Lori Lightfoot’s legacy: A combative mayor who led Chicago through crises, some of her own making

Chicago Mayor Lori Lightfoot will exit office Monday after presiding over the city’s most tumultuous era in generations, one marked by enormous strain on every element of civic life and the twin crises of COVID-19 and civil unrest.

As Chicago’s first Black female and first openly gay mayor, Lightfoot vowed four years ago to make Chicago the safest big city in the country, transform its reputation as a hive for corruption and villainy and lead an overhaul of the long-troubled Police Department. Her ambitious plans were derailed by the pandemic and widespread looting following the Minneapolis police murder of George Floyd, as well as Lightfoot’s own failure to forge or maintain bonds with stakeholders and public officials who could help her push a reform agenda.

It was this confluence of outside forces and self-inflicted wounds that sealed Lightfoot’s fate as she became the city’s first incumbent mayor in 40 years to lose reelection when she garnered only 17% of the vote in February’s election. Her fall from breakout political star to placing third represented a harsh rebuke from Chicago voters across the ideological spectrum.

Since her defeat, Lightfoot has stopped holding regular news conferences and declined to speak with the Tribune for this story. Instead, Lightfoot has given a small number of exit interviews to other media outlets where she defended her record and suggested history will look kindly upon her long-term measures aimed at making Chicago a fairer city.

“When we work to achieve equity, what we really mean is we are looking at our history and the deep scars that systemic racism, machine politics and disinvestment has left,” Lightfoot said in a farewell address last week. The solutions, she said, “won’t come overnight. But our administration created real change and planted seeds for transformation of our city to right these historic wrongs.”

Indeed, where Lightfoot experienced most success was in highlighting Chicago’s inequities and advocating to reverse deeply entrenched segregation, poverty and institutional racism. While she and her administration exaggerated the scope of her Invest South/West program to boost development in Black and Latino neighborhoods, she brought dozens of projects and refocused builders to disinvested communities. She took key steps toward realizing the proposed Red Line extension beyond 95th Street, a move officials hope will boost the Far South Side.

Lightfoot also made moves to stabilize the city’s finances by securing a Chicago casino to help fund pensions, addressing costly legacy debts, and reducing some fines and fees owed by those least able to afford it.

Early in the pandemic, when Black Chicagoans were dying at six times the rate of whites, Lightfoot and her team led by Dr. Allison Arwady worked to address that startling disparity. They provided door-to-door outreach with masks and information in vulnerable communities and, when vaccines became available, prioritized them for South and West side residents.

But Lightfoot also was slow to take action when the pandemic spurred Illinois Gov. J.B. Pritzker to close schools and businesses across the state, following along only reluctantly. She later clashed with the governor over bar and restaurant rules and battled the Chicago Teachers Union in a push to return to in-person learning, even as she faced blowback over keeping the lakefront closed too long. Her supporters praised her effort to make Chicago the largest open city in America, but critics accused her of acting too hastily to loosen restrictions.

Perhaps most devastating to her reelection bid, 2020 ushered in a staggering spike in violence that has yet to fully abate.

Though the recent crime wave was one felt across American cities, the outgoing mayor was dogged by accusations that her response was inadequate and her hand-picked police superintendent, David Brown, out of his league. Officers complained she didn’t have their back, a grievance highlighted by her claim that cops who were forced to work through long stretches without breaks were actually receiving an “incredible amount” of time off. On the left, progressives blasted her for failing to push more holistic approaches to stemming violence.

Amid the upheaval, Lightfoot left top priorities unaddressed or in poor condition. She failed to stamp out aldermanic prerogative over ward development and make ward redistricting independent — centerpieces of her plan to curb City Hall corruption. She allowed police reform efforts to atrophy. After abandoning support for an elected school board, she tried in vain to stop state lawmakers from enacting one anyway in legislation that ultimately stripped the mayor’s power over Chicago Public Schools.

While supporters say an elected board will democratize Chicago’s education system and lead to better results for students, the change also creates a highly uncertain transition period in the nation’s fourth-largest school district after years of declining enrollment.

