have been. I think that somebody I talked to recently said that they thought that the, that Mayor Lightfoot criticizing him in public the way she did sort of turned it into, this is a passion, that this is a job. And, you know, there’s, I don’t, you know, some, some people in this room have been bosses and some people have been employees and some people have been both probably over the course of a lifetime. When you have an employee, when you have somebody that reports you and that you work with, not everybody is motivated the same way. If my boss calls me and says, where the f is the story, I’ll say f off. It’s coming in five minutes and we will laugh, you know, and it’s fine.

And some people, if you call and you say, where the f is the story, they’re going to shut down, right? They’re, they’re going to be like, oh, you know. And so you have to know who you’re dealing with. And I think that, I do think that Brown did not like it. Obviously he, he confided in the state’s attorney about, about how he didn’t like it. And I think that, that diminished his passion. But even if it didn’t, and that theory that people have shared is wrong, he wasn’t here that often. He was not here as much as he could have been. He was not visible.

A very short story I’ll tell is I was, in Christmas time of 2017, I got sent to the house of a woman on the South side, black woman. Her house is raided by police. They got the wrong house because it had the wrong, the number wasn’t clear. So they, they, they meant to be next door. This happens a lot. And, and they go in and she’s upset because she’s about to watch a movie and her kids are there. And, and I’m talking to her and she’s very pissed off at the city of Chicago. And the police superintendent, Eddie Johnson calls her cell phone number and she doesn’t know who’s calling. She looks at her phone, puts it down. When the voicemail comes on, she puts it on speaker. Hello, this is police superintendent Eddie Johnson. I’m very sorry for what happened. Will you give me a call back? She looks at it. She says, fuck him and puts it away. But that’s not about, of course she’s upset in that moment, right? But Eddie made the effort and superintendent Brown didn’t make that kind of effort very often.

LW: So let’s back up a little bit and go back to the beginning and how, how she came to office. And you mentioned that she, you know, kind of backed off on the elected school board and a lot of progressives, a lot of people who were for reform in the city were very disappointed with a lot of the things she did. Was she, she campaigned as a progressive. She campaigned as a reformer. Was she really either one of those things fundamentally?

GP: The short answer is no, but so no, she’s, she would tell you that if she was in this room and she was being honest and had a brandy, which is one of the drinks she likes, or actually she’s more of a whiskey girl. If she was here and she was having a glass of whiskey or scotch, she’s more of a scotch girl. I apologize. The, I regret the error. She would say that she is a progressive that has been left behind by the crazy communists that, that now are Chicago’s progressives. You know, she complains a lot about the teacher’s union and the super left wing.

She’s somewhat progressive, you know, especially on workers issues. I think that she relates to that on a personal level. Her, her parents were hardworking, working people, you know, working hard jobs. She worked in a factory packing a Tony Caccatore Creole sauce, which you can buy at Jewel. It’s good stuff. And so I think she has a heart for those issues. But you got to remember, she was a corporate lawyer and what you do as a corporate lawyer is cover your butt. The job of a corporate lawyer is not to overturn the system. It is to protect institutions and clients. I mean, that is, that is fundamentally what a lot of corporate law does for big law firms.

And I’m not even saying that as necessarily a bad thing. It’s just, it is what it is. It’s what Mayor Brown, where she was, does a lot of. And so she’s not a overturn the system type of person. She is a let’s tinker around the edges. Things are, things are, a lot of things are good. Don’t throw out the baby with the bathwater. And that’s where she is.

So she is a reformer, but she’s not a total reformer. And she’s somewhat progressive, but she’s not really particularly progressive on a lot of issues around here. I used to enjoy watching her dance around the issue of criminal justice, because, you know, she would come out and she would go to the north side and talk about how much Kim Fox sucks. And then she would go to the south side and talk about how great Kim Fox is. And if you think Kim Fox sucks, great. That you’re entitled to that view. That’s a legitimate enough view. If you think Kim Fox is great, that’s a legitimate view.

But we live in a world of Twitter and YouTube and social media. People are going to find out what you’re saying. It’s not like the old sitcom thing where the guy’s going on a date with like two different girls at the restaurant and he’s going back and forth between tables. Surely you’ve all seen these scenarios. A few people have, apparently.

So, it also is pivotal in Mrs. Doubtfire, if you remember Mrs. Doubtfire. And he has to strip down from Mrs. Doubtfire to, I forget what his name is in the movie, but it is spectacular. And it’s on Broadway now, I think. Check it out. So, she won because she said she was going to clean up City Hall. She was going to end corruption. On the day of her inauguration, she stood up during her speech and turned around and pointed at the City Council and said, you know, and said, you’re going to get in line.

LW: What impact at that moment have on her relationship with the City Council?

