Mayor will need more campaign cash to overcome negatives, some observers say

After a first-quarter fundraising frenzy, the mayor has $1.7 million in cash in her primary political account. But veteran political operatives she may need $15 million to mount a successful defense of her record in a re-election campaign.

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Lori Lightfoot on election night in April 2019.

Lori Lightfoot on election night in April 2019.

Ashlee Rezin/Sun-Times

In 2015, an unpopular Chicago mayor who had closed 50 schools and alienated voters with his abrasive personality and top-down management style spent $24.4 million to survive Chicago’s first mayoral run-off.

Four years later and just a month before choosing political retirement over the uphill battle for a third term, Rahm Emanuel had $8.5 million in his campaign chest.

After a first-quarter fundraising frenzy that was her best since taking office, Mayor Lori Lightfoot has just $1.7 million in cash in her primary political account.

However you measure it, Lightfoot has nowhere near the money she’ll need to stand even a chance of being re-elected.

“A minimum is $8 million. A more likely need is probably closer to $15 million” for an unpopular incumbent with a record to defend, said veteran political operative Victor Reyes, who is not consulting for any potential mayoral challengers.

“She’s under water in the polls. She needs to try to turn that around by messaging. She needs to find a way to communicate her message to people who, right now, are not getting a positive message.”

Pressed to pinpoint Lightfoot’s roadblocks to a second term, Reyes pointed to two issues.

“The perception of her personality and then, the crime situation. People need to perceive that they’re safer under her watch. And that’s just not there right now,” he said.

Another political operative, who asked to remain anonymous, said “word has gotten around” that Lightfoot is “not an easy person to work with and doesn’t bring people together.”

“People know who she is. It’s like when Dennis Green said that about the Bears years ago, ‘They are who we thought they were,’” the operative said.

“She’s had so many instances of yelling at people. Picking on the Italian’s anatomy. Et cetera, et cetera. People know who you are at that point. You can’t cover it up. It was much easier for Rahm to do it with a [fuzzy] sweater than it will be for her.”

But the veteran operative argued Lightfoot’s biggest problem is public safety.

“You could spend $10 million on messaging on crime alone. People don’t believe it. They don’t see it. The police have no idea whether they can run to chase somebody, drive to chase somebody, whether they can put handcuffs on ’em,” the operative said.

“This is so muddled, you’ll need millions and millions just to prove that you’re even credible on the subject.”

However, the operative argued, Lightfoot’s “weak and late” fundraising suggests there is at least a remote possibility she may not run for re-election when the moment of truth comes, adding: “Maybe she’s just going through some motions right now.”

The City Council’s Black and Latino caucuses have both done recent polls to gauge voter sentiment for the contentious remap referendum. Both also included questions about Lightfoot.

The Black Caucus poll had her approval at 28%. The Hispanic Caucus had it at 30%.

An incumbent is considered “under water” with an approval rating below 50%.

Even with those numbers, Lightfoot’s first-quarter fundraising was her best yet as mayor, with $715,000 for her primary political fund, Lightfoot for Chicago, and $66,000 pulled in by Light PAC, created to support political candidates of her choosing.

By far the biggest donation — for $59,900 — came from the Lesbian Political Action Committee.

That was followed by the Illinois Black Business Political Action Fund ($25,000); Democratic donor extraordinaire Fred Eychaner and his Newsweb LLC ($24,000); Danny, Marilyn and Rocky Wirtz ($18,000 combined); Jerry, Michael and Nancy Reinsdorf ($16,000 combined); Spothero, Fuel Line Management LLC, Machine Entertainment Group, Laura and Brooke Skinner Ricketts, and Bob and Susan Wislow ($12,000 apiece); Joselito Cruz of EKI Digital ($10,000) and the Southern Glazer’s Wine and Spirits LLC ($8,000).

The $6,000 club includes: Robert Judelson, co-founder of JMB Reality; Theodore Kanellakes, executive director of the Chicago Medical Society; Winston & Strawn attorney Linda Coberly; developer Al Friedman; Erik Johnson of Baldwin Richardson Foods; software executive Mike Gamson; Larry Rogers of the Cook County Board of Review; Mark Aistrope, former president of Meeting Tomorrow and former independent Ald. Dick Simpson (44th).

The most popular donation was for $5,000. Somewhat surprisingly, that long list included only two unions: Chicago Stagehands Local 2 PAC and Roofer & Waterproofers Local 11 PAC. Also contributing $5,000: Cinespace Chicago Film Studios; Chicago attorney Ty Fahner; the law firm of Foley & Lardner LLP; economist Daniel Frisch; David Anderson, CEO of Anderson Royal Industries; Dennis Cook, CEO of WES Health System; Matt Mosher of Park Row Development; accountant Allen White and Rama Dandamudi, president of Studio Snaidero Chicago.

Emanuel’s vast Rolodex and infamous fundraising muscle allowed him to bring in vast sums of money quickly. Six-figure donations were his calling card.

Lightfoot, by contrast, recorded only one contribution over $50,000 in the first quarter, despite fundraising trips to California and Florida and a parade of emailed appeals to small donors ahead of the March 31 deadline.

At this point, she could have a difficult time matching the $5 million she raised and spent to win both rounds of the 2019 mayoral sweepstakes.

That’s particularly true given that mayoral candidates will compete for donations with candidates for governor, Illinois secretary of state, the General Assembly, the City Council and both sides of the remap referendum.

Dave Mellett, political director for Light PAC, noted the mayor is only now “ramping up” her fundraising for the uphill battle ahead.

Millionaire businessman Willie Wilson is likely to make fundraising easier by entering the race and giving himself a six-figure donation, which would lift caps on donations to all mayoral candidates.

“She’s $1.7 million ahead of anybody else who’s running for mayor right now, which is nobody,” Mellett said.

Madison Olinger, a spokesperson for Lightfoot’s re-election campaign, said the mayor “had her strongest fundraising quarter since the last election” and is “preparing to ramp up in the weeks and months ahead. ... We are confident we will have the resources to build a robust, grassroots, citywide operation. Mayor Lightfoot is proud of the progress she’s been able to make, especially while leading Chicago through a pandemic. These numbers show that our broad base of supporters, both at home and across the country, share that pride.”

Jason McGrath, Lightfoot’s pollster, could not be reached for comment. Neither could the mayor’s media consultant, Eric Adelstein.

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