‘The city is up for grabs’: Chicago Tribune reporter’s new book details Lightfoot’s tenure as mayor

CHICAGO — Despite her small stature, Lori Lightfoot loomed large in a city known for its big shoulders. “She fits the great characters of Chicago politics,” said Gregory Royal Pratt, author of a new book about Lightfoot. “Big, brash, bold. Sometimes offensive. Sometimes endearing. She’s a brilliant woman and a dynamic personality.”

Pratt, who covered City Hall during Lightfoot’s tenure, said the former mayor is fascinating figure who led Chicago through a transformative time. “It’s a way for me to document the history of the city we love and the mayor that the city loved and, sometimes, loved to hate,” he said.

The book is entitled “The City is up for Grabs.” The phrase comes from Lightfoot’s own words in a text message to Ald. Rosanna Rodriguez Sanchez during the 2020 riots.  But, in a broader sense, it also describes the political void from which she emerged. “When mayor Rahm Emanuel stepped down in 2018 and said I am not going to run again, that created a power vacuum in the City of Chicago that threw the political establishment up for grabs,” Pratt said.

Lightfoot was initially viewed as a longshot candidate in the crowded field to succeed Emanuel, but her candidacy, Pratt said, was boosted by extraordinary luck. “There’s no doubt if a lightning bolt doesn’t come out of the federal prosecutor’s office and strike Ed Burke right in the head, she doesn’t become the Mayor of Chicago,” he said.

Powerful alderman Ed Burke’s indictment (and later conviction) on corruption charges galvanized voters against the “machine.”  A nimble Lightfoot rebranded as the ‘reform’ candidate. She ended up in a runoff against Cook County Board President Toni Preckwinkle. “It was a really bizarre election in that way where Lori Lightfoot did everything right, and Toni Preckwinkle did everything wrong,” Pratt said.

Lightfoot won in a landslide, sweeping all 50 wards. She made history as the first openly gay person, and first black woman to hold the office.  But, in Pratt’s analysis, she made an immediate error: alienating city council during her inauguration speech, in which she called out corruption in city government.

Pratt’s book argues that the moment was indicative of a theme throughout Lightfoot’s time in office — the impulse to act as a prosecutor instead of a politician. “You can’t slap everybody all the time as though they were a criminal, because that’s just not the way you get stuff done., and she could not adapt her personality and her leadership style,” Pratt said.

Lightfoot did not agree to be interviewed for the book, but Pratt spoke with dozens of city hall insiders, along with Lightfoot’s former classmates, co-workers, and rivals.  “I have four years of the mayor’s text messages with powerful people,” he said.  “I have four years of her emails with her staff, and again, with all sorts of powerful people.”

In an interview with WGN News political host Paul Lisnek in 2023, Lightfoot discussed some of her key accomplishments: Brining a casino to Chicago, and her signature economic development initiative “Invest South-West” which brought projects to historically ignored parts of the city. “I think we planted great seeds for transformation that will inure to the benefit of people, long-term, in the city,” Lightfoot said.

In March of 2020, Lightfoot’s agenda was upended as the world experienced the beginning of the covid pandemic. “I think that mayor Lightfoot should be proud of her work under covid and as a city, the city should be proud of her. That doesn’t mean that it’s that simple or that clear,” he said.

Though we remember the tough leader whose strict stance became a national symbol of responsibility, Pratt says Lightfoot was reluctant to take drastic action and had to be pulled in that direction by Governor J.B. Pritzker. “She was a little bit behind him every step of the way and he complained about that,” Pratt said. “It’s kind of funny how you luck into a reputation that maybe you didn’t earn, but you get anyway and if I was her I’d ride with it too.”

On May 25 of that same year, George Floyd was killed by a police officer in Minneapolis, sparking violent riots and massive racial justice protests across the country.  In Chicago, looters ransacked stores on Michigan Avenue and in various neighborhoods.  “It was a collective failure of the city and its leadership to fully anticipate,” Pratt said.

Pratt says perhaps the most consequential decision of Lightfoot’s term was — in real-time, and in retrospect — her biggest misstep: the hiring of David Brown as police superintendent. Pratt reports that many in Lightfoot’s own circle viewed him as overmatched and outdated.  In the Lisnek interview, Lightfoot defended her choice: “Being superintendent of the second largest police force in the country is not an easy job,” she said. “On any given day, under the best of circumstances, there’s probably less than half a dozen people qualified to do it nationwide.”

Pratt said that argument shows the former mayor’s unwillingness to admit Brown wasn’t successful. “What she ended up arguing to people is that there’s a small handful of people who are capable of being the police department superintendent, which is grossly exaggerated,” he said.

Chicago (like cities around the country) experienced a rise in violent crime during the four years Lightfoot served.

Lightfoot tangled with the police union and the Chicago Teachers Union, which went “on strike” for 11-days in 2019, and engaged in a ‘labor action,’ refusing to return to in-person learning forcing school cancellations in 2022.   “Mayor Lightfoot does not share their politics,” he said.

In the end, Pratt says the Lightfoot years seemed hopeful and hectic, overwhelming, and exhausting. She became the first incumbent not to even make the runoff election.

“When you face historic challenges that literally no mayor has faced, you’ve got to take challenges head on, and you’re not going to please everyone,” Lightfoot told Lisnek.

She finished third behind Paul Vallas, and eventual mayor Brandon Johnson.

“People were just kind of tired,” Pratt said. “It was a little bit like trump in 2020, where it’s something new every single day.”

But Pratt’s conclusion is that the city – which he describes as up for grabs won’t be held down for long. “We are a strong resilient people,” Pratt said. “We like our mayors we like our politics, but that doesn’t mean that any four years can break a city as incredible as this one.”

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