GP: No, hang on, hang on, hang on. They were all very happy about it. They said, you know what, she’s right. We are all crooks and imbeciles. It was an astonishing moment because, and one of the things they resented, and there’s a chapter called Trained Seals in the book, one of the things they resented is she turned and made them clap for the line. And they didn’t quite know what was going on, so they get up and they clap.

So, she sort of provoked this Pavlovian response out of them to applaud her as she’s insulting them. And so, it was just, it was entirely unnecessary, and it’s one of the things that, when I talk about adaptation, you’re no longer on the campaign trail.

And yes, there are 38 aldermen have gone to prison since 1970 in the city of Chicago. That’s almost enough to fill a City Council. That is enough to override a mayoral veto. That is a substantial number of people that have gone to prison, and a lot of them have gone to prison because they do have more power, authority, and leeway culturally and legally than they probably should. That doesn’t mean that the mayor should have turned around on her first day and said, you’re all crooks, because of course, obviously, it’s common sense.

And so, she got off to the wrong foot on day one. And her high school president campaign was get on the right foot with right foot, and this was get on the wrong foot with right foot. And she never recovered from that? No, it was a very damaging moment, because people would remember that, and sometimes, months and even years later, alderman would be ranting about some contemporary issue and be like, and by the way, I haven’t forgotten.

LW: So, I want to talk more about her relationships or the challenges she had with relationships, but in her defense, her supporters would say that she had got dealt a very, very tough hand, you know, the pandemic, the civil unrest. That’s what she had to deal with was monumental and would have been very difficult for any mayor, and she should have been given some slack and that maybe she didn’t accomplish everything that she said she would and she wanted to. What’s your response to that?

GP: That’s absolutely true, or at least true enough. It’s absolutely true that she got dealt a tough hand. It’s absolutely true that she got dealt a tough hand, and it’s absolutely true, and people don’t believe me sometimes when I say this, that I admire a lot about Mayor Lightfoot. I admire that she’s a tough lady, she’s a smart lady. If she walked into this room, she’d be one of the smartest people in this room. She has a lot of brain power. She lacks political skill. Doesn’t mean that she isn’t a brilliant lady. I would hire her to be my lawyer, but the hand she got dealt was really brutal, but she accentuated it with a lot of self-imposed, self-inflicted wounds.

So when Rahm Emanuel, who is as devious and cynical as he is brilliant, would say that COVID was a great thing because it’s an opportunity. I’m being a little playful with that, but Rahm has a line about never waste a crisis. A crisis. COVID was an opportunity to do a lot of transformative work, and actually Mayor Lightfoot was able to increase some funding for some mental health type of stuff, for homelessness efforts.

There was a lot of good things that came out of the pandemic. In some ways, the pandemic is an easier problem to solve than the migrant crisis because the pandemic affects everybody, and the migrant crisis affects a small number of people. So it is easy to get the buy-in, to get the money, to get the programs. Whereas with the migrant crisis, you’re like, “Wait, so 30,000 people showed up here? Fuck them.” And that is the attitude of a lot of people. Whereas when you get a situation like COVID, which again, literally affects everybody, you’re like, “Should we write checks and businesses and programs and do all of these things?”

And people will work, and they will move heaven and earth to build a vaccine, to create the vaccine. So that’s scale and scope, but I am digressing to the question at hand. She got a tough hand. She dealt with it as best she could, and there were a lot of moments in there that I admire and that I think readers of the book will admire, but she didn’t lose reelection because she misplayed COVID or because she misplayed even the riots. She failed because she couldn’t lead the city. She couldn’t bring people together.

LW: You say there are some nice moments. Could you share a moment or two of the good side of Lori Lightfoot?

GP: So I think that when the vaccines were coming out, one of the issues was let’s get black people in the city of Chicago are sicker than white people. They’re poorer than white people. They have worse health outcomes. They have less access to doctors. They have less access to hospitals. The South and West Sides have a variety of these issues which are exacerbated by poverty, by class, by segregation. There was a theory of let’s just get the vaccine out to as many people as possible and eventually herd immunity will start to kick in and we can do it that way.

Mayor Lightfoot put a priority on vaccinating black and brown people who in addition to already starting from a worse position health wise had skepticism about the vaccine. There was enormous distrust of government. There were a lot of cultural issues going on, a lot of discussions in the black community. She said we’re going to push this as hard as we can. They were sending people out door to door, knocking on doors, leaving leaflets. They absolutely saved a lot of lives by putting in that effort. I think that she deserves some commendation for that.

She would talk about equity with some programs like Invest Southwest which was the idea of building on the South and West Side. She exaggerated some of those programs and was somewhat unfair to Rahm Emanuel sometimes with some of those programs. Rahm Emanuel put enormous effort into North Lawndale and Englewood in particular and other places too but he put in a lot of effort into those areas. He gets a reputation as Mayor 1% in downtown and that’s fair because he does care a lot about downtown and the North Side, but he did things too.

