Mayor Lightfoot says the ‘destiny’ of Black Chicagoans is at stake in the 2023 election. But can she win their votes?

At a South Side diner one recent morning, Chicago Mayor Lori Lightfoot served up a cautionary tale about what might happen if Black voters don’t unite behind her reelection bid.

She told the mostly Black crowd at Huddle House on Stony Island Avenue that the city’s first African American mayor, Harold Washington, spent years feuding with a “racist mob in City Council.” When he died in office in 1987, they voted to replace him with Ald. Eugene Sawyer, who they “thought they could control,” but two years later they “dropped him like a bad habit” and “went all in for (Richard M.) Daley,” she said.

The result? Daley’s long tenure at City Hall and “30 years of people struggling,” Lightfoot said.

“Not having the resources and the control of the city government left Black and brown Chicago the worse for it,” Lightfoot said. “So when you think about what’s up on the ballot, in February of next year, our destiny is on the ballot.”

Lightfoot’s comments during a petition kickoff event led to criticism from some who said she had distorted history and disrespected the memory of Sawyer, whose son is running against her. But it also underscored the mayor’s strategy in the 2023 mayoral campaign as her political base of support has shifted from the lakefront to the South and West sides, creating a unique dynamic for Lightfoot as she seeks a second term.

In the first round of the 2019 mayoral race, Lightfoot emerged from a historic 14-candidate field with roughly 18% of the vote. Much of it came from white lakefront residents on the North Side who backed her over more established politicians. Many of those voters are now disenchanted with Lightfoot, and she has been working vigorously to lock in support from the Black community.

To be sure, Lightfoot is expected to campaign for votes across the city but her attempts to build a new political base with Black voters face real hurdles. Five candidates who have announced their campaigns to unseat her are also Black and enter the contest with their own bases of support on the South and West sides. That large field includes businessman Willie Wilson, who won the city’s Black vote in the first round of the 2019 race and has loaned $6 million to his campaign this year. Wilson has more money in the bank than any candidate, including Lightfoot, an unusual development in a city where incumbents have often handily outspent opponents.

If no candidate secures more than 50% of the vote in the February election — as was the case in 2019 — the race will proceed to a second round between the top two finishers. Lightfoot won all 50 wards in the runoff the last time, but whether she can solidify Black support, expand her base and reclaim disaffected supporters remains an open question that will help determine whether she finishes first, second, or out of the running.

For their part, Lightfoot’s rivals say her argument presents an antiquated notion of racial politics in the city. Three of the four leading vote-getters last time were Black, which challengers say proves that an African American can win even in a crowded field.

“It’s fine for her to rely on the Black community and embrace them as her new base because, she’s correct, that’s the base that still is with her. … Black people tend to be relational and white people tend to be transactional,” veteran Chicago political strategist Delmarie Cobb said. “We will stick with you even when we know you’re not the best for us. Proof of that was sticking with Rahm Emanuel because of (his ties to) Barack Obama.”

But, Cobb added, Lightfoot may run into problems keeping the Black community’s support.

“She can make the argument that ‘I’ve done X, Y, Z after almost 40 years of disinvestment and I’ve come along channeling Harold Washington, I understand what these neighborhoods need.’ But someone else can make the argument, ‘Where have you been? Where were you?’ ” Cobb said. “This didn’t happen overnight. There are people who can make that argument, who are going to be running against her, who can show where they were. They weren’t on the North Side in a nice cozy community with all the resources and amenities.”

Political analyst Ameshia Cross said the mayor has “a lot of work to do to regain the ground she lost” and her message that the Black community may struggle if they don’t vote her may not resonate “when you’re in a sea of Black candidates.”

High crime and politically controversial decisions, such as raising bridges downtown during the height of civil unrest, might cause South and West side residents to be wary of her candidacy, Cross said.

“Lori Lightfoot has a problem and it’s interesting for a Black woman to have a Black problem,” Cross said. “It is a large part of her own doing.”

