Lori Lightfoot, who defied expectations four years ago to win the Chicago mayoral race as a political outsider, finds herself once again the underdog as she seeks to fend off multiple challengers in a tough reelection bid.

The city’s top executive is facing a crowded field of eight other candidates. Though Lightfoot campaigned as a reformer in 2019, voters are signaling they might be ready for another fresh start, and she finds herself trailing some of her rivals in recent polls.

Should she fail to become one of the top two vote-getters in Tuesday’s primary, she could become the first incumbent Chicago mayor in more than three decades to lose an election.

“She’s an underdog this time around for different reasons than she was an underdog last time,” said longtime political operative Victor Reyes, who is supporting challenger Rep. Jesús “Chuy” García (D-Ill.) but not advising him.

“Last time, she was an unknown and she was the counter to the traditional political establishment folks, and the vote split was happening in a different way back then. And this time, she’s like the target of everybody’s ire, right?” Reyes continued. “She’s getting attacked from the left; she’s getting attacked from the right. And she doesn’t have any ground footing with any significant solid base of votes.”

Multiple polls over the past month have shown Lightfoot either tied with or trailing a mix of the other three frontrunners: García; former Chicago Public Schools CEO Paul Vallas; and Cook County Commissioner Brandon Johnson. Still, Lightfoot is no stranger to being counted out. During the 2019 Chicago mayoral race, she polled as low as in the single digits ahead of that year’s February primary and surprised many when she made it into the runoff that year along with Cook County Board President Toni Preckwinkle. 

But the reformer candidate who broke barriers as the first Black woman and first openly gay candidate to be elected as Chicago’s mayor is facing a steep path to reelection as she battles perceptions that she’s too combative along with concerns over crime and public safety.

Lightfoot’s campaign argues she has the support be reelected.

“Under Mayor Lightfoot’s leadership, Chicago has made progress like this city has never seen before,” Lightfoot campaign spokeswoman Hannah Goss said in a statement. “In just four years, she has spurred economic development in every corner of the city — not just downtown. The Mayor has secured record investments in affordable housing, expanded access to mental health services, raised the minimum wage to $15, made key reforms to our police department — and more.”

Twyla Blackmond Larnell, an assistant professor of political science at Loyola University Chicago, argued that identity politics are playing a significant role in the race, and that while Lightfoot has courted Black and white voters in the past, it’s not clear if she has their support.

“And so my question has always been who’s going to turn out to vote for [Lightfoot] in this election, at least … vote for her enough to get her to the runoff?” Larnell said.

Lightfoot appeared to nod toward that question while speaking to voters last weekend.

“Any vote coming out of the South Side for somebody not named Lightfoot is a vote for Chuy García or Paul Vallas,” she said, according to footage from NBC5 Chicago. 

She later walked back those statements following criticism for the remarks. “If I said anything other than everybody everywhere needs to vote then I misspoke in the heat of a campaign rally,” she said.

At the same time, Vallas, García and Johnson are not without their own challenges ahead of next Tuesday. Lightfoot, for example, has sought to portray Vallas as a Republican — an insult in the heavily blue city of Chicago — and has pointed to his endorsement from the Fraternal Order of Police. News coverage has also reported on Vallas’s donors, some of whom have given to Republicans in the past.

A spokesperson for Vallas’s campaign suggested those attacks “show a little bit of desperation” and noted that “the facts of it are pretty straightforward: He’s a lifelong Democrat, he’s run for public office multiple times, even statewide office, as a Democrat. He is completely pro-choice and has publicly said that he would make sure that Chicago remains a reproductive safe haven.”

Meanwhile, Lightfoot has sought to tie García to FTX founder Sam Bankman-Fried and disgraced former state House Speaker Mike Madigan (D) in one of her earlier ads.

The Chicago Tribune noted that Bankman-Fried donated $2,900 to the congressman’s campaign while more than $150,000 was spent by a political action committee with ties to the FTX founder to support García’s reelection efforts. More recently, the Tribune reported that an unidentified member of Congress referenced in court documents related to a probe involving Madigan is García himself.

García’s campaign has said that the congressman donated the direct contribution from Bankman-Fried, and the congressman has publicly said he was not involved with the independent expenditure that was made outside his campaign. The campaign also told the Tribune that he is not involved in the Madigan probe or any other related probe. No wrongdoing has been alleged against him.

“Because Lori Lightfoot has no accomplishments of her own to tout, she has resorted to phony, desperate attacks on the Congressman to distract from the fact she has failed to keep Chicagoans safe and has failed to reform city government as she once promised,” García campaign spokesperson Antoine Givens said in a statement to The Hill. 

In a sign that Ligthfoot views Johnson as a possible contender, Lightfoot also released an ad targeting the Cook County commissioner’s previous comments in which he voiced support for defunding the police — an attack line often used by Republicans against Democrats but less often seen among intraparty disputes. 

Johnson would not say directly whether he would cut spending from the Chicago Police Department, noting instead he would be “investing in what works.” But the Cook County commissioner also accused Lightfoot’s and former Mayor Rahm Emanuel’s administrations of defunding city services and institutions.

“She’s not an underdog, she’s a disappointment,” Johnson told The Hill.

“This administration [and] the previous administration have moved on the defunding of all of the critical services that the people of Chicago not only rely upon but deserve,” Johnson said. “I am running to become the investor-in-chief.”

Still, observers argue not to count her out. 

Dick Simpson, professor emeritus of political science at the University of Illinois Chicago who’s long been a fixture in Chicago politics, explained he was supporting her because “she did carry out the ethics of good government reforms.”

“And she is a pragmatic progressive who’s carrying out the agenda of issues like Invest South/West affordable housing, balanced economic development,” he added.