My point is that Mayor Lightfoot did talk about equity. She did work on some equity stuff particularly with the vaccine. She was very successful and I think that that deserves to be applauded.

LW: Speaking of equity, one of her other beasts might be and I know I’ve heard this from her and she’s said this publicly that she feels that she was treated differently or not given the credit that she deserved because she was a black gay woman. What’s your take on that? Is that a fair complaint?

GP: I think she’s right. I think that everybody who had a problem with her is racist, homophobic, and sexist. That is supposed to generate a laugh because I am sarcastic about that. I think so being more serious, any woman who has ever been a boss somewhere understands that people treat women differently in terms of that way. If a woman says hey go did you punch in today at the factory they’d be like wow she’s such a bitch and if a man does it they’re like oh yes sir. There are biases against women in our society. There are biases against people of color in our society. That said, no. Mayor Lightfoot used to say that 99% of her problems were because she’s a black woman and that’s just not true.

There’s an older woman Leslie Harrison who I quote in my book who talks about how sometimes you have to own the fact that you messed up and that you did something controversial and she could never quite do that. Mayor Lightfoot is one of the most defensive people that I’ve ever met.

We talked about that with David Brown. We talked about that with other things and so she doesn’t want to address the fact that she’s made mistakes. I mean some of her harshest critics are black men and women, are Latino men and women.

It’s not just Paul Vallas that has a problem with her although she would want to portray it that way. It’s not only people who look like Colonel Sanders from Kentucky Fried Chicken and which Paul Vales looks like. There’s nothing wrong with that by the way.

The short answer is of course there’s some biases but no, I don’t think that’s fair. She was at the University of Michigan recently and she was talking about this issue. She said that the city voted overwhelmingly for her and that a whole lot of people woke up and realized that she was a black gay woman. That’s really cynical I think because a lot of people voted for her and they were proud to vote for a black gay woman. A lot of people all across the city and so I think that I just don’t think that that is fair to the voters or the residents when she makes that argument.

LW: So I have many more questions but I want to, I know you all probably have great questions and comments so I want to get to you. So I just have a couple more things. One is, is there, I mean you reported the hell out of this book and like I said there’s probably nobody that knows her better as a public official than you. Was there anything that you learned or anything that surprised you coming out of the work you did on this book about her or about Chicago? Anything you learned that you didn’t know or anything that surprised you?

GP: Yes, so you know it’s interesting to really dig into the political psyche of a city and this is actually something that Stacey Davis Gates, the president of the teachers union and I had a conversation about and when she was working on Brandon Johnson’s campaign for mayor, you know, she believed in him. She, there’s some people were like oh they were just running him to run him and they didn’t think he would win. You know they understood the challenges but they thought they could win. They didn’t spend three million dollars to feel warm and fuzzy inside, you know, that’s that that’s not the way anybody does work, even socialists.

And so, so she was talking about how the city of Chicago doesn’t know how to break up with a mayor and it had been 40 years since the city of Chicago had broken up with a mayor, since they had broken up with Jane Byrne. They broke up with Gene Sawyer but that doesn’t really count because they didn’t really pick him in the first place, right? He was so appointed by the city council after Harold Washington died.

So and when you get elected, there’s something it’s like when you get married, right? You get married, you got married for a reason. You like this person. You saw yourself with this person. You’re going to give this person a chance when they mess up, when they when they refuse to take out the garbage every day and you’re like is it time to finally break up with this person? Well you know I did like this person at one time and that’s that’s the voters. That’s the electorate. You vote for someone the first time and you want to give them a second chance.

And Stacy had made this observation to me which I thought was on point. And then when you start to look at the psyche of a city that had a father and son for about 50 years and then Harold was elected for eight years, obviously he passed before he got to eight years. You have Rahm Emanuel elected the eight years. You have a couple of brief interludes.

The I was surprised when you really just take a step back to look at that tradition because a lot of that’s not normal in a lot of cities. I mean New York runs through mayors. LA runs through mayors and in this town we view the mayor as father-mother, problem-solver, troublemaker, and mischief-causer. And that’s changing and that’s something that’s surprises me.

Brandon Johnson, his name’s come up a couple times tonight. I’ve heard of him. You covered him as well. He he’s a new mayor, inexperienced in many ways as Lori Lightfoot was, a progressive, parallels between the two of them and or differences as you see it. And how is he doing so far? So you know I interviewed Mayor Johnson for his 100th day interview and we were, I wanted to talk to him about one of the contrasts between him and Mayor Lightfoot and that’s that Mayor Lightfoot wakes up in a bad mood and Brandon Johnson wakes up in a good mood. And you know Mayor Johnson, Mayor and he laughed you know and that’s absolutely true.

