Lori Lightfoot Credit: Doug McGoldrick

One indication that Lori Lightfoot is not your standard politician came at the end of the Chicago Teachers Union’s forum in December, when mayoral candidates were offered the chance to ask each other questions.

This has become a standard feature of political debates, and it allows candidates to launch “zingers” at each other. The next day’s headlines focused on Toni Preckwinkle’s question to Susana Mendoza about her earlier support of the death penalty and on Mendoza’s question to Preckwinkle about her soda tax.

When it was Lightfoot’s turn, she asked Paul Vallas what he thought about the changes and challenges in Roseland, the far-south neighborhood where he grew up. He gave a thoughtful and reflective answer. She scored no points. It was as if she was just there to have an intelligent conversation about issues facing the city.

Lightfoot is not from central casting. If elected, she would be the city’s first black woman mayor and the first lesbian mayor. In public, she doesn’t offer oratory so much as she presents arguments. One-on-one, she has a quiet focus and a wit that can be affable or cutting; her eyes have a searching intensity that draws you in.

Like most of the other candidates in the race, she’s never held elected office, but she does have an extensive background in government—in her case, in criminal justice and as a troubleshooter in some of the city’s most challenging agencies. Indeed, parts of that background—as a federal prosecutor and as head of the police department’s Office of Professional Standards—have given pause to some activists who might otherwise have been drawn to her call for “a new progressive vision for the city.”

Supporters argue that her working-class roots and what the Sun-Times has called the “independent streak” that’s characterized her career—particularly the leading role she played in pressing Mayor Rahm Emanuel to get serious about police reform—reveal the kind of mayor she would be: one who would stand up to political pressure and reorient city government to serve neglected communities.

Raised in a struggling working-class family in southern Ohio, Lightfoot credits her mother, now 90—a health-care aide who served for 25 years on the local school board—as her role model, someone who “truly was fearless,” who taught her “not to shrink from a challenge, to take on hard fights” without concern for the consequences.

After college Lightfoot worked in the Washington office of the local congressman. Then she went to the University of Chicago Law School, where her independence came to the fore. That time was “really tough,” she told me recently. Despite growing up in a small segregated town, she said, “I never felt more conscious of my race than I did in my three years in Hyde Park.” Each year saw major racial incidents “created or exacerbated” by the law school’s administration. In her third year, when she was president of student government, a friend complained about racist and misogynist comments by a recruiter for Baker & McKenzie. Despite the fact that the law firm was one of the biggest in the world—and a major benefactor of the law school—Lightfoot led a successful fight to have its recruiters banned from campus.

Lightfoot spent six years at the white-shoe law firm of Mayer Brown; in two stints there she’s worked on two lawsuits brought by Republicans challenging congressional redistricting. She now argues her interest was in promoting greater Latino representation, but in 1991 all parties agreed to a new Latino-­majority district; in 2010, “Lightfoot’s filings and arguments in the case clearly contend that the map was unfair to Republicans,” according to Crain’s.

In 1996, urged on by a mentor at Mayer Brown, Lightfoot joined the U.S. Attorney’s Office. She was motivated in part by the fact that the office was “almost exclusively white male”; in her view people of color needed to be represented, particularly given the wide latitude in investigating and charging enjoyed by federal prosecutors. She also cites family history when describing her motivation. Her grandmother’s husband was murdered by a Klansman in the 1920s, when “there was never any thought that the guy would face justice”; an older brother has been in and out of prison, which she has said gives her insight into the impact of crime on families.

She prosecuted violent crime extensively in addition to bankruptcy fraud and public corruption. She helped convict former 15th Ward alderman Virgil Jones of taking a $7,000 bribe in the Silver Shovel scandal. It was the height of the war on drugs, which she now criticizes as resulting from politicians who wanted to look tough on crime without regard for the “devastating” consequences increased incarceration would have on communities. As for her role, she told me, “I was a federal prosecutor enforcing existing federal law.”

Lightfoot became chief administrator of OPS in 2002 and led it for two years. A Chicago Tribune investigation of that period revealed a pattern of cursory investigations, sometimes involving no more than a review of police reports. Lightfoot now says she made numerous recommendations to terminate officers for unjustified shootings, and that the agency for the first time recommended firing officers charged with lying in an investigation, but the recommendations were generally rejected. The problem, she says, was that the agency was part of the department it was charged with investigating.

