On a Sunday morning at a West Side church in March 2019, prominent pastor Rev. Ira Acree became one of the first Black faith leaders in Chicago to endorse then-candidate Lori Lightfoot in the city’s run-off election.

“I marched her down my aisle saying she is the person that can lead us for the next four years … I’m happy we did that because we defeated the machine if you ask me,” Acree said of Lightfoot’s landslide victory over Cook County Board President Toni Preckwinkle in a recent interview with WBEZ.

Acree’s endorsement, along with the support of several other prominent figures, helped Lightfoot gain the support she needed within the city’s Black communities — building on the momentum she garnered among white liberal voters along Chicago’s lakefront. Lightfoot will likely seek support from Black community leaders again as she works to build a base among voters on Chicago’s South and West Sides in her 2023 reelection campaign.

But Acree is one of many who endorsed Lightfoot in 2019 and is not sure whether he’ll make the same choice again.

“She’s made quite a few enemies out here. And her temperament has been kind of, you know, it has a lot to be desired, so it’s gonna be a tough battle,” said Acree, who believes overall that Lightfoot has “done OK,” and may end up supporting her.

Lightfoot has spent the last four years at odds with some of the city’s biggest unions, including the Chicago Teachers Union and the largest union representing Chicago officers, the Fraternal Order of Police. She has engaged in back-and-forth public disputes with Cook County State’s Attorney Kim Foxx over how to stem violence in the city, and has at times had a significantly contentious relationship with the Chicago City Council, contributing at least in part to a pandemic-era exodus of aldermen.

But on the 2023 campaign trail, it’s this tough persona that Lightfoot is embracing, attempting to convince voters that she fights on behalf of everyday Chicagoans, and that she’s been the target of unfair criticism because of her identity as the city’s first gay, Black woman mayor.

Lightfoot comes to the table with a four-year track record that impresses some residents, political allies and community leaders. And though she’s struggled to raise funds in the same way her predecessor, Mayor Rahm Emanuel, did during his reelection campaign, Lightfoot has raised the most money of any candidate aside from businessman Willie Wilson (who is largely self-funding his mayoral run). She also has the name recognition advantage that comes with incumbency.

As Acree put it, with 10 challengers currently aiming to unseat her, “Lightfoot is still the person to beat.” It remains to be seen whether her opponents can build a coalition to defeat her.

“One of the things that works in her favor is that different constituencies … each come with criticisms of her, but they are also opposed to each other, so she does not face a single united front,” said Don Rose, a veteran political strategist who worked for Lightfoot’s campaign in 2019 but is now supporting one of her opponents, Democratic Illinois U.S. Rep. Jesús “Chuy” García.

A South and West side base

After filing what she said were more than 40,000 signatures in her petition paperwork on Monday, Lightfoot is kicking her campaign into high gear. She is banking big on building a base on the South and West sides — painting herself as the mayor who finally invested in some of the most underserved areas of the city after decades of neglect under the Chicago political machine.

Some of the first endorsements she rolled out in 2023 were those of longtime Black Congressmen representing parts of those areas. García’s congressional colleague, Illinois U.S. Rep. Danny Davis, D-Chicago, was among Lightfoot’s supporters as she filed her stack of 2023 ballot petitions — a theatrical display in Chicago politics that’s meant to show a candidate’s strength as campaigns launch.

Lightfoot has also won the support of Ald. Jason Ervin, 28th Ward, who is the chairman of the City Council’s Black caucus. He initially clashed with Lightfoot but has become one of her fiercest council allies.

“I do think that [she’s] looking at the South and West sides as a base of support, and then that’s just not enough to get the job done — you still have to have coalition and other groups across the city that will work with and buy into what you’re doing also,” Ervin told WBEZ in a recent interview.

Ervin said he believes Lightfoot’s record will convince constituents in his West Side ward to help reelect the mayor. He referenced Lightfoot’s signature Invest South/West program, which aims to leverage public funds to attract private investment in 10 high-need areas of the city. A Crain’s Chicago Business analysis revealed, however, that the program has been slow to break ground on any major projects.

Ervin contends that support for Lightfoot is strong even as she faces criticism over her continued support for Police Supt. David Brown — who many of her opponents say they’d fire — and as the city faces high rates of violence, which disproportionately impacts Black and brown residents.

“I think it’s impossible to lay violence at the feet of one individual,” Ervin said. “And it’s an issue that we as a community and African American community need to work with and tackle the underlying fundamentals that create conditions of violence, which I think everyone is looking at and doing,” Ervin said, adding data shows violence is down in the city. Shootings and homicides are down around 15% compared to 2021, which was the city’s most violent year in a quarter century, according to city data.

For Chicagoan Wallace “Gator” Bradley, who is a paid organizer for the campaign, Lightfoot has come a long way since 2019, when he supported Preckwinkle’s mayoral candidacy instead of hers. But Bradley, an ex-gang member who lost his half-brother to gun violence during Lightfoot’s term, said the mayor has won him over. He stood behind Lightfoot as she filed her reelection paperwork on Monday.

