Lori Lightfoot: From ‘kickass trial lawyer’ to Chicago’s next mayor

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Senior class president Lori Lightfoot, left, in yearbook photo. (Provided.); Mayoral candidate Lori Lightfoot, right, in the Sun-Times newsroom Thursday, January 17, 2019. | Rich Hein/Sun-Times

This story was originally published on March 22, 2019.

The moment University of Michigan sophomore Lori Lightfoot stepped inside her Ohio home for Christmas break, she knew something wasn’t right.

There were no decorations, no tree, nothing. And her mother loved Christmas. Always made a big deal of the holiday.

“Something’s wrong,” said her mother.

The older brother who Lightfoot idolized had robbed a bank in Nebraska and shot a security guard. Their devastated parents were considering mortgaging their house to raise bail money. But her brother had spread word that if he made bail, he’d run. Their hardworking parents — her father, deaf, toiled as a janitor and at other menial jobs, her mother a caretaker — could lose their home.

“So here I am, a 19-year-old, the youngest of four,” Lightfoot said in an interview with the Chicago Sun-Times, “and I have to help my parents navigate through this incredibly painful and difficult circumstance, which really kind of reshaped my relationship with them for the rest of my life and their lives, and tell them it would be absolutely foolish for them to take this money out because he was going to flee and that, if he fled, they would lose their house.”

These days, Lori Lightfoot isn’t shy about taking charge. But if you’re tempted to draw a line between her troubled brother, who would spend decades behind bars, and Lightfoot’s career in law, particularly as a federal prosecutor, putting criminals like her brother in prison, don’t. She says that wasn’t the reason.


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High school yearbook photo of senior class president Lori Lightfoot in Massillon, Ohio. | Provided photo

High school yearbook photo of senior class president Lori Lightfoot in Massillon, Ohio. | Provided photo

“It was really economics that drove me to think about the law,” she said. “I just wanted to be able to do something where I would be able to take care of myself financially.”

If that seems a contradiction — such a pivotal moment in her life having zero impact on her professionally — get used to it.

Lightfoot, 56, was elected mayor of Chicago on April 2 in a landslide victory against Cook County Board President Toni Preckwinkle, making her the first African-American woman to do so and also the first openly gay person.

There is a lot to unpack regarding Lightfoot, including many contradictions. And not just because she is 5-feet-1, maybe, yet played on her high school basketball team — point guard — and quarterbacked her intramural football team at the University of Chicago Law School.

“Flag football,” she observed, as if someone might otherwise suspect she were playing tackle.

Lightfoot was an equity partner at Mayer Brown — a global law firm where Lightfoot eventually made around $1 million a year — who frequently cites her humble beginnings in Massillon, Ohio, as the daughter of parents who came North in the Great Migration, fleeing the Jim Crow South, her mother Ann from the hills of Alabama, her father Elijah from Arkansas, where his father was a sharecropper.

Often stonefaced in public, Lightfoot starts to weep when she talks about her father, who died a decade ago.

“This is the second time today I cried about my dad,” she said, tapping the table to compose herself. “He had a very hard life.”

‘Kickass trial lawyer’

Lightfoot ran against powerhouse Preckwinkle and said harsh things about her opponent to her face.

“You are lying,” Lightfoot told her in one televised exchange. “There’s no lie you will not tell. It is sad and pathetic.”

Yet in 2016, she gave $1,000 to Preckwinkle’s campaign fund. Why? “Because she asked.”

A “kickass trial lawyer,” in the words of onetime Illinois Attorney General Ty Fahner, a Mayer Brown partner and former chairman, Lightfoot left big-firm life on several occasions for the grind of government. First to campaign in the 1990s for Dick Phelan, the Cook County Board president who wanted to be governor. She was a prominent critic of the Chicago Police Department, heading the city’s Office of Professional Standards under Mayor Richard M. Daley, and the city’s Police Accountability Task Force and the Chicago Police Board under Mayor Rahm Emanuel — but has been accused of being soft on rogue cops, an accusation she vehemently denies.

