It’s been more than 60 years since A. J. Liebling skewered Chicago in three caustic pieces in the New Yorker, soon after collected into a short book of 30,000 words or so, Chicago: The Second City.

Of course, “caustic” was Liebling’s specialty, so his acerbic reading of the city shouldn’t have come as a surprise to anyone. Yet, ever since, anti-Liebling rhetoric has routinely found its way into print in Chicago.

In 1980, for instance, Chicago Tribune columnist Jack Mabley dismissed the book as the work of “a New York writer [who] once came to Chicago for several months…and interviewed people who came into the bar where he hung out. The essays he sent back to Manhattan were filled with startling inaccuracies which comforted New Yorkers in their oneness. No. 1-ness.”

liebling - second cityFourteen years later, in a Tribune story about his new publishing venture Academy Chicago, Jordan Miller was quoted as describing Liebling as “that creep.” Eighteen years after that, Chicago Sun-Times columnist Neil Steinberg made a significant reference to Chicago: The Second City in his 2012 book about the city.

It had to do with something Liebling writes in an introduction to his book — that, after his New Yorker essays began appearing, he received a postcard from a woman reader which said simply, “You were never in Chicago.” It’s that phrase that Steinberg chose for the title of his own book.

Liebling’s literary gifts

Liebling was no hack, and that, in part, is why his ghost has hung so long over the city’s psyche. And why he’s well worth reading today. His writing is lively, fresh and clear-eyed. And very entertaining, as long as it’s not your ox that he’s eviscerating.

At some deep level, those who have denigrated him over the decades have known that it would have been wonderful to have someone with Liebling’s literary gifts as a fan of Chicago — as wonderful as it has been painful to endure his long-stinging words as a critic.

Consider these turns of phrase:
• Regarding the relationship between the powerful aldermen and the weak mayor of that time, Martin Kennelly: “When [Kennelly] tries to assert himself, they react as if they had been kicked by a stained-glass window.”
• Regarding the Herald-American, a newspaper in the Hearst chain: “[It] is aimed at the intellectual level of a slightly subnormal strip-tease girl.”
• Regarding the Chicago cityscape: “Seen from the taxi, on the long ride in from the airport, the place looked slower, shabbier, and, in defiance of all chronology, older than New York. There was an outer-London dinginess to the streets; the low buildings, the industrial plants, and the railroad crossings at grade produced less the feeling of being in a great city than of riding through an endless succession of factory-town main streets.”
• Regarding the multiple train lines fanning out in all directions from the Loop: “The railroad tracks are the cords that hold the Chicago Gulliver supine.”
• Regarding Chicago-based business leaders of the isolationist American First Committee prior to World War II: “All things, national and international, were manifest to the manufacturers of overalls and breakfast cereals, and the America First letterhead showed that the General [Robert E. Wood, chairman of Sears] and the oatlet [Robert Douglas Stuart Jr., the son of a Quaker Oats vice president] had behind them the man who made Spam and a man who made steel and a man who had investments in salt, teletype machines, and wristwatches.”

“That grim rectangle”

Liebling pointedly dismisses Chicago as “a large place” rather than a big city, “a not-quite metropolis.” The city’s skyline as seen from Lake Michigan “is like a theatre backdrop with a city painted on it.”

He finds off-putting the intense concentration of so much of Chicago’s business, shopping and culture in a downtown girded by elevated railroad tracks:

…the Loop, a rectangle only seven blocks long and five wide, holding most of the major stores, theatres, and big hotels and office buildings, as well as the financial district, components of a city that in Manhattan are strung out from Central Park South to the Battery, a good five miles, and in London from Albert Hall to the Tower, about the same.

The Loop with its lakeside screen, forms a unit like the Kremlin as described by Richard Harding Davis when he attended the coronation of Nicholas II in 1896 — a small city surrounded by a boundless agglutination of streets, dramshops, and low buildings without urban character.