Under Lightfoot, the Chicago Transit Authority went from an effective public transportation system to a poster child for unreliability. And though she vowed to “bring in the light” and run a transparent administration, she followed her predecessor, Rahm Emanuel, in repeatedly breaking public records law.

The city’s business community, particularly downtown, complained her administration belittled their concerns about public safety. The feeling was best illustrated by an incident where her often brash personality took center stage when she told McDonald’s CEO Chris Kempczinski to “educate himself” after he shared business concerns that the city was “in crisis” and without a plan to address crime.

In the midst of her term, the Chicago Bears announced they were looking to leave Soldier Field for Arlington Heights. And while it’s questionable Lightfoot could have prevented the NFL franchise from pursuing a new stadium at the former Arlington Park racetrack, her dismissive reaction illustrated the lack of diplomacy and slowness to recognize a problem that often characterized her term.

Despite all the slings and arrows, Lightfoot betrayed no regrets during rare interviews since her reelection loss, instead casting her record as one that kept the city afloat during unprecedented hardship while at last shifting attention to often-overlooked neighborhoods and residents.

“I leave office with my head held high, knowing that every single day I made a lot of tough but necessary decisions in some of the most difficult, challenging circumstances that any mayor in the history of this city has faced,” Lightfoot said in an exit interview with WBBM radio. “And I feel very comfortable with the way in which we governed.”

Crime spikes, police reform plods

Lightfoot inherited a Police Department at a crossroads in a city that has long struggled with violent crime and officer misconduct.

A sweeping, federally ordered consent decree to overhaul the city’s law enforcement practices debuted in 2019, on the heels of a stunning conviction in the Chicago police murder of Laquan McDonald. The newly minted mayor, who had burnished her police oversight credentials on the campaign trail, entered office with a vow to oversee “full and swift compliance” of the mandated reforms.

Meanwhile, Chicago homicides were steadily tapering for a third straight year. At the start of 2020, Lightfoot hoped to take a victory lap to mark a pivotal shift in Chicago’s gun violence fight.

That optimism was short-lived.

In March 2020, Chicago was brought to a standstill by the pandemic. Two months later, video footage of Floyd’s murder sparked one of modern America’s largest social justice movements, as well as two rounds of destructive looting throughout Chicago.

Under Lightfoot, the city’s approach to reforming its Police Department has generally been viewed as plodding, with residents from areas with the poorest officer-community relations reporting little change while alleging the same pattern of violent and intrusive encounters with law enforcement.

The court-ordered consent decree contains 800 paragraphs of reforms covering use-of-force, search warrant execution, foot pursuit policies and scores of other mandates meant to restore trust in the department and address inequitable policing.

Fulfilling the decree has been plagued with issues. Its independent monitor found 78% of the provisions have reached some level of compliance, but the city has only reached full compliance on 5% in four years. Critics, including former high-ranking city officials within the department and mayor’s office, argue Lightfoot and her team have treated the reform mandates as a box-checking exercise rather than truly overhauling the department.

Brown’s 2022 decision to fire the executive director of constitutional policing and reform, Bob Boik, also drew widespread concerns. Boik had objected to an order moving staff from officer training — a crucial piece of the consent decree — to patrol.

Charlie Beck, who was Chicago police superintendent from late 2019 through April 2020 after leading the Los Angeles Police Department as it exited 12 years of federal oversight, said the consent decree process is “always slow” but must be a high priority.

“If I had any criticism, it’s that there needs to be more effort and more resource put into consent decree compliance,” Beck said.

Illinois Attorney General Kwame Raoul, whose office is involved with the order’s implementation, said Brown never seemed to convince members that constitutional policing could improve their mission.

“I don’t know that he was fully invested in needing to do what we needed to do to embrace the consent decree, so it’s not coming from the top,” Raoul said.

One highlight for Lightfoot was bringing elected civilian oversight of the Police Department. While Lightfoot watered down the proposal creating the Community Commission for Public Safety and Accountability from what she supported as a candidate, commission supporters say it will help bridge divides between the police and citizens. Critics, however, worry that the agency lacks enough teeth to make a difference, as it only has limited power to change department policy.

