Chicago Mayor Lori Lightfoot has been spending campaign money faster than she has been raising it, leaving her with less political cash than she had shortly after winning office two and a half years ago.

The mayor’s two campaign funds have bled $213,000 during that time, as Lightfoot raised $2.67 million but spent $2.88 million, a Chicago Tribune analysis of state campaign finance records found.

As a result, the $1.78 million Lightfoot had on hand in June 2019 has shrunk to $1.56 million, a figure unlikely to ward off any potential challengers in the February 2023 election.

Lightfoot is widely expected to seek a second term, but she has yet to launch a reelection bid. She is likely to announce her intentions by spring or early summer, according to two sources close to the mayor not authorized to speak publicly about her plans.

Typically, incumbents stockpile campaign money during nonelection years, conserving their cash for expensive television ads, direct mail and get-out-the-vote efforts closer to Election Day.

But Lightfoot has outstripped her fundraising by spending steadily on campaign staffers, consultants, polling, digital advertisements, events, travel and more, averaging nearly $100,000 per month in expenses, records show.

Lightfoot’s financial footing is a contrast to her two predecessors, former Mayors Richard M. Daley and Rahm Emanuel, who tapped the advantage of incumbency to build massive campaign war chests aimed at discouraging challengers from entering the race, and then using the cash to quickly define those who did through attack ads.

“I’m really surprised, because I thought once the mayor got into office, her strategy was going to be to amass as much money as possible, in the tradition of Rahm and Daley, to show her prowess,” said veteran Chicago political strategist Delmarie Cobb. “What is she spending her money on? If it were me, I would be holding onto every penny to scare people off who might want to run. She’s not scaring anybody.”

Lightfoot’s tenure as mayor has served as a crash course in crisis management, from the COVID-19 pandemic and destructive civil unrest to a teachers strike and skyrocketing violent crime.

As a result, Lightfoot said in an interview that she has not focused on political positioning but on “working on behalf of our residents who have been through hell and back the last two years.” Still, she expressed confidence her fundraising would be sufficient.

“I’m an incumbent mayor with a national reach,” Lightfoot said. “We’re going to have more than enough resources to be able to get the job done when that time comes. I’m not worried about that at all.”

Lightfoot said the pandemic has affected her campaign fundraising and spending plans.

“What would I have looked like, doing massive fundraising in the middle of a pandemic when people are worried about whether they are going to keep their jobs, worried about whether they were going to be able to meet their daily needs?” she said. “The money that I’m focused on is the money that needs to be in the pockets of the people in this city who are really hurting and in need.”

Steady spending

Fundraising was not a strong suit for Lightfoot when she ran in the February 2019 election as one of 14 candidates, the largest mayoral field in the city’s history.

For that first-round election, she raised $1.6 million, less than five other candidates.

The former federal prosecutor saw an opening to capitalize on the indictment of the city’s most powerful and longest-serving alderman, Ed Burke, who had ties to four front-runners in the race. With donor contributions drying up three weeks before the election, Lightfoot loaned her campaign $200,000 and recorded a TV spot that showed her flipping on a light in a proverbial dark backroom as she pledged independence from the city’s history of political corruption.

The political newcomer stunned the city when she finished first and found herself in an April runoff election with Cook County Board President Toni Preckwinkle.

The money quickly flowed Lightfoot’s way.

An array of business heavyweights and trade unions filled Lightfoot’s campaign coffers. She raised $4.8 million in the runoff, more than double Preckwinkle’s $1.9 million.

After Lightfoot won in a landslide, even more cash poured in. Wealthy donors who sat out the runoff made congratulatory contributions, adding another $1.7 million to the new mayor’s campaign accounts.

Since then, Lightfoot’s campaign fund and political action committee have together spent more money than the mayor has raised.

Her campaign fund, Lightfoot for Chicago, has raised $365,000 and spent $929,000, records show. Her Light PAC, which the mayor uses to cover most of her political expenses, has raised $2.3 million and spent $1.95 million.

Records show the mayor has spent more than $500,000 on fundraising consultants this election cycle, about 20% of the money she has raised. Lightfoot has spent another $350,000 on polling with a Washington, D.C., firm. She spent another $562,000 to pay a Chicago political consultant and her campaign’s political director and deputy political director, state campaign finance records show.

Lightfoot also made $25,000 in political contributions from her Light PAC, gave roughly the same amount to charities and spent another $17,000 on gifts such as flowers and Garrett’s popcorn. The mayor’s campaign also spent more than $17,000 to cover 1,038 ride-share trips around the city for staffers, records show.

Over the last two and a half years, Lightfoot has spent $270,000 on political events, equal to about 10% of the money she has collected over that period.

Among those expenses: $26,500 to rent a room at the Palmer House Hilton for a December 2019 fundraiser and $10,000 for another event at the historic Loop hotel that November. She spent another $36,000 on catering from Offshore Chicago, the Navy Pier venue that advertises itself as the nation’s largest rooftop venue.

