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Chicago’s mayoral race is about to make history

In a race between Lori Lightfoot and Toni Preckwinkle, Chicago will elect its first black woman mayor on Tuesday.

Lori Lightfoot and Toni Preckwinkle, candidates for Chicago mayor.
Lori Lightfoot and Toni Preckwinkle, candidates for Chicago mayor.
The Washington Post/Getty Images
Emily Stewart covers business and economics for Vox and writes the newsletter The Big Squeeze, examining the ways ordinary people are being squeezed under capitalism. Before joining Vox, she worked for TheStreet.

Chicago is poised to make history on Tuesday and elect a black woman as its mayor for the first time.

Cook County Board President Toni Preckwinkle, 72, is facing off against lawyer and former president of the Chicago police board Lori Lightfoot, 56, to determine who will hold the highest office in the third-largest city in the United States. If Lightfoot is elected, Chicago would also become the largest US city to elect an openly gay mayor. The pair were the top two vote-getters in a February contest of more than a dozen mayoral candidates, forcing Tuesday’s runoff election.

The victor will succeed Rahm Emanuel, Chicago’s two-term mayor and former chief of staff to President Barack Obama. Emanuel in September announced he wouldn’t seek a third term. His popularity in Chicago has plummeted in recent years, in large part due to the city’s handling of the 2014 police shooting of Laquan McDonald, a black 17-year-old.

The case gained national attention after video footage released more than a year after the shooting showed that police lied when they claimed McDonald had lunged at the officer who shot and killed him. The officer, Jason Van Dyke, was convicted of second-degree murder and subsequently sentenced to more than six years in prison.

Emanuel’s successor will have to navigate the turbulent relationship between Chicago’s black community and the police and tackle other challenges as well. The city is facing a fraught financial future, as its contribution to four major pension funds will require another $1 billion by 2023. The next mayor will also need to draft a city budget that fills in a $252 million deficit by October.

Toni Preckwinkle versus Lori Lightfoot, briefly explained

Preckwinkle is viewed as the more experienced candidate in the race. Lightfoot, on the other hand, has never held elected office. Both women have claimed the progressive mantle.

Preckwinkle is a former high school history teacher. She served as alderman of Chicago’s Fourth Ward from 1991 to 2010, when she was elected as Cook County board president, becoming the first black woman to hold the post. She is also chair of the Democratic Party in Cook County, which covers Chicago.

As USA Today notes, if Preckwinkle wins, she would be the first person to be Chicago mayor and county Democratic Party chair since Richard J. Daley, the late mayor who held Chicago’s highest office for more than two decades and who famously oversaw the city’s powerful political machine. Former US Commerce Secretary Bill Daley, Richard Daley’s son and brother to former Chicago Mayor Richard M. Daley, lost to both Preckwinkle and Lightfoot in February’s first election.

Lightfoot has gone after Preckwinkle over her ties to Alderman Ed Burke, who was charged with extortion in January after allegedly trying to extort the owners of a restaurant chain who wanted to remodel a Burger King in his ward. Preckwinkle has returned $116,000 raised during a fundraiser Burke held for her before charges were brought.

According to the Chicago Tribune, Preckwinkle has proposed increasing Chicago’s minimum wage to $15 an hour by 2021 (four years ahead of a statewide increase to $15 an hour), creating an office of criminal justice reform focused on policing, and freeing up money for pensions by overhauling Chicago’s workers compensation program and some of its taxes.

The Cook County soda tax, which added a penny to the cost of each ounce of soda and sugary drinks in 2017, has also weighed on Preckwinkle, who championed it. The tax was highly unpopular and repealed just months after it was enacted.

Lightfoot is no stranger to Chicago politics. Both Emanuel and Richard Daley appointed her to positions in the city related to police oversight and accountability. Lightfoot also previously served as an assistant US attorney and most recently as a senior equity partner at Mayer Brown LLP.

Preckwinkle has swiped at Lightfoot over her lack of experience in the electoral realms. According to NPR, she warned that “being mayor is not an entry-level job.” But as Bloomberg notes, others are attracted to Lightfoot’s “clean slate” appeal.

Lightfoot’s primary proposals, per the Tribune, include increasing access to affordable housing, creating an office of public safety to reduce crime and reform policing, and pushing through a graduated real estate transfer tax to help combat homelessness. She also backs abolishing US Immigration and Customs Enforcement.

Heading into Tuesday, Lightfoot appears to have the advantage over Preckwinkle, as polls show her with a large lead. She has also outpaced Preckwinkle with endorsements, having gained endorsements from the media, the business community, and candidates who did not make it to the runoff. Meanwhile, the Chicago Teachers Union has endorsed Preckwinkle. So have Chance the Rapper and Rep. Bobby Rush (D-IL), among others.

Still, voter turnout for this mayoral election cycle has been low.

It’s going to be a big deal for whoever wins — and a tough road ahead

Whether Preckwinkle or Lightfoot prevails on Tuesday, the victory will be historic, because Chicago will elect its first black female mayor, and, if Lightfoot wins, its first openly gay mayor. In a city where race relations have historically been so fraught, and the relationship between the police and the black community is tense, it will be a big deal.

That doesn’t mean the task the winner will take on will be easy. The city is still reeling from the McDonald case. While Van Dyke, the officer who shot McDonald 16 times, was convicted, the police officers who filed reports backing his claims that McDonald had lunged at him were acquitted. During and after the trial, experts and activists claimed the officers’ actions exemplified the “code of silence” among police, which Vox’s P.R. Lockhart laid out:

In recent years, a number of police shootings and excessive force cases against black residents in the city have drawn attention to the systemic problem.

In a 2017 Department of Justice report on the Chicago Police Department, federal observers noted that they found evidence of an agreement between officers to hide wrongdoing. “One CPD sergeant told us that, ‘if someone comes forward as a whistleblower in the Department, they are dead on the street,’” the report notes.

According to the DOJ report, this code is so pervasive in Chicago that “officers and community members know” of its existence, further straining an already broken relationship between the police and black Chicagoans regularly subjected to racist language, police violence, and other discriminatory behavior.

The recent handling of the Jussie Smollett case — in which the actor alleged he was the victim of a hate crime, then was charged with a felony because authorities said he perpetrated a hoax, only for the charges later to be dropped — has put further scrutiny on Chicago’s police force and political apparatus.

To be sure, criminal justice is far from the only issue Chicago’s next mayor will have to tackle. The city is in a tough fiscal situation, and whoever is in charge will face some difficult budget matters as the city will need to direct more money toward pension funding.

The Tribune laid out what the candidates have said about the matter, though neither has definitively weighed in on their exact plans.

Lightfoot has proposed introducing “progressive sources of revenue” and cutting the city government, but details are still lacking. She also hasn’t ruled out tax increases.

Preckwinkle has suggested trying to make Chicago’s workers’ compensation program more efficient and modifying certain downtown taxing rules. She has also mentioned support for a potential tax hike to high-income people in Illinois.

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