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Chicago: The Second City
Many Chicagoans rose in protest over A. J. Liebling’s tongue-in-cheek tour of their fair city in 1952. Liebling found much to admire in the Windy City’s people and culture—its colorful language, its political sophistication, its sense of its own history and specialness. But Liebling offended that city’s image of itself when he discussed its entertainments, its built landscapes, and its mental isolation from the world’s affairs.Liebling, a writer and editor for the New Yorker, lived in Chicago for nearly a year. While he found a home among its colorful inhabitants, he couldn’t help comparing Chicago with some other cities he had seen and loved, notably Paris, London, and especially New York. His magazine columns brought down on him a storm of protests and denials from Chicago’s defenders, and he gently and humorously answers their charges and acknowledges his errors in a foreword written especially for the book edition.Liebling describes the restaurants, saloons, and striptease joints; the newspapers, cocktail parties, and political wards; the university; and the defining event in Chicago’s mythic past, the Saint Valentine’s Day Massacre. Illustrated by Steinberg, Chicago is a loving, if chiding, portrait of a great American metropolis.“Good entertainment. The book is attractively designed, the illustrations are first-rate and Mr. Liebling can write.”—New York Times“Mr. Liebling’s entertaining book can be highly recommended.”—New York Herald Tribune“He has shown his readers in his lively, sardonic style exactly the split-personality city that he feels Chicago to be.”—San Francisco Chronicle
106 pages, Kindle Edition
First published March 1, 2004
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About the author
A.J. Liebling
42 books72 followersAbbott Joseph "A. J." Liebling was an American journalist who was closely associated with The New Yorker from 1935 until his death.
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Displaying 1 - 22 of 22 reviews
April 17, 2023
Chicago is a great American city, one of my favorites; but, A.J. Liebling's title aside, it is no longer "the Second City" of the United States, if one is speaking in terms of population. Upstart Los Angeles has now replaced Chicago as America's "Second City." Whether one is focusing upon city population (L.A. 3.84 million, Chicago 2.84 million) or metropolitan area (L.A. 12.8 million, Chicago 9.5 million), Los Angeles is now the nation's second city. Yeah, but where can you find a good deep-dish pizza in Beverly Hills or Westwood?
In 1952, when A.J. Liebling of The New Yorker wrote his book, Chicago was indeed the second-largest city in the United States; and his Chicago: The Second City made quite an impression from Juneway Terrace to Hegewisch. That impression was not always favorable. As Liebling explains in a foreword, some Chicago-area residents who objected to his characterization of the city "rose to [Chicago's] defense like fighters off peripheral airfields in the Ruhr in 1944" -- a simile that may reveal much about Liebling's own attitude regarding criticism of his book. Comparing one's critics to Nazis? Really? It would seem that Godwin's Law was in operation well before the Internet.
In Chicago: The Second City, Liebling offers a portrait of the Illinois metropolis that might best be described as affectionately critical. Sometimes, Liebling seems to celebrate Chicago's regional character, as when he talks of how he can't repeat Chicago dialect he's heard "without thinking of a city with lifted head, singing." At times, however, he seems to find Chicago's boosterism illogical, as when a Chicago alderman proudly describes his ward as the site of the Saint Valentine's Day Massacre in 1929: "The Alderman's manner, if not his tone, was that of Dr. Douglas Southall Freeman saying, 'There stood Pickett's men.'"
Liebling's brief book is well-written, but is a bit too self-consciously literary for my taste; sometimes it seems as though one can't get through a single sentence without being subjected to a barrage of allusions that will hammer into the reader's mind how erudite and well-read Liebling is. In Liebling's time, The New Yorker was associated with a decided degree of hauteur toward any city that had the unmitigated gall not to be New York; and that old New Yorker attitude does seem to come through at times, as when Liebling describes the Chicago Loop as "a small city surrounded by a boundless agglutination of streets, dramshops, and low buildings without urban character" and adds that "The Loop is like Times Square and Radio City set down in the middle of a vast Canarsie [a Brooklyn neighborhood]." This is very much a mid-20th-century New Yorker's view of Chicago.