Bradley said he believes the television ads Lightfoot’s campaign is running so far will highlight how relatable she is to everyday Chicagoans.

“I saw the human part of her — that she was letting people know: I’m a human being,” Bradley said afterward. “She appeals to me. I went to Lori Lightfoot and told her, ‘I’m with you. And there’s nothing you can do about it.’”

In one of those ads, Lightfoot speaks directly to the camera to say she won’t contend she’s “done everything perfectly” but that her team learns from their mistakes. In another series, Lightfoot delivers pizza to two men playing video games, quipping she’s delivered for Chicagoans, but doesn’t have time to play because she has “work to do for our city.” The ads are meant to speak to older Black and white voters, according to her campaign.

A broader coalition base

But Lightfoot will have to build a coalition across multiple demographics, particularly in a likely run-off election, to secure another four years. And her campaign says she has a track record of success this first term that appeals to all of Chicago.

“We believe there’s something for everybody,” said Valerie Martin, a senior consultant on the campaign. “There are accomplishments for every corner of the city, every pocket of the city.”

Back in 2019, arguably the strongest part of her coalition consisted of white liberal lakefront voters excited about a progressive candidate who’d make history becoming the city’s first openly gay, Black woman mayor.

For the national LGBTQ political advocacy organization LPAC, it’s Lightfoot’s strong personality that helped secure their support for the second time in a row.

“She is unafraid. She took on the coronavirus. She was OK with having cardboard cutouts around the city of herself — being that fierce leader,” said Lisa Turner, the group’s executive director. “She’s also stood up to Fox News, former President Trump. I mean it’s harsh, the criticism that she gets from the right. But she doesn’t take it sitting down. She gets up every day and fights for more equality, more fairness, a more level playing field and the very city that she runs.”

But whether liberal voters along Lake Michigan will show up for Lightfoot in 2023 remains to be seen, and some speculate that a parade of retiring aldermen in the area spells trouble for Lightfoot’s support base there.

Chicago Alds. Harry Osterman and James Cappleman, allies of Lightfoot’s, will retire from the council after this term. Michele Smith abruptly resigned from the council earlier this year. And Ald. Tom Tunney, who is retiring at the end of this term as well, mulled a run against Lightfoot but ultimately decided against it.

At the opposite side of the city, in Chicago’s Southwest Side 19th Ward, voters in 2019 came out in droves to vote for Lightfoot. The ward had one of the highest turnout rates, and 84% of voters cast their ballot for the reform candidate who had the support of their local alderman — Ald. Matt O’Shea.

O’Shea’s endorsement came at a pivotal time and contributed in part to Lightfoot’s win. Heading into 2023, O’Shea told the Sun-Times a Lightfoot endorsement from him would cause a “civil war” in his ward, a majority white area that includes conservative Mount Greenwood and Beverly.

“I think that base is largely gone,” said Rose, the veteran political strategist. “But it could come back in the run-off depending on who she’s running off against. But it was a very important element in the [2019] coalition she ended up with, you know, when she went from 18% of the vote [in the general] to 70% [in the run-off].”

The union base

Lightfoot’s 2019 support featured a long list of unions, including ones representing CTA bus and train workers, the plumber’s union and more.

While major progressive unions like the Chicago Teachers Union and SEIU Local 73 have endorsed her opponent, Cook County Commissioner Brandon Johnson, in the 2023 race, Lightfoot has been rolling out a steady slew of union endorsements herself.

Her reelection team believes the mayor’s pro-union track record is one of the strongest pieces of Lightfoot’s campaign.

But a nod from union leadership doesn’t always influence the entire body. Members of the Plumbers Union Local 130, for instance, which has endorsed Lightfoot, reportedly booed her off stage at at a previous event.

In the last election, another union that secured Lightfoot’s support was Sprinkler Fitters Local 281 — a group representing around 1,500 sprinkler system installers in the city. The union’s leader, Bryan LaRoche, said he’s still deciding who to endorse in 2023, but downplayed the influence of his decision on the mayoral race.

“I don’t think it’s going to sway any of my members,” he said. “I think my members that live in the 19th Ward,” around 500 of them, he said, “have their mind made up.

“[A Lightfoot endorsement] could affect me in my next election [as union leader], is what it could do,” he said with a chuckle.

For Acree — who endorsed Wilson in the first round of the election last time before throwing his support behind Lightfoot in the runoff — it all depends on who’s left standing after February’s election.

If Lightfoot were to face a runoff, and he had to choose between her and one of her more conservative opponents, such as Paul Vallas, Acree said there’s no doubt he’d support the incumbent.

But between García and Lightfoot? That would be more difficult, Acree said.

“If I went with my heart, I would go with Lori Lightfoot. Because she is a Black woman with many struggles. I can relate to them,” Acree said. “But if I went with who I think would be a better mayor, who’s more competent, who’s most prepared? Who has a history of fighting corruption? Then I will go with Chuy García.”

Mariah Woelfel covers city government and politics for WBEZ. Follow @mariahwoelfel.