One area where the mayor acted more assertively was boosting anti-violence funding, said Susan Lee, who was Lightfoot’s deputy mayor of public safety until resigning in fall 2020 to work at the anti-gun violence organization, Chicago CRED.

The city’s wide-ranging network of violence prevention and street outreach groups saw unparalleled public spending in their programs under Lightfoot, Lee noted.

Many of these programs operate by recruiting men who are most in danger of becoming involved in violence and paying them to participate in counseling, job training and other enrichment. Research on their effectiveness is still preliminary, though advocates credit the city for being open-minded to new ways to stop violence.

Chicago gun violence remains worse than it has been in years. Shootings spiked dramatically in 2020. The following year marked the city’s deadliest in a quarter century, with 800 people killed and more than 3,500 shot. Last year saw drops in those categories, a trend that’s continued so far in 2023. But homicides remain 11% higher year to date than in the same period in 2019, when Lightfoot took office.

Lightfoot was unable to convince voters she deserved credit for the decreases but not the spikes. For her part, she blamed public concerns about crime in part on “the 24-hour news cycle and the sensationalization of every issue.”

While Lightfoot faced extraordinary headwinds on public safety, her administration’s policing strategies and polarizing leadership style also played a role in the mixed results.

For instance, Beck said Brown’s decision to centralize the Police Department’s organizational structure and move beat cops from neighborhoods into citywide roving units was an inefficient deployment of resources that weakened community bonds.

As the mayor navigated the harrowing spike in violence, she found herself under fire from both sides of the political spectrum.

During her reelection campaign, the mayor condemned calls from conservative rivals to “let the police be the police” and said that belief fostered the infamous Chicago police torture ring led by disgraced Cmdr. Jon Burge. At the same time, Lightfoot launched attacks on Cook County State’s Attorney Kim Foxx and other progressive leaders of the Cook County criminal courts while also feuding with police advocates over issues including officer wellness.

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A protester breaks through a police barrier during a march in the Loop on May 29, 2020, to bring attention to the May 25 killing of George Floyd by a Minneapolis police officer. (John J. Kim/Chicago Tribune)

Summer 2020′s civil unrest was another flashpoint for Lightfoot. She faced criticism from conservatives for the city’s failure to stop the first round of looting or prevent a second. But her decision to raise downtown bridges during early looting came to be seen by progressives as a symbol of the city’s deep divisions. She defended it as a necessary public safety measure during an unprecedented moment.

“I think that’s the confusion, right, that everyone feels. That on the one hand, she speaks from the heart about giving young people and people who have been exposed to violence real trauma interventions and opportunities,” Lee said. “On the other hand, we have Mayor Lightfoot also talking about pointing fingers at state’s attorney. … I do think there’s been two different sides of the Lightfoot administration’s approach to public safety.”

Turmoil in the schools

COVID-19 monopolized much of the Lightfoot administration’s management of Chicago Public Schools. The widespread disruption prevented her from championing any signature educational agenda, though she succeeded at keeping schools open in 2022 amid a dispute with the teachers union.

Lightfoot’s struggle to forge effective coalitions was on prominent display during schools fights. She lost mayoral control over the district for the first time since 1995 after spurning Springfield lawmakers at the negotiating table over an elected school board. Bargaining conflicts with the Chicago Teachers Union during contract negotiations and then COVID-19 transformed the union into one of her staunchest political enemies. CTU went on strike months into her term and resisted her plans to return to in-person learning throughout the pandemic.

Endemic problems that predated Lightfoot remain: The student population further shrank and a fiscal cliff still looms.

Enrollment has declined from about 400,000 students a decade ago to just over 320,000 this school year. Underused and vacant schools languished as Lightfoot sidestepped thorny discussions of their future. Then, the passage of a state’s elected school board bill imposed a moratorium on CPS closings until 2025.

The first data on CPS achievement following the onset of COVID-19 revealed declines in academic performance that district officials portrayed as both “sobering” and an understandable byproduct of trauma that the predominantly nonwhite, majority low-income student body shouldered during the pandemic.