Perhaps it is no accident that this book's modern reprinting comes not from a Chicago-area university press, like Northwestern University or the University of Chicago, but rather from the University of Nebraska. The book, based originally on three articles published in the New Yorker, is brief and fun to read; the illustrations by Steinberg are engaging. But after reading Liebling's Chicago: The Second City, be sure to consult some other Chicago books, for a more balanced picture of this fascinating city.
In 1952, when A.J. Liebling of The New Yorker wrote his book, Chicago was indeed the second-largest city in the United States; and his Chicago: The Second City made quite an impression from Juneway Terrace to Hegewisch. That impression was not always favorable. As Liebling explains in a foreword, some Chicago-area residents who objected to his characterization of the city "rose to [Chicago's] defense like fighters off peripheral airfields in the Ruhr in 1944" -- a simile that may reveal much about Liebling's own attitude regarding criticism of his book. Comparing one's critics to Nazis? Really? It would seem that Godwin's Law was in operation well before the Internet.
In Chicago: The Second City, Liebling offers a portrait of the Illinois metropolis that might best be described as affectionately critical. Sometimes, Liebling seems to celebrate Chicago's regional character, as when he talks of how he can't repeat Chicago dialect he's heard "without thinking of a city with lifted head, singing." At times, however, he seems to find Chicago's boosterism illogical, as when a Chicago alderman proudly describes his ward as the site of the Saint Valentine's Day Massacre in 1929: "The Alderman's manner, if not his tone, was that of Dr. Douglas Southall Freeman saying, 'There stood Pickett's men.'"
Liebling's brief book is well-written, but is a bit too self-consciously literary for my taste; sometimes it seems as though one can't get through a single sentence without being subjected to a barrage of allusions that will hammer into the reader's mind how erudite and well-read Liebling is. In Liebling's time, The New Yorker was associated with a decided degree of hauteur toward any city that had the unmitigated gall not to be New York; and that old New Yorker attitude does seem to come through at times, as when Liebling describes the Chicago Loop as "a small city surrounded by a boundless agglutination of streets, dramshops, and low buildings without urban character" and adds that "The Loop is like Times Square and Radio City set down in the middle of a vast Canarsie [a Brooklyn neighborhood]." This is very much a mid-20th-century New Yorker's view of Chicago.
Perhaps it is no accident that this book's modern reprinting comes not from a Chicago-area university press, like Northwestern University or the University of Chicago, but rather from the University of Nebraska. The book, based originally on three articles published in the New Yorker, is brief and fun to read; the illustrations by Steinberg are engaging. But after reading Liebling's Chicago: The Second City, be sure to consult some other Chicago books, for a more balanced picture of this fascinating city.
May 8, 2025
100 angry Chicago residents vs 1 New York City journalist, who wins?
July 26, 2013
I’ve lived in Chicago all my life. I understand from others who have moved here that this is a city where they meet a surprising number of ‘natives.’ That, for instance, if you live in New York, you meet a lot of people who aren’t from NY; they’re from any number of other cities and countries. May this is why Chicagoans are so protective of their city. We truly are from here and have internalized the city in some way.
I was introduced to this book when it was mentioned in a recent New York Times Book Review “Chicago Manuals” (one of which took its title from a passage in this book: “You’ve Never Been to Chicago.”) The reviewer received a lot of ‘feedback’ from Chicagoans regarding her review of the three books and I have the same reaction to Chicago The Second City.