Calling for greater transparency with the police, she also has condemned Emanuel for acknowledging a police “code of silence,” fearing that opened the city to lawsuits.

Her image is often severe. But friends and colleagues say that, in private, she is very funny.

“She’s a riot,” said U.S. Magistrate Judge Susan E. Cox, who worked with Lightfoot when she was a hotshot newcomer in the U.S. attorney’s office in Chicago. “She has a great sense of humor.”

Why doesn’t the public see that?

“The things that I’ve been doing in the public sphere are pretty serious topics,” Lightfoot said at her River North campaign headquarters. “So it’s hard to find the laugh line in that.”

Lori Elaine Lightfoot was born on Aug. 4, 1962, in Massillon, a small, industrial town an hour south of Cleveland. Massillon is a mecca of high school football. Its rivalry with nearby Canton, home of the Pro Football Hall of Fame, dates to 1894. Massillon has 32,000 residents, half of whom can fit into Washington High School’s Paul Brown Tiger Stadium. Brown coached at Washington, Lightfoot’s alma mater, before going on to renown as the first coach of the Cleveland Browns.

High school yearbook photo of senior class president Lori Lightfoot (top row, right) in Massillon, Ohio. | Provided photo

High school yearbook photo of senior class president Lori Lightfoot (top row, right) in Massillon, Ohio. | Provided photo

When babies are born in Massillon, then and now a miniature orange Tigers football is placed in their bassinets by a member of the football booster club. Only if the baby is a boy.

Lightfoot did not get a football. Still, the sport took hold in her. She’s been a Bears season ticket-holder for 20 years.

“In Massillon, you either hated football, or you loved it,” Lightfoot said. “On a Friday night in the fall, I don’t know what anybody did if they weren’t at, quote-unquote, ‘The Game.’ Both my brothers played football. My mother had season tickets as a school board member. I was in the band, my sister was in the band. The thing was, the unifying civic activity was obsession over high school football.”

‘I show very little of my full personality’

Lori was the youngest of four Lightfoot children, two boys and two girls, a gap separating the older and younger pairs.

The eldest, Derrick, 12 years older, went off to college when Lightfoot entered first grade. Sister Angela was close behind him. Brian was six years older and was Lightfoot’s idol, their mother said.

“For her, the sun, moon and the stars set around her brother Brian,” said her mother, Ann Lightfoot, now 90, who still lives in the house where her children grew up.

Massillon was and remains a segregated city. Most blacks lived on the East Side. The Lightfoots lived on the West Side.

“We did not live in a black population,” Ann Lightfoot said. “There are very few Afro-Americans on the West Side of Massillon. My children learned to know who they are.”

Brian learned he was drawn to trouble. After his mother dropped him off at Washington, where she was on the school board, he would walk in one set of doors and out another.

“By the time he was in high school, he was almost totally lost to the streets,” said his little sister, who took an opposite path.

Lori Lightfoot sang in the choir. She played trumpet in the famed Tiger Swing Marching band, joined the Pep Club, edited the yearbook.

Lori Lightfoot (left) playing on her high school basketball team in Massillon, Ohio. | Yearbook

Lori Lightfoot (left) playing on her high school basketball team in Massillon, Ohio. | Yearbook

She was elected president three years in a row of her class of mostly white students, running on the slogan “Get on the right foot with Lightfoot.”

“‘Don’t forget you’re Ann Lightfoot’s daughter’ — that was my mantra my entire growing-up years, into my 20s,” Lori Lightfoot said. “What that meant early on was: ‘Don’t go out there and act a fool and embarrass me.’ What it really meant was: ‘Remember you are black and female and from this family, and you have to present yourself in a certain way when you’re out in public.’ So I show very little of my full personality.”

Nevertheless, what she did show made an impression.

