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Chicago Mayor Lori Lightfoot (D) is bracing for a challenging reelection bid as she vies to remain the city’s top executive against eight other candidates in next month’s election.

Lightfoot, who made history in 2019 as the city’s first Black female and openly gay mayor, has faced a slew of challenges in recent years, including confrontations with local unions, the COVID-19 pandemic and rising concerns over crime.

Now the mayor is staring down efforts from within her own party to take her down, though observers suggest ousting Lightfoot will be no easy feat.

“She currently has two challenges. I would call them crime and combativeness,” said Jason DeSanto, a senior lecturer at the Northwestern Pritzker School of Law and a Democratic debate strategist.

Lightfoot’s time in office has at times been marked by contentious relationships with city and state officials. She’s gone head to head with the Fraternal Order of Police president over COVID-19 vaccines while grappling with two Chicago Teachers Union strikes, the first of which was held just months after her 2019 election. Text messages obtained from the Chicago Tribune through a public records request have also shown a frosty relationship at times with other leaders like Gov. J.B. Pritzker (D) and state Senate President Don Harmon (D).

And while Chicago is making some progress on the issue of crime, including seeing lower numbers of murders and aggravated battery over the last year, certain crimes like murder and theft are still above pre-pandemic levels, according to Chicago Police Department data.

At the same time, Lightfoot has sought to remind voters about the city’s track record under her administration since the former federal prosecutor and then-political outsider entered office in 2019. 

“Mayor Lightfoot has led this city through unprecedented challenges with tough, fair leadership — all while undertaking an ambitious agenda to deliver real, tangible results,” said Hannah Goss, a spokesperson for Lightfoot’s campaign, in a statement. “The Mayor is improving public safety, getting guns off our streets and hiring more officers, all while ramping up police accountability and transparency. She’s reversing decades of disinvestment in communities on Chicago’s South and West Sides to create inclusive economic growth.”

“Unlike her opponents, these aren’t just half-baked ideas or values statements,” Goss added.

Yet candidates like Rep. Jesús “Chuy” García (D), former Chicago Public Schools CEO Paul Vallas, Cook County Commissioner Brandon Johnson (D) and state Rep. Kam Buckner (D) are now casting themselves as viable alternatives to the first-term mayor. Alds. Sophia King and Roderick Sawyer, activist Ja’Mal Green and businessman Willie Wilson have also thrown their hats in the ring. 

All of them will make their case to voters during their first televised debate on Thursday ahead of the Feb. 28 election. If no candidate gets more than 50 percent of the vote, the election will head to an April 4 runoff between the top two vote-getters.

Green’s campaign in a statement highlighted the activist’s “bold action, fearlessness, and ardent sentiment to stand up for justice for all,” while Sawyer, the alderman, pointed to his 12 years serving in City Council and nodded to his upbringing as the son of a former Chicago mayor in his own statement. Antoine Givens, a spokesman for García’s campaign, told The Hill in a statement that the congressman was the “only candidate who has the ability to unite Chicago.”

Observers note that Lightfoot’s first task is making it into the April runoff and that Vallas and García could be the most formidable challengers. Both men have run for Chicago mayor in the past. Vallas has honed in on the issue of crime, while García enjoys support from several labor unions, including the influential IUOE Local 150. 

“The path for her is to have the right candidate” to run against, said veteran political operative Victor Reyes, who’s a supporter of García.

“If she makes the runoff with certain candidates, her chances improve dramatically,” he added. 

Lightfoot has already gone on the attack against the pair, accusing Vallas of being “silent” for months on the Supreme Court’s decision to overturn Roe v. Wade while rolling out a 30-second ad earlier this month tying García to FTX founder Sam Bankman-Fried and disgraced former state House Speaker Mike Madigan (D). 

Bankman-Fried gave a $2,900 donation to García’s campaign, and the PAC Protect Our Future, which is also associated with Bankman-Fried, spent over $150,000 independently to boost his campaign, according to the Tribune. The congressman donated the nearly $3,000 direct campaign contribution and said of the PAC money, which was spent outside his campaign, “by law and by definition, I had nothing to do with it.”

Givens, the García campaign spokesperson, in a statement slammed Lightfoot’s ad, saying the mayor was “resorting to more lies and desperate attacks.”

Observers say Lightfoot’s opponents also face the challenge of trying to unseat an incumbent.

“The mayor is in there with 99 percent name I.D. Most have an opinion of her that’s baked in,” said Zach Koutsky, a city lobbyist who’s worked on Democratic and progressive campaigns. “It’s the others that are ill-defined at this point that creates an opportunity for her and for those candidates to introduce themselves or be defined by others.”

At the end of the day, while observers of the race point to Lightfoot’s perceived weaknesses, they also caution against writing her off. After all, Lightfoot was seen as an unlikely contender in the last election, given that polls had shown her polling in the single digits. 

“Anybody who writes off an incumbent is a fool. You never write off an incumbent,” said Reyes, the veteran political operative. “And even though her approval numbers aren’t where they are, she got lightning in a bottle last time.”