Mayor Lori Lightfoot represented a lot of firsts when she became mayor of Chicago in 2019. The city’s first Black, gay woman elected mayor, she promised a new vision for the office and a progressive approach to crime and neighborhood investment on the South and West Sides. In a crowded race, she set herself apart from the political establishment in her climb to the fifth floor.
But in four years, Lightfoot weathered crisis after crisis—from the pandemic to civil unrest and one of the longest teacher’s strikes in decades. As a reporter for the Chicago Tribune, Gregory Pratt often had a front-row seat to the drama as Lightfoot clashed with city council, local officials, and her staff. In The City Is Up for Grabs, Pratt paints a portrait of the person at the center of the storm and the chaos that unfurled.
“It is a brutal hand that she was given, but she misplayed it because she struggled to be a leader. The biggest crises she made were for herself, not the external ones,” he said. “She handled many of them as best as she could, but every day, she invented some new crisis because she couldn’t just shake hands and agree to disagree.”
How did Lightfoot go from a relatively unknown figure in Chicago politics to winning over 70% of the vote? When did longtime allies go from lobbying by her side to cursing her privately and even publicly? Answering why Lightfoot rose and fell becomes a primer on the fallout of Chicago’s political machine and the local institutions rapidly evolving around her.
In our conversation, Pratt talks about what made Lightfoot different from her predecessors, why relationships ultimately caused her downfall, and what lessons Chicago should learn from her four years at the helm.
This interview has been edited and condensed for clarity.
Reema Saleh:
When did you first start writing this book? How did this bleed over from your coverage?
Gregory Pratt:
As soon as I started covering Mayor Lightfoot, I understood early in 2018 that we were potentially looking at a big sea change in Chicago, where you had the big bad, established Mayor Rahm Emanuel, leaving. Now, you potentially had a power vacuum and turnover. I thought this could be a great story. I got more serious about writing a book about this in 2020. I would cover Mayor Lightfoot day-to-day then, which I like to think of as our soft apocalypse here. Because it was crazy, right? You had the pandemic, you had civil unrest, you had a lot of institutions being remade and tested. I remember thinking, there’s more here than just what’s in the daily news. It was mostly doing the day job and then, at night, sitting around and daydreaming about writing a book, which is probably common.
Reema Saleh:
Why did Lightfoot feel different when she came on the scene in 2019?
Gregory Pratt:
Lightfoot is an interesting historical figure because she is so different from most people who are mayor. For most of Chicago’s history, her as a mayor would be unthinkable because you had two white guys, father and son, running the city for about fifty years. Then, you had one of their protegees running the city for eight years, Mayor Emanuel. And Mayor Lightfoot comes in, and she is not totally an outsider, but she effectively is an outsider. She comes in, guns blazing. And you can see, “Wow, things are really going to change, and this could be interesting.” Of course, some of her efforts were short-circuited by COVID-19. Some of them got short-circuited by her own leadership flaws. It was a situation where you almost had the famous Chicago legend of the “nobody nobody sent” become the somebody in charge at City Hall and see what happens.
Reema Saleh:
What made Lightfoot stand out in that election race? How did she go from someone relatively unknown in Chicago politics to winning over 70% of the vote?
Gregory Pratt:
Lori Lightfoot is a wickedly smart person. She’s very intelligent, and she is a tremendous diagnoser of problems. Take policing, which she made a big name for herself with the Police Accountability Task Force. You can put her on their panel to say what the problems with policing are, and she can figure out there’s an element of racism, staffing problems, and a lack of training, and she can diagnose those problems very well.
When Alderman Ed Burke’s office was raided by the FBI in 2018, and the race started to become about corruption and about the way Chicago government works and doesn’t work, she was able to use her experience as a prosecutor and her big brain to diagnose very clearly what the problems are and talk about taking them on head-on. All her major opponents were connected to the machine, so even if they understood the problem as clearly as she did, they couldn’t take it on as openly because they were beholden to the same machine. Life is about good luck and timing, and she had a window open for her.
Reema Saleh:
While we’re here, what is the machine? And how does it work?
Gregory Pratt:
The machine has various iterations, but it’s the idea that we’re going to use government and the levers of government to benefit ourselves and our people over the everyday citizens. We’re going to use government to take power, keep power, hold on to power, and profit off power. With the first Mayor Daley, who had a big machine, we have all these jobs. We give them to our friends. We give them to the people who campaigned for us, and that’s how we keep and hold on to power. The Illinois Speaker Michael Madigan, the longest-serving speaker in Illinois and US history, had his organization of workers on the payroll. They go out, they do politics, and they get priority.
The political machine is not uniquely Chicago because New York had a machine. Kansas City had a machine. Other places have had machines. But those machines died out a long time ago. In Chicago, up until recently, you had the first Mayor Daley, who took office in the 50s and then died in the 70s, and two of his protegees and allies and people that he knew, Alderman Burke and Speaker Madigan, were still in power forty years after Mayor Daley has died. That’s the machine. It’s using the government to build a political organization to support yourself politically and financially.
