Both Chicago Mayoral Candidates Claim to Be Progressive. Here’s a Close Look Into Their Records.

Lori Lightfoot and Toni Preckwinkle have each run under the “progressive” mantle. Yet their records—and conversations with movement organizers—tell a more complicated story.

Camille Erickson

On April 2, Chicago voters will make the choice between Lori Lightfoot and Toni Preckwinkle as their next mayor. (Getty Images)

Chicago is barreling into the April 2 mayoral runoff election, pitting former prosecutor Lori Lightfoot against seasoned politician Toni Preckwinkle. Both candidates are cautiously responding to heat from community organizers in a race to win the progressive crown. Regardless of the outcome, Chicago — the nation’s third largest city — will replace Rahm Emanuel with the first Black woman serving as mayor.

To a political outsider, Lightfoot and Preckwinkle’s positions may sound nearly identical. But to community organizers with ears to the ground, the candidates’ track records say otherwise.

Both mayoral hopefuls trumpet what they call progressive agendas, promising sweeping criminal justice reform, equitable education and affordable housing for all Chicagoans. To a political outsider, Lightfoot and Preckwinkle’s positions may sound nearly identical. But to community organizers with ears to the ground, the candidates’ track records say otherwise. The tight race requires looking deeply into their backgrounds for a more accurate picture.

As Democrats across the country lurch left in order to benefit from grassroots progressive energy, many have leapt onto issues once considered politically taboo — abolishing ICE, tackling climate chaos or supporting universal healthcare.

This national shift left has been mirrored in Chicago, where candidates from the city council to the mayoral level have embraced progressive priorities.

I’m glad that we’re at a time in Chicago when the candidates are fighting to get the progressive vote,” says Tania Unzueta, legal and policy director at Mijente, a national Latinx organization fighting to protect immigrants.

But as progressive values swim into the mainstream, Candis Castillo, organizing director at United Working Families, says winning the progressive vote requires more than just lip service. It’s fashionable to be considered quote, unquote progressive,” she says. You can call yourself progressive all day, but where is your work?”

The machine

Current Mayor Rahm Emanuel’s legacy will forever be stained by the alleged cover-up of a video showing 17-year-old Black teenager Laquan McDonald’s murder at the hands of white Chicago Police Department (CPD) officer Jason Van Dyke. On Sept. 4, 2018, just weeks before a jury found Van Dyke guilty of second-degree murder, Emanuel announced he would not to run for a third term as Chicago mayor.

Preckwinkle, 72, jumped into the mayoral race soon after. She has served as president of the Cook County Board — which covers Chicago — since 2010, and before that as a city alderman representing the 4th Ward on the city’s South Side for 19 years. But Preckwinkle’s long political history has largely served as a liability during the campaign.

Critics like Dick Simpson, former Chicago alderman and professor of political science at the University of Illinois at Chicago (UIC), say that despite Preckwinkle beginning her career as a self-declared independent progressive, she is far too entangled with the infamous Democratic machine.”

This same machine helped allow the longest-serving alderman of 50 years, Edward Burke of the 14th Ward, to get re-elected despite facing an ongoing FBI investigation. Burke has been tied to Preckwinkle throughout the campaign due to their political relationship.

She also must overcome backlash for defending former Cook County Democratic Chairman Joe Berrios, who was found responsible for discriminatory property tax assessments during his time in office. 

Bryce Fields, an organizer with One People’s Campaign, supports Preckwinkle. One reason, Fields explains, is that they see Preckwinkle as having a proven history of being open to working with and for community organizations and the people they represent. In determining what is progressive means that your track record matters a lot,” Fields says. “[It’s] not just what you say and what you promise, but what you have done.”

Lightfoot, 56, a former federal prosecutor for the Northern District of Illinois and partner at the corporate law firm Mayer Brown, is seen by many of her supporters, including Simpson, as a disruptor — and just what City Hall needs. Yet she too is no political novice and has her own connections to the machine, though they don’t run as deep as Preckwinkle’s.

