CHICAGO — As Chicago Mayor Lori Lightfoot gears up for her expected reelection campaign after three tumultuous years, she finds herself in a familiar position: on the defensive.

Lightfoot the rookie politician won in 2019 in part because of her credentials as an outsider, but Lightfoot the incumbent does not have that advantage. And in recent days — still more than 10 months before the municipal Election Day — two candidates have announced plans to run for mayor with expectations several more will join the field.

During her three-plus years in office, Lightfoot has faced spikes in crime, hasn’t run as transparent an administration as promised, and engaged in constant fights with unions representing Chicago teachers and police — all while struggling to forge good relationships with politicians or leaders in the city’s business community.

“I have never met anybody who has managed to piss off every single person they come in contact with — police, fire, teachers, aldermen, businesses, manufacturing,” Ald. Susan Sadlowski Garza, 10th, a onetime close Lightfoot ally, said recently in explaining why she wouldn’t endorse the mayor for reelection. “I said it. That’s it. I don’t care.”

The situation is rare for an incumbent mayor. Richard M. Daley — the longest-serving mayor in city history — had his problems but rarely had tough competition come election time. His successor, Rahm Emanuel, faced steeper challenges than Daley but overcame them with massive fundraising.

“She has the position, she doesn’t have the power,” said veteran Chicago political strategist Delmarie Cobb, who isn’t currently advising any mayoral campaigns. “You may be the mayor but you don’t have the power that a Daley had or a Rahm Emanuel had and that’s because they came in with that kind of power. They didn’t have to gain it, they actually had it when they walked in the door. She needed to achieve it and create the illusion of inevitability or being invulnerable.”

Still, Lightfoot can’t be dismissed.

Incumbency in any form has power. She’s earmarked roughly $3 billion in federal funds for city projects and she’s launched a series of programs aimed at reversing one of the biggest criticism’s of Emanuel’s tenure — disinvestment in Chicago’s neighborhoods, especially on its South and West sides. Lightfoot also can argue she deserves more time to finish the job after having faced the unprecedented COVID-19 pandemic and some of the city’s most significant civil unrest since the 1960s.

“Everybody keeps telling me, ‘she’s done, she’s done, she’s done,’ ” said Ald. Nick Sposato, 38th, a Lightfoot ally. “But you’ve got to have somebody to beat somebody.”

Earlier this week, businessman Willie Wilson — who has lost two previous bids for mayor and endorsed Lightfoot in 2019 — joined Ald. Raymond Lopez, 15th, as an announced candidate for mayor in 2023. Lopez has garnered a large amount of attention for his consistent attacks on Lightfoot, mostly focused on crime, but it remains unclear if he’ll be able to raise enough money to run citywide or counter criticism he nitpicks her unnecessarily. Wilson has significant personal wealth to help fund his campaign and previously generated strong support from Chicago’s Black voters, but he hasn’t been able to expand his base and make a runoff.

In response to the Lopez and Wilson announcements, Lightfoot’s campaign this week said the mayor is focused on “keeping our streets safe from gangs and guns, pushing historic levels of economic investment in the South and West sides and creating jobs and opportunities for all Chicagoans. We have a long road ahead — candidates for mayor will come and go, but Mayor Lightfoot won’t be distracted from the big challenges at hand of economic recovery and public safety as we emerge from the pandemic.”

Asked Monday about Wilson’s strong support from Black voters, Lightfoot said, “I don’t know that that assumption is correct.”

Even though Lightfoot has not formally announced her reelection bid, she’s expected to and made clear that she’s watching the landscape carefully to avoid being upstaged.

After Wilson gave away $1.2 million in gas all over Chicago and nearby suburbs, Lightfoot followed by proposing $12.5 million in city funds be used for 50,000 prepaid gas cards worth $150 each as well as 100,000 passes that will cover $50 worth of CTA fares. The plan still needs to be approved by the City Council.

U.S. Rep. Mike Quigley, who has polled about running for mayor and last week created a Quigley for Chicago campaign committee, recently sent out an anti-crime mailer that touted a federal gun buyback program he’s supported. Lightfoot announced a $1 million gun buyback of her own shortly after.

She also last year unveiled a $31.5 million guaranteed basic income program after opposing a similar initiative by Ald. Gilbert Villegas, 36th, who weighed a potential mayoral run before deciding instead to run for Congress.

University of Illinois at Chicago political science professor Chris Mooney said Lightfoot’s campaign will need a bigger overarching message than some of her more recent announcements.

“You could say she’s assessing the landscape and looking for threats. One might argue that’s one aspect of an incumbent’s campaign. The other, more important aspect of an incumbent’s campaign is to be able to tell a story about what he or she has been doing and how things have happened,” Mooney said. “This is the story they tell in a reelection campaign. I am agnostic on if she has a good story to tell but if she’s having to rely on giving gas away, that suggests she doesn’t but maybe her campaign has to figure that out.”

