Facing stiff headwinds, Lightfoot launches campaign for a second term

After a video release and fundraiser on Tuesday, the piece-by-piece rollout of a campaign that has long been a given continues Wednesday with five campaign stops — in Ashburn, Greater Grand Crossing, Little Village, Garfield Park and Boystown.

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A happy Lori Lightfoot on the night of her landslide win over Toni Preckwinkle in the 2019 mayoral runoff election.

A happy Lori Lightfoot on the night of her landslide win over Toni Preckwinkle in the 2019 mayoral runoff election. Whether she is as happy on election night next year remains an open question.

Sun-Times Media

Facing stiff headwinds, Mayor Lori Lightfoot on Tuesday started her uphill climb to reelection with a River North fundraiser and a video embracing the combativeness that some view as her greatest weakness.

The piece-by-piece rollout of a campaign that has long been a given will continue on Wednesday with five campaign stops — in Ashburn, Greater Grand Crossing, Little Village, Garfield Park and Boystown.

“They say I’m tough. They say I get angry. They say sometimes, I take things personally. You know what I say? They’re absolutely right,” Lightfoot says in the video, an updated version of the infamous fuzzy sweater commercial that a dictatorial Mayor Rahm Emanuel used to win a second term.

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“When we fight for change, confront a global pandemic, work to keep kids in school, take on guns and gangs, systemic inequality and political corruption only to have powerful forces try and stop progress for Chicago, of course I take it personal — for our city. Change doesn’t happen without a fight. It’s hard. It takes time. And I’ll be the first to admit: I’m just not the most patient person. I’m only human. And I guess sometimes, it shows. But just because some may not always like my delivery, doesn’t mean we’re not delivering.”

The 2-minute, 35-second video easily could be carved up into campaign commercials, assuming Lightfoot can raise the $10 million to $15 million political observers say she needs to convince an angry electorate fed up with inflation and violent crime to give her a second chance.

After a first-quarter fundraising frenzy, her best since taking office, Lightfoot still had just $1.7 million in cash in her primary political account.

Since then, millionaire businessman Willie Wilson joined the fray and contributed $5 million to his own campaign, blowing the cap on fundraising for all 2023 mayoral candidates.

But Lightfoot has, so far, failed to benefit from it, receiving just a handful of five-figure contributions, and none higher than that.

Her largest recently have come from: Rockwell Construction LLC ($25,000); Peter Kadens of Vision Management Services ($24,000); philanthropist MaryJo Schuler ($15,000); Cboe Markets, Inc. ($12,000) and Anthony Chase, chairman and CEO of ChaseSource LP ($10,000).

It still looks like Chicago’s big-money interests are on the sidelines, waiting for a candidate.

Lightfoot can only hope that changes — starting with the take from Tuesday’s fundraiser in the Ivy Room at Tree Studios, 12 E. Ohio, in River North. The room holds 200 people, and contribution levels range from $250 to the $5,000 or $10,000 needed to access a “special sponsor reception.”

Lightfoot’s entry makes it four Black candidates in the field. The others are Wilson; Ald. Roderick Sawyer (6th), son of former Mayor Eugene Sawyer; and state Rep. Kam Buckner. Also running: former Chicago Public Schools CEO Paul Vallas and Ald. Ray Lopez (15th).

South Side Ald. Sophia King (4th), state Rep. La Shawn Ford, D-Chicago, former Democratic candidate for state’s attorney Bill Conway, former Gov. Pat Quinn and former mayoral challenger Gery Chico are still thinking about it.

Lightfoot’s speech to the City Club of Chicago in late April laid the groundwork for her reelection campaign.

She claimed Chicago was poised for “the best economic recovery of any big city in the nation, bar none” — despite “what the naysayers” have to say.

After the speech, she challenged the media to “find another mayor” who faced the “unprecedented challenges” that confronted her. There was “no honeymoon period for me,” she said.

“A pandemic, historic economic meltdown, civic unrest, spiking violence” and all “within about a six-month period,” Lightfoot said that day.

Chicago Mayor Lori Lightfoot gets a booster shot of the Pfizer-BioNTech COVID-19 vaccine.

Mayor Lori Lightfoot gets her COVID-19 booster shot in November. The coronavirus pandemic upended her first term in office, and has made her quest for a second term more challenging.

