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Chicago's 'Blood Sport' Politics, Lesbian Mayor Probed in New Doc

Lori Lightfoot

Above: Lori Lightfoot celebrates with her wife, Amy Eshelman, and daughter, Vivian, in the background. All photos courtesy Chicago Story Film LLC.

In the free-for-all Chicago mayoral race of 2019, few people would have predicted that a progressive Black lesbian who’d never held elective office would emerge victorious. But that’s just what happened, and a new docuseries takes viewers through the process — and goes on to show how Mayor Lori Lightfoot dealt with the challenges of 2020.

“The fact that Lori Lightfoot became mayor is remarkable,” says Steve James, the director of the five-episode City So Real, which will be shown in its entirety Thursday on Nat Geo and will be available on Hulu the next day.

James, the filmmaker behind such acclaimed projects as Hoop Dreams and America to Me, had thought for years that it would be great to do a profile of Chicago, where the Virginia native has lived for 35 years. He decided the time was right in the summer of 2018.

That was when Rahm Emanuel, a former congressman and White House staffer, announced he wouldn’t seek a third term as mayor. That led to the most wide-open mayoral race ever, with 21 candidates initially seeking the office; the field was eventually whittled down to 14.

The early fall of that year also saw the long-awaited trial of a white Chicago police officer, Jason Van Dyke, for killing a Black teenager, Laquan McDonald, four years earlier. In this period, “Chicago is at a moment when its future is very much on the line,” James says.

The first four episodes of the series track the mayoral race, the Van Dyke trial, and other tumultuous events in the nation’s third largest city, including the indictment of a powerful alderman on corruption charges. After finishing those episodes, which were screened at the Sundance Film Festival this year, James decided to make a fifth episode, showing the city dealing with the COVID-19 pandemic and uprisings over racial injustice, and revisiting many of the people — politicians, activists, business owners, and more — who had figured significantly in the first four. “It was satisfying to be able to get back there and check in,” he says.

Lightfoot is among the most prominent of those figures. She had been a federal prosecutor and an attorney in private practice, held appointed positions in city government, and served on police oversight bodies, which documented widespread police misconduct. She was a longtime community activist as well, having been on the boards of liberal organizations such as NARAL Illinois and the state’s branch of the American Civil Liberties Union. But early on, no one expected her to become mayor.

Despite Chicago’s diverse population, its mayors have been almost all white men. One powerful family in particular has dominated city politics since the mid-20th century — Richard J. Daley was mayor from 1955 until his death in 1976, and one of his sons, Richard M. Daley, held the office from 1989 to 2011. Another son, Bill Daley, entered the 2019 race after having held positions in two presidential administrations, those of Bill Clinton and Barack Obama. Some political observers thought he would become the third Mayor Daley.

Other competitors in the race — officially nonpartisan, although Chicago is heavily Democratic — included Cook County Board President Toni Preckwinkle as well as an Illinois comptroller, a former Chicago police superintendent, a former Chicago Public Schools CEO, a wealthy businessman, attorneys, and activists. In the first round of voting on February 26, 2019, Lightfoot and Preckwinkle, two Black women, one gay, one straight, emerged as the top two vote-getters. A few weeks later, Lightfoot won a runoff election in a landslide.

“The fact that two Black women ended up in the runoff was remarkable,” says James, whose documentary shows how they got there, in addition to following other candidates on the campaign trail through the city’s many and varied neighborhoods during a typically brutal Chicago winter. Initially, he adds, “none of the pundits gave Lori Lightfoot a chance at all of being in that runoff.” But she found her message, charmed voters with her approachable manner, won the endorsement of the Chicago Sun-Times — one of the city’s two daily newspapers — and, in the runoff, the support of some former rivals. She also overcame a few homophobic attacks.

City Hall protest

Lori Lightfoot in Humboldt Park

Top: Protesters march at Chicago's City Hall; bottom: Mayor Lightfoot meets with residents in the city's Humboldt Park neighborhood.

But campaigning is different from governing, as the fifth episode demonstrates. When the pandemic led to a shutdown of Chicago businesses and Lightfoot scolded people for holding large gatherings in parks, she was featured in numerous internet memes conveying that she was watching Chicagoans wherever they were. That was lighthearted and welcome attention for the mayor.

However, when Chicago was rocked by protests over racism and police brutality, as many cities were in the summer of 2020, she received criticism from across the political spectrum. Some denounced her as an establishment politician who didn’t understand the rage of most Black people, while others contended she couldn’t keep order in the city. James gives time to both the mayor and her critics, and lets viewers make up their own minds about her performance in office.

James says he set out to offer a close-up look at Chicago’s rough-and-tumble politics, described at some points as “blood sport.” “I hope that people get a ringside seat for the political process in Chicago, but not in the usual way,” James says of his intentions for City So Real. He’s sought to show what the process means to so many people in the city, not just those in power.

He has also sought to convey that for all its problems — economic inequality, gun violence, and more — Chicago is a diverse, vibrant city, not the hellhole conjured by the likes of Donald Trump. The city is beautiful, he says, and not just because of its stunning skyline. “There’s incredible people, there’s incredible passion, there’s incredible neighborhoods,” he says. “Chicago’s problems are America’s problems, and its passions are America’s passions.”

City So Real will be shown Thursday at 7 p.m. Eastern/6 p.m. Central on Nat Geo and will be available to stream on Hulu beginning Friday. Below are two clips from the series, showing Lightfoot voting with her wife, Amy Eshelman, and daughter, Vivian, and at a candidates’ forum.

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