This matchup, which took shape late Tuesday as election results rolled in and contender after contender conceded defeat, did not seem likely when the campaign got underway. Lightfoot had been a relative unknown in the race, but with more than 95 percent of precincts reporting, she had gained more votes than any other candidate.
She seemed likely to face Preckwinkle, who had the second-highest vote total late Tuesday. Bill Daley, former chief of staff to President Barack Obama and the brother and son of former mayors, was in third place and conceded. Willie Wilson, another contender, had not conceded as of late Tuesday, his staff reported, but he trailed Lightfoot and Preckwinkle by several percentage points and tens of thousands of votes.
They were all among a record crowd of mayoral contenders seeking to fill the job once held by Harold Washington and two Richard Daleys, looking to replace Mayor Rahm Emanuel (D), who abruptly announced last fall that he would not seek a third term. An election that would have hinged on Emanuel instead became remarkably wide open, with a diverse field of candidates jostling to respond to voter concerns about crime, schools, the city’s finances and public corruption.
The slate of candidates had been relatively slim before Emanuel’s announcement, but it grew, with nearly as many names on the ballot as there are players on the Chicago Bulls roster. The candidates were also diverse, with people of color making up nearly half the ballot and polls showing three women among top contenders.
Some voters said the number of people running made it difficult to pick a candidate. “It’s hard to choose the best person if everyone has the microphone,” said Tony Lowman, 40, who added that he was disgusted by the endless marketing.
As it was responding to this bloodshed, the Chicago Police Department was also the subject of a federal civil rights investigation and repeated protests spurred by the 2014 death of Laquan McDonald, a black 17-year-old who was fatally shot by Jason Van Dyke, a white police officer.
Video footage of the shooting was released the following year. Chicago officials had sought to keep it from being made public, and the video emerged only after Emanuel was elected to a second term and the city council had approved a $5 million settlement with McDonald’s family.
The graphic footage set off waves of public unrest. The Justice Department opened an investigation that concluded Chicago police routinely violate the constitutional rights of residents, particularly those of color. A task force Emanuel organized amid the fallout from the video’s release also found that the Chicago police face a “justified” lack of trust from the community.
Issues of law enforcement and police reform also infused the candidacies of some on the ballot Tuesday. Among the contenders were Lightfoot, the former federal prosecutor involved in issues of police reform; Garry McCarthy, who said Emanuel made him a fall guy by forcing him out as police superintendent after the McDonald video was released; and Preckwinkle, who criticized Emanuel for his handling of police reform.
When Emanuel announced that he would not seek another term in the office he has held since 2011, it was at a tense moment in Chicago — just one day before Van Dyke’s trial was set to begin. Van Dyke, now a former police officer, was convicted of second-degree murder.
A race that had begun by focusing on Emanuel’s tenure — responding to the controversies that dominated his terms, including policing issues, gun violence, skyrocketing pension debt and his decision to close more than 50 public schools — shifted.
The campaign was a referendum on the Chicago establishment, pitting a tier of candidates connected to the “Machine” system of the Cook County Democratic Party against those who argued they were independent enough to spark long-needed reform.
Chelsea Brown, 29, who voted for Lightfoot, said she viewed her as the least tainted by the Chicago system of politics.
“She’s the least in the pocket of the Machine,” Brown said. “She’s interested more in people than politics.”
Much of this had been in response to events in the area. The offices of Chicago Alderman Edward Burke, a powerhouse in Illinois state politics who has held that job since 1969, were raided by federal agents. Burke was accused of attempted extortion and trying to steer business in his ward to his private law firm. He has denied any wrongdoing. The scandal also extended to Alderman Danny Solis, who reportedly recorded conversations with Burke for authorities after being confronted with allegations of misconduct.
The Burke allegations sent shock waves through the Democratic political establishment, primarily because few candidates have been untouched by Burke’s power, influence and fundraising clout. Caught inside the net of allegations were Preckwinkle and Illinois Comptroller Susana Mendoza, both mayoral candidates who are close to Burke. Both returned campaign contributions from him but struggled to shed their associations.
Burke was also linked to two other candidates in the race: former Chicago Board of Education president Gery Chico, who received Burke’s endorsement, and Daley, whose family Burke has worked closely with and supported with contributions for decades.
Voters in the Albany Park neighborhood on Chicago’s North Side expressed anti-Daley sentiments, pointing to his familial history — both his brother and father had served as mayor.
“We’ve had enough Daleys,” said Jenny Schatz, 45. “It’s time for someone new. I’m about done with old white men in general.”
For others, they were not confident in any choice.
“No one knows who to trust,” said Gilbert Pereiro, 50, a Chicago Streets and Sanitation Department worker. “That’s unfortunate. We’d be better off throwing a dart and praying for the best.”
Other candidates in the race who were damaged by ethics issues were Amara Enyia, a community organizer endorsed by music star Chance the Rapper, who did not declare $20,000 on her 2017 federal tax return, among other financial missteps, and Cook County Circuit Clerk Dorothy Brown, who was removed from the ballot in January for not having enough valid signatures. Her office has been under a federal investigation for years.
Since the Burke raids, not a week went by without new allegations connecting the establishment candidates to dark money or other charges of Chicago-style cronyism making headlines. The back-and-forth resurrected stereotypes associated with the city’s reputation for rough-and-tumble politics.
Among establishment candidates, Daley represented the benefits and drawbacks of having a prominent name and history in the city’s politics.
In one way, his name recognition was an asset: He entered the race late, but polling repeatedly showed him as a front-runner, and with nearly $7 million in campaign cash, he was also the best-funded candidate on the ballot, according to data from Reform for Illinois, a nonprofit watchdog group. Yet his name also comes with heavy baggage. His brother and his father, Richard J. Daley, led Chicago for a collective 43 years, leaving a legacy that includes segregated public housing under the elder Daley and record financial debt and billions in unfunded pension liabilities left for Emanuel by the second Daley.
Berman reported from Washington.