You Were Never in Chicago

In 1952 the New Yorker published a three-part essay by A. J. Liebling in which he dubbed Chicago the "Second City." From garbage collection to the skyline, nothing escaped Liebling's withering gaze. Among the outraged responses from Chicago residents was one that Liebling described as the apotheosis of such criticism: a postcard that read, simply, "You were never in Chicago."

Neil Steinberg has lived in and around Chicago for more than three decades—ever since he left his hometown of Berea,...