Pat Nabong/Sun-Times

Tuesday’s video continues that theme — but in a more uplifting way, aimed at reminding voters of Lightfoot’s tough-as-nails leadership during the pandemic and why they chose her in a 2019 mayoral campaign dominated by the corruption scandal still swirling around indicted Ald. Edward Burke (14th).

“I get it: I don’t look or sound like any other mayor we’ve ever had before. And I’ve had to fight to get a seat at the table. And like so many in our city, I’ve had to fight to have my voice heard. That’s why I’ll never back down in fighting every day to turn your voice into action,” she says in the video.

“You love the city as much as I do. ... Because of you, Chicago is coming back. When we got knocked down by COVID, we came together as a city and we got right back up because that’s who we are. And that’s how we’ve been able to make so much progress in spite of all that’s been thrown at us. Of course, there are tough challenges ahead. We have a lot of work to do because change just doesn’t happen overnight. But together, we will make our city safer, fairer and more equitable for all. Now, let’s get back to work.”

Recent polls by other declared or potential mayoral candidates and for the City Council’s Black and Hispanic caucuses show Lightfoot facing strong headwinds.

Her public approval is 25%, according to Ald. Brian Hopkins (2nd), a potential challenger whose $50,000 poll is the most recent.

Mayor Lori Lightfoot and Chicago Police Supt. David Brown at a July 2021 press conference in Lawndale.

Mayor Lori Lightfoot and Chicago Police Supt. David Brown outside the 11th District CPD headquarters in Lawndale, in July 2021.

Anthony Vazquez/Sun-Times

With violent crime foremost on voters’ minds, veteran political operative Victor Reyes said Lightfoot is at a tremendous disadvantage.

With a runoff all but certain, her best — and, possibly, only — hope is to make it into that runoff with “45% of the vote or better” against a candidate who “can’t raise money to get their message out,” Reyes said.

“I don’t see too many other paths. … When you’re the mayor and crime is going through the roof, you wear the jacket, no matter what. There’s a personality trait that appears, at least to the outside world, like ‘my way or the highway.’ That’s turned off voters at a time when they’re looking for collaboration,” Reyes said.

Lightfoot’s biggest problem, Reyes said, is that politically, she’s like the man without a country, with a “very small base” of potential voters.

“I don’t think she has the lakefront vote like she had against [Toni] Preckwinkle. I don’t think she has the Latino vote. The Southwest and Northwest side bungalow belt [dominated by police officers and firefighters] are not likely. ... And her popularity in the Black community is primarily older African American women” who might gravitate to Wilson or Sawyer, he said.

Mayor Lori Lightfoot delivers her inaugural address at Wintrust Arena on May 20, 2019.

Mayor Lori Lightfoot’s first inauguration was held at Wintrust Arena. Her route to a second term remains difficult.

Ashlee Rezin/Sun-Times

The Chicago Federation of Labor and its member trade union leaders appear to be lining up behind Lightfoot after helping her convince the City Council to approve Bally’s $1.7 billion casino plan.

Still, “their members are not necessarily supportive. They have concerns about crime, taxes and services” just like everybody else, Reyes said.

“I wouldn’t count her out completely. I really wouldn’t. But, she has a very difficult challenge ahead. Some of her own doing. Some of it just institutional problems.”

Veteran political consultant Peter Giangreco represents U.S. Rep. Mike Quigley, D-Chicago, who, like former U.S. Education Secretary Arne Duncan, skipped the mayor’s race. He also advised mayoral challenger Susana Mendoza in 2019.

Giangreco noted polling for Quigley, Duncan and other prospective candidates shows Lightfoot nowhere near the half-plus-one tally she needs to avoid, or win, a runoff.

“She’ll still get some votes on the lakefront. But it doesn’t add up to more than 50% because there’s a lot of white progressives who are disappointed in her. There’s more somewhat-liberal folks — the kind of people who voted for Hillary Clinton and Rahm Emanuel — who have left her in droves. And she’s got real problems in the Hispanic community as well,” he said.

“Her path to victory is to hope and pray that she gets into a runoff with Paul Vallas,” then paint Vallas “as a Republican in a city that’s 70% Democrat. That’s her only path, in my mind,” Giangreco said.

Though he expects Lightfoot to make it into the runoff, “I would bet that we have a new mayor in 2023,” he said.

“When you win with 76% of the vote, you have a once-in-a-lifetime chance to unite the city, and she managed to fritter it away both in terms of performance and inability to keep quality staff. But mostly, it’s crime. If things were better on crime, no one would care what her personality was like.”


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