From Outsider To Incumbent Under Siege: Chicago Mayor Lori Lightfoot’s Rocky Road To Reelection

CHICAGO ― On a rainy morning in the historic Bronzeville district earlier this month, Lori Lightfoot, Chicago’s embattled first-term mayor, was fired up. Flanked by more than a dozen Black clergymen and small-business owners, she recounted the biblical story of Joshua, who brought down the walls of the city of Jericho with the trumpeting of horns. So, too, Lightfoot insisted, would her second term in office tear down the barriers to investment in the city’s underserved communities.

“This, ladies and gentlemen, is our Jericho moment!” she declared, prompting cries of affirmation from the ministers standing behind her.

But then, as lyrical speeches gave way to a brief question-and-answer period with reporters, a veteran Chicago journalist brought the discussion back to the prosaic matter of Lightfoot’s treacherous path to victory.

Given the hostility that Lightfoot faces from both her right and her left, the reporter asked, what “base” of voters in the city can she claim as her own?

“My base? My base is all over,” she replied. “You listen to people that have stood up and endorsed me ― all over Black Chicago, brown Chicago, white Chicago. From the tip of the city, from Roseland, all the way up to Rogers Park ― East and West.”

Voting in Chicago’s nonpartisan, citywide elections comes to a close on Tuesday. (Early voting in the race to lead the country’s third-largest city began on Jan. 26.)

If no candidate for mayor gets more than 50% of the vote, a two-person runoff will decide the winner on April 4.

Lightfoot has eight challengers: Paul Vallas, a former CEO of Chicago Public Schools and past city budget director; U.S. Rep. Jesús “Chuy” García (D); Cook County Commissioner Brandon Johnson (D); businessman Willie Wilson; activist Ja’Mal Greene; Illinois State Representative Kambium “Kam” Buckner (D); and Chicago City Council members Sophia King (D) and Roderick “Rod” Sawyer (D).

The crowded field alone virtually guarantees that no one will get an outright majority in the first round. The outstanding question is whether Lightfoot, who is barely holding on to second place in a recent poll, will make it to the runoff, let alone win a second term.

Vallas, a centrist and the only white candidate, is the consistent polling leader in Tuesday’s election, and some prognosticators believe he’s the front-runner. Vallas’ ties to more right-wing figures and groups have at once spooked progressives and emboldened Lightfoot, who portrays herself as the only viable alternative to Vallas’ bid.

HuffPost spoke to more than 30 rank-and-file Chicago voters, two Christian ministers, four City Council members (often referred to as aldermen) and the top-five polling candidates in the mayor’s race.

What emerged is a portrait of a mayor with considerable accomplishments, beset both by crises that are not entirely in her control and some problems of her own making.

Lightfoot, who is both Chicago’s first Black woman mayor and its first openly gay mayor, faces headwinds that would test any leader’s mettle. She is one of the first incumbent, big-city mayors seeking another term in office after presiding over the onset of the COVID-19 pandemic, the unrest following the police killing of George Floyd and a rise in violent crime that has swept the country.

The spike in crime has hit the racially segregated Windy City especially hard, given the disproportionate level of violence already plaguing predominantly Black, high-poverty neighborhoods on the city’s South and West sides.

But if Lightfoot falls short, it will also be because her hard-to-pin-down ideology and her reputation for abrasiveness have left her with precious few allies.

“When you are plotting a course that bounces between ideological lanes or some other category, you’re in this weird mush zone,” said Alyssa Cass, a New York City-based Democratic strategist who has advised candidates in similar situations. “You can say you’re not left and you’re not right, but that’s really hard to do. Are there enough people supporting you when you piss off the people on the left and the people on the right?”

“It’s sort of like a Goldilocks problem,” Cass added. “It’s easier to be too hot or too cold. But it’s harder to, say, sear something medium-rare.”