You know Mayor Lightfoot wakes up looking to put her boot in someone’s butt and Mayor Johnson wakes up you know in a much better mood. And they’re very different contrasts in terms of how they approach but what I said to Mayor Johnson at that time he had been in office for a hundred days which is a little more than three months and he had an appointed a housing commissioner, he had an appointed a planning commissioner. There were like five key vacancies and I said, I said when are you going to fill them?

And he hemmed and hawed a little and I said well no seriously I mean you know and people think you weren’t prepared for the job because these are key appointments. Housing is one of the most important issues for the political left in the city of Chicago and you don’t have a housing commissioner and they didn’t have one until December is when they appointed one. That’s seven months in the office.

So there is a real learning curve that they are working through there and I think that there are things that he does well actually. I think that there and you know the thing about you’re pissed off and you’re happy. Voters and residents and people like optimism. In general being the optimistic person is much more attractive than being the negative person. That’s true in everything in life. I think he’s doing much better than people give him credit for on policing. I think people are unfair to him on policing because first of all crime there there been some decreases in crime. Some of it is natural. Some of it is in police department.

But Brandon Johnson comes from political groups that do not like the police department, that do not like that approach and he hired a guy who is true blue Chicago police who everybody in that world respects and he more or less lets him do his job. He’s not sitting there saying you know don’t arrest people. I don’t know what else you could want from him. You know from Mayor Johnson. He’s not micromanaging the police department and telling them to whatever it is some people think that he’s going to do when he took office. I think that he’s starting to show some signs. He’s shown some flashes of pragmatism that are important for any mayor because you don’t want to be someone who doesn’t believe in anything but you have to be pragmatic.

And for instance downtown isn’t a big priority for him and for his side of politics but he just did a big deal with with some RFPs for LaSalle Street for bringing some more housing to LaSalle Street which has had some business issues and some vacancies. So let’s bring people down here which is something Mayor Lightfoot wanted something that Alderman Bill Conway wanted that is certainly not a CTU guy. And so I think that that said those are some positive things. Those are some things that I think he’s learning from. I think that there’s still there’s still a real learning curve.

But if he asked me about it I would say to him like I would say to you that if I was mayor I would rather start a little like this and then come back up then start then start up here and come back down and which is what Mayor Lightfoot did right. And so he’s got room to improve but he’s you know there there are positive things there too.

LW: Do you think you know people are voters I hear from all the time and some of them are in this room are people who voted for him already getting a sour on him because they’re concerned about the way he’s handled policing fine but the migrant situation some of the mistakes he’s made he’s got he’s had challenges in terms of some of his relationships with his peers. Is it is he running out of time to to to win that support back or to keep that support or?

GP: I think I think he has time but sometimes and actually I said a lot of positive things so I’ll say something negative. The sometimes I say that Mayor Johnson resembles a teacher that has lost control of their classroom and he’s a teacher and he was a teacher and where that happens is there have been four instances where the aldermen are trying to kick each other out of committee chairmanships.

There have been two incidents where the aldermen have put their hands on each other in various capacities. There it’s like the Jerry Springer show and you guys all remember Jerry Springer and and and so do I and my favorite it’s what I grew up with. So there are days that the city council is goofy and he doesn’t have as strong a grasp on that as he could. I think that there are times that residents watch him at press conferences which he doesn’t do enough of although he’s he’s getting a little better but he doesn’t do enough of them and sometimes he seems unsure of himself and sometimes he needs to he needs to stray straight in those types of things.

And I do think that there are people that have lost or are losing confidence but again I think he has plenty of time to win that back and as I as I point out in the book elections are not about who is your perfect candidate you know who you would like your perfect candidate to be up there but you’re often voting between this and that and you might not like this but you like it better than that.

And so that’s that’s what elections come back to so he has he has time he has things to work on projecting confidence maintaining control of the room maintaining control of his initiative having a message and a vision that he is articulating to the public these are issues that they that they’ve had.

One other thing I mean when they fired Dr. Allison Arwadi they didn’t have they they have a perfectly justifiable series of arguments that they can articulate about why they wanted to make a change. They fired her abruptly. It was a bad play and they didn’t have an explanation. Their explanation would be that they that they have different views of public health infrastructure that they want to have more government owned clinics and you can disagree with that you can agree with that but there’s an actual vision they didn’t articulate anything they just fired her abruptly didn’t explain themselves. So you you end up with the with a vacuum there. Why why why did what you said what you laid out as the logical approach why did they do it the way they did it? That that is such a good question. If I if you know I don’t I mean sometimes people just screw up I hear somebody in the crowd say amateurs and and that may you know there’s whatever the graceful way of saying that is probably correct. I mean when you’re just learning when you’re just starting people people make mistakes and the growing pains is the nice way to say that.

LW: All right a lot more to talk about. Anybody have questions or comments?