Was A.J. Liebling right about Chicago? Decades after the New Yorker's ‘Second City,' time for a second reading

Chicago Tribune

24-06-2025

Exactly 100 years ago the New Yorker magazine first landed on newsstands. Its influence on the cultural and civic history of the nation (if not the planet) is hard to overstate. A pair of new doorstop-sized books on my desk prove it: 'A Century of Fiction in the New Yorker 1925-2025,' at 1,119 pages, boasts stories assigned to school kids for generations (Shirley Jackson's 'The Lottery,' James Thurber's 'The Secret Life of Walter Mitty') and authors who defined decades (Susan Sontag, J.D. Salinger, George Saunders, Alice Munro). 'A Century of Poetry in The New Yorker 1925-2025,' at 959 pages, overflows with so many essential voices of the past 100 years as to be mocking: Langston Hughes, Sylvia Plath, W.B. Yeats, W.H. Auden, Joy Harjo, Pablo Neruda.
And I haven't even mentioned the magazine's milestones of nonfiction — 'Hiroshima,' 'Silent Spring,' the moral accounting of Hannah Arendt, the criticism of Pauline Kael.
But then there's 'Chicago: The Second City.'
Arguably nothing in 100 years of the New Yorker landed on Chicago with more oomph than A.J. Liebling's infamous 1952 three-part profile of the city. No, wait, strike 'arguably' — that I'm writing this piece soon after my colleague Rick Kogan's piece on how Liebling gave Chicago another nickname and inspired a certain comedy troupe, that alone suggests Liebling got under this city's skin with a precision few can claim.
Seventy-five years ago, he moved to the Gold Coast with a new wife and stepdaughter (who enrolled at Frances W. Parker School) in late 1949, stayed through part of 1950 and returned briefly in 1951. New Yorker editor Harold Ross warned him he wouldn't like the Midwest. He didn't. Liebling, who had never been west of Buffalo when he first came here a decade earlier, took the role of the Eastcoaster's Eastcoaster, reflexively judgy, a personification of Saul Steinberg's famous New Yorker cover, 'View of the World From 9th Avenue,' showing a huge Manhattan in the foreground, a smaller empty rectangle of a country after New Jersey, then, just beyond, off in the distance, the Pacific.
He deposited on Chicago a catalog of cultural crimes, an unflattering character study, a hair shirt of self-consciousness and a charge of provincialism so gleeful he didn't seem to recognize he was hiding behind New York's own brand of small-mindedness. Trash pickup? . Drinking water? . Chicagoans were too proud. Chicagoans were not proud enough. Local fashion? Dull. Every political ward was a rat's nest of corruption.
And my favorite: Lake Michigan was cold.
Letters from pissed-off readers flew out of Illinois to Ross and Liebling. One letter reads now like the precursor of social media snark: So aggrieved was this city that, 60 years later, when the Sun-Times' Neil Steinberg wrote his own book-length profile of Chicago, the title came from an especially biting insult lobbed by one of Liebling's critics: 'You were never in Chicago.'
To make ugliness even uglier, when Liebling collected his Chicago series into a book, he included this criticism — then dismissed it with glib bemusement, the sort that suggested he thought of Chicago with all of the seriousness of royalty visiting, well …
Buffalo.
And yet, at least psychologically, 'The Second City' would become one of the most influential things written about Chicago since Daniel Burnham's 'Plan of Chicago.'Seventy-five years after he left, we should just accept: Liebling was right.
The nickname, of course, was metaphor: Chicago seemed second to New York in all things, an also-ran of a city, closer to a 'large place,' or worse, a 'not-quite metropolis' that could only view itself in relation to New York City. Plus, Chicago was the second largest city in the country in 1952. (Though Liebling saw Los Angeles's rapid growth about to bounce Chicago to third place, it didn't happen until the 1990s.) When Liebling moved to Chicago, the city seemed to have abandoned Burnham's vision. It would not be the next Venice or Paris or New York City. It was at an ebb, if not decline. Yet another Chicago was just around the bend: The mayor was Martin Kennelly ('a bit player impersonating a benevolent banker'), but Richard J. Daley was up next. Businesses were leaving the city, and even the stockyards that graced poetry were struggling. The tallest building was still the Chicago Board of Trade. Though Liebling notes (rightly still) that many of the city's biggest boosters fled to the North Shore every night, the white flight that transformed the South Side was just percolating. The Eisenhower was under construction, the Skyway was years off, and even O'Hare was not yet open for commercial air travel.