Lightfoot appeared pleased as she stood next to three political heavyweights within Black Chicago in June. Underneath the DuSable Museum’s black-and-white mural of African American faces, U.S. Reps. Robin Kelly, Bobby Rush and Danny Davis sang Lightfoot’s praises as they endorsed her for reelection.

Combined, their speeches aimed to paint the mayor as a stalwart for the city’s majority-Black neighborhoods, where she has launched the Invest South/West program to fund business development in disinvested neighborhoods.

Lightfoot returned the love and described the trio as “three of the most iconic Black leaders in our country.”

The session highlighted an important aspect of Lightfoot’s strategy: Standing with the Black political establishment. To that end, she also recently announced the backing of outgoing Secretary of State Jesse White, and most of her endorsements from sitting aldermen come from Black and Latino officials.

It wasn’t always like this. Much of the Black political establishment supported Cook County Board President Toni Preckwinkle in 2019. During the runoff that year, Davis knocked Lightfoot’s lack of experience holding elected office, while Rush had said her supporters would “have the blood of the next young Black man or Black woman” killed by the police on their hands. White also supported Preckwinkle.

More than three years later, that hatchet seemed long buried as Rush shrugged off his past criticism.

“That was then, but now is now,” Rush said, drawing a round of laughter from Lightfoot and her supporters.

She has also worked to establish friendlier ties with Black politicians she has previously criticized. Early in her term, Lightfoot feuded with Black Caucus chairman Jason Ervin, who she once slammed in a text as “full of crap.” Lightfoot also battled Ervin’s wife, city Treasurer Melissa Conyears-Ervin, after the mayor’s administration stripped her of her security detail.

But in recent years, Ervin has emerged as one of her closest allies. After Ald. Sophia King announced her bid for mayor, Ervin released a statement warning that “with so many Black candidates in the race and more expected to enter, we run the risk of losing it all.”

“As a community, it behooves us to come together and figure this out or end up walking away with nothing,” Ervin said.

In August, Lightfoot took the stage at the Black Women’s Expo in Bronzeville where she gave shout-outs to Black elected officials including Conyears-Ervin and “our great state’s attorney,” Kim Foxx.

“Keep fighting that fight, keep fighting that fight,” Lightfoot told Foxx from the stage.

Lightfoot’s comments raised eyebrows in political circles because the mayor has been critical of Foxx and the criminal justice reforms she has pushed. Lightfoot has publicly attacked Foxx’s office at least twice and has long spoken out against bond reform, though she often aims her criticism toward judges rather than naming Foxx.

Race is a recurring theme when Lightfoot is defending her actions. She has said “about 99%” of the criticism she gets is because she’s a Black woman.

Lightfoot created an uproar when she refused to grant interviews to white journalists for her two-year anniversary. She said that was meant to highlight the lack of diversity in the press corps, but it led Brandon Pope, president of the Chicago chapter of the National Association of Black Journalists, to later tell WBEZ, “It does feel like we were used for political props.”

Lightfoot also stumbled during an interview with the Triibe, a Black news website, where she was asked about Black businesses she frequents and didn’t name any except one on the South Side.

The Bud Billiken Parade has long been a highlight of campaign season that can illustrate potential pitfalls for a candidate. Glad-handing along the route last month, Lightfoot received a warm reception from the crowd — but so did other candidates.

One paradegoer, Erica AnnMarie Vassell, said she’d found comfort in the mayor’s words in the scary early days of the COVID-19 pandemic. She recalled an April 2020 news conference in which Lightfoot said she personally drove around neighborhoods scolding people who weren’t social distancing.

Vassell, 51, has worked as a nurse’s assistant is now bouncing around shelters on the West Side. She has never voted but is planning to cast a ballot for Lightfoot in 2023, saying she found the mayor’s confidence as a woman inspiring.

“Lori Lightfoot? She’s strong,” Vassell said. “I’m very strong. So I see the strongness that is in me in her. I respect her for being a woman that stands up to so many challenges and changes that’s been going on. She never backed down.”

Carla Johnson, 66, waved a Pan-African flag on the sidelines of the parade as she watched Wilson march past her, wearing a shirt with his face on it.

