No matter who wins the April 2 mayoral runoff, Chicago will make history: an African American woman will become mayor of the nation’s third-largest city. The candidates are Lori Lightfoot and Cook County Board of Commissioners President Toni Preckwinkle. If elected, Lightfoot would also be the city’s first openly gay mayor.

Lightfoot and Preckwinkle emerged from a crowded field, riding a national wave of support for racially diverse female candidates that swept the country during the 2018 midterm elections.

But neither candidate won a majority of the city’s black vote. While Chicago has a long history of pioneering black political leaders, from the Rev. Jesse Jackson to President Barack Obama, their successes have not translated into improved conditions in the city’s worst neighborhoods, leaving black voters in Chicago skeptical.

White liberals have flocked to Lightfoot, 56, who casts herself as an outsider and candidate of change, but her background as a federal prosecutor worries many black voters. Preckwinkle, 71, also touts herself as a reformer who has pushed for stricter rent control laws and a reduction in the county jail population. But some black residents blame her for facilitating a wave of gentrification that has pushed working-class residents out of Chicago’s South Side.

“People still aren’t any closer to figuring out who the next mayor should be,” said Jawanza Malone, director of the Kenwood-Oakland Community Organization on Chicago’s South Side. “It’s great that they’re trying to ‘out-progressive’ each other now, but Toni Preckwinkle has a checkered past with this community, and so does Lori Lightfoot.”

That tension became clear during the Feb. 26 mayoral primary, when Democratic voters rejected decades of control by the city’s political machine and by Mayor Rahm Emanuel (D), who abruptly decided not to seek reelection in September amid fallout from a policing scandal.

“This is the first time in generations there wasn’t a dominant candidate, which demonstrates that the Chicago Machine has broken down over time. Now it’s just a bunch of rusty spare parts,” said David Axelrod, a former Obama adviser and a veteran of Chicago political campaigns. “That alone is a harbinger of change in Chicago.”

Criticism and praise for the candidates

As a former prosecutor, Lightfoot has faced questions about whether she may be too cozy with police. At the bar earlier this month, she also was asked whether Preckwinkle is fair to suggest that her background as a corporate attorney leaves Lightfoot out of touch with regular Chicagoans.

“I’m a kid who grew up in a low-income family, who struggled hard every day and, frankly, saw firsthand how racial discrimination can tear apart individuals’ families and communities,” Lightfoot told a mostly white crowd at a recent event on Chicago’s affluent North Side

She noted that a relative was killed by the Ku Klux Klan in the 1920s and that her brother spent years in and out of jail and prison.

Lightfoot’s call for unity received a major boost when former opponent Willie Wilson announced that he is backing her for mayor. (Joshua Lott/for The Washington Post)
Lightfoot’s call for unity received a major boost when former opponent Willie Wilson announced that he is backing her for mayor. (Joshua Lott/for The Washington Post)

In a contest where violent crime and policing policies loom large — and the incoming mayor will have to deal with a mandated overhaul of the Chicago Police Department — Lightfoot has also had to account for her time serving as president of the Chicago Police Board, an independent body that oversees disciplinary cases. Activists have been critical of her tenure, saying too many officers avoided punishment.

“When I saw Lori Lightfoot running this campaign on a progressive platform and talking about police reform, I was honestly shocked,” said activist Trina Reynolds-Tyler, a graduate student in public policy at the University of Chicago.

“She was a huge part of enabling police officers to be immune to accountability. ... We need a mayor who will be more vigilant and does not necessarily have such a checkered past with the Chicago Police Department and with Mayor Rahm Emanuel.”

Lightfoot says that the percentage of officers who were fired after being accused of misconduct under her leadership rose from 37 percent to 72 percent. She notes that she led a task force after a white police officer shot and killed black teenager Laquan McDonald in 2014 that issued a scathing report about systemic racism in the police department. She says that better policing, including tackling the city’s dismal rate of solving murders, is a top priority.

“Look at the actual evidence,” she said. “My record of accomplishment on police reform and accountability sets me apart and is a far cry from my current opponent.”

On the North Side, many voters are enthusiastic about Lightfoot. Mohammed Arzek, who recently moved here from New York, said he was eager to vote for a liberal candidate and was pleasantly surprised to see black women in the race.

“I’m looking for someone who represents the tide of [Reps.] Ilhan Omar or Alexandria Ocasio-Cortez, who is making more progressive decisions,” said Arzek, 48, referring to newly minted members of Congress from Minnesota and New York. “Issues like mass incarceration and segregation are being taken more seriously now. They’re more in the zeitgeist for the average schmuck.”

This month, Lightfoot received a major boost when her former primary opponent Willie Wilson announced that he is backing her for mayor. In the primary, Wilson, a flamboyant businessman who handed out cash to locals who were behind on their property tax payments, won the predominantly black neighborhoods, while Illinois Comptroller Susana Mendoza, the daughter of Mexican immigrants, performed well in some of the city’s Latino areas.

“They’ve been so long neglected,” Wilson said of the residents on the South and West sides who supported him. “They’re seeking a change — for the better, not for the worse.”