But Elaine Allensworth, a director at University of Chicago’s Consortium on School Research, noted that while math scores fell, the drops in reading proficiency were not statistically significant and graduation rates reached record levels.

“I don’t think we need to panic or see the district as somehow in disrepair,” Allensworth said. “The school district has not suddenly started doing terribly. Actually, it is a school district that has been showing a lot of improvement over the last 15 years.”

Daniel Anello, CEO of the local education nonprofit Kids First Chicago, said the academic setbacks during the COVID-19 era — sometimes referred to as “learning loss” — are part of a bigger story about the legacy of unequal investment in CPS. He noted the Lightfoot administration did make inroads such as bridging the digital divide via a free internet program for CPS households called Chicago Connected.

“For a lot of children in Chicago, particularly Black and brown families across the city, learning loss has been around for a long time,” Anello said. “This administration, I don’t think that they did harm, but I still feel like they were weathering the pandemic and we’re just getting to a place where we can start to address it.”

Lightfoot also walked back her 2019 support for an elected board during the campaign. She said the reversal was in part because the General Assembly’s proposal was flawed, and increasing the board’s size to 21 members was unwieldy.

State Rep. Kambium “Kam” Buckner, a chief architect of the school board bill who ran for mayor this year, said he understood Lightfoot’s concerns, “but the best way to fix that is to be at the table and to have conversations with those lawmakers.”

“Unfortunately, a lot of it was negotiated through the media and not in person,” Buckner said. “The truth of the matter is we didn’t need to fight on this bill. We needed a negotiation.”

Under the legislation that passed in 2021, the Chicago Board of Education will move to a half-elected, half-appointed panel in two years and transition to a fully-elected board by 2027.

Lightfoot had introduced her own versions of a hybrid board that would retain mayoral control over the majority of members. Buckner said that indicated the mayor was perhaps not unlike her predecessors who wanted to hold on to their tremendous influence.

“No one wants to give up power, right?” Buckner said. “But this is not the same Chicago that Rahm Emanuel governed. This is not the same Chicago that Rich Daley governed. And what was clear was that people have made up their mind about direct representation.”

But conflict with the teachers union was a hallmark of Lightfoot’s tenure, during which classes were canceled three times amid teacher work stoppages. The first was the bitter strike over the union’s contract. The latter two were standoffs over returning to in-person learning during the pandemic. The mayor frequently accused CTU of politicizing education, wielding undue influence and contributing to enrollment loss.

Union President Stacy Davis Gates scoffed at the notion teachers were holding their students hostage, a common criticism from Lightfoot.

“As a candidate, she was basically on the same page of the schools Chicago students deserve, the policy changes that this union has advocated for since 2010,” Davis Gates said. “When Mayor Lightfoot became mayor, those things quickly changed, and it never actually made sense. She never upheld her end of the bargain. That was our issue with Mayor Lightfoot.”

The 2019 CTU strike — Chicago’s longest teachers’ walkout in decades — ended after 11 days and set a discordant tone between the union and the mayoral administration early on. Though she praised the final contract’s commitments to class size limits and a nurse and social worker in every school, Lightfoot also trashed the union afterward and quipped to the Tribune, “I’m assuming that they’re coming after me in 2023.”

She was right. The former longtime CTU organizer and Cook County Commissioner Brandon Johnson will officially succeed her as mayor on Monday.

CPS finances remain a key concern going forward. The $9.4 billion public schools system is in the midst of a financial crunch as federal COVID-19 relief funds run out. District officials are projecting a $628 million deficit for the 2025-26 school year, and have called on state officials to provide more funding.

Adding to the pressure is Lightfoot’s decision to shift costs the city previously carried onto CPS’ books as a way to balance budgets. The district is already weighed down by a heavy debt burden and considered below investment-grade by rating agencies.

Lightfoot has long supported more state funding for CPS, as most mayors and candidates for that office have, but accomplishing that is easier said than done. The district is more than $1 billion per year below a state-set funding target based on student need.

But without strong allies in Springfield to grant relief, the district has continued to rely on raising its property tax levies. The business-backed watchdog Civic Federation opposed last year’s proposed $140 million hike, noting spending and personnel “continue to increase with no apparent cost containment strategies” and “no public long-term financial plan outlining how the district will address its challenges going forward.”