Reema Saleh:
You write about the ways Lightfoot would use her race, gender, or sexuality as stand-ins for her progressive values when that wasn’t accurate. How was she straddling the line between being progressive and moderate?
Gregory Pratt:
She would use it as armor to defend herself from criticism that she was not fulfilling the progressive politics. Mayor Lightfoot is more progressive than some groups would probably give her credit for, but she’s not that progressive. People wanted to see her deliver some more. Early on, she interviewed with a national publication, Think Progress, where she was trying to ride the wave of Alexandria Ocasio-Cortez in New York at the time, and it fell flat because she didn’t have a progressive answer for everything they asked her. She would often go back to race, gender, and sexuality as signifiers, but once you passed that, she was a pretty moderate politician. That balancing act alienated people because you have to portray yourself the way you are and not try to do some false advertising.
One of the best examples is the story I relay in the book, which was first reported in the Sun-Times, about how she was angry that Bernie Sanders and Elizabeth Warren hadn’t reached out for her endorsement, saying, “They were very supportive of the Chicago Teachers Union strike but didn’t feel it was necessary to talk to the new Black LGBTQ mayor.” What does being Black LGBTQ have to do with being progressive? There are plenty of Black LGBTQ moderates, liberals, centrists, and even a few conservatives.
I talked in the book about universal basic income, which, by the time it came to Chicago, was an idea that had been tried out in other cities. Mayor Lightfoot was against the Universal Basic Income program. She told Alderman Villegas, “I’d rather give people jobs…I want to see people work.” And that’s not that’s not very progressive. It misunderstands the nature of welfare. Many people are working very hard, and they’re not getting by because they don’t get paid a living wage. She constantly struggled to balance her side as a corporate lawyer with her desire to be progressive but not necessarily understanding what it meant.
Reema Saleh:
When did that balancing act stop working?
Gregory Pratt:
I think that Mayor Lightfoot never recovered from the civil unrest and riots in 2020. I think that her worldview shifted. She was angry about what had happened around the city, and rightfully so. I drove around all of the South Side as looting was happening, and it was horrible. You had big stores like Jewel-Osco, and then you had all these small stores, outlet malls, and corner stores getting looted. I don’t think she ever really reclaimed her mojo after that. She started lashing out at State’s Attorney Kim Fox, which took her off her political base a little.
By the time 2021 had happened, she was shrinking further and further into being angry with the media and legislators. She lost control of the school board. I think people started to tune out and get tired of Mayor Lightfoot not necessarily having answers to questions but picking fights with everybody. I think 2021 is the year that she lost the city because that was when, after COVID and civil unrest, crime kept going up, and she didn’t have good answers. She started withdrawing from answering questions and talking to the public more directly. I think that’s when the shine came off.
Reema Saleh:
It seems like relationship-building is the thing she struggled with—whether that was the city council or her staff. Why did it get so bad?
Gregory Pratt:
Everybody has their personality and way of addressing stuff. For Mayor Lightfoot, she was a prosecutor. When the prosecutor gets to the alleged criminal, you can hammer them and beat them, and there isn’t a lot that they can do because the Feds aren’t bringing cases unless they’ve got you dead to rights. When she went into private practice and worked for Mayer Brown, those big law firms paid $250,000 to start. They get to talk to you however they want for that kind of money.
Then you come into city government, where nobody is making $250,000 except the police superintendent and the mayor. You’ve got these hard-working, intelligent people working for minimal money under tough conditions with annoying people like me in the media second-guessing everything they do. She would treat people like she was still at a big law firm or like she was still at the US Attorney’s Office, and that doesn’t work. Some of her people would tell you that she could never stop being the hammer. That was the problem with her and relationships. She would probably still be the mayor if she could have dialed that back.
Reema Saleh:
It feels like many institutions around Lightfoot were also in flux. How were city institutions changing around her while she was in the office?
Gregory Pratt:
We’re still very much in a state of flux as a city. The book’s title, “The City is Up for Grabs,” comes from a text message she sent during the civil unrest in 2020. There was looting downtown, and she’s talking about how the city is up for grabs. And she was annoyed with an alderman who was, in her opinion, too concerned with the civil rights of the people downtown. But “The City is Up for Grabs” applies to the fact that policing was in flux because it was under a new consent decree and facing calls for reform. The school district was in flux because the Chicago Teachers Union was dead set on taking control of the school board and taking it away from the mayor. The city council was in flux because many of the old veteran aldermen like Danny Solis, Ed Burke, and Carrie Austin were on their way out, leaving the City Council facing criminal cases, public scrutiny, and embarrassment from scandals.
