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Person of the Year: Mayor Lori Lightfoot: Legal career, work ethic laid the groundwork for historic run to City Hall

December 05, 2019
By Jordyn Reiland
Chicago Lawyer correspondent

It’s a brisk fall Saturday afternoon in Lincoln Park.

Lori Lightfoot has just finished calling bingo numbers at a church ready for this interview just two days removed from accomplishing her most consequential task since being sworn in on May 20 as Chicago’s mayor.

On that particularly snowy Halloween Thursday, Lightfoot officially announced a contract agreement to end an 11-day strike by the Chicago Teachers Union — its longest since 1987’s 19-day strike — after a lengthy meeting with CTU President Jesse Sharkey.

The agreement was the culmination of weeks of tense negotiating and bargaining between the mayor’s office and union officials, a type of dealmaking the longtime lawyer has had plenty of experience with.

Almost a year-and-a-half earlier Lightfoot made a different kind of announcement, one that began her trajectory toward the city’s top leadership position.

Joining only a handful of candidates prepared to run to unseat then-Mayor Rahm Emanuel, the former federal prosecutor and Mayer Brown partner touted her role as a political newcomer and her desire to dissolve machine politics.

After Emanuel announced in September of last year that he would not seek re-election, the number of candidates looking to replace him only grew.

Nevertheless, Lightfoot forged ahead.

Come the municipal general election on Feb. 26, Lightfoot and fellow candidate Toni Preckwinkle topped a field of 14, forcing the race to an April 2 runoff between the two. After five weeks of extra campaigning, Lightfoot went on to sweep all 50 Chicago wards, becoming the first African American woman and openly gay person elected mayor.

Reflecting on a busy few months, Lightfoot recognizes she will face many more challenges during her time as mayor — the job requires it.

Just as she did ahead of a big trial or court hearing, Lightfoot plans to similarly approach any issue that comes her way with a similar thread: Be prepared.

“I really understand the necessity of total preparation,” she said, speaking to her effectiveness as an attorney. “There’s nobody who is going to outwork me, there’s not going to be an argument that I haven’t anticipated and am ready to respond to.”

According to her colleagues in both the political and legal realms, the qualities that made her a strong lawyer are what give her the potential to be an equally strong mayor.

“She’s an incredibly smart person. She is extremely principled and she can critically think through a problem and see various sides of it,” said U.S. Magistrate Judge Susan E. Cox, who has known Lightfoot since the two were federal prosecutors in the U.S. Attorney’s Office in Chicago.

Lee N. Abrams, senior counsel at Mayer Brown, thought when Lightfoot announced her intention to run for mayor that she would be the right candidate.

“I thought she would make a terrific mayor all along because of the characteristics that she has of being so insightful into the issues, problems and possible solutions,” he said. “That openness and willingness to listen to other people, I think, is a unique gift.”

The law student

For Lightfoot, going to law school started off as a “practical and pragmatic decision.”

As it turned out Lightfoot loved being a lawyer.

“It’s the best, the best, the best,” she said with a smile.

From as early as elementary school the Massillon, Ohio, native saw herself as an advocate who cared about social justice and equity.

Her decision to become a lawyer, however, didn’t come until several years later.

Lightfoot graduated from the University of Michigan in 1984 with a bachelor’s degree in political science. After college she took a few years away from schooling, believing she would eventually come back and get a Ph.D. in history or political science.

While spending time working for multiple congresspeople in Washington, D.C., Lightfoot started thinking about what she could do professionally to ensure her financial stability. She did not know any of her hometown lawyers and didn’t have any family connections to the legal world, but after speaking with several she came across during her time in Washington Lightfoot decided a law degree was something she could build a life on.

She moved to Chicago in 1986 after earning a full scholarship to attend the University of Chicago Law School. She was president of the Law Student Association, quarterback of the school’s intramural women’s football team and wrote for the now-defunct law school student newspaper, The Phoenix.

As student association president, she advocated a law firm be banned from on-campus interviews for one year after an interviewer made racist and sexist comments to an African American female student.

Having been discriminated against herself, that moment hit home.

“I remember it like it was yesterday,” she recalled.

After some investigating it turned out the interviewer had made similar comments to other students in the past. At that point Lightfoot felt she had no other choice.

“I felt like employers coming to the campus, it’s a privilege not a right,” she said.

Lightfoot did what she felt was right at that time, and “doing right” has been a mantra she has lived by throughout her life.

“That theme is something that is kind of baked into my DNA,” she said. “I just think that people need to be treated fairly and you’ve got to have the courage to be able to step up and advocate for the things that you believe in … Right was right and we needed to do the right thing.”

Her time as quarterback of the intramural women’s football team not only fueled her love of the sport, but it got her through the difficulty of her first year in law school. The team was undefeated and unscored upon for the three years she was there, she said, relying on a series of rolls, bootlegs and 15- to 20-yard passes to get the job done.

“Being able to go out on the athletic field and bond with the incredible women in my class really got me through the tough periods in my first year,” she said.

The lawyer

Upon graduating from law school in 1989, Lightfoot began her legal career as an associate at Mayer Brown one year later. She recognized she was far from a legal expert at that time and knew she wanted to work at a firm where she would receive “first-rate training.”

“You don’t come out of law school and you’re ready to argue a Supreme Court case or you’re ready to take on complex litigation,” she said. “It’s a trade you get better at the more experience you have, the more mentors you have and the more opportunities you have.”