In 2002, she was appointed by former Mayor Richard M. Daley as the chief administrator of the CPD’s Office of Professional Standards. And again in 2015 she was appointed, this time by Mayor Emanuel, to head the Police Accountability Task Force. Her record in these roles has also been the cause of much scrutiny. 

Criminal justice and policing

Preckwinkle supporters are quick to point out her successes in reforming a punitive criminal justice system. She led impactful bond reform, allowing defendants to secure release on recognizance before trial. While she was board president, the Cook County Jail population fell below 6,000 for the first time in decades. The notorious Cook County Jail, which Preckwinkle holds sway over in her position as board president, is one of the largest jails in the country. A vast majority of people incarcerated face charges for low-level, non-violent crimes, but sit locked up waiting for a day in court simply because they cannot afford bond. She also fought to raise the age children would be transferred to adult jails from 17 to 18 years old.

As for her plans for office, Preckwinkle pledges to pump funding into an Office of Criminal Justice, support a civilian oversight system for the police department to increase democratic accountability and advance the city’s consent decree (a court order monitored by a federal judge that requires the city to address CPD’s systemic pattern of abuse).

Preckwinkle also was a supporter of eliminating Cook County’s gang database, a system replete with errors. As of July 2018, it listed 25,000 names of overwhelmingly Black and Latinx individuals suspected of gang involvement, according to data obtained by ProPublica. Law enforcement could turn undocumented suspects on the list over to ICE due to exceptions outlined in Chicago’s welcoming city ordinance. In January, the county’s database was officially terminated.

And when it comes to the city’s gang database, which has attracted fierce criticism for being over-inclusive and discriminatory, Preckwinkle unequivocally calls for its elimination. Lightfoot, for her part, says she will overhaul” or have CPD institute a replacement database.”

In 2017, Wilmer Catalan-Ramirez endured a violent arrest by ICE agents. With his name showing up on the gang database, he was placed in detention for 10 months. But, following outcry, the city ultimately settled the case, removing his name from the list.

If not for that database that the police have, I don’t think Wilbur would have spent that time in the detention center,” says Rosi Carrasco, a Chicago resident of 25 years and community organizer with Organized Communities Against Deportations (OCAD). Strengthening the welcoming city ordinance and eliminating the gang database are both imperative if the next mayor is going to protect immigrant communities, she says.

At a packed forum at Malcolm X College on March 19, Preckwinkle leaned forward when answering how she would address public safety.

If we’re really going to address issues of violence, we have to address the challenges that communities suffering from the most violence face,” Preckwinkle said. These are communities that have the highest levels of unemployment, the lowest levels of educational attainment, and they have under-resourced schools. They are often food deserts. We have to look at community needs.”

Lightfoot says she is also committed to criminal justice and immigration reforms, and cites her success during her time as co-chair of the Police Accountability Task Force.

At the March 13 forum, Lightfoot outlined her intent to reform police and the prison system while also increasing public safety. We need to do more, frankly, than send our officers to the DuSable Museum [of African-American History]. We have to deal with the practical problem of race and policing,” Lightfoot said.

But some activists, especially those seeking to abolish police and prisons, consider her former position as a federal prosecutor as a red flag.

When you’re a hammer, everything looks like a nail,” says Janaé Bonsu, co-director of Black Youth Project 100, referring to Lightfoot’s history representing police officers in court.

Bonsu is concerned with Lightfoot’s faith in current criminal justice and policing systems. The city already spends over a third of its budget on police and racial justice organizers are tired of communities of color being over-criminalized. Bonsu wants a candidate who will invest in schools, affordable housing, grocery stores, after-school programs and mental health services to address public safety concerns.

Others are also weary that Lightfoot’s prosecutorial background will make her too cozy with the CPD. It makes sense that someone who was a prosecutor believes that prosecuting people is one of the ways in which we resolve problems,” Unzueta says.

While working in CPD’s Office of Professional Standards under Mayor Daley, Lightfoot sustained (or found in violation of policy) very few complaints of abuse between her time leading OPS between 2002 and 2004, according to the Citizens Police Data Project. And many of her critics have spoken out against her decision to declare the shooting of 17-year-old Robert Washington in 2000 by police officer Phyllis Clinkscales justified.