Liebling's vision of Chicago would be unrecognizable today.
Gentrification and development had not yet taken hold, so he saw neighborhoods strictly by ethnicity alone, which defined how people voted; an Italian, he wrote, was only politically loyal to Italian ward captains. Also, Chicago had few restaurants worth visiting, only barbecue joints (for which he had grudging respect). The culture and life of the city was found in the Loop alone, clustered together. The opera was dark, and Chicago Symphony Orchestra too hard to hear over the loud whine that it wasn't Boston or New York. The city was so empty of literature he runs constantly into Nelson Algren at house parties: 'A diet of turkey, Virginia ham and cocktail shrimp apparently agreed with him.'
Theater?
Hang on. Liebling found the 'smart' local attitude to be: If you knew better, you avoided attending Chicago theater. To attend local theater was to admit that you didn't know real (New York) theater, or you were too poor to buy a plane ticket, or you were 'indifferent to nuance and might, therefore, just as well go back to Fond du Lac, Wisconsin, where you went to high school.'
Double .
Some of this was accurate, and some of this was Liebling, who seemed to get as much wrong as he got right. He saw, for instance, no enthusiasm at all for the Cubs or the White Sox. Chicagoans were so boring, he suggested, because the temperature at the lake might be 20 degrees different from the suburbs and we couldn't even make small talk about our weather. We shared little. Today, we would call this lazy reporting or drive-by journalism. Thomas Dyja, in his definitive 2013 cultural history, 'The Third Coast: When Chicago Built the American Dream' (partly a chronicle of the mid-century period when Liebling lived in Chicago), called Liebling's series 'deeply incurious, if not dishonest.'
And still, as even Liebling's critics have come to decide, he 'got many things right.'
In fact, one of the depressing things about revisiting Liebling's series is how little has changed, despite the city being a more vibrant place full of Chicago flag tattoos and T-shirts. Liebling would have seen that as a part of the civic boosterism he loathed while living here, a characteristic he read as a symptom of chronic low self-esteem, and not merely local pride in your home. You can see now why Chicagoans wrote those confused letters:
That said, that these questions remain in the water, picked over and picked over, as much a part of Chicago's character as hot dogs — no, Liebling wasn't totally wrong, though he was harsh. Liebling saw Chicago's ambivalence and suspiciousness towards homegrown talent (before they become stars) as 'a sign not of maturity but of a premature old age.' As an East Coaster myself, I never totally understood why Chicagoans claim certain locals as their own and ignore others: Bill Murray can do no wrong, yet Kanye (even before his impossible-to-defend behavior took hold) was a civic eye-roll. Murray showed his roots casually while Kanye was apocalyptically boastful.
Liebling took this characteristic, the public shows of modesty (and less public tribalism), as good old fashioned Midwestern provincialism. Alex Kotlowitz, in his own Chicago book, 'Never a City So Real,' also reckons with Liebling, as any writer on Chicago must, and decides Liebling mistook the insular nature of certain neighborhoods as a citywide provincialism — which then manifested into a civic disappointment with itself. Kotlowitz, who has lived here for decades, describes the city with vastly more shading, as a place 'grappling with its promise, alternately cocky and unsure.' That sounds more like 2025.
Then again, so do Liebling's portraits of aldermen who block the construction of new housing, presumably afraid to soil their own rock-solid constituencies. Paddy Bauler, who served the 43rd Ward for 30 years, and was never anyone's vision of transparency in local government, told Liebling that he had to do favors for everyone in his ward, whether or not they asked, because some people are too 'stupid' to know they need a favor. Bauler's motto was 'Everybody gets something,' insuring Bauler got something himself at election time. The problem, Bauler complained, was the Republicans in his ward (Lincoln Park, Old Town, Gold Coast) 'expected more than than their fair share.'