After a stint as a summer associate at Mayer Brown, the decision to work there was a no-brainer. She felt a genuine connection and bonded with those who worked at the firm. She also had the flexibility to explore what she wanted to do without making a commitment to a specific practice area immediately.

She felt fortunate to be in the company of people who helped her expand her legal skills, including partner Tyrone C. Fahner.

Lightfoot said while people may not have initially thought the two had much in common, given their age difference and political backgrounds, the time she “spent under his wing” not only made her a better lawyer but it also introduced her to the notion of on-the-job public service.

“He’s 20 years older than me, white guy, Republican from Detroit, but he’s a working-class guy. His father worked in one of the auto factories and he was just somebody who was, I thought, a consummate professional,” Lightfoot said.

Based on her own experiences Lightfoot finds pro bono work meaningful because it allows lawyers to not only pursue their passion but gives, especially younger lawyers, another opportunity to get experience they may not be getting day-to-day at the firm. At Mayer Brown, Lightfoot worked on criminal defense, civil rights and immigration pro bono cases.

“I used to say to the young associates who worked for me, ‘The objective every day is to maximize your happiness quotient’ and pro bono I think really fills that void for a lot of people,” she said.

Lightfoot left Mayer Brown in 1996 to join the U.S. Attorney’s Office, a move she said occurred “kind of by chance.”

She didn’t consider working as a federal prosecutor until after she defended a case against them. She got an offer to join the U.S. Attorney’s Office in November 1994 but delayed accepting it so she could try a big case she was working on at the time at Mayer Brown.

That case ended up settling but, around the same time, the U.S. federal government shutdown twice for a total of 26 days between November 1995 and early January 1996, which postponed Lightfoot’s start at the U.S. Attorney’s Office until April 1996.

“The moral of that story is never wait. When the opportunity presents itself jump on it,” she said.

Despite the delay, Lightfoot quickly learned she loved being a trial attorney and all the preparation and work that came along with it.

From the outset Lightfoot prosecuted bank robberies, violent crimes and drug cases. Those cases gave her a perspective of the city she did not already have. It also gave her an opportunity to learn more about city government.

“I was the kind of lawyer that I didn’t sit in my office and let the agents have all the fun,” she said.

Lightfoot prosecuted former 15th Ward Ald. Virgil Jones, who took two payoffs totaling $7,000. He was indicted as part of Operation Silver Shovel, a 1990s FBI probe into political corruption in Chicago.

In 2002, Lightfoot was named a high-ranking official in the Chicago Police Department Office of Professional Standards and, later on, the Chicago Department of Procurement Services. Lightfoot returned to Mayer Brown as an equity partner in 2005, while leading the Chicago Police Board and the Police Accountability Task Force.

Abrams said Lightfoot is “extraordinarily effective in a courtroom” and can react well to the changing dynamic that can often occur during a hearing or trial.

“I’ve had the pleasure of practicing law for a very long time and there are a lot of good lawyers who are not very good at the aspect of dealing with people,” Abrams said. “She is very good at it.”

During her time as a Mayer Brown partner, Lightfoot had a number of associates working with her, including Michael Frisch. Frisch is now senior adviser and legal counsel for the city, a job he has held since Lightfoot took office.

Frisch also considers Lightfoot his No. 1 mentor.

“She advocates strongly for what she believes in [as mayor] and that’s the way she practices law as well,” he said.

During the teachers’ strike specifically, Frisch saw Lightfoot use her “no nonsense, straightforward approach that she takes to both legal cases and negotiations.”

He said when an independent fact-finder determined a 16% raise was appropriate for the teachers Lightfoot and her bargaining team ultimately decided to bring that number to the table instead of starting somewhere lower because she knew it was the right thing to do.

“She’s not one for playing games or for considering the political ramifications of something when she sees something that is right,” he said.

In May 2018, Lightfoot resigned from Mayer Brown to run for mayor.

The mayor

Since hitting the ground running Lightfoot has stressed the importance of being physically present. Whether it’s greeting city residents outside public transit stops, interacting with students in the classroom or calling bingo at a church, Lightfoot wants people to know she’s there.

“I hear all the time, ‘We’ve never seen a mayor in [this] neighborhood. I’ve never met a mayor [she’s heard] from older Chicagoans,’” she said. “The notion that we are going to use the power of the mayor’s office and the city government to really be out in communities that have really suffered from disinvestment, that’s magical to me.”

What she has heard both on the campaign trail and as mayor is being incorporated into policy. For example, Lightfoot spoke with several small business owners during the campaign who were concerned about the fact that it took between eight months and two years to get a sign for a new business.

As a result of those conversations, her office has proposed legislation that would provide a business owner with a sign at the same time they get a business license.

Lightfoot has also made it a goal to make Chicago a city of opportunity for its young people. Before calling out those Saturday afternoon bingo numbers, Lightfoot attended part of Simeon High School’s first playoff football game where she briefly addressed members of the team.

The high school’s state championship hopes were in jeopardy due to the length of the teachers’ strike but after a deal was struck they were able to play. Lightfoot told the players that she was proud of them for persevering despite difficult circumstances.

“Those young men worked their tails off and they were performing at a very high level,” she said. “I didn’t want to see that opportunity taken away from them.”

For Cox, none of this comes as a surprise. She knows firsthand what relationship building means to her former colleague and friend.

Fully recognizing that her election was a historic moment for the city, Cox was especially honored to be the one who swore Lightfoot in.

“I think she could have had any judge she asked. She did that because what she values more than anything is friendship and the people in her life that make a difference. To me that says a lot,” she said. “She’s not going to forget the people she’s met along the way.”

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