Mr. Liebling originally published this book in 1925, so it’s quite dated. However, some of the criticisms in this book continue to this day; warranted or not. ( Yes, the city government is corrupt. You’ll get no argument from me on that. Just look at the recent deal that our ‘reform’ mayor made for expressway billboards: http://tinyurl.com/m8csnr8 )
However, the social criticisms in this book are specious at best. Mr. Liebling is from New York and this is little more than a New Yorker’s screed against a city he feels is inferior to New York (I would bet that he could have written this book about any other city on earth. New Yorkers don’t think that any city measures up to their own. ) Many of these criticisms stem from an isolated interaction or event and he extends that as a universal truth about the entire city and its population.
Mr. Liebling also says that he had “a considerable circle of Chicago acquaintances [some of which he enumerates] …whom my wife and I had met at cocktail parties in New York.” Apparently a primary activity of this group was to get together and complain about what Chicago lacks. Our architecture isn’t any good (the Tribune Tower should have been “finished …off with a gigantic scoop of ice cream, topped by an illuminated cherry.” Our theatre is horrible, but when it’s good, our audiences didn’t recognize it and “laughed in all the wrong places.” Our sports fans don’t have good teams to cheer for and we also lack the heart of Brooklyn fans, who again and again revive their spirit. Our restaurants are no good, yet the restaurateurs complain that Chicagoans don’t go out to eat.
Again, this is an old book, and maybe some of these complaints were valid, but it seems to me this is just a diatribe by somebody without the capacity to enjoy life outside New York. Because of his limitations, the narrative is pretty snide and therefore not pleasant to read. Because of the date of the book, the language is formal and old-fashioned.
Not a book I would recommend to anybody.
I was introduced to this book when it was mentioned in a recent New York Times Book Review “Chicago Manuals” (one of which took its title from a passage in this book: “You’ve Never Been to Chicago.”) The reviewer received a lot of ‘feedback’ from Chicagoans regarding her review of the three books and I have the same reaction to Chicago The Second City.
Mr. Liebling originally published this book in 1925, so it’s quite dated. However, some of the criticisms in this book continue to this day; warranted or not. ( Yes, the city government is corrupt. You’ll get no argument from me on that. Just look at the recent deal that our ‘reform’ mayor made for expressway billboards: http://tinyurl.com/m8csnr8 )
However, the social criticisms in this book are specious at best. Mr. Liebling is from New York and this is little more than a New Yorker’s screed against a city he feels is inferior to New York (I would bet that he could have written this book about any other city on earth. New Yorkers don’t think that any city measures up to their own. ) Many of these criticisms stem from an isolated interaction or event and he extends that as a universal truth about the entire city and its population.
Mr. Liebling also says that he had “a considerable circle of Chicago acquaintances [some of which he enumerates] …whom my wife and I had met at cocktail parties in New York.” Apparently a primary activity of this group was to get together and complain about what Chicago lacks. Our architecture isn’t any good (the Tribune Tower should have been “finished …off with a gigantic scoop of ice cream, topped by an illuminated cherry.” Our theatre is horrible, but when it’s good, our audiences didn’t recognize it and “laughed in all the wrong places.” Our sports fans don’t have good teams to cheer for and we also lack the heart of Brooklyn fans, who again and again revive their spirit. Our restaurants are no good, yet the restaurateurs complain that Chicagoans don’t go out to eat.
Again, this is an old book, and maybe some of these complaints were valid, but it seems to me this is just a diatribe by somebody without the capacity to enjoy life outside New York. Because of his limitations, the narrative is pretty snide and therefore not pleasant to read. Because of the date of the book, the language is formal and old-fashioned.
Not a book I would recommend to anybody.
May 9, 2020
I can understand why all true Chicagoians were a bit up in arms. I do love Liebling.
August 15, 2012
Chicago is a great American city, one of my favorites; but, A.J. Liebling's title aside, it is no longer "the Second City" of the United States, if one is speaking in terms of population. Upstart Los Angeles has now replaced Chicago as America's "Second City." Whether one is thinking in terms of city population (L.A. 3.84 million, Chicago 2.84 million) or metropolitan area (L.A. 12.8 million, Chicago 9.5 million), Los Angeles is now the nation's second city. Yeah, but can you find a good deep-dish pizza in Beverly Hills or Westwood?