“She was not 6-9, but she had power to command, to get people to do what she wanted to do,” her English teacher remembered.

How? “By example. By voice. By her ability to organize. To be able to focus on different things and get them done.”

Her longtime friend Michael Mann, who was student council vice president while she was president, said Lightfoot at times defied expectations of both racial groups at school — that some black students would question her because her precise diction struck them as being white, while whites rejected her because of the color of her skin.

“After a while, Lori’s not black or white,” Mann said. “She kind of broke that image.”


In pageant, ‘she should have won’

Lori Lightfoot’s chain of early successes ended at the Miss Massillonian contest, a pageant in which a dozen Washington seniors competed — at an exclusive country club the Lightfoot family did not belong to — based on grades, activities, essays and standing onstage in formal gowns while answering judges’ questions, including one about how to “get that new boy at school to ask you out.”

“She should have won,” her mother said.

“My view is I should have been Miss Massillonian, and I wasn’t,” Lori Lightfoot said, the injustice rankling nearly 40 years later. “I think the reason I wasn’t was because I was black. Frankly, I was told later I should have been. But they were afraid if they elected a black girl as Miss Massillonian, it would have been a scandal.”

Lori Lightfoot in a yearbook photo from her high school in Massillon, Ohio.

Lori Lightfoot in a yearbook photo from her high school in Massillon, Ohio.

Despite her popularity and involvement in high school, she never considered staying in Massillon. She followed another trumpet player in the band to the University of Michigan, hoping to be a systems engineer because her oldest brother advised her that was the thing to be.

“I had no idea what that was,” she said.

After college, she worked for two years for her congressman, Ralph Regula, a Republican, and capital life pushed her toward lawyering.

“In D.C., there are a lot of lawyers,” she said. “I started talking to people about the legal profession. It seemed the right fit for my personality.”

Lightfoot ended up going to the University of Chicago Law School with a full scholarship. The decision had nothing to do with her brother’s troubles, she said.

“My brother was also a pimp,” she said. “He forced women, beat women to go out on the street and sell their bodies for him. I’m an ardent feminist. That’s something I didn’t agree with, obviously. We had a very different way of living our lives for a really long time.”

They didn’t see each other for decades.

Chicago is where Lightfoot also came out as a lesbian. Though she hasn’t been active in public LGBTQ+ causes, some of her earliest political contributions were to openly gay candidates.

She joined Mayer Brown — working on cases for powerful Republicans such as Henry Hyde and Dennis Hastert on redistricting matters, against African-Americans suing over race discrimination, on behalf of casinos, airlines and other such clients of the multinational firm.

She left in the late 1990s for the U.S. attorney’s office — which she would later unsuccessfully seek an appointment to run — prosecuting drug cases while her brother faced his own charges, later sending felons to the same prison where he ended up.

She was part of the team that prosecuted Ald. Virgil Jones (15th) for corruption, part of the broader Operation Silver Shovel investigation of political corruption in Chicago.

‘A responsibility to give something back’

While a prosecutor, Lori Lightfoot ran into trouble of her own, attracting a rare rebuke from highly respected federal Appellate Judge Richard Posner, who issued a stinging criticism of her “professional misconduct” related to a motion Lightfoot filed in the case of a Norwegian national who was fighting extradition. Lightfoot eventually was exonerated.

Still, she said, “That stays with me. That incident occurred in the summer of 1999 and stayed with me every single day of my legal career. Every time I applied to get admitted to another jurisdiction, it came up. I’ve had opponents bring it up.

“What I did was no different than anybody else,” she said. “Frankly, I couldn’t help but suspect I was this disposable black girl that nobody gave a s— about and that it didn’t matter if I was hurt in any way.”

But she said, “I had no choice but to bounce back. I knew I didn’t do anything wrong.”

Her reputation was solid enough for police Supt. Terry Hillard to tap her in 2002 to head the Chicago Police Department’s Office of Professional Standards, investigating complaints against officers. She vowed then not to let herself become “window dressing,” saying, “I feel like, as an African-American woman, I have a responsibility to give something back.”