Disappointing Progressives

Lightfoot, a former federal prosecutor and trial lawyer, had never served in elected office before running for mayor in 2019. She turned that inexperience into an advantage, running as a bold reformer who got results as a watchdog for the city’s troubled police force under then-Mayor Rahm Emanuel.

Leveraging an especially strong showing in the affluent “lakefront liberal” neighborhoods on the North Side, Lightfoot came in first place against 13 other candidates in the first round of municipal elections and romped to a landslide victory in the runoff. In her inaugural address, Lightfoot laid out a progressive vision for the city in which development would not be limited to the gleaming skyscrapers of the downtown Loop, public schools would provide a path to upward mobility and underprivileged residents would live without either fear of violent crime or police misconduct.

Almost immediately, the city’s sizable community of progressives and leftists, which had grown into a veritable force in the preceding years, became disillusioned by Lightfoot’s leadership.

Lightfoot’s critics on the left fault her for restoring previously slashed mental health care funding through private providers rather than city-run clinics, watering down a civilian police oversight board that she had run on erecting and fighting the creation of an independent, elected school board after campaigning on its adoption.

The lack of consequences for police officers involved in the 2019 police raid of social worker Anjanette Young’s home also heightened progressive criticism of Lightfoot early on in her tenure. Young, who was pursued based on a bad informant tip, was left naked and handcuffed for the length of the raid. The city then tried to block the release of the cops’ body-camera footage.

“She campaigned as a progressive reformer and then governed like Rahm 2.0,” said Alderman Carlos Ramirez-Rosa (D), a member of the Democratic Socialists of America.

Ramirez-Rosa is supporting Johnson, a former Chicago Teachers Union organizer who has his union’s backing. If elected, Johnson would likely be the most progressive mayor in Chicago’s history. The heart of Johnson’s agenda is a budget plan that would raise an estimated $1 billion in new revenue through a cluster of progressive tax hikes that are simultaneously designed to spare homeowners an increase in property taxes.

Johnson is perhaps the only candidate in the race who is not promising to immediately fill the police department’s 1,600-person deficit from its 2019 levels, proposing instead that the city find $150 million in efficiency savings that he would use to add 200 more detectives through internal promotion.

“My public safety plan is an investment plan that gets at the root causes while also addressing the immediate crisis that we are experiencing right now,” Johnson told HuffPost in an interview.

Progressives aligned with Johnson also note that the Chicago police budget has actually gone up 15% since 2019, and that the size of its per capita presence in the city has nearly tripled since 1964.

Johnson is experiencing something of a last-minute surge. He landed in third place, behind Vallas and Lightfoot, respectively, in the most recent public poll, which was conducted by Victory Research, an independent firm. If the results are accurate, Johnson will have surpassed García, once the city’s most influential progressive.

But that same rise has made Johnson a juicier target for his mayoral rivals, who ganged up on him in the final pre-election debate on Feb. 13.

Lightfoot is airing two ads painting Johnson as a proponent of “defunding the police,” based on his sponsorship of a resolution in July 2020 calling for Cook County to “redirect” resources from law enforcement and incarceration to social programs.

Her digital ad uses video footage from a radio interview in which Johnson uses the word “defund” to describe his efforts to direct resources away from law enforcement.

“I don’t look at it as a slogan. It’s an actual real, political goal,” Johnson says in the ad.

Currently, Johnson has ruled out cutting Chicago police funding, according to a statement his campaign provided the Chicago Tribune recently. He also insisted to HuffPost that his fundamental position has not changed since he sponsored the countywide resolution in 2020.

“You have to do what safe American cities do all over the country: You invest in people – that’s what the [Cook County] resolution calls for,” he told HuffPost.

For progressive voters worried that Johnson goes too far, García, a veteran of the City Council and Cook County Board of Commissions before heading to Congress, offers a more familiar and less radical alternative.

García has argued for pairing recruitment of police officers with additional investment in underprivileged neighborhoods. It’s a platform similar to Lightfoot’s, but García says that new, more competent leadership is necessary to actually get it done.

