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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, 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.


 "[A] rollicking newspaperman’s memoir . . . and a strong case for Second City exceptionalism."

New York Times

"A triumph."

Patrick Ryan | Toronto Star

“In this wonderful book, Steinberg weaves a poetic mosaic of his life and the life of Chicago—past, present, real, imagined. Like many of its citizens, he came here from elsewhere, drawn by its brawny allure. He lives in Chicago and Chicago lives in him.”—Roger Ebert

Roger Ebert

“I grew up in Chicago. And reading You Were Never in Chicago reminds me why I still think of Chicago as home even though I haven’t lived in the city for more than twenty years. Steinberg brilliantly explores the historical and contemporary city and how each of us makes (or loses) our way in it. Whether you’re a native or you just arrived at O’Hare, read this book: it will make you feel at home in Chicago. Even better, it will you make Chicago yours.”

Dan Savage

“A lot of people have tried to take the measure of Chicago, capture it between the covers of a book. Many more have failed than have been successful, and that’s easy to understand. Chicago is ever elusive. But this writer and this book get it. If you know Neil Steinberg from his Sun-Times column, and God love you for still reading a newspaper, you will not be unfamiliar with the high quality and distinctive style of his writing. But here you will also find people and places and sentiments that will surprise, enlighten, and entertain you. It is, of course, his own take on the city. And it’s a keeper.”

Rick Kogan

"Despite his long residence in the city and its suburbs, Steinberg feels and writes as an outsider, which allows him to see and describe aspects of Chicago from a fresh and enthusiastic perspective....This is a well-done paean to a diverse, vibrant metropolis."


"Like Studs Terkel before him, Steinberg mixes memoir, history, and travelogue in You Were Never in Chicago as he takes readers along on an engaging tour of the characters—and character—of his adopted city, past and present."

Kristin Baird Rattini | American Way Magazine

"If you love Chicago, you’ve got to read Neil Steinberg’s new book You Were Never In Chicago. It’s not a guide book. You won’t find a listing of restaurants. It’s not the history of our great city. It’s one man’s perception of this complex, compelling and confounding community we call sweet home Chicago. . . . He has the skill and curiosity of a great writer."

Terri Hemmert | XRT

"[O]n display in You Were Never in Chicago, a memoir interwoven with local history just published by the University of Chicago Press . . . is [Neil’s] curiosity, insight, amusing self-awareness and enormous talent."

Eric Zorn | Chicago Tribune

"Steinberg’s greatest gift is his ability to build Chicago in our imaginations as a city that has grown from the efforts of people willing to make it their home, sometimes against unbelievable odds. He weaves wonderful stories of people we now take for granted – Upton Sinclair, Julia Louis Dreyfus, Carl Sandburg, the Rev. Jesse Jackson, Theodore Dreiser, Jelly Roll Morton – all who were not born in Chicago, but for whom Chicago became the backdrop onto which they achieved greatness."

Shyam K. Sriram | PopMatters

"Steinberg’s new book is a pleasing blend of what makes him and his city distinctive. You Were Never in Chicago is a sort-of memoir of his professional life, a kind-of love letter to the city—a scrapbook, as it were, of Chicago eccentricities. Unlike most columnists who get called ’humorists,’ Neil Steinberg is a funny writer." 

Andrew Ferguson | The Weekly Standard

"You Were Never In Chicago by Chicago Sun-Times journalist and author, Neil Steinberg is the directional refrain that echoes throughout this very readable poetic memoir, historic excavation and contemporary exploration; Steinberg portrays a vastly nuanced city, breathtaking in its myriad facets like a rare diamond, painstakingly, slowly cut and lovingly polished."

Chicago Life

"Steinberg . . . takes the reader on a rollicking tour of Chicago history, writing with engaging fascination about the famous characters who’ve made the city home—from jazz great Louis Armstrong to mobster Al Capone to celebrity columnist and talk-show host Irv Kupcinet—as well as those on the margins that play just as much of a role in the reality of Chicago, such as prostitutes, crack babies, and owners of failing businesses. He has an eye for the tiny details, the quirks that turn a regular Joe into someone to remember and bring celebrities down to a human level."

Mary Mann | Bookslut

"Steinberg revels in the unusual, the underground, the unique, sharing stories about a Chicago that most readers—even many locals—would usually overlook."

Chicago Book Review

Table of Contents

One   Manus manum lavat

Two   “God, I am in Chicago”

Three   “A tolerance for rubes”

Four   “Give her my regards”

Five   “Your show of shows”

Six   “I’ll get you a judge”

Seven   In the sleeping room

Eight   “How long is it supposed to last?”

Nine   Annals of the paper tube trade

Ten   “A byutafl day in the palka”

Eleven   “You gave the money away?”

Twelve   A visit from the Angel Nacht

Thirteen  “A lot of broken hearts”

Fourteen  Driving with Ed McElroy

Fifteen   “Gee, ya think?”

Sixteen   The city in fog



Society of Midland Authors: Midland Authors Award

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