‘Reform is here’

Portraying herself as an outsider compared to her runoff opponent, Cook County President Toni Preckwinkle, who had ties to indicted 14th Ward Ald. Edward Burke, Lightfoot campaigned against the “broken and corrupt” political machine.

She vowed to curb aldermanic prerogative, the informal practice of giving City Council members near-total power over developments in their wards. That pledge became a focal point of Lightfoot’s campaign as she argued residents and businesses shouldn’t have to “kiss the ring” to get their projects approved.

Keeping promises is easier than making them, however, and Lightfoot always faced an uphill battle to kill aldermanic prerogative, as any such efforts would have to be approved by the City Council itself. Days before she was sworn in, Lightfoot denied reports her administration would allow aldermen to keep power over zoning while limiting their influence on permits and other administrative functions.

“We can’t really successfully change aldermanic prerogative but say carte blanche when it comes to zoning,” Lightfoot said. “We’re not going to do that. We’re going to drive change there as well.”

Instead, Lightfoot signed a largely symbolic executive order against aldermanic prerogative on her first day in office but dropped her promise to take on aldermanic control over zoning. Steps that her supporters said did reform City Hall include pushing a law forbidding aldermen from holding jobs that conflict with the city — like Burke’s job as a property tax attorney — and increased fines for ethics violations. Housing officials also have made it more difficult for aldermen to bury affordable housing proposals in City Council committees.

Her initial package of ethics reforms was weaker than an ordinance proposed by the Board of Ethics, an agency often criticized as being milquetoast. She also unsuccessfully opposed an effort by Aldermen Matthew O’Shea, 19th, and Michele Smith, 43rd, to ban lobbying by elected officials.

“She led on some things and allowed City Council reformers to lead on others. But she had chances to do much more than she did,” said Alisa Kaplan, executive director of Reform for Illinois, an organization Lightfoot previously served as a board member.

Kaplan pointed out Lightfoot’s 2019 ethics package passed unanimously in the 50-member council, but that Lightfoot let the momentum fizzle, later showing reluctance at raising fines for ethics violations: “She was elected on a wave of pro-reform sentiment, and she really didn’t ride it the way she could have. Some of her decisions were downright puzzling considering her promises and the political environment.”

In the end, the aldermanic culture and practices Lightfoot railed against largely remain intact. Incoming mayor Johnson has deflected questions about aldermanic prerogative, saying he doesn’t know what the phrase means and vowing to collaborate, an implicit acknowledgment he won’t pursue the issue.

She didn’t run as transparent an administration as promised, best exemplified by the Anjanette Young scandal, where her administration withheld videos of a disturbing police raid from the social worker while arguing that the footage painted a misleading picture of what happened. When WBBM-Ch. 2 obtained the footage, which showed Young naked in tears as police raided her home on an errant tip, Lightfoot lawyers attempted to have her sanctioned.

For her part, Lightfoot repeatedly denied any knowledge of the incident but later acknowledged receiving a detailed email about it, which she had responded to and demanded a meeting to discuss. She explained the discrepancy by saying she simply had forgotten the exchange. For critics, the episode illustrated a lack of regard for transparency and police reform that belied her campaign promises.

Similarly, Lightfoot pushed an ordinance allowing the city’s release of certain high-profile inspector general reports but refused to use it on any incidents that happened during her administration, including the Young report and an investigation into Hilco’s botched 2020 smokestack implosion that covered Little Village in dust.

Another critical piece of reform Lightfoot heralded, then dropped, was the idea of having an independent redistricting process for the city’s ward remap, which happens only once every 10 years after the census.

“Obviously, aldermen should have a role, but what they’ve done before is go behind closed doors and carve up the spoils of the city,” Lightfoot told WTTW-Ch. 11. “We’ve got to have a map that fairly represents neighborhood and community interests, and not just the interest of the local elected official.”

But when it came time to remap Chicago wards, in 2021, Lightfoot attempted to bring aldermen to deal, failed, and then largely left them to their own devices as they negotiated a backroom deal that served City Council’s interests.

