Chicago Prepares to Elect Its First Black Female Mayor

When Lori Lightfoot won the first round of voting for Chicago mayor, in February, she did something typically shrewd. With news cameras broadcasting live, Lightfoot, who until recently had been an afterthought in polling, delivered a polished speech introducing herself to viewers tuning in to her campaign for the first time. She had outworked thirteen opponents, some with bigger names and deeper pockets, but now she was in a runoff against Toni Preckwinkle, the head of the Cook County Democratic Party. To win, she needed a lot more people to know her story.

Lightfoot spoke of the skeptics who told her that she had good ideas but no path to victory against Bill Daley, a well-funded candidate whose father and brother were Chicago mayors, or Susana Mendoza, a rising star repeatedly elected citywide, or Preckwinkle, who hasn’t lost a race in thirty-two years. “And it’s true,” she told the cameras and the buoyant crowd, “that not every day a little black girl in a low-income family from a segregated steel town makes the runoff to be the next mayor of the third-largest city in the country.”

Whoever wins, Chicago will elect its first black female mayor on April 2nd, to replace the two-term incumbent Rahm Emanuel, who announced last fall that he would not seek reëlection. The race isn’t over, and pundits have been wrong before, but money and momentum are flowing toward Lightfoot, a fifty-six-year-old corporate lawyer and former Assistant United States Attorney, who served as the president of the Chicago Police Board until she resigned to launch her campaign. On policy, little separates Lightfoot and Preckwinkle, who talk of spreading the wealth of a booming downtown and gentrifying inner core to the city’s tattered, violent outer reaches. But Preckwinkle, who turned seventy-two this month, has been in office for nearly thirty years, and has built alliances with unsavory politicians. Lightfoot has not.

“This was always going to be a change-versus-old-guard election,” Pete Giangreco, a Chicago political strategist who most recently worked for Mendoza, told me. “Lori got on the air with a really good ad, telling a story about putting an alderman away, as a prosecutor. That dovetailed with being an African-American woman, being gay, being a mom—all of these attributes that, particularly, younger white progressives like. People said, ‘We want change,’ and there was nothing Toni could do to stop it.”

Lightfoot grew up in Massillon, Ohio, where she was a five-feet-one-inch point guard for the high-school basketball team and a three-time class president. Her father worked low-paying jobs, including as a janitor, shoeshine man, and barber. Before she was born, he fell into a yearlong coma and lost his hearing. Her mother was a health-care aide who served on the school board and, like her daughter, liked to be in charge. Lightfoot graduated from the University of Michigan and the University of Chicago Law School. Of her three siblings, one became a postal worker and one a city planner, while the third spent most of his adult life in prison. Now in his early sixties, with only a high-school education and no work experience, he is struggling to build a life. Lightfoot mentioned this in her Election Night speech, to signal to skeptics that she understands the impact of policing and incarceration, the most contentious issues in the campaign.

There were five hundred and sixty-one murders in Chicago last year, more than in New York and Los Angeles combined. The police department, which is plagued by corruption, overwhelmed by the frequency of violence, and often unable to get help from mistrustful witnesses and victims, solves fewer than one in five homicides. Residents are moving away from the city, particularly African-Americans upset by the violence and a large number of poor public schools. Emanuel moves easily among the downtown élite and commands loyalty from the fifty-member city council, but he has never persuaded working-class black Chicagoans that he understands them or has their backs.

Preckwinkle, who is formidable without being entirely popular, is trying to paint Lightfoot as similarly disconnected from the city’s most troubled black precincts. She chides her for living on the city’s more prosperous North Side, and for making millions at one of the country’s largest and richest law firms, Mayer Brown. In a fractured city with 2.7 million residents and a budget of nearly four billion dollars, Preckwinkle does not hide her disdain for Lightfoot’s thin public-service résumé, telling an audience at Chicago State University, “I think it’s easy to talk about change. It’s hard to actually make change, and that’s what I’ve done my entire political career.”