In a recent interview with ABC7 News, Lightfoot responded to criticism by stating, The superintendent rejected the finding that it was an unjustified shooting, so by the time this case got back to me, there was very little I could do.” Rather than facing charges, Clinkscales instead received a 30-day suspension.

Lightfoot later transitioned to head of the Police Accountability Task Force which was launched to ease tension between community and CPD in the wake of McDonald’s murder. The task force aimed to provide independent oversight of police misconduct.

In 2016, community activists and family members attended a police board meeting to demand the firing of Dante Servin, a Chicago detective acquitted of involuntary manslaughter charges after killing 22-year-old Rekia Boyd while off duty.

At a 2016 police board meeting, Boyd’s brother Martinez Sutton offered an emotional plea. When he went over the allotted two-minute time limit, he was escorted from the room by security. Lightfoot’s response to the series of events is forever imprinted in Bonsu’s memory. Instead of responding with empathy and understanding, I saw Lightfoot just be stone-face, stoic,” she says. Servin resigned and continues to receive a pension, despite continued calls from activists for justice. People remember that and have resentment around that,” Bonsu says.

Still, Lightfoot supporters say her leadership is key to any sustained police reform, citing her claim that when she was the head of the police board, officer firings increased from 37 percent to 78 percent. Simpson, who came out in support of Lightfoot early in the race, sees her prominent involvement in setting the stage for Chicago’s consent decree—intended to rein in the rampant abuse in CPD — as evidence of her fitness for office.

The consent decree is what is legally binding for the city to carry out,” Simpson says. Lori would no doubt carry out the consent decree.”

Both Preckwinkle and Lightfoot have voiced opposition to a $95 million police training academy to be built on Chicago’s West Side, approved this month by Emanuel and City Council. 

This decision came despite dogged protests by residents and organizers from #NoCopAcademy who contend the city moved forward without enough community input. They argue that the funding for the project should be funneled to other vital resources such as education and job training.

While Lightfoot criticized the top-down rollout of the academy during debates, Unzueta says her solutions to public safety often involve investing more resources in CPD. At the March 13 forum, Lightfoot suggested reallocating the $95 million to convert some of the 38 closed Chicago schools into police academies, a proposal that received immediate blowback from many community members directly hit by the school closures. She later walked backed her statement saying she would not move forward without intensive community engagement.” The editorial staff at the Chicago Tribune—which endorsed Lightfoot — championed the proposal as out of the box thinking.”

But her comment has stayed on the mind of Castillo, a mother of an 8-year-old son.

I have a real problem with using our closed schools for mini-police academies in communities that are already over-policed instead of using that for the educational enrichment for our children,” Castillo says. The over-policing of Black and Brown children, especially boys, has a lot to do with what is wrong in our communities, and what is wrong with the city of Chicago.”

And despite widespread calls for equity and justice for the city’s most marginalized residents, both candidates do believe in the existing criminal justice system. Organizers with BYP100 keep their eyes on a more seismic solution: a city that, according to Bonsu, no longer needs prisons, jails, detention centers or other mechanisms of surveillance.” 

Taxes and pensions

On day one in office, the new mayor will have no choice but to confront Chicago’s swelling pension liability, not to mention a city budget in the red.

For decades, the city failed to remit necessary payments to pension funds and racked up 28 billion dollars in pension debt, placing the future lives of public service workers on the line. Both candidates have made promises to preserve workers’ pensions and reduce the city’s debt, but have provided few specifics.

Amisha Patel is the executive director of Grassroots Collaborative and Grassroots Illinois Action, organizations fighting to win economic and racial justice for Chicagoans. She’s been disappointed with the lack of solutions proposed by both of the candidates to manage the city’s unwieldy budget.

I think both Preckwinkle and Lightfoot really struggle here,” Patel says. Neither have been able to articulate a clear progressive vision when it comes to economic policies in the city of Chicago.” That indecisiveness is cause for concern, she says. For decades, an austerity agenda” has reigned king in the city and hit working people, especially people of color, hard.

Emanuel rolled back taxes for corporations after taking office with little regard for low-income communities, many activists say. And after his reelection in 2015, Emanuel announced he would tackle the pension crisis by cutting benefits for workers and increasing property taxes.