Liebling is being a bit unfair here, of course. Still, he is right in focusing on the Loop as an essential element of what makes Chicago Chicago. Indeed, he mentions the great affection that “one of my most astute Chicago friends” has for the Loop:

He loves that grim rectangle, bounded in its iron crown of elevated-railroad tracks, and says that during the war, when he was overseas and he thought of Chicago, it was always of the Loop in the ra1n, with the sound of the low-pitched, bisyllabic police whistles, like seas birds’ cries.

On the money

A.J. Liebling

A.J. Liebling

Liebling is also on the money when he looks with wonder — and humor — at the interconnection of Chicago’s inveterate boasting and its inferiority complex.

In the first half of the 19th century, scores of speculative cities were optimistically laid out by would-be land developers. Most came to little. Some never saw a single home built. So, winning the game meant having something to sell — in Chicago’s case, its location on Lake Michigan and its proximity to the planned Illinois & Michigan Canal that would link to the Mississippi — and selling it well.

That’s where boosterism came in.

Boosterism played a significant role, especially in the early years, in the rise of Chicago from a settlement of fewer than 100 people living in wood cabins in 1830 to the second largest city in the nation with just under 1.1 million residents in 1890. In many ways, boasting is woven into Chicago’s DNA.

No other city in world history had ever grown so large so fast. And the city’s boosters saw no reason to expect that growth to end.

In their classic 1909 Plan of Chicago, Daniel Burnham and Edward Bennett noted that one contemporary urban expert was predicting that, by 1952, Chicago’s population could rise to more than 13 million people. “Chicago,” they wrote, “is now facing the momentous fact that fifty years hence, when the children of to-day are at the height of their power and influence, this city will be larger than London: that is, larger than any existing city.”

They weren’t talking about a guess or prediction. They were talking about a “fact.”

It just so happens that 1952 was the year in which Liebling’s three essays appeared, as well as his book. It was also when Chicago’s population began to fall, according to the data in Wesley G. Skogan’s Chicago since 1840.

Those numbers show that, in 1951, the city had 3,618,500 residents. A year later, the figures had slipped by 3,300. As of 2010, the population was down to 2.7 million.

Nowhere near 13 million.

“The slain deer”

Liebling doesn’t mention the Burnham Plan, but, from across the decades, he records deliciously over-the-top examples of those selling Chicago — and believing their own rhetoric.

For instance, he writes that, in 1857, an editorial writer for the Tribune looked forward to the day when “the last rival in the race for greatness is left behind.” Noting that the writer meant what he said, Liebling goes on:

So, probably did another Tribune man, who wrote, thirty-six years later, during the Columbian Exposition, “In her white tent like Minnehaha, the arrow maker’s daughter, stood Chicago yesterday morning and gazed out on a sapphire lake, under a blue and cloudless sky, and her Hiawatha, her World Lover, came to her, and laid at her feet the slain deer, the tribute of universal admiration and love.”

To which, Liebling adds: “At the world’s feet, Chicago, in return, laid a butchered hog.”

“Heiress of all the ages”

In that same year, he points out, yet another Tribune editorial asserted: “Heiress of all the ages, [Chicago] stands in the foremost files of time.”

Contemporary “civic self-approbation” was easy for Liebling to find during his time in Chicago as a resident (for nearly a year) and a visitor.

North Michigan Avenue exhibited a sign trumpeting that it was “lined with the most beautiful buildings and the finest and most luxurious shops in the World.” A Loop restaurant offered chowder “said to be a favorite soup of Ernest Hemingway, believed by the natives of the Bahama Islands to promote virility and longevity.”

And, then, of course, there was the Tribune which, on its masthead, described itself as “The World’s Greatest Newspaper.”

“The expectation of a legacy”

Yet, the facts at mid-century were that, despite Chicago’s high hopes, it wasn’t the largest city in the world. Or even in the United States. And its hold on second place was coming under increasing threat from Los Angeles.

The hopes for all-round preeminence, to come as an automatic bonus for being biggest, have faded, too. Still the habit of purely quantitative thinking persists. The city consequently has the personality of a man brought up in the expectation of a legacy who has learned in middle age that it will never be his.

It is here, I think, that Liebling, for all his sarcasm, is most perceptive.

Just as a trauma in youth will color the perceptions and actions of a person through the rest of life, this lost-legacy realization has evidenced itself down the years in Chicago’s feeling of inferiority.

