What to Know About Chicago’s Mayoral Election

CHICAGO — As residents of Chicago prepare to elect a mayor, they are staring at a highly uncertain picture: a race so wide open that even the incumbent, Mayor Lori Lightfoot, who won every ward in the city in the final balloting four years ago, is not assured a spot in an expected runoff election.

Chicagoans will pick on Tuesday among nine candidates at a pivotal time to lead the city, which has wrestled since the pandemic with a spike in homicides and an emptier downtown. At least four of the candidates are seen as serious contenders to make it to an April 4 runoff, and Ms. Lightfoot finds herself in between candidates casting themselves to her political left, and also to her right.

In the final days of the race, Ms. Lightfoot has attempted to embrace her spot in the middle, arguing that the city needs to stay the course with her. Before a crowd at a union hall over the weekend, she accused one opponent of being an undercover Republican. Another, she said, would raise taxes and cut policing.

In addition to Ms. Lightfoot, the top tier of candidates includes Jesús G. García, a progressive congressman; Brandon Johnson, a county commissioner endorsed by the local teachers’ union; and Paul Vallas, a former public school executive with a far more conservative platform on policing and education.

Those candidates all describe themselves as Democrats, an unofficial prerequisite for winning citywide office, but have vastly different visions for Chicago. Here is what is shaping the race to lead the country’s third-largest city:

The incumbent is on shaky ground.

Ms. Lightfoot leveraged outsider status and a promise for sweeping reforms to win her seat in 2019, becoming the first Black woman and first openly gay person to serve as Chicago’s mayor.

But she will enter this Election Day with uncertain prospects, dogged by diminished popularity, homicide rates that soared to generational highs and frequent feuds with labor unions and City Council members. Her campaign’s own polling in the weeks before the election showed her in the lead, but with only 24 percent of the vote.

Ms. Lightfoot has spoken about a need to attract more people to Chicago. But while the city’s population grew slightly between 2010 and 2020, census estimates show that the number of residents has declined since then.

Facing a crowded field, Ms. Lightfoot has portrayed herself this time not as a political outsider but rather as a serious, experienced leader who stabilized Chicago after being dealt a lousy hand. She has emphasized her investments in long-overlooked neighborhoods, defended her handling of the virus and noted that homicides have declined from their pandemic peak.

Paul Vallas wants to talk about crime.

When Mr. Vallas, a former chief executive of Chicago Public Schools, ran for mayor four years ago, he received just over 30,000 votes and finished in a distant ninth place.

But this time, he has emerged as perhaps Ms. Lightfoot’s biggest electoral threat by portraying Chicago as a city in crisis and promising to crack down on lawbreakers. His campaign website describes the city in almost dystopian terms, saying it appears Chicago “has been surrendered to a criminal element that acts with seeming impunity in treating unsuspecting, innocent people as prey.”

Mr. Vallas has called for increasing the number of police officers, replacing the police superintendent and improving arrest rates for serious offenses. But as he has made electoral inroads, emphasizing some of the issues that Mayor Eric Adams of New York City campaigned on in 2021, some have questioned whether he is out of step with Chicago’s overwhelmingly Democratic electorate.

In a city with a powerful teachers’ union and a long-troubled Police Department, Mr. Vallas’s calls to invest in charter schools and prosecute more misdemeanor crimes have unnerved left-leaning residents and led Ms. Lightfoot to suggest his true loyalties are with the Republican Party. Then, in the final run-up to the election, The Chicago Tribune reported that Mr. Vallas’s Twitter account had liked an array of tweets about the mayor that used offensive language or described Ms. Lightfoot as a man. Mr. Vallas, who calls himself a lifelong Democrat, said he did not like those posts and suggested that his Twitter account was breached.

Key union endorsements could cut both ways.

Two powerful labor unions that Ms. Lightfoot clashed with repeatedly — the conservative local branch of the Fraternal Order of Police and the liberal Chicago Teachers Union — have steered their supporters to two of her opponents. How much those endorsements will help or hurt remains an open question.

Mr. Vallas received the police union endorsement, which could be crucial in consolidating support among right-leaning voters and supporters of the police. But that endorsement has been used as an attack line by Ms. Lightfoot, and it may be a liability among Chicagoans who do not trust the Police Department or who disapprove of the union’s frequently brash rhetoric and coziness with Republican politicians, including Gov. Ron DeSantis of Florida.

