An early look at the race for mayor of Chicago

The exit of former U.S. Education Secretary Arne Duncan leaves field wide open, and increases the likelihood that a runoff election will again be needed between the top two vote-getters.

SHARE An early look at the race for mayor of Chicago
Lori Lightfoot on election night in April 2019.

Lori Lightfoot celebrates at her election night rally at the Hilton Chicago after defeating Toni Preckwinkle in the 2019 Chicago mayoral election. Lightfoot carried all 50 wards in that race, but her path to re-election will not be nearly so easy in 2023 — if she runs at all.

Ashlee Rezin/Sun-Times

Mayor Lori Lightfoot may feel like she dodged the big one when former U.S. Education Secretary Arne Duncan decided not to enter the 2023 mayoral race.

But Duncan’s exit left the field so wide open, so early, for other challengers, the embattled incumbent might end up being worse off.

Duncan likely would have had formidable financial support from a business community disenchanted with Lightfoot. His decision not to run leaves business leaders and business money on the sidelines.

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It also increases the likelihood of another crowded mayoral field — and a runoff between the top two vote-getters. Lightfoot’s now-dismal approval ratings also mean there’s at least a remote possibility she wouldn’t make a runoff.

Who, then, are the top-tier candidates and possible challengers in an election almost certain to be a referendum on the embattled incumbent — unless Lightfoot pulls a Rahm Emanuel and makes an eleventh-hour decision not to run for reelection?

There are many intriguing and not-so-intriguing possibilities, though some depend on the outcome of this year’s races.

Mayor Lori Lightfoot chats with U.S. Rep. Mike Quigley on Wednesday, June 2, 2021 after a news conference about a project to replace four stations on the CTA’s Red Line.

Mayor Lori Lightfoot chats with U.S. Rep. Mike Quigley in June 2021 after a news conference about a project to replace four stations on the CTA’s Red Line.

Ashlee Rezin/Sun-Times

U.S. Rep. Mike Quigley

The North Side congressman has told the Sun-Times in recent days he was “being encouraged” to run for mayor and was all ears because of, as he put it, “the situation” in Chicago. But he wouldn’t say if business leaders were among those encouraging him — or if the “situation” referred to violent crime.

A political centrist from a North Side ward with a progressive bent, Quigley started in politics as a top aide to then-Ald. Bernard Hansen (44th) during the battle over lights at Wrigley Field. After a stint on the Cook County Board, he landed in Rahm Emanuel’s congressional seat after Emanuel became chief of staff to President Barack Obama.

Quigley’s high name recognition and almost nonexistent negatives have only increased since Russia’s invasion of Ukraine. Running for mayor could intrigue him, particularly if Democrats lose control of Congress.

City Clerk Anna Valencia marching in the Bud Billiken Parade in Bronzeville on Aug. 14, 2021.

City Clerk Anna Valencia marching in the Bud Billiken Parade in Bronzeville on Aug. 14.

Pat Nabong/Sun-Times file

City Clerk Anna Valencia

With surprise endorsements from retiring Illinois Secretary of State Jesse White, Gov. J.B. Pritzker and her old boss, U.S. Sen. Dick Durbin, D-Ill., Valencia is giving front-runner Alexi Giannoulias a run for his money in the race for secretary of state. But if Giannoulias’ four-to-one fundraising advantage carries him over the finish line, Valencia might parlay a strong showing into a mayoral campaign. She’d be the city’s first Latina chief executive.

Valencia has been a rising star on the political scene ever since Emanuel appointed her to succeed Susana Mendoza as city clerk after Mendoza (one of many unsuccessful 2019 mayoral candidates) was elected Illinois comptroller. And everybody who knows her knows her ultimate goal is to be elected mayor.

State Rep. Kam Buckner

Chairman of the Black Caucus in the Illinois House of Representatives, Buckner is “strongly considering” a run for what he calls the “greatest job in American politics.” But the timing may not be the best for someone who championed the sweeping criminal justice reform bill that Republican leaders contend went way too far.

He does not want to repeat what he called the mistakes politicians made in responding to the 1990s crime surge. Illinois is on track to eliminate cash bail, and Buckner said he will make sure that happens.

Buckner said he’s working on bills targeting organized retail theft, carjackings, “ghost guns” and the theft of catalytic converters. But with violent crime foremost on the minds of Chicagoans, those changes might not be enough to satisfy voters.

Bill Conway

With a law-and-order pedigree and a billionaire father who bankrolled his 2020 Democratic primary campaign for state’s attorney, Conway is a somewhat intriguing possibility in the 2023 mayoral race. His father, William E. Conway Jr., helped found the private equity firm the Carlyle Group and has a net worth pegged at $3.5 billion in 2020.

Despite being outspent three-to-one, and dogged by her handling of the Jussie Smollett case, incumbent Kim Foxx won easily, with 50.5% of the vote. Still, in his first run for elected office, Conway got 31.1%. If his dad was willing to write a $10.5 million check to bankroll that race, he might be willing to contribute at least as much to a mayoral campaign.

Conway, 44, spent six years as an assistant state’s attorney under Richard Devine and Anita Alvarez. He later served as a U.S. Navy intelligence officer, helping disrupt the Taliban’s flow of cash for illegal narcotics.

“Conway could write his own check” because of his father, said veteran political operative Victor Reyes. “Everyone else is gonna struggle to raise money.”

Mayoral candidate Gery Chico is interviewed by reporter Fran Spielman.

Mayoral candidate Gery Chico, interviewed by reporter Fran Spielman during in February 2019 during that year’s mayoral campaign.

Rich Hein/Sun-Times

Gery Chico

He’s fallen far short in two previous campaigns for mayor, but the third time could be the charm for Chico — in part because he’s among a precious few who could actually do the job.