Like an anthropologist, Liebling painstakingly examines the many ways in which this feeling of unworthiness was expressed in his era:

Plays at Chicago theatres, for example, are always locally assumed to be inferior versions of the New York productions, or, if they are the New York productions, with original casts intact, the actors are presumed to be giving inferior performances.

It’s the same, he writes, with regard to women’s clothing: “Women who wouldn’t think of going to a show in Chicago told [Liebling’s wife] they wouldn’t think of buying a dress in a Chicago store, either.” And sports. “The fans don’t want to believe in their teams.”

Such pessimism about local products and talent, Liebling says, is “a sign not of maturity but of a premature old age.”

And it continues today with local leaders of all sorts wring their hands over whether Chicago is truly a world-class city. That not a question in Paris or New York. (Or, for that matter, Memphis or Pittsburg.)

“Five-dollar bills”

The over-fueled braggadocio and its twin, the less-is-me complex, result in what Liebling describes as the Chicagoan’s ambivalence about the city.

People you meet at a party devote a great deal more time than people elsewhere talking about good government, but they usually wind up the evening boasting about the high quality of crooks they have met.

At every social gathering, abuse is heaped upon the head of every politician in public view, the standard complaint being that the fellow is not sufficiently idealistic. The male guests carry five-dollar bills folded in their drivers’ licenses. Upon being stopped by a traffic policeman, they present the license, the cop takes the fin and returns the license, and the transaction is closed.

Further, Liebling writes about a similar two-faced attitude regarding political corruption. Robert Merriam, an honest alderman, tells him, “Chicago is unique. It is the only completely corrupt city in America.” And, when Liebling mentions a few other morally odiferous places, Merriam becomes defensive: “But they aren’t nearly as big.”


The city’s gangsters get the same treatment:

I have known Chicagoans who claim that they are embarrassed, when they are traveling abroad, at being quizzed about les gangsters. I have never believed them, because they invariably tell it like a funny story.

Indeed, one newspaperman, bemoaning Chicago’s mid-century decline, told Liebling: “It was a wonderful place when I was a kid. Guys would be shot down every day on the busiest street corners. It was romantic.”

Similarly, a Chicagoan whom Liebling describes as “a non-practicing lady novelist…who once won the Pulitzer Prize” — apparently Margaret Wilson whose novel The Able McLaughlins was the 1924 winner — was excited to tell him about the St. Valentine’s Day Massacre. That’s the name given to the gangland killing of seven men on February 14, 1929, in a garage at 2122 N. Clark St., a half block from her daughter’s school.

“How I remember that afternoon! I went around to Francis Parker to call for my daughter. But all the children had cut classes and gone to view the scene! Those were wonderful times!”

No shame

True, some things have changed since Liebling’s era. Chicago’s theater scene is nationally and internationally renowned. Indeed, his designation of Chicago as Second City was adopted as the name of the nation’s premier comedy troupe, a major force in American entertainment for more than half a century.

And, occasionally, over the years, a Chicago sports team has found a way to win a championship, as long as its name wasn’t the Chicago Cubs.

Still, Al Capone, whose short violent and energetically self-publicized career ended in 1932, remains still one of the most famous Chicagoans around the world. Regular bus tours take visitors and local people to important locations in the gangster’s life — as if he were some sort of saint or hero.

Political corruption is so expected that no one feels shame if yet another alderman is put up on trial. During a 26-year period ending in 1999, prosecutors sent 25 sitting and former City Council members to prison on corruption charges. The fact that such a roster was drawn up in the Tribune is an indication of the continued fascination of Chicagoans with the city’s political dark side.

And it was a Chicago politician, the son-in-law of an alderman, Rod Blagojevich, who, as Illinois governor, made the city and state a national laughingstock for blatant corruption, including an effort to sell the U.S. Senate seat of newly elected president Barack Obama.

First or nothing

There’s an odd kind of triumphalism at work here.

If the city can’t have the cleanest government, it can have the dirtiest. If none of the city’s sports teams is a perennial contender (like the New York Yankees), Chicago can boast of the Cubs, a team that has gone more than a century since winning a championship.