Although the Illinois Supreme Court ruled cutting of benefits for workers unconstitutional, efforts are still underway to either make a constitutional amendment or garner taxes from casinos and legalized marijuana, as announced by Emanuel in December 2018.

Preckwinkle pledged to work with the state to capture some revenue from gambling and marijuana, provide discounted buyouts for some workers or institute a graduated state income tax.

But Patel remains skeptical. With Preckwinkle, I think there’s a bit of a muddy history,” she says.

Confronted with Cook County’s exorbitant budget, Preckwinkle has secured a reputation as a pragmatist. In 2015, she supported pension reform that would have raised the retirement age and whittled away at workers benefits multiple times (the plan did not move forward). And though she initially campaigned in 2010 on not raising the county’s sales tax, in 2015 she attempted to do just that. Preckwinkle also pushed through a controversial soda tax in 2016 that fueled furious reactions, mostly from retailers and trade interests, to the point that the county repealed the law.

Lightfoot says she aims to keep the promise of a pension for workers, but also has signaled her intent to overhaul the pension system for incoming workers starting in 2020. What that means exactly remains unclear.

Ultimately, Patel says, the candidates missed the opportunity to propose creative revenue-generating solutions such as a graduated city income tax or a public bank. Patel also thinks the city needs to reinstate a corporate head tax so that corporations stop receiving tax breaks or handouts from pools of tax increment financing, or TIF, dollars.

They know that there isn’t an easy way forward,” Patel says, and they’ve been very careful to not talk about what they’re going to do.” In the end, she says, what matters is having a candidate willing to sit down and listen to organizers on the ground who have solutions to the crises.

Campaign support

Although the Grassroots Collaborative’s Patel believes both candidates are deeply flawed,” their positions do diverge dramatically, most notably when it comes to campaign contributions, she says.

Contributions tell a pretty clear story and they are very different stories when it comes to Lightfoot and Preckwinkle,” she says. 

Preckwinkle’s campaign has collected donations from major donors with suspect backgrounds — including through the aforementioned Ald. Ed Burke — but the majority of her funding has come from union support, including from the openly left-wing Chicago Teachers Union and SEIU Healthcare Illinois & Indiana.

Patel is most concerned with the number of corporations and Emanuel-backers doling out funds for Lightfoot’s campaign, including Craig Duchossois, CEO of a $3 billion company called Duchossois Group. She also received support from John Canning, a private equity investor who had previously backed Rahm Emanuel as well as a number of Republican politicians.

Patel is concerned that Lightfoot will fail to challenge corporate interests, even when the interests of working people are at stake, because of the strings such donations carry. Lightfoot has also received scrutiny for $40,000 in donations accumulated in a 501(c)(4) called Change Chicago, which WBEZ referred to as a dark money” group.

It sends a pretty clear message about where business thinks they’ve got their best shot of maintaining an agenda that puts them at the center and the rest of us on the margins,” Patel adds.


Chicago Public Schools have long suffered under shoestring budgets and closures. Over the course of just two decades, the city of Chicago shuttered or restructured over 200 public schools.

Essentially we have created a two-tier public system,” says activist and educator Jesse Mumm. We have boutique schools that get lots of funding and attention, are very hard to get into and are increasingly for the elite and disproportionately white families. And then we have neighborhood schools which sporadically get attention but are essentially allowed to rot.”

And it’s not just public schools that have come under scrutiny in recent years. In a span of three months, nearly 700 charter school teachers went on strike as charter school networks face heightened scrutiny from organized labor over the treatment of teachers and students.

Organizers with CTU have grown hoarse in their calls for reduced class sizes, higher teacher wages, more special education resources and equitable fiscal reform within Chicago’s charter school.

Chicago’s families have suffered for years under the Rahm/​Rauner/​Daley agenda of privatization, austerity and public subsidies for private corporate interests at the expense of working-class families and neighborhoods,” says CTU’s President Jesse Sharkey in a statement.

