Shouldering the Burden

Steve James' latest ode to Chicago is masterful

Often when I watch a documentary, a Darren Rovell tweet comes to mind. “I feel bad for the country,” it goes, “but what tremendous content!” I inhaled City So Real, Steve James’ latest documentary about the surprising, crowded, frustrating 2018 Chicago mayoral race and the additional challenges of Covid, protests, and the reckoning of police violence in wake of George Floyd’s murder. After watching, I felt bad for Chicago—but what tremendous content!   

James’ subject is always Chicago. He made America to Me, about a public school in Oak Park, as well as Hoop Dreams and the Roger Ebert documentary Life Itself. In City So Real, Chicagoans tell their stories to an unseen, unheard cameraperson as we jump from Logan Square to Hyde Park and elsewhere. An on-screen map orients the viewer as the documentary skips from the North Side to the South Side to the West Side in this “city of neighborhoods.”  

It’s also a city with a lot of problems, as Fox News is happy to remind you. Corruption, gentrification, and a system of local government that doesn’t lend itself to accountability pushed the city to the brink. Willa Paskin said City So Real is like “if the wire and the good wife had a documentary baby,” and I love this analysis. Even with all the good intentions in the world, if there’s not the political will or structural ability to change things, it doesn’t do much good. Yet the city keeps on going. 

A few themes stick out. Local politics are humiliating. We see Paul Vallas’ campaign manager corral people outside Daley’s Diner, inviting them to sit with Vallas. “He’s right inside. Would you like a cup of coffee with him?” Lori Lightfoot canvasses from door to door, in the snow, introducing herself. It’s cringe-inducing to imagine saying “Hi, I’m running for Mayor,” to strangers for most of us, but shaking hands and earning votes, like Lightfoot does, “because you came to my house” are the oldest form of politics for a good reason. How can you represent people if you don’t know who they are? 

Chicago’s broken system for vetting signatures to get on the mayoral ballot features prominently in City So Real. Candidates must collect a minimum number of signatures to make it onto the ballot. They are forced to collect far more than they need because, after the petitions are filed, those signatures can be challenged by other candidates, claiming the signatures don’t match, the names don’t match, the addresses don’t match... voting issues that you may have seen mentioned of late. The two parties sit on either side of an election administrator who rules whether the challenge is sustained or overruled. They do this for every signature that is challenged. Afterward, most campaigns object further so those challenged signatures are set aside, to be ruled on later by the Board of Elections. Lawyers enter into the process, which can cripple campaigns without the financial resources to defend their signatures. It’s a deeply flawed way to field candidates for mayor. When Willie Willson’s campaign manager, an old-school operator well versed in the art of Black politics in Chicago—later, he’s handing out walking-around money to people to put up signs above the Expressway—explains his reasoning for challenging certain candidates and not others, it sounds more like a strategy for Risk than a vision of democracy in action. 

Chicago is thirty percent Black and thirty percent Latino, so racial politics are as impossible to ignore for the viewer as they are for the campaigns. The campaign operators themselves see things ethnically and racially because it’s their job to count votes, not worry about what those categories mean to society at large. 

As the race for mayor unfolds, the documentary follows candidate Garry McCarthy, Chicago’s former police superintendent, who was fired after Laquan McDonald’s murder. At the house of some McCarthy supporters during a televised mayoral debate, as candidate Amara Enyia, a Nigerian public policy expert in her thirties endorsed by Chance the Rapper, answers questions from the moderator, one of McCarthy’s supporters opines that she “seems like she’d do a blunt on the way home” before noting that busing and integration ruined Chicago’s public schools. I guess the two of them didn’t overlap at the London School of Economics. Visiting with the same supporters later as they watch a newscast about rioting and looting in Chicago this summer, another notes that “this happens every time one of them get killed.”   

In the end, Lightfoot emerges from the campaign victorious, winning her runoff. I wonder if the country likes to elect Black leaders only when things are at their worst, in part so they can blame them later, in part because the better-off people in the city don’t intend to see things through anyway. Their relationship to Chicago is extractive. Make money gentrifying new areas of the city, push out the lower income people, and fight against any redistribution of wealth, lest it go back to the city instead of paying for private school for their kids out in the burbs. 

That all said, City So Real is not a categorical downer. It’s a celebration of the fact that, despite the institutional, generational, racial, and financial roadblocks cities face in the years to come, we will, just barely, make things work. Got to. This America, man.

[City So Real is on Hulu and Nat Geo