Lightfoot went on to be a top administrator at the Office of Emergency Management and Communications in 2014; she has recalled getting dirty looks from officers who’d been assigned to the 311 call center as a result of disciplinary actions she had recommended. In 2005 Lightfoot was appointed deputy chief of the procurement department under Mary Dempsey, in the wake of a scandal involving minority contractor fronts run by a white family close to Mayor Richard Daley.

According to the Sun-Times, Dempsey and Lightfoot “made waves by taking on powerful targets,” including wheeler-dealer Tony Rezko, who was later convicted on corruption charges. She and Dempsey also went after top Daley fund-raiser Elzie Higginbottom. (Higginbottom is a part owner of the Reader.) Mayor Daley reportedly felt they had gone too far.

Lightfoot left after a few months, concerned, she now says, that corruption wasn’t being adequately addressed.

Dempsey was Daley’s longtime library commissioner—she resigned after Emanuel’s first budget included deep cuts for libraries—and her assistant commissioner was Amy Eshelman, who is now Lightfoot’s wife. They married on the day Illinois made gay marriage legal. Dempsey is now a top donor to Lightfoot.

Lightfoot returned to Mayer Brown, and in 2015 Emanuel appointed her president of the Chicago Police Board. The board was notorious for overriding disciplinary recommendations by the police superintendent. Under Lightfoot it changed course, terminating officers in 72 percent of the cases it heard. As board president she was sometimes the target of vociferous protests, particularly calls for the firing of Detective Dante Servin, who shot and killed Rekia Boyd, though at the time his case wasn’t before the board.

A few months into Lightfoot’s tenure at the police board, a judge ordered the city to release video of Laquan McDonald’s shooting by Officer Jason Van Dyke. The U.S. Department of Justice announced an investigation of CPD, and under fire for having kept the video under wraps, Emanuel appointed Lightfoot to head a Police Accountability Task Force.

Issued in April, the task force report was scathing and systematic. “The community’s lack of trust in CPD is justified,” it found, citing pages of data about disproportionate shootings, tasings, traffic stops, and street stops of black residents. The report also found an “utter lack of a culture of accountability” in the department, and charged that union contracts have “essentially turned the code of silence into official policy.”

From that point Lightfoot became a leading voice pushing Emanuel to move on police reform, sometimes occupying a middle ground between protesters and the mayor, but often criticizing Emanuel sharply. She slammed him when he tried to head off a federal consent decree with a memorandum of understanding with the Trump Justice Department, saying the proposed agreement was “fundamentally flawed” and “sets the police department up for failure.” She pressed publicly for measures to increase the independence of the new Civilian Office of Police Accountability and called the mayor out for failing to follow through on a community oversight board. She has repeatedly pointed to the many task force recommendations that Emanuel has ignored. She criticized the proposed state-city consent decree for lacking bans on chokeholds and shooting into crowds and for failing to mandate a foot-pursuit policy. She has also been a forthright critic of the leadership of the Fraternal Order of Police.

When her police board term expired, Emanuel hesitated, but under public pressure and after a long meeting—where he reportedly pressed her about her intentions to run against him—he reappointed her.

Given that history, it wasn’t a surprise that less than a year later Lightfoot announced she would run against Emanuel. She promised a progressive campaign that would challenge the status quo. She raised hundreds of thousands of dollars, much of it from the legal community—nothing near the millions Emanuel had amassed, but enough to position her as a challenger, perhaps even his foremost challenger.

But when Emanuel dropped out, several more established candidates entered the race, and Lightfoot dropped back in the pack. Lightfoot has focused her fire on County Board president Toni Preckwinkle, another black woman who casts herself as a reformer. Lightfoot charged Preckwinkle with trying to “bully” her out of the race, and as the Ed Burke scandal unfolded, she hit Preckwinkle repeatedly for her slow response.

With more than a dozen candidates, the election has a horse-race aspect that tends to overshadow the merits of individual candidates. That doesn’t help Lightfoot. Her most prominent supporter, former reform alderman Dick Simpson of the 44th Ward, says “she has the background, qualifications, temperament and policies that we need in a mayor.” She does seem like the antithesis of Rahm Emanuel—calm, focused, principled, and independent. The question her campaign poses is an old one: Is Chicago ready for reform?  v