It's those clear-as-day contradictions — modesty suspicious of ambition, corruption outraged by grabbiness — that Liebling seemed to find confusing, and one reason we should cut Liebling (who died in 1963) some slack. Besides, when he came to Chicago, he was pretty tense. He left the New Yorker that spring to write for Colliers, including a profile of Colonel Robert McCormick, the Tribune publisher. He found this newspaper, to put it mildly, a bit much: 'The Tribune reader issues from his door walking on the balls of his feet, muscles tense, expecting attacks by sex-mad footpads (thieves) at the next street corner, forewarned against the smooth talk of strangers with a British accent and prepared to dive behind the first convenient barrier as the sound of a guided-missile approaches — any minute now — from the direction of northern Siberia.'
Weeks before he moved here, he also finalized a divorce, then got remarried to his mistress. Then, just as he arrived, his Colliers deal fell apart (they said his work was too critical). He began his time in Chicago unemployed, and yet, as he wrote friends back home in New York, his new wife became so enamored of the stores in the Gold Coast that shopkeepers raised their prices when they saw her coming. By the end of the year, the New Yorker welcomed him back to its pages, but what he was writing about Chicago, according to biographer Raymond Sokolov, became 'the fullest record of Liebling's state of mind,' his discontent with his Midwest lifestyle 'pouring out in one vindictive spurt.'
About a decade later, before he died at 59 of pneumonia, Liebling saw himself as something of a literary failure, far from the best-seller lists; the collected 'Second City' alone, the book version, sold only 3,500 copies and was already out of print by 1960.
But as a piece of writing, it's still joyously rangy, hilariously mean. ('A masterpiece of modulated contempt,' Steinberg wrote.) It was also an early example of what Sokolov called a new 'mature Liebling style.' The journalist, who had covered World War II and boxing and restaurants with a sharp, if sniffy, upper-crust New Yorker tone, finally found a voice in Chicago that was not fussy, 'shifting nonchalantly from Augustan to breezy.'
Perhaps 'Second City,' in its own way, was about embracing the freedom in inconsistency. Late in life, Liebling continued to puzzle over the response to 'Second City,' writing once it 'survives as an ectoplasmic itch' in Chicago, though him always intended the series as a 'soothing ointment — but (Chicagoans) are hard to soothe.'
Not sure I buy that, but more than one letter writer did wonder, generously, if the series should be read as tough love, pushing Chicago to consider its potential and improve. Certainly Liebling knew the city's literary traditions were already celebrating Chicago's contradictions: Carl Sandburg famously found the bluntness of the city's working class as a point of pride, and Algren, the same year that Liebling was in Chicago, published 'Chicago: City on the Make,' a lyrical ode that compares loving Chicago to 'loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real.' (Kotlowitz took the title of his own book from Algren's embrace of dissonance.)
There's plenty of 'The Second City' that hasn't aged a wink. Liebling meets local corporate leaders involved in an America First movement who show unbounded hubris. ('All things, national and international, were manifest to the manufacturers of overalls and breakfast cereals.') There's the perverse pride in a history of gang violence, and the reputation of University of Chicago undergraduates. ('The greatest magnet for neurotic juveniles since the Children's Crusade.') He finds the rumor about a suffocating Midwest friendliness throughout Chicago quickly extinguished by airport employees.
But some itches evolve.
He finds Chicago's infamous weakness for superlatives — 'greatest newspaper in the world,' 'the most beautiful buildings' — part of an ingrained 'all-or-nothing psychology.' He would have had a field day with politicians and civic leaders who still boast of Chicago as a 'world-class city,' somehow deaf to how that would sound to actual world-class cities. But reading 'The Second City' again, I wondered how Liebling would have seen the amateur satirists and social media influencers on TikTok who show off the city without a drip of self-loathing, who juxtapose political talk of Chicago as a 'hell hole' with footage of pastoral lakefront strolls, who never once seem to want to be anywhere else. He might have read them as yet another case of all-or-nothing overcompensating.
Or he might have seen a new day.
Certainly, if A.J. Liebling was around today, social media wouldn't have cared much. He would have been mocked, and he would have cycled in and out of feeds in 24 hours.
Besides, who asked him anyway?