In 1952, when A.J. Liebling of the New Yorker wrote his book, Chicago was indeed the second-largest city in the United States; and his Chicago: The Second City made quite an impression in the city that was his subject. That impression was not always favorable. As Liebling explains in a foreword, some Chicago-area residents who objected to his characterization of the city "rose to [Chicago's] defense like fighters off peripheral airfields in the Ruhr in 1944" -- a simile that may reveal much about Liebling's own attitude regarding criticism of his book.
In Chicago: The Second City, Liebling offers a portrait of the Illinois metropolis that might best be described as affectionately critical. Sometimes, Liebling seems to celebrate Chicago's regional character, as when he talks of how he can't repeat Chicago dialect he's heard "without thinking of a city with lifted head, singing." At times, however, he seems to find Chicago's boosterism illogical, as when a Chicago alderman proudly describes his ward as the site of the Saint Valentine's Day Massacre in 1929: "The Alderman's manner, if not his tone, was that of Dr. Douglas Southall Freeman saying, 'There stood Pickett's men.'"
Liebling's brief book is well-written, but is a bit too self-consciously literary for my taste; sometimes it seems as though one can't get through a single sentence without being subjected to a barrage of allusions that will hammer into the reader's mind how erudite and well-read Liebling is. In Liebling's time, the New Yorker was associated with a decided degree of hauteur toward any city that had the unmitigated gall not to be New York; and that old New Yorker attitude does seem to come through at times, as when Liebling describes the Chicago Loop as "a small city surrounded by a boundless agglutination of streets, dramshops, and low buildings without urban character" and adds that "The Loop is like Times Square and Radio City set down in the middle of a vast Canarsie [a Brooklyn neighborhood]." This is very much a mid-20th-century New Yorker's view of Chicago.
Perhaps it is no accident that this book's modern reprinting comes not from a Chicago-area university press, like Northwestern University or the University of Chicago, but rather from the University of Nebraska. The book, based originally on three articles published in the New Yorker, is brief and fun to read; the illustrations by Steinberg are engaging. But after reading Liebling's book, be sure to consult some other Chicago books, for a more balanced picture of this fascinating city.
In 1952, when A.J. Liebling of the New Yorker wrote his book, Chicago was indeed the second-largest city in the United States; and his Chicago: The Second City made quite an impression in the city that was his subject. That impression was not always favorable. As Liebling explains in a foreword, some Chicago-area residents who objected to his characterization of the city "rose to [Chicago's] defense like fighters off peripheral airfields in the Ruhr in 1944" -- a simile that may reveal much about Liebling's own attitude regarding criticism of his book.
In Chicago: The Second City, Liebling offers a portrait of the Illinois metropolis that might best be described as affectionately critical. Sometimes, Liebling seems to celebrate Chicago's regional character, as when he talks of how he can't repeat Chicago dialect he's heard "without thinking of a city with lifted head, singing." At times, however, he seems to find Chicago's boosterism illogical, as when a Chicago alderman proudly describes his ward as the site of the Saint Valentine's Day Massacre in 1929: "The Alderman's manner, if not his tone, was that of Dr. Douglas Southall Freeman saying, 'There stood Pickett's men.'"
Liebling's brief book is well-written, but is a bit too self-consciously literary for my taste; sometimes it seems as though one can't get through a single sentence without being subjected to a barrage of allusions that will hammer into the reader's mind how erudite and well-read Liebling is. In Liebling's time, the New Yorker was associated with a decided degree of hauteur toward any city that had the unmitigated gall not to be New York; and that old New Yorker attitude does seem to come through at times, as when Liebling describes the Chicago Loop as "a small city surrounded by a boundless agglutination of streets, dramshops, and low buildings without urban character" and adds that "The Loop is like Times Square and Radio City set down in the middle of a vast Canarsie [a Brooklyn neighborhood]." This is very much a mid-20th-century New Yorker's view of Chicago.