To have a chance of winning, Preckwinkle will have to attract a commanding majority of voters in predominantly black working-class wards on the South and West Sides, something she struggled to do in the first round, when she finished with sixteen per cent of the over-all vote, one and a half percentage points behind Lightfoot, in a fourteen-candidate field. “We’re working hard to strengthen our base in the African-American community,” she told me, after a rally with health-care workers in Douglas Park. “I’m an African-American elected official and I start with the African-American community. That’s my base, and we’re going to move out from there.”

The challenge is evident in the Twenty-eighth Ward, on the West Side, where Preckwinkle opened a storefront office in December, in a one-story building next to a vacant lot. Staff and volunteers ran phone banks, distributed signs, and knocked on doors. Yet, in the ward, Preckwinkle finished far behind Willie Wilson, a wealthy businessman who handed out tens of thousands of dollars in cash, saying he wanted to help Chicagoans in need. He won fourteen predominantly black wards, with Preckwinkle finishing second in all of them. He then endorsed Lightfoot.

At the field office the other day, Bertrice Hall, a retired union worker and former precinct captain from the South Side, was on her cell phone, trying to persuade a reluctant voter to cast a ballot for Preckwinkle. “Vote for Toni,” she said each time the man paused describing his difficulty in finding a job. She listened patiently and told him that she would pray for him: “You’ve got to ask God for what you want in life. He doesn’t always come when you want, but he’s always on time. You have a blessed day, and don’t forget what I told you.”

Between calls, Hall, who was seated near a hand-painted sign that read “Smile when you dial,” explained that Preckwinkle may not be pristine, but she gets the job done. “Ain’t nobody going to run over her,” she said. “That’s what I like about her. She’s paid her dues here in the city.” And Lightfoot? “Never been elected to nothing. She’s an attorney. She’s not a negotiator. She’s not a proven leader. Who jumps right to the top? Go and run for alderman or commissioner or something.”

Preckwinkle has played the experience card early and often. “Look, this is not an entry-level job,” she told me. “I think it’s really important that the mayor of the city of Chicago know how to govern.” And then she laughed. Repeat visitors to an endless series of candidate forums might recite her record of nineteen years as an alderman, followed by eight years on the Cook County Board of Commissioners, and also her work in building affordable housing and her efforts to straighten out the budget, expand health care, and reduce the number of nonviolent offenders in the Cook County Jail. They know that she wants a police superintendent who, as she put it to voters at Malcolm X College, “acknowledges there’s a code of silence in the police department and there’s racism in the police department.”

It’s a significant record, but Preckwinkle has been undone by the friends and allies she courted along the way. Nearly three dozen members of the Chicago City Council have been convicted of crimes since the early nineteen-seventies, most recently on March 21st. Preckwinkle looked likely to coast into the runoff until federal prosecutors charged the alderman Edward Burke, then the chairman of the city’s finance committee, with attempting to extort favors from the owners of a Burger King located in his Southwest Side ward. In addition to trying to steer business to his law firm in return for city permits, prosecutors said, he allegedly sought one of the owners’ attendance at a Preckwinkle fund-raiser at his home. The owner did not attend but contributed ten thousand dollars to the campaign, prosecutors said. Preckwinkle, who has not been accused of wrongdoing, returned the money, yet many voters weary of corruption see her as tainted. (Burke denied the allegations and won reëlection in February.)

“Preckwinkle is part of the old Cook County party. She’s the chairman! How are you going to remove yourself from that?” Deborah Echols, a South Side resident, said, after listening to Preckwinkle and Lightfoot speak at Trinity United Church of Christ, the former church of Barack and Michelle Obama. The link leaves Preckwinkle with little room to maneuver. “The dynamic started with the Burke indictment,” Giangreco, the political strategist, said. “It changed the race from the usual schools—crime, pensions, and jobs—to, Are we really going to stay with the Chicago Way and let the system be the system? It played into Lori’s hands.”