Both Preckwinkle and Lightfoot have pledged to stop the accelerated privatization of schools, institute a fully elected school board — rather than the current mayoral-appointed one — and place a moratorium on public school closures. And in January, Lightfoot released a comprehensive 15-point plan for funding and protecting public schools in Chicago. 

But as an educator, Mumm remains skeptical of Lightfoot. She has literally no experience whatsoever dealing with the education system,” he says. That’s not simply a matter you can brush up on a couple of weeks in advance.”

And CTU says Lightfoot’s donors alone are grounds for alarm. Donor John Canning, who also contributed to former mayoral candidate Bill Daley, champions the education voucher program and privatization. Lightfoot would be beholden to these private interests at the expense of families, CTU argues.

Before entering elected office, Preckwinkle served as a teacher for a decade, a qualification that she’s relied on in numerous debates. She also received the endorsement from the powerful CTU. But when she wore the hat of alderman of the 4th Ward, she supported the opening of charter schools under a plan to address underperforming public schools. She’s defended her decision in an interview with Chalkbeat, noting that times were different and it was the best choice she had to address deteriorating conditions of public schools.

Healing ties with Chicago’s South and West Sides

Both mayoral candidates’ agendas fall in sharp contrast to those carried out during Mayor Emanuel’s tenure. This is a new day for Chicago,” Castillo says. Regardless if it’s Lori or Toni, neither of them will have the rolodex of Rahm Emanuel or either of the [former-Mayor] Daleys.”

UIC’s Simpson calls the election a harbinger of a new day in American politics.”

Emanuel, first elected mayor in 2011, leaves behind a trail of neglect as he pumped millions of dollars into Chicago’s glittering downtown at the expense of poor and working-class communities of color, many activists say. Progressive voices across the city point to the city’s South and West Sides for proof. Home to the majority of Chicago’s Black and Lantinx residents, these neighborhoods have endured chronic disinvestment from city government and often live with high rates of unemployment, poverty and violence.

Emanuel attempted to remedy the city’s debt by imposing austerity measures that many residents pilloried as cruel — including the closing of 50 public schools and half of the city’s public mental health clinics. His administration reinforced segregated divisions chiseled deep into Chicago’s landscape, activists say. 

OCAD’s Rosi Carrasco says the city’s systematic neglect of immigrants and communities of color has had profound consequences. For 25 years, I have seen our neighborhoods become poorer,” Carrasco says. The government of the city is not paying attention.” When Emanuel disclosed he would not seek a third term, she says she felt hope that change would come.

Under Emanuel’s watch, murders in Chicago jumped by 58 percent between 2015 and 2016, according to the University of Chicago Crime Lab, with a significant proportion of homicides befalling communities of color chronically starved of sufficient public services. And a teetering pile of misconduct complaints against the Chicago Police Department (CPD) led the city to dish out taxpayer money to the tune of over $600 million for police misconduct settlements and fees over the span of just 12 years.

Chicago’s Black population declined by nearly 25 percent between 2000 and 2017, with more expected to leave in coming years, according to the Urban Institute. Mumm blames City Hall for not properly serving Black residents. I think it’s also because these communities don’t see themselves having a seat at the table in city government,” he says. They don’t see a future for themselves.”

The next mayor will have to suture these wounds and rebuild severed ties with communities outside downtown.

A question of accountability

Neither candidate is perfect,” BYP100’s Bonsu says of Lightfoot and Preckwinkle. Regardless of who wins this election, they will still have to answer to and work with organizers and people of the community.”

It’s one thing to promise an all-elected school board or halt the building of a police academy, as both candidates have said they would support, but it’s another thing to actually implement progressive promises, especially since every mayor must win majority support of the city’s aldermen too.

Organizers often have their fingers on the pulse of a city’s political climate, and their positions on the mayor’s race expose the backbone of progressive politics: No matter how justice-oriented a platform, politicians must be held accountable.

I’m excited to say we are going to have our first Black female mayor in the city of Chicago,” says Christopher Cook of 100 Black Men, an organization mentoring Black youth in Chicago. But when that’s all said and done, what changes are they going to make? We can’t really predict right now, but we can hold them accountable.”

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Camille Erickson is a writer and graduate student at Northwestern University.
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