“The type of leadership on the fifth floor makes a world of difference,” García told HuffPost, referencing the floor of City Hall that the mayor occupies.

Lightfoot has attacked García on the TV airwaves early and often, hitting him for benefiting from the largesse of FTX founder Sam Bankman-Fried’s pandemic preparedness super PAC, which spent nearly $200,000 on García’s behalf in a Democratic primary in which he was uncontested. García has said he knew nothing about the spending or the reason for it and plans to honor a request by Bankman-Fried’s creditors to return Bankman-Fried’s individual $2,900 contribution to the clients whom Bankman-Fried allegedly swindled.

Critiquing Lightfoot’s Style – And Substance

That Chicago progressives now favor other candidates despite Lightfoot’s reforms is only more evidence that Lightfoot should have never tried to accommodate them in the first place, according to Alderman Raymond Lopez (D), one of the City Council’s most conservative members and a harsh critic of her handling of civil unrest in 2020.

“Now that they have completely rejected her for one of their own, she’s trying to come back to the middle and say, ‘Look, I’m as common-sense as you are,’” said Lopez, who has endorsed Willie Wilson, a multimillionaire self-funder who wants cops to “hunt [criminals] like a rabbit.” “And people like myself and others are not going to let anyone forget that she’s nothing like us.”

Indeed, as Lopez’s outspokenness attests, progressives aren’t Lightfoot’s only critics – or even her main ones. A deterioration in public safety has sparked a more generalized sense of dissatisfaction with the mayor.

Amid the COVID-19 pandemic and heightened tensions with police following the May 2020 murder of George Floyd in Minneapolis, Chicago followed the national trend of higher crime ― only the effect was worse, because the city was starting from a higher baseline. There were 800 murders in Chicago in 2021, far more than in either New York City or Los Angeles, cities with much larger populations and which also experienced a spike in violence.

Murders in the city dropped by 14% from 2021 to 2022 but stayed at their fourth-highest level since 1999. Meanwhile, robberies and car thefts, which went up over the same period, are now orders of magnitude higher than they were at this point three years ago.

As usual, the crime wave has hit the city’s poorest neighborhoods hardest. But a rash of incidents in Chicago’s downtown business and shopping districts have been especially shocking to the city’s professional class, costing Lightfoot the support of many of the middle-class and affluent voters who put her in office.

Diane Andrews, a real estate agent from the South Loop, had voted for Lightfoot in 2019, appreciating what she saw as Lightfoot’s “fresh perspective.”

But Andrews was wearing a Vallas pin after a meet-and-greet with the former school district chief at an Italian restaurant on the near South Side earlier this month.

Andrews dislikes Lightfoot’s “combative style” and associates it with the city’s problems.

“It’s not productive,” she said. “Crime has gone up.”

Lightfoot, whose tenure has been marked by feuds with the city’s influential police and teachers unions, some business leaders, and numerous members of the City Council, has repeatedly admitted that her delivery sometimes rubs people the wrong way.

She is hoping voters judge her instead on the progress that she believes she’s made under difficult circumstances, touting her investment in economic development in underprivileged communities, a steady reduction in the city’s COVID-era budget shortfall and the arrival of major new businesses, including a long-sought-after casino. A Lightfoot TV ad in January even notes that she has presided over increases in police funding.

“We’re not at the finish line,” she told HuffPost. “But there’s been a lot that’s been done to move things in the right direction.”

She has also suggested that criticism of her style often stems from racism and sexism.

Kimberly Miller, a criminal investigator from the South Loop, shared that view, arguing that Lightfoot was being judged too harshly because she is a woman.

“She came in when we had a lot going on in the city ― the pandemic ― but I think they need to give her a chance to play out her strategies with the police department, the community, crime and everything else,” Miller told HuffPost.

Even if concerns about bias are well-founded, though, complaints about Lightfoot’s demeanor and heavy-handed approach to governance have not been limited to white Chicagoans or conservatives who would disagree with her anyway.