Chico has served as president of boards overseeing the Chicago Board of Education, the Chicago Park District, City Colleges of Chicago and the Illinois State Board of Education. He also was chief of staff to Mayor Richard M. Daley.

As school board president, Chico recused himself from dozens of votes to avoid conflicts of interest with his private law firms. Those recusals helped sink his previous mayoral campaigns, despite formidable labor support, including the police and firefighter unions. Chico’s collaborative style contrasts starkly with Lightfoot’s combative approach. He could be the candidate business leaders are looking for — if he’s willing to take the chance of having to rebuild his private law practice for a fourth time, as he did after two mayoral campaigns and a failed U.S. Senate race.

“The path for both Chico and Conway is similar. They need to win a majority of the white and Latino vote. Then they would only need 15% to 20% of the Black vote,” Reyes said.

Paul Vallas speaks at a mayoral candidate forum at Greater St. John Bible Church, Saturday, Nov. 10, 2018.

Paul Vallas speaks at a candidate forum in 2018 during his campaign for mayor of Chicago.

Tyler LaRiviere/Sun-Times

Paul Vallas

The former Chicago Public Schools CEO finished in the single digits behind Chico in the 2019 mayoral race. He’s been a constant critic of Lightfoot’s performance on city finances and public safety.

Vallas recently served as an unpaid adviser to the Fraternal Order of Police, helping deliver a police contract that guaranteed rank-and-file Chicago Police Department officers a 20% raise over eight years. After serving as former city revenue director and budget director under Daley, Vallas knows city finances intimately but lacks Chico’s leadership skills and has a dedicated enemy in the Chicago Teachers Union.

“Paul’s biggest challenge is getting into the runoff. If he does, he could beat Lightfoot,” Reyes said.

Jesus “Chuy” Garcia, concedes to Mayor Rahm Emanuel April 7, 2015, in Chicago’s first mayoral runoff election.

Jesus “Chuy” Garcia, conceding to Mayor Rahm Emanuel on April 7, 2015 in Chicago’s first-ever mayoral runoff election. Garcia has since been elected to the U.S. House of Representatives, but could decide to run for mayor again in 2023.

Ashlee Rezin/Sun-Times

U.S. Rep. Jesus “Chuy” Garcia

Garcia has all but ruled out a mayoral run — even after saying Lightfoot faces the toughest reelection challenge of any Chicago mayor in 40 years.

But, he did leave himself an out.

“If somebody could show me where there’s a significant pot of gold … to usher in a real era of equity in Chicago, that would be really moving and convincing to me,” Garcia told the Sun-Times.

If Democrats lose control of Congress, maybe, just maybe, millions in fundraising could convince Chuy to reprise the energetic 2015 mayoral campaign that forced Emanuel into Chicago’s first-ever mayoral runoff.

Other possibilities

Jonathan Jackson, son of civil rights leader Jesse Jackson Sr., could run if he doesn’t win the crowded race to replace retiring U.S. Rep. Bobby Rush. Ald. Gilbert Villegas (36th) could do the same if he loses his congressional race to State Rep. Delia Ramirez. So could Ramirez, for that matter. Kari Steele, president of the Metropolitan Water Reclamation District, also could enter the mayor’s race if she loses to Cook County Assessor Fritz Kaegi.

Judy Frydland, acting commissioner of the Department of Buildings for the city of Chicago, in her office at City Hall on Friday, July 24, 2015.

Judy Frydland in her City Hall office in 2015. She served as Buildings Commissioner but now is a possible candidate for mayor.

Ashlee Rezin/Sun-Times

Longshots to run — or to win

This laundry list of would-be candidates includes Chicago Teachers Union Vice President Stacy Davis Gates; former mayoral challengers Mendoza, Willie Wilson, Illinois state Rep. La Shawn Ford and Ja’mal Green.

Also: former City Treasurer Kurt Summers; former Buildings Commissioner Judy Frydland; Illinois Attorney General Kwame Raoul; former state Comptroller Dan Hynes; Deputy Gov. Christian Mitchell, a former state representative; and former Chicago Urban League President Cheryle Jackson.

And don’t forget other City Council members who might have mayoral ambitions: Brian Hopkins (2nd), Rod Sawyer (6th), Anthony Beale (9th), Ray Lopez (15th), Carlos Ramirez-Rosa (35th) and Brendan Reilly (42nd).

Stacy Davis Gates, vice president of the Chicago Teachers Union, speaks during a June 2020 rally in Federal Plaza.

Stacy Davis Gates, vice president of the Chicago Teachers Union, speaks during a June 2020 rally in Federal Plaza.

Ashlee Rezin/Sun-Times file

No matter who enters, what is certain to be a crowded mayoral field, the race will be a referendum on Lori Lightfoot.

Assuming she runs.

Last summer, Lightfoot said seeking reelection was “not a gimme,” cracking the door open to joining Atlanta Mayor Keisha Lance Bottoms in saying one term is enough.

Since then, Lightfoot has sounded very much like a candidate for a second term.

She’s raised money furiously, spending it faster than it comes in.

She’s touting a “remarkable record of accomplishment” while leading Chicago during the pandemic. And she downplays the continuing focus on her inability to get along with others, even with her closest allies.

The problem is, polls conducted for other politicians continue to show Lightfoot’s approval rating at about 30%, maybe lower. That’s at least 20 percentage points below where she must be to win and avoid a runoff.

If Chicago continues to struggle with its highest rates of homicides, shootings and carjackings in a quarter century and suffers through what some fear will be a violent summer, it’s not outside the realm of possibility that Lightfoot could walk away rather than risk a humiliating defeat.

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