Perhaps it is no accident that this book's modern reprinting comes not from a Chicago-area university press, like Northwestern University or the University of Chicago, but rather from the University of Nebraska. The book, based originally on three articles published in the New Yorker, is brief and fun to read; the illustrations by Steinberg are engaging. But after reading Liebling's book, be sure to consult some other Chicago books, for a more balanced picture of this fascinating city.
October 23, 2013
I had never heard of this book before, let alone seen a copy, until I came across a nice, clean remaindered copy in a St Cloud, MN used bookstore. At about 150 pp (including the "Foreword" he added to the book publication of these 3 essays on his life in Chicago, first published in the "New Yorker")I read it in 2 quick evenings.
Liebling lived in Chicago for about a year, 1949-50 (he never says why) and I hope he never went back after these essays were published. Because any true son of Chicago would have punched him in the nose. The Chicago he writes about is not the Chicago of today, and it actually sounds a lot like the NYC of the 1970's through the '90's - a desolate wasteland filled w/ the poor in an almost Dickensian city.
But it was fun to hear the names of some of the places which still had some aplomb when I was growing up in the metro area in the '60's and '70's. The Pump Room, the College Inn, the Ambassador Hotels, columnist Kup. And his stories of Colonel McCormick, a Chicago strip club visit, and his attack on Hutchinson and the U of Chicago (not "the U of C" - the real, and older, one is out on the West Coast) exhibits much of the wit Libeling is known for in his journalistic writing.
A "must read" for any Chicago resident - and before you get too pissed off, remember that he is writing about a city 60 years ago. He is accurate - and a LOT has changed. This collection is not included in the LOA volume of Libeling's writings. "New Yorker" illustrator Saul Steinberg does not add much to the book.
Liebling lived in Chicago for about a year, 1949-50 (he never says why) and I hope he never went back after these essays were published. Because any true son of Chicago would have punched him in the nose. The Chicago he writes about is not the Chicago of today, and it actually sounds a lot like the NYC of the 1970's through the '90's - a desolate wasteland filled w/ the poor in an almost Dickensian city.
But it was fun to hear the names of some of the places which still had some aplomb when I was growing up in the metro area in the '60's and '70's. The Pump Room, the College Inn, the Ambassador Hotels, columnist Kup. And his stories of Colonel McCormick, a Chicago strip club visit, and his attack on Hutchinson and the U of Chicago (not "the U of C" - the real, and older, one is out on the West Coast) exhibits much of the wit Libeling is known for in his journalistic writing.
A "must read" for any Chicago resident - and before you get too pissed off, remember that he is writing about a city 60 years ago. He is accurate - and a LOT has changed. This collection is not included in the LOA volume of Libeling's writings. "New Yorker" illustrator Saul Steinberg does not add much to the book.
December 11, 2018
I think that the Chicagoans who didn't like Liebling's opinions should understand that he was writing about Chicago in the 1940's (and yes, he did live there, not just visit). At the time The Chicago Tribune was run by Robert McCormick, a narcissistic nutcase who had considered himself a war hero and insisted on being called "The Colonel". He was a Nazi sympathizer and isolationist who railed against everyone and felt the sting of a superior New York press and culture and whined about those slights in his newspaper, whose motto he coined: World's Greatest Newspaper. (WGN radio was owned by him.)
It's the Chicago pretensions of that time that Liebling writes about. But that was a long time ago; people should get over it.
It's the Chicago pretensions of that time that Liebling writes about. But that was a long time ago; people should get over it.