The same redistricting gamesmanship happened as council factions fought. Latino Caucus chairman Ald. Gilbert Villegas, 36th, had his ward redrawn into a parody that has been compared to a snake, a seesaw and soup cans connected by a string, while conservative Northwest Side aldermen helped secure Ald. Jim Gardiner’s reelection by carving cop- and firefighter-heavy neighborhoods into the 45th Ward while drawing out more progressive neighborhoods.

And Englewood, one of the largest geographic neighborhoods on the South Side, remains divided among a handful of aldermen, a recurring criticism Lightfoot previously made about city maps.

“It was a clear-cut (broken) promise that just further fuels residents’ cynicism and erodes their trust in their city’s government,” said Madeleine Doubek, executive director of CHANGE Illinois, which has long advocated for reform to the redistricting process. “This isn’t some esoteric exercise. How wards are shaped determines whether people have an easy or hard time getting trees trimmed, garbage picked up and myriad other needs addressed.”

Shoring up city finances, with help from COVID money

While Lightfoot entered office with “an (outsized) structural deficit, a persistent and growing pension debt, and other costs that” threatened Chicago’s financial stability, as she put it in her inaugural speech, perhaps the brightest part of her legacy will be a series of moves to shore up the city’s finances.

The first deficit Lightfoot faced totaled $838 million and was soon compounded by a pandemic that clobbered city revenues.

But four years later, Lightfoot leaves her predecessor with a surplus, leveled-off debt service payments, a slew of upgrades from ratings agencies, and pension payments that are expected to climb at a more manageable rate for future budget-makers.

After a series of high-profile reports revealed how city fines and fees weighed disproportionately on low-income people of color, Lightfoot also worked to reform charges around city vehicle stickers, drivers licenses, utilities and booting and impoundment. The city said those reforms have saved “residents and businesses $262.6 million of debt without significantly impacting the city’s revenue structure.”

She came into office as lawmakers in Springfield were negotiating a massive gambling expansion that would finally authorize Chicago’s long-sought casino, along with five other licenses for gambling halls in the suburbs and downstate. The new mayor’s main contribution to the measure was the inclusion of a feasibility study to determine whether the approved tax structure was workable and whether city-proposed sites would make a good location for a future casino.

After a 2019 study concluded the approved plan wasn’t viable because of “very onerous” taxes and would fail to draw enough tourists, Lightfoot went to work. She launched what arguably became her most successful lobbying effort at the statehouse, convincing lawmakers to modify taxes for the casino to make the project more attractive to potential developers.

Though some aldermen pushed back on the selection of Bally’s as the operator and their plans to locate at the vacant Medinah Temple and the Chicago Tribune’s printing plant, Lightfoot’s pick prevailed, with support from organized labor. Pending state approvals, the temporary casino at Medinah is expected to open later this year. It’s estimated the casino will bring in $140 million in gaming revenues and $100.4 million in other revenues for the city and other taxing bodies by 2028.

But the gaming infusion will cover only about one-tenth of annual pension costs, city officials estimate, just one piece of the offensive to tackle the city’s mounting debts. Emanuel spearheaded both the change to state law to ensure any eventual gaming revenues were dedicated to police and fire pensions and creation of a payment ramp to get Chicago’s four pension funds to 90% of funding by the mid-2050s. It’s work that Lightfoot’s team argues it built on and exceeded.

But the mayor did not secure promised structural pension reforms, including a campaign proposal to put new workers into 401(k) plans rather than pensions, or a subsequent plan to consolidate city pensions with smaller funds downstate. Instead, she worked to carve out revenues for steep pension payments, which have grown from $1.3 billion in 2019 to $2.6 billion in last year’s budget.

Amanda Kass, an assistant professor at DePaul’s School of School of Public Service who has long studied Chicago pensions, said Lightfoot deserves plaudits for climbing the ramp Emanuel’s administration built. Lightfoot has also taken “prudent” steps to be proactive, Kass said, including a $242 million additional pension payment in her 2023 budget that helped offset pension fund investment losses last year. Officials estimate the extra payments will save $2.6 billion in the long term.

