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, Ohio, to attend Northwestern—yet he remains fascinated by the dynamics captured in Liebling's anecdote. In You Were Never in Chicago Steinberg weaves the story of his own coming-of-age as a young outsider who made his way into the inner circles and upper levels of Chicago journalism with a nuanced portrait of the city that would surprise even lifelong residents. Steinberg takes readers through Chicago's vanishing industrial past and explores the city from the quaint skybridge between the towers of the Wrigley Building, to the depths of the vast Deep Tunnel system below the streets. He deftly explains the city's complex web of political favoritism and carefully profiles the characters he meets along the way, from greats of jazz and journalism to small-business owners just getting by. Throughout, Steinberg never loses the curiosity and close observation of an outsider, while thoughtfully considering how this perspective has shaped the city, and what it really means to belong. Intimate and layered, You Were Never in Chicago will be a welcome addition to the bookshelves of all Chicagoans, be they born in the city or forever transplanted.