She was chosen to head the city’s Office of Procurement in 2005 as Mayor Richard M. Daley (“a really interesting and complicated guy,” Lightfoot said) attempted to escape the shadow of the Hired Truck scandal. She said that post gave her “a very deep knowledge of how the city works,” which is also one reason she didn’t stay long.

“Procurement, in particular, we saw a lot of things that were right on the edge of criminal activity,” she said. “I didn’t want to spend my life in the federal grand jury reporting on things I had seen or heard. It was a tough environment in which to work then. It was time for me to leave.”

‘Rubbed people the wrong way’

At a friend’s house, she met Amy Eshleman, who worked for the Chicago Public Library. The two got married in 2013 on the day same-sex marriage became legal in Illinois. They have an 11-year-old daughter, Vivian, whom Eshleman, 57, cares for as a full-time mom in their Logan Square home.

In 2015, Lori Lightfoot was back on police watchdog duty. Her brisk manner on the Chicago Police Board governing officer misconduct was not always soothing.

“She … rubbed people the wrong way, rubbed families the wrong way,” said Ja’Mal Green, the Black Lives Matter activist who briefly ran for mayor himself. “I think she could have been more receptive to the families. Families felt they were disrespected.”

Lori Lightfoot, then the Chicago Police Board president, at announcement of the Chicago Police Department’s newly revised use-of-force policy on May 17, 2017. | Santiago Covarrubias / Sun-Times

Lori Lightfoot, then the Chicago Police Board president, at announcement of the Chicago Police Department’s newly revised use-of-force policy on May 17, 2017. | Santiago Covarrubias / Sun-Times

Lightfoot acknowledges her reputation for toughness. “I’m certainly demanding on people. I’m tough on people and demanding, but I also care about people who work for me.”

And for her family. She talks with her mother almost every day on the phone and is more in touch with her brother Brian, now 62, who’s free now, and helping care for their mother.

“He’s now involved in the family church,” Lightfoot said, noting that, with his record, he can get only manual labor jobs. “It’s hard. It would be easy for him to slip back into that life.”

Watching Emanuel in action pushed her to decide to run for mayor even before he decided not to run again.

“I came to be very committed to the fact he could not have a third term,” she said. “Because I felt that there were way too many black and brown people, particularly young men, who were going to be left behind and never, ever have a shot, an opportunity, the thing that really transformed my life.

“And when nobody else would stand up, and I started looking at the people early announcing they were going to run against him, I didn’t think those people were ever going to address the issues that I thought had to be addressed or in the way I knew they had to be addressed. That’s what got me really started thinking about this.”

Lightfoot knows that, if she is elected, she will draw criticism, too.

“It comes with the territory: I’m a black woman who operated in a very white world,” she said. “And whether it’s to my face or otherwise, it’s just what happens.

“I know who I am. I have a very, very clear sense of myself. I have a great wife and daughter, good family, a very tight circle of friends. They love me. They support me. They also don’t hesitate to tell me when I’m full of crap and keep me centered. So the external criticism, it comes from the territory of being out there in the public.”

How does she handle being critiqued?

“I listen to it, for sure. I check in with myself about whether or not there’s any legitimacy to it. When I think there is, I adjust accordingly. When I think there isn’t, I keep plowing ahead.”

She is plowing ahead now, as she prepares to bring her complicated life experience to the fifth floor of City Hall.

“I think I’ve had a lot of experience in helping run most challenging city agencies,” Lightfoot said. “I have a very deep knowledge of how the city works, both from that experience, and also I helped a lot of different individuals in business navigate a lot of byzantine processes in the city.

“But I also really value collaboration, and I look forward to the possibility of assembling a really great team of experts and also people who really love the city and recognize, if I win, it’s a mandate for change in a fairly profound way that gives us an opportunity to really do big bold things.”

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