September 4, 2007
i dunno, i'm just not diggin the liebling. i was given a copy of another book of his (one about eating) by a friend whose taste i respect, but i was never able to get into that one and this one didn't do anything for me either. my complaints are: i find his style overly showy with too many look-at-me-i'm-clever allusions and a general air of superiority to his subject matter and the world in general that bugs me. but, as i say often, i'm often wrong, and i could be wrong about liebling as well. if anyone has another book of his that they think might convert me, please let me know.
August 17, 2007
I've read that Liebling is considered by some to be a father figure to the New Journalism. He's a great writer, always entertaining, and, man, he hates Chicago. As a Chicagoan, it's fun to read such a humorously disparaging account of our fine city. A lot of the things that chafe Liebling are things that I define as charming, such as the inferiority complex that Chicagoans collectively suffer from. Also, there's a very entertaining description of Nelson Algren.
December 6, 2009
A. J. Liebling coined the phrase "Second City" in reference to Chicago. The book is a compilation of essays he wrote for the New Yorker in early 1952. Originally a critique (and withering criticism) of Chicago, it now stands as a fascinating glimpse of that City in mid-century American, straddling the depression/war era and renewal. Reading this is like inhabiting 1950s Chicago. Highly recommended.
May 6, 2008
The best thing about this book is that it made me appreciate Algren's "City on the Make" more. As I told a friend, it is one thing for your own brother to call you fat and ugly and quite another when his retarded college friend visiting from New York City does so.
January 11, 2013
Enjoyed the collection. It is either about a Chicago I have never experienced (the Michigan Avenue crowd), or a society long lost from the time it was written. Either way, it was a fun series of essays.
August 20, 2007
A fun look at Chicago half a century ago. The three-part series, which ran in the New Yorker, offended a lot of Chicagoans at the time for its unsentimenal look at the Second City.
June 22, 2012
There's nothing better than a concentrated dose of A. J. Liebling to cheer a reader up. His love of writing and spinning a tale is palpable and makes for a great reading experience.
Read
August 5, 2012Meh. The good thing is that I did not devote more than a couple of hours to the book.
February 6, 2018
This is the book (series of articles) to which You Were Never In Chicago by Neil Steinberg is an answer of sorts. It's a flyby view of Chicago. You know, like when you tell someone where you are going on vacation, and they tell you all of the reasons you'll hate it, and finish up with "But you might like it." It's an interesting opinion piece designed to solicit response, and it certainly did in it's time (almost 60 years ago), but if you want a real taste of Chicago, just read Steinberg's book.
February 12, 2022
“Christ, what an asshole.”
Last essay is a solid run on wards and the historic gaze back onto Capone (which hasn’t evolved in 70 years? Fascinating). The rest is yawn and everything you’d expect from a mid century New Yorker writer on assignment with working stiffs.
Interesting material on how Chicago has more or less always imagined itself as on the decline while forcing the approaching zenith.
Last essay is a solid run on wards and the historic gaze back onto Capone (which hasn’t evolved in 70 years? Fascinating). The rest is yawn and everything you’d expect from a mid century New Yorker writer on assignment with working stiffs.
Interesting material on how Chicago has more or less always imagined itself as on the decline while forcing the approaching zenith.
November 30, 2022
Hilarious, if a bit outdated. As a former resident of New York City and someone who is pretty familiar with Chicago, Liebling's take on the Second City (and the reactions he got from readers) is spot on. Not only spot on, but his writing style betrays certain stereotypes about acerbic New York writers, so it's sort of a hilarious two way street.
October 23, 2020
Dated.. sort of funny. Meh
January 15, 2025
This reporting is interesting, in that it’s conisderably worse than I would have expected.
July 26, 2025
can't believe i got ragebaited by a new yorker writer from 75 years ago
September 3, 2008
Only Chicago history buffs will enjoy this long essay, the best parts of which appear near its end in riffs on the University of Chicago, Alderman Paddy Bauler, and the St. Valentine's Day Massacre.
Displaying 1 - 22 of 22 reviews