Wilson said he thinks Lightfoot will do more to help businesses there succeed, noting that she plans to boost vocational education programs and has proposed creating more tax increment financing districts, where a portion of property tax dollars are earmarked for investments to revitalize neighborhoods.

“I think she’s going to really make an impact in those areas,” Wilson said.

Preckwinkle, he said, “is the old guard.”

“She is the leader of the party,” he said. “So, I don’t see no change there at all.”

Preckwinkle, who is backed by several unions, racked up two other prominent endorsements this month — from Alderman Walter Burnett Jr. and Secretary of State Jesse White, both of whom have long been elected with strong support from black and white voters. She touted her own appeal to a racially diverse base, noting that she was elected alderman in Hyde Park, a diverse ward.

“Chicago is 77 communities. We’re going to go everywhere to ask for help and support — African American communities, Latinx communities, majority [white] communities,” Preckwinkle said, using the non-gendered term to refer to Latino people. “I think it’s important you carry the campaign everywhere.”

The historic moment of electing a black, female mayor comes as the city is losing African American residents by the thousands. About 200,000 have left since 2000, census data show, a reversal of the Great Migration from the Jim Crow South that turned Chicago into a hub of blues, African American literature and political activism.

Frustration and hope

Solidly middle-class neighborhoods have emptied out, hit hard by the 2008 housing crisis and Emanuel’s decision in 2013 to close dozens of low-performing schools. In some black and Latino neighborhoods, 10 to 25 percent of the housing stock was abandoned, according to a 2017 study by the University of Illinois at Chicago’s Institute for Research on Race and Public Policy.

Under Emanuel, the city created a Neighborhood Opportunity Fund in 2016 that is supposed to steer density fees charged to downtown developers toward construction grants for businesses in struggling neighborhoods. Of the $38 million collected so far, only $20 million has been paid out.

Preckwinkle says she wants to streamline the grants so they reach entrepreneurs faster and has a plan to raise the minimum wage to $15 an hour by 2021.

Chicago mayoral candidate Toni Preckwinkle arrives for a news conference at her campaign headquarters on March 6. (Joshua Lott/for The Washington Post)
Chicago mayoral candidate Toni Preckwinkle arrives for a news conference at her campaign headquarters on March 6. (Joshua Lott/for The Washington Post)

“We can’t have a world-class city in which we allow this kind of tremendous inequality,” she said in an interview. “All of our neighborhoods have to be thriving.”

Lightfoot has said she wants to create business incubators on the South and West sides and use more property tax dollars to revive those neighborhoods.

But Stephanie Hart, whose Brown Sugar Bakery is on 75th Street in Chatham on the city’s South Side, said local businesses are in need of more urgent help. The city has done little to spur a mini-revival in the area after several older businesses closed following the 2008 recession, she said. And several employees and customers have been affected by gun violence tearing across the area.

In one recent case, a bakery worker’s girlfriend was hit in the head by a stray bullet while she was home sleeping. The woman lived, but the trauma of it caused the employee to move away.

Across the street from the bakery is a weed-filled church parking lot that Hart and other business leaders have tried unsuccessfully to get city officials to convert into parking for local businesses.

“I probably wouldn’t have said this five or 10 years ago, but I’m ready to leave Chicago,” Hart said.

“I’m dragging along, doing what everyone says needs to be done. And, while the words of support I hear feel good, it’s never executed. I love Chicago, but I’m tired of that.”

Pastor Jonathan Brooks of Canaan Community Church, on Chicago’s South Side. (Joshua Lott/for The Washington Post)
Pastor Jonathan Brooks of Canaan Community Church, on Chicago’s South Side. (Joshua Lott/for The Washington Post)

Jonathan Brooks, pastor of the Canaan Community Church in the nearby Englewood neighborhood, sees powerful symbolism in the fact that a black woman will be leading the country’s third-largest city — akin to the hope that surrounded the 1983 election of Harold Washington, the city’s first black mayor.

As church members have either died or moved away, shrinking his congregation by one-third to about 130 people over the past 13 years, Brooks and some of his neighbors have worked to persuade young black professionals to move back to the area and invest in it.

Their group — known by its acronym RAGE — was a driving force in the Emanuel administration’s move to lure a Whole Foods store to the area in 2016. The store now anchors a bustling plaza in an area of the city that is otherwise a desert of healthy food choices.

A black woman as mayor could encourage more African Americans to return to the city and reinvest, said Brooks, a 39-year-old father of two young daughters.

“It doesn’t really matter which one of them wins; it is a hallmark time in our country and in our city,” he said.

But as the campaign heats up, the candidates’ attacks against each other have escalated. They sparred in a debate this month, with Preckwinkle tagging Lightfoot as a wealthy corporate lawyer and Lightfoot dismissing Preckwinkle as a product of the “broken, corrupt political machine.”

“I’d hate to see the magnitude of this moment for my two little girls get squashed,” Brooks said.

“No matter who wins, it’s going to be a black woman running the city of Chicago. I want my two daughters to be able to revel in that.”

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