It is as if, feeling inferior, the city had decided to be world-class at inferiority.

Liebling called this Chicago’s “first-or-nothing psychology.” And he saw it as ambivalence in the face of a lost legacy.

Yet, it’s deeper than that, older than that.

Birth and rebirth

As the meeting point of East and West — its reason for existence from the beginning — Chicago has always been looking in two directions at once. No wonder, then, that the city and its people have developed a character comfortable with dualities — with good and bad, beauty and grime, old and new.

miller---apocalypseIn American Apocalypse: The Great Fire and the Myth of Chicago, Ross Miller describes Chicago’s core identity as “an ingrained and finally institutionalized schizophrenia…in part, compensation for the strains of the city’s meteoric growth and expansion.”

The duality of Chicago’s birth was intensified by the duality of its rebirth.

Chicago began in 1830 when surveyor James Thompson subdivided the land along the three branches of the Chicago River for sale. Within 40 years, it had grown into one of the most important cities in the nation.

Then, in 1871, the Great Fire erased all of the city’s central business section — its banks, its newspapers, its department stores, its government facilities. But, with the help of Eastern capital, that downtown area was well on its way to being rebuilt before the first anniversary of the blaze.

Chicago was essentially re-created from scratch. It was reborn out of the ashes, a phrase that was and still is continuously repeated.

Celebrating its death

Ever since, Chicago has celebrated its death — because that dying permitted its resurrection as a phoenix, another phrase endlessly applied to the city then and now.

“Chicago’s incongruities,” writes Miller, “became part of any portrait of the city. Praise, set off by examples from the city’s other side….there was a certain pride in the city’s divided nature…”

Nelson Algren captured this duality in his paean to the city Chicago: City on the Make.
Originally published in truncated form under the title “One Man’s Chicago” in Holiday magazine in October, 1951 (three months before Liebling’s New Yorker series began), the essay was issued as a book with its present title before the end of the year.

nelson algren

On its final pages, Algren wrote of the dualities that make Chicago:

Remembering nights, when the moon was a buffalo moon, that the narrow plains between the billboards were touched by an Indian wind. Littered with tin cans and dark with smoldering rubble, an Indian wind yet finds, between the shadowed canyons of The Loop, patches of prairie to touch and pass.

Between the curved steel of the El and the nearest Clark Street hockshop, between the penny arcade and the shooting gallery, between the basement ginmill and the biggest juke in Bronzeville, the prairie is caught for keeps at last. Yet on nights when the blood-red neon of the tavern legends tether the arc-lamps to all the puddles left from last night’s rain, somewhere between the bright carnival of the boulevards and the dark girders of the El, ever so far and ever so faintly between the still grasses and the moving waters, clear as a cat’s cry on a midnight wind, the Pottawattomies mourn in the river reeds once more.

“One rusty iron heart”

Those Indians had been replaced by skyscrapers, two-flats and elevated tracks and, Algren wrote, left behind nothing but a dirty river “While we shall leave, for remembrance, one rusty iron heart. The city’s rusty heart, that holds both the hustler and the square.”

The hustler and the square — A.J. Liebling beheld the duality of Chicago’s personality and found it ridiculous. And, perhaps, it is ridiculous.

But, maybe, it’s also realistic.

Maybe Chicago isn’t so much schizophrenic as it is balanced in recognizing and finding accommodation with its contradictions — in holding them together in “one rusty iron heart.”

Either way, it is what it is. You can’t have Jane Addams without George Pullman, the lakefront without the slums, the Chicago Symphony Orchestra without Al Capone, the Haymarket martyrs without Rod Blagojevich.

For all its boasting, Chicago has always been rooted deep in the mire from which it sprang.

Patrick T. Reardon

Written by : Patrick T. Reardon

For more than three decades Patrick T. Reardon was an urban affairs writer, a feature writer, a columnist, and an editor for the Chicago Tribune. In 2000 he was one of a team of 50 staff members who won a Pulitzer Prize for explanatory reporting. Now a freelance writer and poet, he has contributed chapters to several books and is the author of Faith Stripped to Its Essence. His website is

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