Twenty years ago an editor for the Chicago Sun-Times told Neil Steinberg—at the time a young reporter for the paper—that he might someday become the next Sydney J. Harris, and Steinberg, for reasons unclear, did not punch him in the kneecaps. Harris was dead by then, but from the 1950s to the 1980s he had tortured Sun-Times readers with a column composed of nothing but aphorisms, sententious squibs, little dollops of uplift that were so banal or dubious they perversely compelled a reader’s attention.

“The greatest enemy of progress is not stagnation, but false progress,” Harris would write, letting the sentence hang there all alone in a sea of newsprint until an asterisk pulled a reader’s eye, kicking and screaming, down to the next one: “The time to relax is when you don’t have time for it.” And so on, for a good 10 inches or more, day after day, four days a week. No reporter could have pondered a career as a neo-Sydney J. Harris without a soul-deep shudder.

Maybe Steinberg is a more forgiving guy than he lets on. As it happens, he did grow up to be a columnist for the Sun-Times—and a four-day-a-week man, too, like Harris. The two columnists are alike in one other (and only one other) respect: They are both distinctively Chicago products. It’s hard to imagine, I mean, another newspaper market in which such odd ducks could not only survive but flourish, developing large and loyal readerships. But then the history of Chicago journalism is rich in newspapermen who were, as they seldom say in Chicago, sui generis—from George Ade to Carl Sandburg and Ring Lardner; Ben Hecht to Mike Royko and Bill Mauldin.

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. A nebbish, too. One of his first books, A Complete and Utter Failure, was a “celebration” of history’s greatest flops and disappointments. The reluctance of readers to wallow in unhappiness helped the book live up to its title, at least commercially.

Another book ventured into the hottest genre in publishing: chronicles of the business world—except the story Steinberg chose to chronicle was the collapse of American hat manufacturing. He also wrote about a transatlantic voyage he took with his estranged father in a touching attempt at reconciliation; by the book’s conclusion, the two disliked each other more than they had at the beginning. A memoir of his harrowing struggle with alcoholism was accompanied by an acknowledgment that, knowing himself as he did, he’d probably start drinking again before too long. Imagine Mitch Albom—if Albom had spent 35 straight winters in Chicago.

A celebration of Chicago just now might seem like another of Steinberg’s adventures in perversity. Nobody knows, of course, whether the rough patch the city is moving through at the moment is merely a glum episode or a further stage in a long and irreversible decline. Its newly minted status as the murder capital of the world is just the start. It also has the largest street-gang membership of any city in America, and, by many measures, the worst public schools. And while most cities of comparable size face the same fiscal cyclone of unfunded debt obligations, the refusal of Chicago’s political class to reckon with impending solvency is San Bernardino-like in its obstinate stupidity.

All 50 city council members are Democrats. True to their faith, they have created a tax and regulatory environment ferociously hostile to any business they don’t like. It took Walmart nearly a decade of petitions and hearings and waivers to open a store where residents of the forsaken South Side could work and shop. The city levies one of the highest sales taxes in the country and imposes a head tax on suburban commuters.

If you tax something, the economists say, you get less of it, and so fewer and fewer people bother to seek work in the city. The private sector has shrunk accordingly. The top two employers in Chicago are the federal government and the public school -system, followed close behind by the city and county governments. The city lost 200,000 residents between 2000 and 2010.

Still more shocking, according to recent data, 25,000 of those who fled Chicago in the last decade chose to move to Rockford, Illinois. Have you ever seen Rockford?

And yet: Maybe you have to see Chicago close up to understand the glories it’s still capable of—and the love it can inspire in the beating heart of a stubborn enthusiast, of whom there are millions, Steinberg included. As a writer he’s not given to flights of poetry—not even the rough-hewn, horny-handed, tough-guy prose poetry of other Chicago boosters like Nelson Algren and Sandburg. But at moments the place can leave him a little breathless, as on a fog-wrapped night downtown, with the spires disappearing upwards into the mist: “It is an eerie, marvelous sight, this city of mystery and beauty, half-seen, half hidden, distant yet right there.” He’s quite good at evoking the skyline, the lakefront, and the neighborhoods beyond. He knows that the city’s sheer size and variety are both intimidating and consoling, especially for scribblers.

“A small town is lucky to boast one or two central elements,” he writes. Chicago, on the other hand, “can be whatever a writer wants it to be. .  .  . It can be a city of theater and plays, or music and concerts, or food and restaurants. God knows there’s politics—election and corruption. A bottomless pit of crime, if you prefer, a city of murders and murderers.”

The Chicago that Steinberg has constructed for himself as a columnist has pieces of all of the above. Well, not politics, which bores him and about which, on the evidence here, he has nothing interesting to say. He has an eye for the colorful, an ear for the quirky. Anachronisms please him very much. His favorite haunt in Chicago over the years has been the Division Street Russian Baths, the last survivor of the public bathhouses that once dotted the city; as late as 1965 the park district operated eight of them. They were built for working men.

The baths were always open, twenty-four hours a day, because people worked three shifts. Men labored in steel mills and slaughterhouses and coal yards—not the type of filth and grime you wanted to wash off in your own home if you could avoid it.

The baths bore no resemblance to the health spas outfitted for today’s urban sophisticates; no sweet-smelling cedar paneling, no chipper attendants in polo shirts. They were subterranean rooms tiled in ceramic and running the length of barns, with lead pipes gushing tap water into pickle buckets and roaring ovens that customers tended themselves with discarded two-by-fours.

The baths were pre-ironic Chicago. This is a Steinberg specialty: a functional enterprise that had essential uses before the age of affluence arrived to place them in self-conscious quote marks—before anyone got the idea to refurbish decaying tenements with exposed brick walls and Viking ovens, or to open faux “diners” with gouda cheese fries and make-believe “dive bars” selling $12 mocha-appletinis. People lived in that older Chicago not for its cultural amenities or its bistros serving fusion cuisine or its “walkability” or its bikeshare racks; they lived there because it’s where the work was.

They earned their livelihoods in the factories that Steinberg shows us in the moments before they vanish: the Jays potato chip factory at 99th Street and Cottage Grove; the Chicago Mailing Tube company on North Leavitt; the Brach’s candy plant on Kinzie, which is the largest candy manufacturing plant in the world.

Or was. Like the baths, most of the manufacturing that enthralled Steinberg as a Chicagoan and a columnist are gone. He’s a clear-eyed nostalgist, however. He knows it’s in the nature of cities to change texture and shape—and in the nature of city dwellers to lament the passing of the golden age, which always seems to have ended the day before yesterday.

Pick whatever era in history seems most exciting, most distinctive, real and alive, then examine that period closely; you will find that Chicagoans of the time were also nostalgic, also troubled by what they considered society’s decline, also confronting a problematic present while mourning some imagined superior past.

In Chicago, the point holds true even in the face of a declining population, the coming fiscal calamity, the murder rate, and those combat-zone schools. Every new era brings its compensations, and even a member of the vast Chicago diaspora will recognize some of them: Neil Steinberg, for example, has replaced Sydney J. Harris. Every reader of this funny and touching book will be grateful.

Andrew Ferguson is a senior editor at The Weekly Standard.

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