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\u2019t like the Midwest. He didn\u2019t. Liebling, who had never been west of Buffalo when he first came here a decade earlier, took the role of the Eastcoaster\u2019s Eastcoaster, reflexively judgy, a personification of Saul Steinberg\u2019s famous New Yorker cover, \u201cView of the World From 9th Avenue,\u201d 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. <\/p>\n
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\u2019t seem to recognize he was hiding behind New York\u2019s own brand of small-mindedness. Trash pickup? Ech. Drinking water? Ugh. Chicagoans were too proud. Chicagoans were not proud enough. Local fashion? Dull. Every political ward was a rat\u2019s nest of corruption.<\/p>\n
And my favorite: Lake Michigan was cold.<\/p>\n
Letters from pissed-off readers flew out of Illinois to Ross and Liebling. One letter reads now like the precursor of social media snark: \u201cOkay, we give up \u2026 who asked you?\u201d So aggrieved was this city that, 60 years later, when the Sun-Times\u2019 Neil Steinberg wrote his own book-length profile of Chicago, the title came from an especially biting insult lobbed by one of Liebling\u2019s critics: \u201cYou were never in Chicago.\u201d<\/p>\n
To make ugliness even uglier, when Liebling collected his Chicago series into a book, he included this criticism \u2014 then dismissed it with glib bemusement, the sort that suggested he thought of Chicago with all of the seriousness of royalty visiting, well \u2026<\/p>\n
Buffalo.<\/p>\n
And yet, at least psychologically, \u201cThe Second City\u201d would become one of the most influential things written about Chicago since Daniel Burnham\u2019s \u201cPlan of Chicago.\u201d<\/p>\n
We doth protest too much.<\/p>\n
Seventy-five years after he left, we should just accept: Liebling was right.<\/p>\n
The nickname, of course, was metaphor:<\/strong> Chicago seemed second to New York in all things, an also-ran of a city, closer to a \u201clarge place,\u201d or worse, a \u201cnot-quite metropolis\u201d 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\u2019s rapid growth about to bounce Chicago to third place, it didn\u2019t happen until the 1990s.) When Liebling moved to Chicago, the city seemed to have abandoned Burnham\u2019s 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 (\u201ca bit player impersonating a benevolent banker\u201d), 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\u2019s 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\u2019Hare was not yet open for commercial air travel.<\/p>\n Liebling\u2019s vision of Chicago would be unrecognizable today.<\/p>\n 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\u2019t Boston or New York. The city was so empty of literature he runs constantly into Nelson Algren at house parties: \u201cA diet of turkey, Virginia ham and cocktail shrimp apparently agreed with him.\u201d<\/p>\n Theater?<\/p>\n Hang on. Liebling found the \u201csmart\u201d local attitude to be: If you knew better, you avoided attending Chicago theater. To attend local theater was to admit that you didn\u2019t know real (New York) theater, or you were too poor to buy a plane ticket, or you were \u201cindifferent to nuance and might, therefore, just as well go back to Fond du Lac, Wisconsin, where you went to high school.\u201d<\/p>\n Double oomph.<\/p>\n 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\u2019t even make small talk about our weather. We shared little. Today, we would call this lazy reporting or drive-by journalism. Thomas Dyja<\/a>, in his definitive 2013 cultural history, \u201cThe Third Coast: When Chicago Built the American Dream\u201d (partly a chronicle of the mid-century period when Liebling lived in Chicago), called Liebling\u2019s series \u201cdeeply incurious, if not dishonest.\u201d<\/p>\n And still, as even Liebling\u2019s critics have come to decide, he \u201cgot many things right.\u201d<\/p>\n In fact, one of the depressing things about revisiting Liebling\u2019s 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: Which was it? Are we self-conscious? Or not self-knowing enough?<\/p>\n That said, that these questions remain in the water, picked over and picked over, as much a part of Chicago\u2019s character as hot dogs \u2014 no, Liebling wasn\u2019t totally wrong, though he was harsh. Liebling saw Chicago\u2019s ambivalence and suspiciousness towards homegrown talent (before they become stars) as \u201ca sign not of maturity but of a premature old age.\u201d 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.<\/p>\n![\"A](\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2025\/06\/CTC-L-ENT-SECOND-CITY-BOOK-BORRE10.jpg\")
A Saul Steinberg illustration in first-edition copy of A.J. Liebling’s “Chicago: The Second City” from the collection of the Newberry Library on March 19, 2025. (E. Jason Wambsgans\/Chicago Tribune)<\/p>\n
![\"Liebling's](\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2025\/06\/CTC-L-ENT-SECOND-CITY-BOOK-BORRE12.jpg\")
Liebling’s observations about the Chicago Tribune in a page of his book, from a copy at the Newberry Library on March 19, 2025. (E. Jason Wambsgans\/Chicago Tribune)<\/p>\n![\"A](\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2025\/06\/CTC-L-ENT-SECOND-CITY-BOOK-BORRE08.jpg\")
The cover of a first-edition copy of A.J. Liebling’s “Chicago: The Second City” from the collection of the Newberry Library on March 19, 2025. (E. Jason Wambsgans\/Chicago Tribune)<\/p>\n