How Lori Lightfoot lost Chicago

The rise -- and fall -- of a one-time Democratic star

In 2019, Lori Lightfoot was seen as the (or at least a) next big thing in Democratic politics. She had taken on the Chicago political establishment — in the form of Mayor Rahm Emanuel — and won. (Emanuel announced he would not seek a third term six months before the election; Lightfoot went on to win.)

Four years later, it was all over. Lightfoot lost her bid for a 2nd term — finishing third in the Democratic primary and becoming the first Chicago mayor in 40(!) years to lose a reelection bid.

So, what the heck happened? Gregory Royal Pratt, a reporter at the Chicago Tribune, wrote the book on it. Literally. It’s called “The City Is Up for Grabs: How Chicago Mayor Lori Lightfoot Led and Lost a City in Crisis.”

I reached out to Gregory to chat about the book, Lightfoot and what her rocky four years tells us about being a big city mayor in this day and age.

Our conversation, conducted via email and lightly edited for flow, is below.

Chris: Tell me why you decided to write this book. What about Lori Lightfoot — and Chicago more generally —  jumped out at you?

Gregory: First, Lori Lightfoot is a fascinating character. She's brilliant. She's funny. She can pierce to the heart of an issue and make you understand it clearly.

At the same time, she's hot-tempered, profane, and can be wildly entertaining. When she entered the city's political scene, she was brave enough to take on “Goliath” -- Rahm Emanuel -- and when he dropped out of the race it left the city's political elite up for grabs. The stakes for Chicago were high in the race to succeed Emanuel as the city confronted financial challenges and other issues. Those stakes rose dramatically with COVID and the civil unrest in 2020. 

Chris: Lightfoot was elected as a breath of fresh air after the always-political Rahm Emanuel. How long did that last?

Gregory: Rahm Emanuel used to say that her political support was a mile wide and an inch deep. Lightfoot kept a honeymoon until the 2019 teachers strike. After that, she continued to have a veneer of strength with aldermen and the media, although it was starting to fade. She had campaigned on a series of progressive promises but governed as a moderate. Her promises to support an elected school board quickly unraveled. 

Chris: Lightfoot was the first mayor in 40 years not to get reelected.  What happened — and what does it tell us about big city mayors?

Gregory: This is a critical point: The powerful teachers union president, Stacy Davis Gates, told me Chicago doesn't know how to break up with its mayors. That was the uphill battle faced by Emanuel’s rivals before he dropped out and Lightfoot critics in 2023.

A few different things happened. First, successful people adapt their style. Lightfoot approached everything as a prosecutor, but every problem isn't a criminal. She couldn't govern collaboratively.

Being positive is a winner. Lightfoot was always complaining about her rivals, her enemy, the media, and eventually people tune that out, even if you've got a point.

Along those same lines, you can't take everything personal. In politics, there are no permanent friends, no permanent enemies, just permanent interests.

Chris: Chicago is regularly cited by conservatives as an example of a big city where violence and crime runs amok. Is that a fair characterization: Why or why not?

Gregory: Definitely not.

In fairness to Lightfoot, Emanuel and Mayor Brandon Johnson, the perception isn't new. When you travel and tell people you're from Chicago, they often bring up Michael Jordan or Al Capone. Capone died in 1947 but that image lingers. People who talk about Chicago don't know Chicago. There is crime, but there are people fighting it every day -- from police to neighborhood groups and clergy. (You sometimes hear a bogus and unfair claim that folks don't protest crime, but they do.)

We have real problems but they aren't as bad as people make them seem. It's a big city with big city problems. We do have real issues with professionalism in the police department compared with New York and Los Angeles, especially, and there's a real belief that the administration failed to really implement necessary reforms.

Chris: Finish this sentence: “The lesson national politicians should take from Lori Lightfoot’s rise and fall is_____________.” Now, explain.

Gregory: One of her longtime aides texted me this after the election: “You can’t run on a platform and then completely abandon it. You can’t run against the status quo, and then fill your administration with the status quo. And you can’t be mean to everyone who tries to help you.” 

To that, I would add that mayors have to be clear to their vision and mission. One moment, Lightfoot would be talking about the need to fire a police officer who flipped off a protester, based on pictures she saw in the news.

Minutes later, she'd be calling an alderman to say that “animals” attacked a police officer. It leads to identity confusion. Are you the progressive mayor? Are you the Rudy Giuliani crime mayor?

You have to have clear articulated values and execute on them. Some of her aides think one of the worst things that happened for her is winning by a landslide because it meant she thought she won because of her, without understanding the broader context she won under.

Lightfoot was the beneficiary of her outsider status after Ald. Edward Burke was charged -- and later convicted -- of corruption charges. That doesn't mean she didn't work hard or capitalize intelligently, but you have to understand why you won. It's almost never because you are the magnetic cult of personality.