Retiring Alderwoman Leslie Hairston (D), a member of the City Council’s progressive caucus who is neutral in the mayoral race, had long respected Lightfoot as a fellow Black woman attorney coming up at a time when there weren’t that many.

She grew dismayed, though, by what she perceived as Lightfoot’s deliberate lack of consideration for members of the City Council, faulting her for failing, at times, to invite aldermen to mayoral announcements in their wards or sidelining them when she did manage to invite them.

Noting the famously foul temper of Rahm Emanuel, Lightfoot’s predecessor, I asked Hairston whether being a hard-ass might not just be part of the Chicago mayor’s job description.

“I would never use the word ‘easy’ and Rahm in the same sentence, but you could understand where he was coming from,” Hairston replied. “Sometimes with this administration, there’s no rhyme or reason. She makes it more difficult.”

Asked by HuffPost whether her political relationships might improve in a second term, Lightfoot suggested that they would.

Acknowledging that she had not known the “vast majority” of the City Council members prior to taking office, Lightfoot concluded, “This has been a learning curve for both of us.”

At the same time, critics to Lightfoot’s right have a more ideological argument for why crime has gone up under her watch: that her efforts to rein in police abuses, however modest by the activist left’s standards, have made police officers afraid to act aggressively enough to be effective.

“She don’t let the cops do their job,” said Guadalupe Dominguez, an electrician from the North Side who is supporting García.

A particular sticking point is the Lightfoot administration’s implementation of a policy that forbids police officers from engaging in foot chases with people suspected of committing minor offenses or with people who run away from officers. The policy, designed to avoid the kind of frivolous police killings that the federal government has concluded are too common in Chicago, still allows officers to pursue someone they suspect of committing a felony. The change came about specifically in response to the controversial police killings of Adam Toledo and Anthony Alvarez in the course of police foot pursuits in 2021.

But some Chicagoans argue that cops are now too worried about running afoul of the rules to exercise the kind of discretion that is needed to keep people safe.

“People talk about racism. It’s not racism,” said Leon Scott, a contractor from the Bronzeville district who is Black and wants foot pursuits fully reinstated. “Nine times out of 10, if you think they have a gun on them, they have a gun on them.”

For her part, Lightfoot interprets the criticism of her from the left and the right as a vindication of the balance she is striking.

“That tells me I’m probably right where I need to go,” she told HuffPost.

Vallas’ Tightrope Walk

Vallas, the centrist favorite in the race and current polling leader, is something of a serial urban technocrat, having been hired to turn around troubled school districts in Philadelphia, New Orleans and Bridgeport, Connecticut, following his stint in Chicago. He also ran unsuccessfully for mayor in 2019, for Illinois lieutenant governor in 2014 and for the Democratic gubernatorial nomination in 2002.

This time, Vallas, who is known as a charter-school proponent unafraid to battle teachers unions, has focused relentlessly on restoring public safety.

HuffPost interviewed Vallas as voters like Andrews, who had come to hear him speak on Feb. 11, were filtering out of the Italian restaurant on the near South Side. Vallas offered a two-fold pitch on policing. He echoes law enforcement complaints about the foot-pursuit policy and other liberal reforms, lamenting the “general lack of support that [police officers] feel from the mayor’s office.”

But he also laid out a multifaceted tactical critique of Lightfoot’s police strategy and controversial police superintendent, David Brown, that candidates with more progressive views share. Vallas wants to replace Brown, return to a community-based policing model and use additional funding to shorten officers’ shifts ― all changes he maintains will “slow the exodus” of cops from the city’s force.

Likewise, he touts his work negotiating the Chicago Police Department’s newest eight-year contract on behalf of the Fraternal Order of Police (FOP), the city’s police union. Lightfoot herself has touted the contract’s new clauses increasing accountability for police misconduct, including an end to the practice of allowing cops to change their testimony about an incident after viewing video of what occurred.