“Yeah, Wilson!” Johnson shouted with both her arms up.

Johnson said she was a Lightfoot voter in 2019 but is planning on backing Wilson this time. One reason? The sentiment that Lightfoot has caved to the whims of politicians instead of everyday residents like Johnson.

“Willie Wilson is more in tune with what the community is looking for,” Johnson said. “He has gotten out more with the people and got in touch and listened to our needs and our concerns more than I feel Mayor Lightfoot has. I feel like she’s caught in the system.”

Johnson said this year’s spike in gas prices has worried her, and she found Wilson’s multiple rounds of gas giveaways impressive. Though Lightfoot passed her own measure giving away tens of thousands of dollars in free gas and CTA cards in April, Johnson said she had hoped the mayor could have used her influence to freeze the city fuel tax.

Lightfoot’s opponents have been critical of her remarks about Black voters and pledged to compete for their support and others.

State Rep. Kambium “Kam” Buckner, whose district includes downtown and a large segment of the South Side, said he’s offended by the idea pushed by Lightfoot and Ervin that the Black vote will split. He pointed out that four of the six leading vote-getters in the first round of the 2019 race were Black.

“Black folks are not a monolith, and those of us who have spent lifetimes in the Black community in this city know that,” Buckner said. “There are differing opinions that are going to be across the board, but we saw in 2019 that splitting the Black vote trope is not a thing.”

Still, Buckner said he has doubts about her appeal to Black voters.

“The question that’s going to be asked by many people of the Black community is, ‘Where were you?’, not just the last four years, but the four years before that and the four years before that,” he said. “Frankly, I don’t think the mayor has an answer to that that’ll be in line with what my neighbors want to hear.”

Activist Ja’Mal Green, another challenger, said it’s “just incorrect” to assume “that the majority of people will vote based on ethnicity. … Chicagoans will vote based on the leadership they want to see going forward and many ethnic groups will coalesce together behind candidates that represent their values.”

Wilson, who won most of the Black wards in the first round of 2019 voting, said he expects to be “even stronger this time” on the South and West sides.

He contended no other candidate “showed the minority community, particularly people of color, that they care about them. I’ve been supporting the Black community … for the last 30 to 40 years,” Wilson said of his practice of giving away money to needy people. “I haven’t seen anybody else do that.”

South Side Ald. Roderick Sawyer, who’s also in the race and whose father was the subject of the mayor’s breakfast comments, said Lightfoot’s version of history was “reckless and irresponsible,” one of Lightfoot’s go-to lines against critics. Sawyer predicted it wouldn’t be effective and that candidates should be playing to as broad a field of support as they can.

“I think her pandering to the Black community is going to be seen as just that. In order to run an effective race, you should be appealing to everybody in Chicago,” Sawyer said. “And I’m speaking as someone who’s proudly Black, been active in Black causes all my life, not just recently.”

Fellow contender Paul Vallas, former Chicago Public Schools CEO, criticized Lightfoot’s pitch to Black voters as “one of rhetoric and one-off projects on the South and West side.”

“With all the talk of equity, whether it’s her record on crime, schools or her taxes and fines, it’s been the city’s African American residents that have been hurt the most,” Vallas said in a statement. “The growing number of Black candidates in the race reflect the great dissatisfaction with her in the Black community.”

Another mayoral candidate, Ald. Raymond Lopez, whose ward includes Back of the Yards and West Englewood, dismissed Lightfoot’s comparison of herself with Washington.

“She has not delivered for the Black community and they know it. She has never worked or lived their experience, and they haven’t forgotten that,” Lopez said. “And now at the eleventh hour trying to portray herself as the victim of racial politics? I don’t think people are going to buy it.”

Ald. Sophia King, who has criticized the argument made by Ervin and Lightfoot about dividing up the Black vote, said the mayor “is failing to keep Black Chicagoans safe, just like she’s failing to keep everyone else safe.”

“I will keep making the case to voters of every race, that I’ll be a mayor who brings public safety and investments to every neighborhood,” King said.

gpratt@chicagotribune.com

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