Chicago Mayor Lori Lightfoot facing stiff headwinds as 8 challengers vie for her job

Forty years ago, the first woman ever to serve as mayor of Chicago was turned into a one-termer by a defeat that paved the way for another first: the election of Harold Washington as Chicago’s first Black mayor.

Now, Lori Lightfoot is trying to avoid following in Jane Byrne’s footsteps by suffering a defeat that could set the stage for yet another piece of political history: the election of Chicago’s first Hispanic mayor.

In all, nine candidates will face off Feb. 28: Lightfoot; millionaire businessman Willie Wilson; two retiring alderpersons, Sophia King (4th) and Roderick Sawyer (6th); Illinois state Rep. Kam Buckner; Cook County Commissioner Brandon Johnson; former Chicago Public Schools CEO Paul Vallas; U.S. Rep. Jesus “Chuy” Garcia; and community activist Ja’Mal Green.

Two high-profile would-be challengers — U.S. Rep. Mike Quigley and former U.S. Education Secretary Arne Duncan — took a pass.

That fractured field virtually guarantees no single candidate will reach the vote threshold — 50% plus one — that’s needed to avoid an April 4 runoff between the top two finishers.

With violent crime and the perception of it foremost on voters’ minds, Lightfoot is facing stiff headwinds.

Mayor Lori Lightfoot’s first term was marred by the pandemic, civil unrest, a teachers strike (above), battles with the Chicago Teachers Union over the reopening of schools and a string of public arguments with City Council members and other elected officials.

Ashlee Rezin Garcia/Sun-Times

Turbulent first term

Her first term was marred by the pandemic, civil unrest, a teachers strike, battles with the Chicago Teachers Union over the reopening of schools and a seemingly endless string of public arguments with City Council members and other elected officials. She has a public approval rating stuck in the mid-20s, according to polling done for other candidates.

Lightfoot is counting on African American voters to help her over the finish line and compensate for the support she has lost among lakefront voters disappointed with her record on reform, transparency and crime. She points to an Invest South/West plan as proof that no mayor — not even Washington — has done more for the African-American community.

But the more divided the Black vote, the more roadblocks there will be on the narrow path to a Lightfoot victory. 

No wonder Ald. Jason Ervin (28th), chair of the City Council’s Black caucus chair and one of Lightfoot’s staunchest supporters, has warned that with seven Black candidates and a divided and diminished African American vote, the Black community risks “losing it all.”

So far, Ervin’s behind-the-scenes efforts to get other Black candidates to drop out have fallen flat.

Only one candidate — Ald. Ray Lopez (15th), the first to announce he was running for mayor — has withdrawn from the race. Lopez said he endorsed Wilson in hopes of easing historic political tensions between Blacks and Hispanics.

Four years ago, Wilson won 13 of 18 Black wards on the strength of his church-based constituency and his lifetime of charitable giving. But it was Lightfoot and Cook County Board President Toni Preckwinkle who advanced to the runoff.

In that runoff, Lightfoot won all of those wards and all 50 wards citywide after Wilson endorsed her over Preckwinkle in a race dominated by the corruption scandal still swirling around indicted retiring Ald. Edward Burke (14th).

Wilson, whose recent gas and food giveaways have made him even more popular, has since called his Lightfoot endorsement a “helluva mistake.”

No endorsement this time

Garcia knows the feeling.

He also gave Lightfoot a pivotal 2019 endorsement, only to regret it so much, he joined the 2023 race himself. Garcia ran for mayor in 2015 and forced then-Mayor Rahm Emanuel into the city’s first mayoral runoff.

But this time, Garcia hesitated before jumping in, and by then, a Chicago Teachers Union that was his biggest contributor in 2015 had already endorsed one of its own in Johnson.

Johnson has since put together a powerful coalition of progressive politicians, labor unions and community groups that includes SEIU Local 73, SEIU Healthcare, the CTU, the American Federation of Teachers, United Working Families and two newly elected members of Congress: Rep. Jonathan Jackson and Rep. Delia Ramirez, both Democrats.

No matter. Garcia has said he is confident he will make the runoff and that the progressive family will unite behind his candidacy when he does.

“Folks know me. … They know what I’ve done. I know we will eventually get their support. I’m the only guy left from the Harold Washington coalition. … No one in Chicago politics today has been involved in fighting the old corrupt and racist and sexist Chicago machine [longer] than myself,” the 66-year-old Garcia has said.

“I’m certain our movement will come together. We have a shared set of values.”

Lightfoot is treating him as a formidable opponent — with a cartoonish commercial tying Garcia to two indicted political powerhouses: cryptocurrency mogul Samuel Bankman-Fried and former Illinois House Speaker Michael Madigan.

She has also attacked Vallas as a “Republican”— even though he is a lifelong Democrat who ran for governor and lieutenant governor as such — and Johnson as a champion of the de-fund the police movement. Johnson has fired back by accusing Lightfoot of “breaking every single promise she made” to progressive voters.

Crime is key issue

Garcia is trying to remain above the fray while moving to the middle, particularly on the issue of violent crime.

“I know some people are surprised to hear a guy like me who spent decades as a community activist … supporting hiring police officers. But building violence prevention programs in Little Village was only possible by having an understanding with police,” he said.

“Yes, we have to hold police accountable. But we cannot treat them like the enemy and expect things to get better. … As long as police officers feel attacked, nothing will change,” he said.

All eight mayoral challengers have outlined plans to deliver Chicago from violence. All eight have promised to start by firing Chicago Police Supt. David Brown, the former Dallas police chief who was picked by Lightfoot to run the Chicago Police Department. In hiring Brown, Lightfoot went around the Police Board, on which she once served as president.

Share This article on

Leave a Reply