“Lightfoot had to manage those jumps and did,” Kass said.

When city revenues collapsed during the onset of the pandemic, Lightfoot’s budget team pitched a return to oft-criticized, kick-the-can tactics known as scoop and toss borrowing. The practice, which involves paying off old bonds with the proceeds from new ones, would have cost future taxpayers tens of millions of dollars in future years.

The city was only able to amend those plans and indirectly pay back its short term debt thanks to a $1.9 billion influx of federal American Rescue Plan funds. In all, the city used $1.3 billion of the money to replace lost revenues over three budgets, avoiding layoffs and drastic service cuts.

Combined with fresh borrowing, her administration allocated the remainder of those funds on a series of investments centered on housing and support for homelessness programs, climate investments, violence prevention and youth opportunities, and other community development initiatives over the coming years.

“Federal stimulus played a very large role” in the city’s current, improved financial status, said Fitch analyst Michael Rinaldi. “I don’t think we can think about the city’s credit quality and how it was able to get through the pandemic challenges without thinking about the stimulus.”

While the skies are clearer, the four pension funds are at an average 23% funded ratio and remain among the worst-funded of its big city counterparts.

A ‘wide open’ door to equity

Former mayors Daley and Emanuel were both criticized for their focus on the Loop at the expense of neighborhoods, especially on the South and West sides, and Lightfoot campaigned on making equity and inclusion “our guiding principles.” She spoke often about her desire to help reverse decades of disinvestment and segregation.

Not long after taking office, she launched what was arguably her highest profile initiative on that front — Invest South/West, a series of requests for proposals to spur developments in underinvested communities that has launched numerous projects.

Still, the city failed to meet its goal to have shovels in the ground on city-subsidized projects within 18 months, according to a Crain’s analysis last fall. A Tribune analysis separately found $409 million of the $757 million in city-funded projects included as Invest South/West projects were either already underway when Lightfoot took office, dedicated to standard building repairs or were still in the conceptual phase. And despite promises that spending would be community-driven, the Illinois Answers Project also spoke to several community leaders who said Lightfoot’s administration was opaque about how winning projects were selected.

But backers are unequivocal that Lightfoot’s laser focus on the program’s goals have set the stage for continued community-led investment with resources and support marshaled by government.

Anton Seals Jr., lead steward of Grow Greater Englewood and the chair of South Shore Works, said Invest South/West efforts in South Shore helped create “activity and buzz” around the 79th Street corridor about how to “grow and attract businesses into communities and having the community being the safeguard.”

“People saw real effort to make investments into our community, it highlighted how difficult and complex that really is,” after generations of white leadership that focused on wealthy downtown interests, Seals said. “That was the most important part: that somebody in power (said) Black communities need this kind of investment.”

Lightfoot brought the same equity focus to the newly constituted housing department. She tapped as its leader Marisa Novara, who had authored a report at her previous job at the Metropolitan Planning Council about the monetary cost of segregation.

The mayor’s equity approach to housing was “pretty revolutionary,” Novara said. “To actually have someone throw the door wide open and say, ‘Come on in and do it and I’ll back you on this’ was quite exciting.”

That freedom also allowed Lightfoot to say no to aldermen who resisted her department’s efforts. “There was a firewall between any grievances or alliances or anything, and it was strictly the ability to say, ‘This is a really strong development that this community really needs,’” Novara said.

The department went on to tweak its developer requirements to provide affordable units in new builds, limit demolitions in gentrifying areas in Pilsen and near The 606 and implement some protections for residents near the incoming Obama Presidential Center.

But critics say Lightfoot fell short on providing sufficient services for the homeless. She dropped an early campaign promise to push for a hike in the real estate transfer tax to provide a dedicated funding stream for homelessness.

And the migrant emergency has reached a fever pitch in Chicago, with hundreds of refugees sleeping in police station lobbies and thousands others seeking shelter elsewhere after coming from southern border states — a complex crisis that is in many ways out of Lightfoot’s control but nonetheless frustrating to aldermen who say her response showed teamwork and communication deficiencies.