Sharp, serious, and ever disciplined, Lightfoot delivers well-ordered prescriptions for a city where the have-nots are afraid of becoming the never-wills. After her runoff victory, she picked up a wide array of endorsements and campaign cash, allowing her to run television advertisements in English and Spanish while Preckwinkle, low on cash, mostly went dark. The star of one ad is Albert Cleveland, who spent twenty-one years in prison on a murder conviction before Lightfoot and her colleagues, working pro bono, managed to free him. In another ad, Lightfoot’s eleven-year-old daughter, Vivian, hams it up, doing a Fortnite dance and playing a trumpet in the background while Lightfoot emphasizes her own ability to focus. She is the first openly gay candidate to run for mayor. At campaign events, she speaks of her partner, Amy Eshleman, a fifty-seven-year-old former Chicago Public Library executive. They married in 2014, on the first day that gay marriage became legal in Illinois.

While polls show her with a large lead, Lightfoot is facing attacks from voters and activists on the left who contend that she is a progressive in name only, and that she too often took the side of the police department when she led the nine-member Chicago Police Board, a civilian body that rules on police-misconduct cases. During Lightfoot’s tenure, the board sided with police less often in disciplinary conflicts, firing roughly seventy-five per cent of officers whose actions were under consideration, compared with forty per cent in previous years. Later, appointed by Emanuel, she chaired the Police Accountability Task Force, which noted “a long, sad history of death, false imprisonment, physical and verbal abuse and general discontent about police actions in neighborhoods of color.” The task force declared that the department had woefully failed to hold officers accountable and called for substantial reforms.

“With Lori Lightfoot, we don’t have a record of public service, and that which we do have is not a progressive record,” Eve Ewing, a University of Chicago assistant professor and social critic whose book, “Ghosts in the Schoolyard,” focusses on school inequities, told me. “This city is really hurting. How are we going to critically address the culture—not the few bad apples, but the culture—of our police department?” A more vociferous critic is Charlene Carruthers, a founding national director of Black Youth Project 100, better known as B.Y.P. 100, part of the Movement for Black Lives. She contends that Lightfoot pays too little attention to victims of police brutality. She told me, “Lightfoot’s record shows where she has invested her time, and it hasn’t been as a public servant improving our communities but as a representative of the state and a system that we know has committed systemic harms against our people.”

In a pair of conversations as she campaigned, I spoke with Lightfoot about policing and the city’s violence, which lies at the heart of her argument for election. More than twenty-one thousand people have been shot in Chicago in the past seven years, according to a database maintained by the Chicago Tribune. She sees the city’s violence as an epidemic and argues that it should be treated as a public-health crisis. “Reframing it in that way forces us to look at the root causes of the violence,” she said. “These explosions of violence—the underpinning is about poverty. It’s about lack of opportunity. It’s about neighborhoods that have seen no investment and are living in Depression-era conditions for decades, and feeling like the promise and the prosperity of our gleaming, beautifully welcoming downtown is a mockery of their daily existence.”

Ever measured, Lightfoot tends to speak in a soft voice, and shows little emotion in public. This is what she has to say about the work of police officers: “They are thrown into the midst of a lot of circumstances that are way beyond their ability to be able to understand or solve. Don’t get me wrong. I’m not absolving the police for anything, because I think they’ve got a lot of literal blood on their hands, for a number of transgressions going back really to the beginning of our republic as we know it. The modern policing model. But they walk into very volatile situations every single day and see firsthand, up close and personal, the results of our collective neglect of people, families, and neighborhoods.”

I asked how she will prove to her critics that she can be trusted to remake the beleaguered department. “My north star is very clear,” she said. “I care a lot about police reform and accountability. I care a lot about making sure that we bring safety to our neighborhoods. For the small crew of activists, I don’t know that I can convince them. I just have to keep doing what I’m doing.”

On the campaign trail, the relationship between the candidates is icy at best, with Lightfoot increasingly pointed in calling out what she sees as low blows by the Preckwinkle camp. If she wins on Tuesday, as expected, she will need to work with Preckwinkle, who will remain the president of the board that runs Cook County, the second-most populous county in the country, with 5.2 million residents. For some voters, the prospect of two strong black women holding power in Chicago for the first time is exciting. “I’m looking for good government,” Thomas Wortham, a retired Chicago police officer, said, after watching Lightfoot and Preckwinkle at the Trinity United Church of Christ forum. “These women, they’ve got gumption. No one can intimidate them. They’re going to get in there and do what they need to do.”