Vallas’ hybrid message ― amplified with the help of deep-pocketed, right-leaning donors ― has helped him assemble a fragile coalition. He has the support of virtually all of the city’s most conservative voters, who are concentrated in largely white, blue-collar areas on the far northwest and far southwest sides, but he has also made inroads with the so-called lakefront liberals on the city’s North Side ― many of whom backed Lightfoot in 2019.

Members of the “lakefront” group ― composed mostly of white, affluent professionals ― share their working-class counterparts’ desire for lower crime, but are more turned off by reactionary rhetoric or the whiff of racism.

Linda Buckley, a retired businesswoman in River North (not, strictly speaking, a lakefront enclave), supported Lightfoot in 2019 and is now choosing between Vallas and García.

She wants the city to take a firmer hand on crime, as Vallas promises, but also told HuffPost she is “a little nervous about an overreaction.”

Vallas’ ties to Chicago’s police union, the FOP, which has endorsed his bid, underscore the precariousness of his political balancing act as he seeks to lock down voters like Buckley. Chicago FOP President John Catanzara is something of a right-wing caricature, with a history of misconduct allegations and racist or reactionary comments. (His rhetorical rap-sheet includes a 2017 Facebook post in which Catanzara said that Muslims are “savages who deserve a bullet” and public apologetics for the U.S. Capitol riot on Jan. 6, 2021, which he claimed resulted in “very little destruction of property.”)

Asked for his response to Catanzara’s remarks, Vallas initially turned the question around, arguing that he shouldn’t have to answer for Catanzara’s remarks any more than he should have to answer for controversial statements made by Chicago Teachers Union President Stacy Davis Gates.

“You should see some of the stuff that Stacy Davis Gates said. Google it!” he told HuffPost, noting that as mayor, it would be his job to negotiate with public-sector unions regardless of who their elected leaders are. “Despite some of the most outrageous stuff that she has said, I’m going to have to negotiate with her.”

Vallas also noted that Catanzara is up for reelection and thus may not be in charge when the next mayor takes office.

But Vallas’ relationship to Catanzara is fundamentally different from his ties to other union leaders, since Catanzara is a prominent supporter of Vallas’ bid. Davis Gates, who has not been credibly accused of racism, is not. Vallas even spoke alongside Catanzara at an FOP event for retired cops earlier this month.

Pressed to clarify his views on Catanzara’s comments, Vallas affirmed that he disagreed with the bigoted remarks and noted that he had publicly expressed revulsion about the U.S. Capitol riot.

The headaches that the FOP is causing Vallas keep coming. On Feb. 17, after news broke that the Chicago FOP invited Florida Gov. Ron DeSantis (R) to speak at a rally with rank-and-file police officers, Vallas condemned the event unequivocally, citing DeSantis’ “record of trying to erase the LGBTQ community” and “banning books on Black history.”

Vallas, who describes himself as a “lifelong Democrat” in TV ads and has a campaign contribution record consistent with that description, has nonetheless given his rivals more than enough material with which to paint him as a closet Republican hoping to prey on the city’s racial demons.

In remarks to supporters in late January, Vallas told supporters that his campaign is about “taking back our city.” When the comments resurfaced recently, Lightfoot accused him of pandering to white racists with the “ultimate dog whistle.”

Vallas’ campaign said in a statement responding to the charge that it would not let Lightfoot “distract” Vallas from his mission to “put crime and public safety first.”

Lightfoot is “desperately lashing out in every direction to cling to a spot in the runoff, even going as far as to suppress the vote if it helps her politically,” the Vallas campaign added.

When HuffPost asked Vallas in person about a similar accusation that Lightfoot had leveled in mid-February, Vallas touted his commitment to preferential treatment for women- and minority-owned businesses in city contracting, and his history of employing a racially diverse staff. (For example, Cozette Buckney, a Black woman who was Vallas’ chief of staff at Chicago Public Schools and followed him to New Orleans and Bridgeport, remains a friend and adviser.)