Bad relationships

Through all four years in office, Lightfoot floundered when it came to developing productive and respectful relationships with other elected officials, feuding with the City Council, state legislators and, at times, the governor.

Some have noted the former federal prosecutor employed a domineering style reserved better for the courtroom, though at times her tough talk was just profane. (A former Park District lawyer in a lawsuit accused her of boasting she had “the biggest d--- in Chicago” while she mocked him, which she has denied.)

These episodes provided fodder for critics and political observers, but her at times abrasive, confrontational manner had real consequences — a characterization she disputes.

“I’m not going to and certainly not here in my final days as mayor give in to the narrative, which I think is frankly pejorative and offensive that, you know, ‘Mayor Lightfoot was mean and too tough,’” she said during a celebratory Friday tour of development projects under her term. “Nonsense, and because we’re family-oriented, I won’t use the other word that almost came out of my mouth. I mean, the notion that I’m tougher, more combative than Rich Daley or Rahm Emanuel is a joke. If I was a man, if I was a white man, we wouldn’t be having these discussions.”

Contrary to Lightfoot’s point, Emanuel’s abrasive personality did receive extensive attention and criticism, including from her. Unlike Emanuel, “I’m not going to lead with my middle finger,” candidate Lightfoot said in 2019.

And Lightfoot’s failures to pass the real estate transfer tax, prevent the General Assembly from stripping City Hall of school control or stop lawmakers from passing a pension bill she said would boost firefighter retirement debt by millions stand as a strong counterpoint.

At a local level, Lightfoot faced resistance in passing her budgets, even when they weren’t particularly controversial. Her 2020 spending plan, which had a minuscule property tax increase, passed 29-21. By contrast, Emanuel pushed through Chicago’s largest ever property tax hike in 2015 with only 15 “no” votes. Lightfoot also was unable to stop aldermen from renaming Lake Shore Drive against her wishes, so she came out in favor of the plan at the last minute.

Many of Lightfoot’s top policy achievements occurred early in her administration, but key parts were already on the runway when she took office. The $15 minimum wage and the fair workweek scheduling ordinance, for instance, were long in the works but bottled up by Emanuel. Lightfoot’s first round of fines and fees reforms was a package built and pushed by city Clerk Anna Valencia.

As time went on, Lightfoot fell short of translating her political goals into policy wins. She resisted efforts by Ald. Villegas to implement a universal basic income program in Chicago, saying she would prefer to give people jobs, before eventually adopting it as her own initiative.

The mayor struggled to fill key positions at times. Deputy mayor jobs for public safety and education, for instance, remained open for months.

She was generally able to pass her initiatives in City Council not because she had good relationships but due to fractures within the body and a broad culture of deference toward the Fifth Floor that continues. Progressives, conservative whites, Latinos and the Black caucus rarely coalesced enough to block her agenda and were often in different combinations of conflict with each other. Unlike the 1980s, when Burke and Ald. Ed Vrdolyak led efforts against Harold Washington, Lightfoot rarely faced well-organized opposition.

During the first months of Lightfoot’s term, Black Caucus chairman Ald. Jason Ervin, 28th, rallied aldermen for two big battles against the mayor — over marijuana sales and the so-called emergency powers ordinance at the start of COVID-19 — but failed to defeat her. In a twist, Ervin later became one of Lightfoot’s closest allies, and she fought to hide allegations of misconduct involving the office of city Treasurer Melissa Conyears-Ervin, his wife, in a court case against the attorney general’s office that remains ongoing.

When it came time for Lightfoot to pursue reelection, she had relatively few allies supporting her from City Council. Several of her hand-picked committee chairmen turned their backs on her, including powerful Budget chair Pat Dowell and Ald. Susan Sadlowski Garza, who delivered a remarkable summary of how the mayor was viewed in an interview with Chicago Reader columnist Ben Joravsky.

“I have never met anybody who has managed to piss off every single person they come in contact with — police, fire, teachers, aldermen, businesses, manufacturing, and that’s it,” Sadlowski Garza said.

Chicago Tribune’s Madeline Buckley and Dan Petrella contributed.

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