Lessons learned from former Mayor Lightfoot’s Chicago tenure

Over the course of one tumultuous term since winning election in 2019, former Chicago Mayor Lori Lightfoot faced more than her fair share of challenges.

A rapid uptick in crime, teacher strikes and the COVID-19 pandemic presented major issues she had to wrestle with. Closer to home, Lightfoot struggled to build relationships and trust with members of the Chicago City Council and Illinois state legislators, as well as some local activists and voters.

Meanwhile, the city continued to deal with its long-standing issues like poverty, segregation and institutional racism, as well as a deep mistrust of the Chicago Police Department after numerous scandals, including several officer-involved shootings.

Lightfoot lost her bid for reelection last year, and was replaced by Brandon Johnson, who has faced his own difficulties, like the bussing of migrants from Texas and Chicago Public Schools’ dramatic budgetary struggles.

Gregory Royal Pratt, a reporter with the Chicago Tribune, had a front-row seat to Lightfoot’s term and recounted those challenges in his book, “The City Is Up for Grabs: How Chicago Mayor Lori Lightfoot Led and Lost a City in Crisis.”

He reflected in a recent interview with Route Fifty on how Lightfoot’s confrontational, prosecutorial style rubbed many in Chicago the wrong way, and how her broken campaign promises came back to haunt her in office. And Pratt noted that while Chicago is unique among big cities in many ways, the lessons Lightfoot learned as mayor can apply to most other municipal leaders.

This interview has been edited for clarity and brevity.

Route Fifty: When did you first become aware of Lori Lightfoot? What was the sense that you got when you first met her?

Gregory Royal Pratt: My first impressions of Lori Lightfoot were around the police accountability work that she got hired to do by [former Mayor] Rahm Emanuel, and she was feisty, she was tough, she was combative. You had a sense that she wanted to get it right. This is a city that has really struggled with police misconduct, and more than other big cities because we had a police torture scandal. We've had all sorts of really big, entrenched scandals, not one offs like every city has, but we've had a lot of issues and she really cared about getting it right and trying to address that after the shooting murder of Laquan McDonald. That's about when I was starting to get an awareness of her.

Route Fifty: I know no politician is going to say, “Yeah, I really want this.” But did you get a sense she really wanted to be mayor, that she felt it in her bones?

Pratt: She had a genuine desire and belief in herself, but she wasn't one of these people that just thinks they’re certainly going to win. She's a realist; she is a pragmatist. I don't know if she ever had the full delusion that a lot of candidates have where they just think that they entered the race and are Super Mario with one of those [invincibility] stars, and that nothing can touch them or hurt them. I don't think she was ever there. I think she was always much more of a realist, but she did think she could win, and she certainly wanted to win. There was an element of getting back at Rahm too.

Route Fifty: I was really struck in the book by Lightfoot managing to piss seemingly everybody off in the city in a short space of time. What went wrong?

Pratt: When you're in politics, you have to adapt or die. I'm not talking about dropping and shifting core values, but I'm just talking about your style, your approach, sometimes compromising on different issues. Lori Lightfoot won because she was an outsider, the race became a referendum on “The Machine,” and she was the only major candidate without ties to The Machine, and that's why she won. She thought that she won because she was the smartest and the toughest and the fairest with the best plans and the hottest jokes, and that's not why she won.

A lot of politicians make that mistake. They don't understand how and why they won. She refused to adapt from her prosecutorial skills. She was a lawyer, she was a defense lawyer, she was a prosecutor, and what she learned to do was fight, fight, fight. In most campaigns, being able to prosecute a case is very, very meaningful. But she couldn't adapt from fight, fight, fight, and that was a big part of her undoing. Then she never really understood that her base was a mile wide, but an inch deep. She didn't realize that she had to maintain these relationships. 

I tell a story in the book, and I think it's an illustrative story. Willie Wilson, a local businessman who gives away a lot of money, spent a lot of time vouching for her in the black community, taking her into churches and clubs and all sorts of places, and she thanked him by dumping him before she was even sworn in. She just didn't have any use for Willie anymore, so she ended that relationship. That's somebody who was not playing the long game, and that's somebody who wasn't really understanding that, yes, you swamped Toni Preckwinkle, but it's not because of your own innate greatness. There were all these people that helped you, and you do have to try to maintain relationships with them.

Route Fifty: What kind of role did COVID-19 play in impacting her leadership and how she had to approach things? How big a deal was it?

Pratt: Speaking broadly about cities and governments, COVID was an easier problem in some ways than some smaller problems, because it affected everybody, and so government was able to truly mobilize and work on it. While you had a relatively small number of people that were anti-mask and anti-vaccine, they were a very vocal minority, but they were definitely a minority. The federal government moved into action. It gave a lot of money. It gave a lot of effort. It sped up. The Trump administration spent all these resources and energy helping mobilize the vaccine.

You compare that with a problem like the migrant crisis, where the governor of Texas has sent tens of thousands of people to the city of Chicago who can't get jobs and who need shelter, and it's really screwed with the city, even though it's a far smaller problem in terms of the scale of COVID. COVID was really tough because government had to use muscles that they don't always use. Mayors don't run for office — and governors don’t run for office — thinking about public health, and if they tell you that they are thinking about public health, they're lying, except for stuff like mental health, which is real and valid too. They weren't thinking about a pandemic in any meaningful sense, so it was really challenging.

Big picture-wise, I think sometimes that gets misconstrued, where people think that COVID was an easier problem in some ways than some of the bigger, more intractable problems, because everybody could mobilize. It was a real crisis and an immediate crisis. When it comes to Chicago, COVID came with a lot of money, a lot of resources, a lot of opportunity for leadership. In a lot of ways, it's one of the times where she shines, sometimes by misunderstanding. People feel good about her toughness during that, but really she was following the governor's lead on a lot of that stuff. COVID was a time that she really got to shine, and it was a hard time because they were working 24/7.