Records show that the bulk of Lightfoot’s spending on events, most of them fundraisers, came in 2019, before the pandemic, and in 2021, after vaccines were available. The mayor’s fundraising also dropped substantially in the beginning of 2020, as the pandemic emerged.

“No one could have predicted COVID, of course, and I’m sure that slowed down her fundraising, but the one thing about Daley and Rahm is their fundraising wasn’t dependent on events,” said Cobb, the political strategist. “They could work the phone and get their money, which you’ve got to be able to do in times like these. It looks like Lori is struggling some with that.”

Campaign finance reports covering the final three months of last year show an uptick in Lightfoot’s travel and fundraising.

Her Lightfoot for Chicago campaign fund, largely dormant since her election win, reported raising $231,000 in the fourth quarter of 2021 while spending $153,000. Her Light PAC raised $306,000 but spent $322,000 for the same period.

Records show Lightfoot went on a fundraising swing through New York in November while holding December fundraisers in Washington, San Francisco, Los Angeles and Chicago. Lightfoot’s California fundraisers brought in $69,000 in contributions, but she also spent $9,000 on hotels for the trip and another $6,000 on airfare and rental cars to cover travel costs for her political staff and security detail, records show.

‘I’m yielding to no one’

As she eyes another run, Lightfoot has begun to cash more campaign checks.

Her largest contributions have come from the building trades — unions representing operating engineers, carpenters, electrical workers, laborers, plumbers and truck drivers. She also has received a number of contributions from wealthy business executives, including some who were prominent donors to Emanuel.

With just 10 months until candidates for mayor must file their petitions to get on the ballot, Lightfoot said she is girding herself for plenty of potential challenges.

“I’m not naive. I think there will be a lot of people — and there have been — putting their toe in the water,” she said. “But what I would say is, ‘When that time comes, you better be ready, because my work is not done, and I’m yielding to no one.’”

The most prominent potential challenger discussed to date has been Arne Duncan, a former U.S. secretary of education and former Chicago Public Schools CEO, whose most recent efforts have centered on anti-violence work in the city.

Duncan has yet to announce a run. That, however, didn’t stop Lightfoot from taking a preemptive shot at the former Obama administration official with an attack line usually used by supporters of former President Donald Trump: She likened Duncan’s push to spend more on community anti-violence measures to “defunding the police.”

“If that’s where he’s at, I’m on the other side of him,” Lightfoot said at an unrelated news conference earlier this month. What the mayor didn’t mention: She has eliminated hundreds of vacant police positions during her tenure while hundreds more officers have been lost through retirements and attrition.

Lightfoot has political liabilities of her own on policing.

She gained prominence as a police reform advocate in the wake of the Laquan McDonald police shooting and vowed as a candidate to ensure “full and swift compliance” with a federal consent decree aimed at forcing reform in a police department with a history of excessive force and misconduct.

But as mayor, Lightfoot has been criticized repeatedly by activists for failing to meet deadlines set by a federal court-monitor to ensure reforms, compelling a Chicago police leader who worked to implement the changes to resign last summer and accuse the Police Department of failing “to even feign interest in pursuing reform in a meaningful manner.”

On the other end of the political spectrum, controversial Chicago Fraternal Order of Police President John Catanzara has teased a mayoral run, which Lightfoot has said would “be a gift,” given his pro-Trump worldview in a deep blue city. Another former CPS CEO, Paul Vallas, who finished ninth in the 2019 mayoral race, also continues to be a highly visible Lightfoot critic.

Regardless of who runs for mayor, the political turbulence Lightfoot faces extends beyond the typical pandemic-related headwinds other mayors and governors across the country have faced.

She and the Chicago Teachers Union just resolved the third work stoppage of her tenure, the last two standoffs over COVID-19 protocols in the city’s schools. The city’s 800-plus homicides last year are the most Chicago has seen in decades, which have fueled feuds with Cook County Chief Judge Tim Evans and Cook County State’s Attorney Kim Foxx as Lightfoot has insisted more must be done to keep violent criminals behind bars. She has also battled the FOP over vaccine rules and reform efforts.

Even though Lightfoot promised as a candidate not to lead “with her middle finger,” she has struggled at times to maintain strong working relationships with aldermen, state legislators and Gov. J.B. Pritzker, because of her combative style.

While some see a politician eager to pick fights and slow to build consensus, Lightfoot’s political donors see a mayor fighting for Chicagoans who have long been ignored by City Hall.

“If you go out in the neighborhoods, and you talk to the vast majority of people who live in the city of Chicago, they like a fighter, and she is a fighter,” said former Democratic gubernatorial candidate Chris Kennedy. “There is nobody who is going to emerge in this race who is a bigger warrior than Lori, and I just can’t imagine the people of Chicago, faced with two choices, and choosing the one who is not the best fighter in the ring. They don’t do that.”