Then, on Thursday, the Chicago Tribune reported that Vallas’ campaign Twitter account had liked racist and insensitive tweets, including comments mockingly dubbing the mayor “Larry Lightfoot” and claiming that she had hired the police chief only because he is Black.

In a statement, Vallas attributed the “likes” to staff, claiming he does not run the account himself. He said the tweets’ “abhorrent and vile rhetoric does not represent me or my views.”

Vallas has fewer good answers when pressed to explain his flirtations with the Republican Party. He openly considered running as a Republican for president of the Cook County Board of Commissioners in 2009.

He told HuffPost that he had entertained the idea after being approached by people who wanted him to do it and because the county Democratic Party was an arm of the Chicago-area political machine. Ultimately, though, Vallas found that he had “too many fundamental differences” with the GOP, including his support for abortion rights, the mayoral candidate recalled.

But in a lengthy 2009 TV interview that has become fodder for attack ads, Vallas sounded far less ambivalent about affiliating with the Republican Party, describing himself as “more of a Republican than a Democrat.” He also told the interviewer that he would “probably” register as a Republican.

‘They’re Never Going To See You’

Lightfoot’s broadsides against Vallas don’t solely aim to polarize the race along partisan lines.

Lacking a clear ideological base on the left and hemorrhaging the upper-middle-class white support that propelled her in 2019, Lightfoot is hoping to ride Black support to a spot in the April runoff.

The presence of six other Black candidates on the ballot presents a critical obstacle to this goal, however. Wilson, in particular, has demonstrated an ability to win votes, not least among more conservative Black voters on the South Side who helped him pick up nearly 11% of the citywide mayoral vote in the first round of voting in 2019.

So Lightfoot has launched a last-minute push to convince Black voters that she is the only Black candidate capable of winning.

“None of those folks who are on the ballot ― they’re never going to see the inside of the mayor’s office unless I invite them in!” Lightfoot told a friendly audience in the predominantly Black, impoverished West Side neighborhood of Austin on Feb. 11.

Then, in remarks that sounded somewhat at odds with her claims to a multiracial, cross-city “base” at the clergy press conference two days earlier, she laid out the stakes of ensuring continued Black control of City Hall.

“Any vote for somebody not named Lightfoot is making sure that Chuy García or Paul Vallas runs your city,” she said. “And you know what’s going to happen if one of those jokers is in charge: They’re never going to see you! They don’t see the West Side.”

During the final candidate debate, Lightfoot also suggested that García is out of touch with Black voters. When García claimed that Lightfoot’s INVEST South/West development money is not reaching its intended targets, she responded by inviting him to tour communities where her signature project is making a difference.

“I know you don’t know Black Chicago that well,” she quipped.

García noted that he lives in “K Town,” a nickname for a cluster of West Side neighborhoods with many Black residents. “Maybe you don’t come there from Logan Square,” he shot back, referencing Lightfoot’s home in a gentrifying, historically Latino neighborhood on the northwest side.

In Chicago, which is roughly evenly divided among Black, Latino and white residents, many voters still believe that one race’s well-being must come at the expense of another’s.

As a result, Lightfoot’s appeals to this zero-sum mentality resonate with some of her supporters.

García will “have to cater to those who put him in office,” Rev. Cy Fields, a Baptist minister and Lightfoot ally, told HuffPost. “He has history with former Mayor Harold Washington, but I think his allegiance will be to the Latino community. And I think that will really change the political power shift for the Black community here in the city.”

García, who immigrated to Chicago from Mexico as a young man in 1965, would be Chicago’s first Latino mayor. But, aware of Black voters’ fears of being pushed aside, he has emphasized his pioneering support for Washington, the city’s first Black mayor in the 1980s, at a time when much of white Chicago was in open revolt against Washington.

That history has made an impression on at least some Black voters, including Scott, the contractor from the Bronzeville neighborhood.

“I think he’s going to take it to another level,” he said of García. “The Hispanics are moving up in the world today. They’re strong people. I work with them all the time.”