Every major institution in Chicago’s government was swirling around and facing enormous upheaval. That was challenging, but it was also an opportunity for Mayor Lightfoot. There are mixed results on some of those because the police department did not have a good four years when it came to reform. It badly needs reform because it lacks trust in the eyes of too many people in Chicago. I am a proud graduate of Chicago Public Schools, which is facing major turnover. The fates of these institutions will also play a big part in whether Mayor Johnson ends up being a one-term mayor or has more success.
Reema Saleh:
When Lightfoot went up for reelection, what changed about what she offered the city?
Gregory Pratt:
It’s no longer about what you’re promising. It’s about what you deliver and how you sell it. It’s a referendum on what you did in office, and people will try to make it a referendum on their opponent, and they usually don’t succeed. Lightfoot hoped that she would end up in a runoff against Paul Vallas, and she would tell the city, “Hey, Paul Vallas is a Republican. He’s an old white Republican, so don’t vote for him. Vote for me.”
She could no longer be the empty slate that people portrayed their hopes and dreams on which she was in 2019. She had to defend her record, and there were a lot of people who were disappointed in how she governed. The people who put her into office and voted for her in the first round of 2019 were white, progressive, LGBTQ-friendly, and LGBTQ people from Lincoln Park to Andersonville and Edgewater. Those people bailed on her in 2023 because they were tired of the constant fighting. They felt she didn’t fulfill her campaign promises about transparency, public safety, or reforming the police department. They went with Brandon Johnson, and they went with Chuy Garcia. Some of them still supported her, but that didn’t leave her with a lot left to go with.
She tried to reinvent herself with her base being Black voters on the South and the West Sides. But Willie Wilson took up a chunk of those voters, which hurt her because if she had won some of those voters instead, maybe she would have made the runoff, and maybe she would have beat Paul Vallas. One of the remarkable things is Willie Wilson, the prominent Black businessman who gives money away across town and is one of the greatest characters in the city. He did a lot to help her get elected in 2019. And she dumped him before she was even inaugurated. That was a big mistake because if she had him stay allied, things would have been different. There’s a pattern where Mayor Lightfoot would use you when she needed you, completely forget about you, take you for granted, sometimes throw you away, and then come back asking for your support. That’s not how it works in politics, especially not if you’re in a position of weakness.
Reema Saleh:
What are the challenges of reporting a book like this? Do you think anything was lost by Lightfoot not interviewing for it?
Gregory Pratt:
Reporting is always challenging because you’re trying to distill various perspectives on what happened, why, and where. You and I could go to Chipotle today, and in two days, if someone asked you what I had to eat, you might have a different recollection than I do. You must talk to as many people as possible, try to make sense of events, and get to the deeper meaning, purpose, history, and why it matters. I talked to many dozens of people, including inner circle people, friends, allies, enemies, and frenemies, which is what you need to do when you’re reporting. I would have liked Mayor Lightfoot to have sat down with me in depth to talk about these things because she is an intelligent woman with a story to tell.
Our relationship started very positively, then became more negative and contentious. I would have liked to have sat down and talked about these issues more with her. But I talked to plenty of people. I got her text messages and emails, and I have a variety of firsthand accounts that help support this. I hope that if she ever writes a book herself, she is honest and, to use one of her words, fulsome in telling the story because it would be interesting to hear it all—warts and all—from her.
Reema Saleh:
What is the epilogue for Lightfoot?
Gregory Pratt:
She started a nonprofit that will help support other nonprofits and do economic development on the South and West Sides. The city should wish her success because neighborhoods need support from all sorts of avenues. She’s done a little speaking at Harvard and the University of Chicago now, and that’s very interesting. At some point, I’m surprised she doesn’t have a job yet as a lawyer. I’m surprised she’s not making it rain at a law firm right now. But I think she wants to do some policy stuff that supports some of her core values: the pandemic, health, and neighborhood investment.
Reema Saleh:
What lessons should Chicago or other cities learn from Lightfoot’s legacy here?
Gregory Pratt:
You have to carry out your promises as best you can. If you can’t keep your promise, you need to be upfront about why and what happened. You have to work with people. You have to have relationships, even with people that you don’t like. Sometimes, you have to have relationships with people you don’t respect. If you’re the mayor of a city, and you think that a guy on the city council is a jackass, that’s great. He’s still somebody you have to work with.
I think that you need to set concrete goals and go after them. Mayor Lightfoot never articulated a clear vision for Chicago schools aside from happy students learning a lot. But if you put a gun to my head, I cannot tell you what Mayor Lightfoot’s actual agenda was for the classroom. She was very fierce about not closing down over COVID again, and she won a battle with the teachers’ union about that in 2022. But aside from that, there wasn’t a clear mission and goalpost. When you’re in leadership, you need to set clear goals, directions, and guidance, or else institutions will misunderstand.
NONFICTION
The City is Up For Grabs
By Gregory Royal Pratt
Chicago Review Press
Published April 2, 2024
