(Bloomberg) -- Chicago Mayor Lori Lightfoot has been making personal appeals for support to the city’s top business leaders ahead of a challenging reelection bid – surprising some of them with direct outreach after she was often seen as holding corporate executives at arm’s length.

Lightfoot has been calling chief executive officers and other top leaders of several of the city’s largest businesses in recent months, people familiar with the conversations said. In each case, the people said, the mayor and her team were seeking support in the Feb. 28 election, which many took to mean donating to her campaign. The people asked for anonymity to discuss the private conversations.

Craig J. Duchossois, executive chair of Duchossois Group Inc., a privately held investment firm headquartered in Chicago, said he received a call from the Democratic mayor about two and a half months ago where he tried to stress the gravity of the city’s problems but felt that Lightfoot pushed back. 

“From my perspective, she really doesn’t appreciate that the city’s in a crisis,” he said, recounting that he told the mayor, “My answer is, ‘I’m not going to support you. I know you’re well intended, but you’re not effective.’”

The business outreach by Lightfoot, 60, comes as she faces criticism for rising crime and corporate departures including Boeing Co. and billionaire Ken Griffin’s Citadel hedge fund. She’s set to face as many as 10 challengers in her reelection bid, including US Representative Jesus “Chuy” Garcia — seen as the biggest threat to her second term. 

In some cases, top executives hadn’t heard from Lightfoot for several years until recent months – leading some to consider her contact too little, too late. It’s unclear how many of the executives will agree to support her reelection bid, financially or otherwise, the people familiar with the matter said.

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Lightfoot’s campaign said the mayor has had a close relationship with the city’s business community, citing her success in working with the corporate leaders during the Covid-19 pandemic, attracting or keeping more than 200 companies in Chicago, and earning several credit upgrades.

Just this quarter, the city’s debt was upgraded by Fitch Ratings Inc. for the first time in more than a decade, while Moody’s Investors Service elevated Chicago out of junk status. Much as with a person’s credit, the better bond ratings will allow the city to cut borrowing costs and save Chicago billions when the city taps debt markets.

“Mayor Lightfoot has been a consistent and committed partner to the business community over the last three and a half years,” campaign spokeswoman Christina Freundlich said in a statement. “None of this would be possible without a strong relationship between Mayor Lightfoot and the city’s business leadership, and she looks forward to their continued work and partnership together in the years ahead.” 

Duchossois said he had supported Lightfoot the first time she ran and considers her a person of integrity trying to do a difficult job. But he said that he, like other business leaders, is troubled by the rise in crime and threats to personal safety in the city.

“She says she’s going to hold people accountable. I cannot see where she’s holding people accountable. Crime continues,” he said. “She’s working hard. She’s giving it everything she’s got. It’s just not working.”

Change in Approach

Lightfoot came to office in 2019 offering herself as a stark alternative to predecessor Rahm Emanuel, whose pro-business agenda focused on attracting corporations to Chicago’s downtown. Emanuel, a Democrat, had worked as managing director at investment bank Wasserstein Perella & Co. and served on Freddie Mac’s board of directors before becoming White House chief of staff under Barack Obama.

“It was sort of either a throwaway line or a rumor, but Rahm Emanuel was talked about as actually being secretly a Republican mayor of Chicago,” said Allen Sanderson, a senior instructional professor in the department of economics at the University of Chicago. “And the reason he was seen that way was that he was friendlier to the business community.”

Emanuel famously counted cranes on the city’s skyline as a marker of his success and lobbied for CME Group Inc. and Cboe Global Markets Inc. to stay when they threatened to leave over a tax spat with the state.

Emanuel also was key in speeding up McDonald’s Corp.’s relocation from the suburbs back to the city, while Conagra Brands Inc. also moved to Chicago from Nebraska under his tenure. He tapped his close relationship with the business community to get Griffin to donate $12 million to the Chicago Parks District to separate the pedestrian and bike paths at the Lakefront.

Lightfoot, a former federal prosecutor who had never held political office, initially won some key business support, with the city’s Chamber of Commerce endorsing her candidacy four years ago. But her relations with the businesses have turned stiff, with executives grumbling that she didn’t fight for their interests in the same way Emanuel did. The Chamber of Commerce didn’t provide a comment. 

Lightfoot focused her administration on reducing segregation in the city, with a project to boost investments in the under-served south and west sides. Her signature economic development plan, Invest South/West, is raising some $2 billion to promote development in those neighborhoods.

That approach rankled some business leaders in “The Loop,” as the downtown business district is known, as they felt that area and its surroundings were getting short-shrift even though some of the city’s best-paying jobs and most prestigious companies are there.

In one high-profile exchange, Lightfoot sparred with McDonald’s CEO Chris Kempczinski after he told a meeting of the Economic Club of Chicago this year that the rise in violence was making it harder to lure executives to the city. A few days later, Lightfoot said at a news conference that Kempczinski needs to “educate himself” on the matter.

Bob Clark, executive chairman and founder of developer Clayco, said he has been in contact with Lightfoot since she was elected and served on the mayor’s Covid Recovery Task Force.

“Personally, I think she is somewhat misunderstood,” he said. “She can come across as abrasive, but so can Rahm.”

“I’d rather be constructive even if I disagree with her,” he said. “She could do more outreach, but it’s not her style. The business community has the responsibility to reach out to her too.”

‘Ongoing Dialogue’

Publicly, the mayor has also been seen more often with business leaders. In October, she moderated a panel at an event run by the Executives’ Club of Chicago with leaders from Google, Discover Financial Services and Health and Care Service Corp. She was also photographed with Dara Khosrowshahi, the CEO of Uber Technologies Inc., and McDonald’s USA President Joe Erlinger.

Michael Fassnacht, the city’s chief marketing officer and CEO of World Business Chicago, says the mayor is able to hold more in-person meetings now that pandemic lockdowns have ended. He cites an increase organization’s board members to 103 now from 85 in 2019 as evidence the business community is interested and engaged.

“I talk with her almost daily business topics, and I feel like over the last couple years since I’ve worked with her, she has an ongoing dialogue with business leaders,” he said. “I think we are even doubling down on how can we create a prosperous, healthy business ecosystem, but not just for one particular neighborhood, but for all 77 neighborhoods.”

Lightfoot’s approval ratings – hovering at less than 30% in polls taken during the summer – also took a hit from rising crime. Just this year, overall crime in the city jumped 41%, with an area that includes the central business district experiencing a 64% surge. Corporate departures added to the sense that Chicago was becoming less friendly toward business on Lightfoot’s watch.

Duchossois agrees that people are concerned about safety when coming into town.

“Although it hasn’t yet impacted our ability to hire quality people, it’s a subject that comes up more often,” he said. Chicago is “just tough to manage. It’s really, really tough to manage. You need to be a magician in so many ways. You need to compromise.”

Lightfoot recently notched an important victory, striking a deal for Google to buy a building that takes up a whole city block. She also approved Bally’s Corp.’s proposed $1.7 billion casino, which will generate revenue to help her plug the city’s ballooning pension debt. 

Still, Google’s new offices are currently being renovated and aren’t expected to bring in employees until 2026. Lightfoot’s main opponent, Garcia, has highlighted rising crime and the need to keep companies in the city as key areas to be tackled. 

--With assistance from Jason Hoffman and Elizabeth Campbell.

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