It’s been said a trillion times: Chicago is a city of neighborhoods. With some 246 of them, it would stand to reason that the task of choosing the city’s worst would be nigh impossible. After all, what makes a particular neighborhood worse than any other? Is it the crime rate? Underperforming schools? Undesirable housing stock? Lack of cultural amenities? As I chewed the question over, I kept landing on the same answer: Chicago’s worst neighborhood is the one that is least representative of the city—demographically, politically, culturally. The neighborhood whose annexation to the nearest suburb would be seen as a win for Chicago. On those terms there was one place that seemed to be actively campaigning for the dubious designation.
The clash between the two groups spoke to the demographics of Mount Greenwood, which is nearly 90 percent white and has a high concentration of residents who work as police and firefighters. In a 1992 piece for the New York Times, Isabel Wilkerson, author of the Great Migration history The Warmth of Other Suns, juxtaposed Mount Greenwood with its opposite, mostly black Roseland: “They are separated by two miles, a highway and fear and suspicion so deep that many people in one community would not dare set foot in the other.” She described Mount Greenwood as “an insular, Leave It to Beaver world where white people can live out entire lives without ever getting to know a black person, where people rarely venture beyond understood borders.”