The Chicago Teachers Union, basically the political opposite of the police union, gave its endorsement to Mr. Johnson, a Cook County commissioner and teacher running on an unabashedly progressive platform.

The teachers’ union has emerged over the last decade as a powerful player in Chicago politics, engaging in repeated work stoppages, fighting with the last two mayors and putting forth a liberal vision for the city that extends beyond education issues. Its endorsement is now a coveted seal of approval on the progressive left.

But after a bruising fight between that union and Ms. Lightfoot over Covid-19 school reopenings and precautions, and in a city where many residents name crime and public safety as their top concern, it is not yet clear what impact the teachers’ endorsement might have.

Race has long been a factor in Chicago politics.

Chicago, which has a long history of racial and ethnic groups voting as blocs, has roughly equal numbers of white, Black and Hispanic residents. This year’s mayoral field has seven Black contenders (including Ms. Lightfoot and Mr. Johnson), one white candidate (Mr. Vallas) and one Hispanic candidate (Mr. García).

Beyond the four candidates leading in the latest polls, others retain significant support and hopes of squeezing into the runoff. Willie Wilson, a businessman who is locally famous for giving away gasoline and $100 bills, finished in fourth place in the 2019 mayoral election and is running again this year on a promise to clamp down on crime. Though Mr. Wilson, who is Black, has a strong base of working-class Black supporters, he has struggled in past campaigns to win votes outside of the South and West Sides.

Some Black leaders have expressed concern that the makeup of the field could dilute the voting power of Black residents and lessen the chances of electing a Black mayor. In parts of the city with more Black and Hispanic residents, voter turnout is sometimes lower than in North Side wards where many white people live.

Other Black candidates in the race include Kam Buckner, a state legislator; Ja’Mal Green, a civil rights activist; and Sophia King and Roderick Sawyer, both members of the City Council.

But while race plays a role in Chicago politics, that role is not necessarily decisive.

Four years ago, two Black women, Ms. Lightfoot and Toni Preckwinkle, built multiracial coalitions and emerged from a large, racially diverse slate of candidates to make the runoff. And eight years ago, Mr. García, who would be Chicago’s first Hispanic mayor, qualified for the runoff by uniting Hispanic voters with political progressives of all backgrounds.

Electoral suspense has been a rarity in the past.

Chicago voters of a certain age came to expect, for better or worse, a level of continuity at City Hall. Richard J. Daley led the city for more than 20 years, from the 1950s into the ’70s, as did his son Richard M. Daley, who served as mayor from 1989 until 2011. Elections still came around every four years, but they became more of a formality than a referendum.

Even when the younger Mr. Daley left office 12 years ago, there was little uncertainty about who would take over. Rahm Emanuel, fresh off a stint as President Barack Obama’s chief of staff, returned to Chicago and won a majority of the vote, clinching the job without a runoff. (If no single candidate gets a majority of votes in the first election, the top two finishers advance to a runoff.)

Since then, mayoral elections have become far less predictable. Mr. Emanuel won a second term in 2015 but was forced into a runoff in a surprisingly close race with Mr. García. That runoff was the first since Chicago began holding officially nonpartisan elections in 1999.

Four years ago, after Mr. Emanuel decided not to run again, Ms. Lightfoot emerged in somewhat surprising fashion from a broad group of candidates that included several more established figures, including William M. Daley, a former White House chief of staff, and Susana Mendoza, the Illinois comptroller.

Whoever wins will face a changed City Council.

To enact their agenda, every Chicago mayor must navigate the city’s 50-member City Council, a body known for its clubbiness, its members’ frequent criminal indictments and the immense control it can exert over development.

As mayor, Ms. Lightfoot, who eliminated some of the sweeping privileges that Council members were historically given to govern their wards, has engaged in highly public disputes with some members even as she worked with them to raise the minimum wage and approve construction of a casino.

But the Council is in the midst of a transformation. Several long-serving members have resigned or decided not to seek another term, leaving voters across much of the city to choose new representation.

With all 50 seats up for election, and redrawn ward maps being used for the first time, voters will decide whether to empower more moderate or conservative candidates who have focused their campaigns on public safety issues, or elect progressives and Democratic Socialists calling for structural change. The outcomes of those races could determine what policies Ms. Lightfoot or her successor can pursue in the next four years.