Kennedy said he supports Lightfoot because of her toughness and applauded her insistence that schools remain open for in-person learning during the most recent standoff with the teachers union.

“Kids are back in school,” said Kennedy, the son of slain U.S. Sen. Robert F. Kennedy. “That’s the critical barometer for me.”

Kennedy, who finished third in the 2018 Democratic primary for governor, called talk of Lightfoot’s fundraising “inside baseball.” Kennedy and his wife, Sheila, have given a combined $25,000 to Lightfoot, including $10,000 in October.

“Do I think fundraising totals are a measure of the value of an incumbent or the attractiveness of the candidate?” Kennedy said. “No, I don’t.”

Laura Ricketts, a prominent Democratic donor and co-owner of the Chicago Cubs, said she hopes Lightfoot runs and wins a second term, citing her “strong, competent and steady leadership. It is exactly what Chicago needs right now.”

Ricketts and her wife, Brooke Skinner Ricketts, served on the host committee for a Lightfoot fundraiser last month at the Theatre on the Lake in Lincoln Park, according to the event’s invitation.

Ricketts, who has contributed $86,000 to the mayor’s campaign, credited Lightfoot with investing in South and West Side neighborhoods and leading the city through the pandemic.

“She deserves a second term to continue her efforts to build a more prosperous, safe and more equitable Chicago,” she said.

A prominent Rahm donor

One Lightfoot campaign donor has been more closely involved than most in helping to shape City Hall policy — Michael Sacks, the CEO of GCM Grosvenor, an international investment firm based in Chicago.

Sacks is best known in Chicago political circles as the close friend, confidant and No. 1 campaign donor to former Mayor Emanuel. Sacks, his wife, Cari Sacks, and Grosvenor employees contributed more than $4 million to political funds that helped Emanuel win election to City Hall.

Sacks and his wife gave a combined $100,000 to Lightfoot’s campaign shortly after she won election.

To some progressives, Sacks is a symbol of the “Mayor 1%” criticism leveled at Emanuel, which contended he did more to serve the city’s wealthy elite than working-class families.

It’s a line of criticism Lightfoot echoed at times during her mayoral run. Yet these days, the mayor and Sacks exchange text messages about City Hall strategy, according to records obtained by Tribune under the state’s open records law.

During the October 2019 teachers strike, Sacks texted Lightfoot with words of encouragement, to which the mayor replied, “I will not cave.” Sacks referred to negotiations with CTU as a “brutal horrible process.”

“I think you can come through it well and they massively overreached,” Sacks texted during the walkout. “You’re being more than fair, and you have the whole city behind you.”

“Well, I hope you are right,” Lightfoot texted back.

In two separate text exchanges, Sacks referred to having phone calls with U.S. House Speaker Nancy Pelosi. In one exchange, he consulted with Lightfoot on what message she would like him to deliver on the city’s behalf.

“We need to have more direct dollars, not filtered through the county and the state,” Lightfoot texted Sacks at the beginning of the pandemic in April 2020. She emphasized the need for an anti-poverty plan and an infrastructure bill, texting “we need to put people back to work and lift people up.”

Perhaps most notably, Sacks was closely involved in Lightfoot’s unsuccessful effort to fight against state legislation creating an elected school board for CPS. Sacks texted about having contacted Senate President Don Harmon and strategized on various compromises the city could seek at the State Capitol.

“(I’m) thinking that the most important message and the most important thing is you don’t walk away and don’t blow up,” Sacks texted in the final days of last year’s legislative session. “You just want to keep working and keep trying to make this work for progress and let them get frustrated and walk.”

“Agreed,” Lightfoot responded.

In the end, their efforts to stall and shrink the size of an elected school board failed.

In an interview, Sacks called the teachers union representatives “effective, skilled and tough negotiators” and said he offered his support to Lightfoot during the strike because “I think it’s always better to maintain a cool head in negotiations.”

On the elected school board, Sacks said he couldn’t see how a board of 21 members would effectively govern, so he “felt it was important to try to help.”

Lightfoot described Sacks as “someone who I have a great working relationship with.”

“Michael is a guy who cares about Chicago deeply and is fundamentally a good human being. That’s exactly the kind of person who we need to be engaged in this really challenging fight for the life of our city,” Lightfoot said. “I really appreciate his support. I appreciate his wise counsel. He has been very close to the line of fire and understands the challenges a mayor faces.”

Sacks and his wife last contributed to Lightfoot in December 2020, when each wrote a maximum $11,600 check to the mayor’s Light PAC.

Asked if he planned to support a likely reelection bid from Lightfoot, Sacks was noncommittal.

“I am still recovering from the last election cycle,” he said of the 2020 presidential race. “But I will let you know when I reengage.”

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