Lori Lightfoot was elected mayor of Chicago on Tuesday, defeating Cook County Board of Commissioners president Toni Preckwinkle. Lightfoot, who swept all 50 city wards, won by a 74-to-26 margin that rivals the biggest election routs of Richard M. Daley. She becomes the city’s first black female mayor, making Chicago the largest city ever to elevate a black woman (who is also gay) to executive power.

In choosing Lightfoot, Chicago has clearly voted for change. Though she’s worked in government for years, Lightfoot is a political outsider by Chicago standards. She previously served as a federal prosecutor, then held several posts in city government, including chief of staff and general counsel of the Office of Emergency Management and Communications. For the Chicago Police Department, she worked in the department of procurement services as chief administrator of the Office of Professional Standards. She also recently served on the civilian Chicago Police Board, which reviews disciplinary cases against officers, and as chair of the Chicago Police Accountability Task Force.   

Nevertheless, Lightfoot had never run for elected office, and she’s never held a post or been especially involved in Democratic politics. A lawyer, she spent her earlier career at the prestigious Chicago firm Mayer Brown, returning later and becoming a partner in the litigation group. Though Lightfoot ran as a reform candidate, she comes from a pragmatic, big-business background. She stressed her progressive bona fides in the campaign, but she hasn’t been a hard-core progressive activist.

By contrast, her vanquished opponent Preckwinkle is the consummate political insider, having built an early reputation as a good-government reformer within the system before stumbling as head commissioner of Cook County. In that position, Preckwinkle reinstated a sales tax after making its repeal a central plank of her original campaign, and she tried unsuccessfully to impose a soda tax. In a change election, her deep ties to the Democratic establishment—she is also chairman of the Cook County Democratic Party—worked against her. Her vast political network made it easy to link her to scandal-plagued figures like indicted alderman Ed Burke and Cook County State’s Attorney Kim Foxx. For an experienced politician, Preckwinkle ran a surprisingly inept campaign, even with $8 million in funding, overwhelmingly provided by unions. Her defeat demonstrates conclusively that the political machine in Chicago—in the traditional sense of a patronage-based, jobs-for-loyalty system that creates a nearly unbeatable get-out-the-vote engine—is defunct.

Lightfoot now faces the challenge of governing Chicago. Unlike outgoing mayor Rahm Emanuel, who took office after a decade of economic malaise, Lightfoot inherits a booming downtown economy that has reached record-high employment. Under Emanuel and Daley, the mayor governed in an alliance with the business community. Given Lightfoot’s professional background, there’s no reason to believe that she will disrupt that cozy relationship.

Lightfoot also benefits from a downward trend in the city’s violent-crime problem. The murder rate, though still elevated, was lower last year and has fallen by 30 percent so far in 2019—welcome news for the city. Other crimes are down, too. If the economy keeps humming and the positive crime trend persists, Lightfoot will have some breathing room to establish herself.

Not that there’s any shortage of other challenges. Chicago has enormous financial problems, headlined by unfunded pensions and high levels of debt. She faces a deficit of as much as $800 million in next year’s budget. She’ll have to negotiate contracts with the police, firefighters, and teachers. The teachers have been in a confrontational mood for years and went out on strike during the Emanuel years. Lightfoot gave little indication of how she’d solve the city’s financial problems during the campaign, but she has floated various ideas for tax increases, include a value-added tax on professional services—a surprising suggestion, considering her background in Big Law. Then there’s the challenge of spreading prosperity beyond the city’s downtown and North Side to other, left-behind areas—a task with no easy answers.

Lightfoot also needs to staff her administration. A political outsider who has never run an organization of substantial size, Lightfoot doesn’t have a ready-made team to bring on board. She’ll likely have to hire experienced players who understand the machinery of municipal governance, and thus risk—as many outsider candidates do—getting co-opted by the entrenched political class.

She’ll also face off with a feistier city council. Under Daley and Emanuel, the council acted as little more than a rubber stamp, with only a small dissident caucus, mostly made up of wonkish good-government types. Several progressive insurgents have just won election to the council, though, unseating several veterans, including Pat O’Connor, Emanuel’s city council floor leader. The incoming progressive class includes Andre Vasquez (who enjoyed backing from the Democratic Socialists of America), Maria Hadden, and Daniel La Spata, who wants to enact rent control. Though making up only a minority on the council, they will likely be vocal, and local and national press can be expected to play them up, as they have other progressive leaders around the country.

Finally, Lightfoot will need to repair Chicago’s battered reputation. The city’s murder problem has made global headlines for years. Incidents ranging from the unjustified police killing of Laquan McDonald to the recent Jussie Smollett hoax generated enormous, and deserved, negative press for the city. Though Lightfoot will rightly focus on the city’s internal problems, she can’t neglect bolstering its global appeal. Daley and Emanuel worked tirelessly to promote Chicago, but the Windy City’s brand needs a reboot.

Chicago is heading into a period of transition not experienced in a generation; Daley and his protégé and successor Emanuel have run the city since 1989. Lightfoot’s emergence as an unlikely outsider-mayor represents a genuinely democratic transition of power, to which Chicagoans are not accustomed. Lightfoot has a hard job ahead, but she also has an opportunity to make a lasting mark—by fundamentally changing the “Chicago Way” of doing business.

Photo by Scott Olson/Getty Images


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