After Wilson announced his intention to run for mayor, Lightfoot said at a news conference that she wasn’t copying Wilson’s idea when she proposed financial relief for drivers and commuters.

“I don’t react to what other people do other than the residents of our city,” she said.

Villegas, who previously was Lightfoot’s floor leader before having a falling out with her, said Lightfoot taking ideas from other places “is just an example of her inability to collaborate with people and want to share in the ideas and try to make them as good as possible.”

“Once an idea is proposed, what we see is her and her team just take the idea, run with it, have it half-baked, and then try to work on it as they move along instead of just working with the person who has done the hearings, has done the research, and has had their team do research,” Villegas said. “It’s just par for the course.”

To be sure, Lightfoot is not the first mayor to face challenges as she runs for reelection.

Emanuel was the first Chicago mayor to be pushed into a runoff. To win in 2015 versus Jesus “Chuy” Garcia, Emanuel raised more than $24 million to defend his record and famously cut a campaign ad where he wore a sweater to try to soften his hard-charging image.

Lightfoot is a far less prolific campaign fundraiser than Emanuel and does not have his extensive Rolodex of potential contributors. She has also broken with standard practice for politicians by spending big from her campaign funds.

A Chicago Tribune report earlier this year found she had less political cash on hand than she had shortly after winning office 2 1/2 years ago. The mayor’s two campaign funds bled $213,000 during that time, as Lightfoot raised $2.67 million but spent $2.88 million, a Chicago Tribune analysis of state campaign finance records found.

Typically, incumbents stockpile campaign money during non-election years, conserving their cash for expensive television ads, direct mail and get-out-the-vote efforts closer to Election Day.

But Lightfoot has outstripped her fundraising by spending steadily on campaign staffers, consultants, polling, digital advertisements, events, travel and more, averaging nearly $100,000 per month in expenses, records show. Her next quarterly fundraising report is expected to be filed in the coming days.

The popular consensus that Lightfoot alienates broad constituencies is a stark flip from the position she found herself in in the April 2019 runoff election, when she carried all 50 wards in a landslide victory against Cook County Board President Toni Preckwinkle, who is also head of the Cook County Democratic Party.

But Lightfoot’s standing with voters is more complex and always has been.

In the first round of the mayoral campaign in 2019, Lightfoot emerged from a historic 14-candidate field with roughly 18% of the vote. While that was enough for her to take first place and move her to the final round versus Preckwinkle, it still shows that 4 out of 5 voters in that first round chose someone else. In that initial February 2019 election, Lightfoot rode broad support from lakefront voters on the North Side, who are often liberal.

What’s more, Preckwinkle was battered by her ties to Ald. Edward Burke, 14th, whose public corruption charges dominated the election cycle, as well as Preckwinkle’s past support for the “pop tax,” which boosted Lightfoot’s outsider campaign against an unpopular insider.

Since then, Lightfoot’s fortunes have shifted. She has polled particularly poorly with white voters in the city as well as Latinos, according to sources who were not authorized to speak publicly. Chicago’s population is roughly one-third white, one-third Black and one-third Hispanic, but the city’s 17 majority-white wards accounted for 44% of the vote in the first round 2019 election.

Toss in two other majority-Hispanic wards that also are home to predominantly white neighborhoods with a high number of public employees and that’s 19 wards that represent roughly half of the city’s vote.

Those are voters Lightfoot will have to win over as she runs for reelection.

Lightfoot critics and allies generally agree she is polling better with Black voters than others, but that is potentially threatened by Wilson’s entry into the race. He won most of the Black wards in 2019 and helped boost her campaign on the South and West sides with his endorsement.

Cobb, the political strategist, said she thinks Lightfoot will be able to get support from many living in the majority-Black wards but that vote won’t be universal for the incumbent mayor.

“I don’t know that they’re going to be overwhelming for her and if there are other candidates out here who are viable, and who have a record of being with the Black community, she may not have them for long,” said Cobb, who is Black. “She certainly is not in a strong position as an incumbent.”

Still, in the hours after Wilson announced his intention to run, Lightfoot previewed one of her main reelection arguments and geared directly at voters on the South and West sides.

“There has never been a mayor in the city’s history who’s invested as much as my administration has in majority-Black wards,” Lightfoot said, touting her plans to spend money on projects in Black and brown neighborhoods, including proposals to redevelop long-challenged corridors. “These neighborhoods have been starved for resources for decades, decades, and when you starve people of opportunity, you starve them of hope.

“We’re on the right path, we’re on the right path, and this is about the future of our city,” she continued. “This is about who we want to be coming out of this pandemic and whether we’re going to bring everybody along or whether we’re going to return to the days when a few people got all the resources on the table and there’s no room for anybody else.”

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