Route Fifty: Chicago sounds like a difficult city to run based on all the factors and all of the groups swirling around. Is it more difficult than any other city? Is it just different?

Pratt: Chicago is unique. Chicago has a very deep history of segregation that's deeper than most big cities. It's this profoundly deep segregation problem. We have a lot of poverty; we have a lot of crime. You have people that don't really interact with each other very much due to the segregation. Lincoln Park and Avalon Park don't cross, and those worlds don't really collide. It's one-third white, one-third black, one-third Latino. You have shifting alliances. You have a lot of conflict. The teachers’ union is very engaged with broad social issues from the left. You have a strong and loud Fraternal Order of Police here.

I think it's uniquely challenging. I think all big cities are challenging. And for the mayor, Lori Lightfoot lost control of the school board for herself and for future mayors. Literally, they took it away. As I write about it in the book, Chicago was unique. In Chicago, the mayor controls the trains, the schools, the parks and everything else in city government, so it is unique in that sense too. Now the mayor's office lost control of the school board. The sheer amount of power concentrated in one person is also unique.

Route Fifty: I keep thinking about what you said earlier, about people voting in an outsider. Is it a surprise that people keep on plumping for outsiders when they vote? Does it really need an insider?

Pratt: Generally speaking, you should be skeptical of outsiders, because they're coming in and it's very easy to promise and say this is all fixable. With the city of Chicago, the unions are so strong, and they're all under contract, so you can't just come in and snap your fingers and change different things. That said, fresh eyes are always valuable. Fresh eyes can challenge the status quo, fresh eyes can go after things. The benefit of insiders is that they know how things work, and then they know how to pull the levers of power.

One of the shocking things when the riots were happening [in 2020] and they went to raise the bridges, there was a delay, because there's only 10 people who know how to raise the bridges in Chicago. You had to go find them and get them downtown to raise the bridges. You don't think about that, but it speaks to the specialization sometimes in government. One of my good sources used to talk about how, in government, there are employees who don't do anything except one thing, and their job is to push that one button one time. You can say that's an inefficiency or whatever, and you may be right, but it is what it is, and you have to know that and deal with that. That's the benefit of institutional knowledge.

In some ways, Lori Lightfoot looked like she was primed to be the perfect mayor because she had some insider experience. She problem-solved for a couple of mayors on a few issues. She's a very smart person. She's one of the smartest people I've ever met. She has integrity. Nobody's perfect, but she has integrity. You thought she could properly shake it up and make it work, and it didn't work out because she wasn't able to transition enough into politician mode and work on the relationships, and that's a real shame. Someone like Lori Lightfoot, but with better political skills, might well be an ideal political leader.

Route Fifty: I'm curious for your thoughts on the current mayor, Brandon Johnson, as well. What have you made of his tenure so far? Do you think he's learned lessons from his predecessor?

Pratt: Mayor Johnson is facing a lot of challenges. He's had a lot of staff personnel turnover. He's attempting very hard to wrest control of the school district from the CEO. He chose to keep Lightfoot’s CEO and now he's upset with him over some stuff. He's upset with him about the district's finances and whether or not there'll be cuts to deal with the budget crisis that's going on because of the one-time money that came from the federal government that they use to prop up the district. He’s struggled with personnel issues, just like she did.

I think they both had a focus on loyalty, and both had an insularity that doesn't serve them all the time. Mayor Lightfoot used to play the race card a lot. She would talk about how 99% of the criticism she gets is because she's a black woman, and Mayor Johnson has started to play the race card more and more. To the extent that they have a point, it's also very off-putting for a lot of people. A lot of people hear that, and they just put up a wall. He hasn't learned that lesson from her. One of the lessons for her, politically, is that you need to expand your base, not shrink it. Mayor Johnson sometimes has done things that have shrunk his base and I think they're both struggling for those reasons. I think that neither one of them had been a chief executive before they became mayor, and they've had growing pains in those roles. They're a little different. Whereas Mayor Lightfoot was a micromanager, Mayor Johnson is probably a little too hands off.

Route Fifty: Chicago is its own city, but based on Lightfoot’s experiences, are there lessons that other leaders could take from her experience into their cities? Is there anything that you think translates broadly across municipal leadership?

Pratt: People want candor, people want to trust you. Mayor Lightfoot came in and almost immediately dropped some of her campaign promises, like the elected school board. She campaigned for an elected school board, then dropped it and the [Chicago Teachers Union] took it from her. You shouldn't be making empty promises. They want to see that you're carrying through on certain things. I think you're better off talking broadly and then giving specifics, and then executing on those specifics, instead of just talking very broadly. There was a lot of dissatisfaction with Lightfoot, in terms of, she promised all these things, and she didn't keep any of them. A few she did keep, but there was a perception she wasn't keeping her promises. You have to keep your promises, you have to be clear eyed about how you're governing, and you always have to work with people.

People like accountability. So the thing where she would say, 99% of my criticism is because I'm a black woman, people don't want to hear that, because it feels like a deflection. Whether it's true or not, it feels like a deflection. Some of the more important chapters are about policing and how the police department ran. She takes over, and she says, “I'm going to have my weekly meeting with them. I'm going to call it Accountability Mondays.” Then 2020 happens and crime shoots up. In January 2021, she sent an email to all her brass, which is in my book, and she talks about, “We need to do better, and we will.” And guess what? 2021 was worse than 2020 and she didn't fire anyone. And this is the accountability mayor. People tune that out. People want to see results, and when they're not seeing results, they want to see strong leadership.