Through all of this, he was funny. Liebling had made up his mind about Chicago long before his 1949 sojourn. He had interviewed the America First leaders in the spring of 1941 and Collier’s wanted a demolition job on the Tribune. In the space of less than a hundred pages of Chicago: The Second City, he manages to bad-mouth everything about the town from its bars to its cultural life, which he diagnosed as marginal, if not terminal. In the book version he was able to write a Foreword firing back at the outraged citizens who protested the original insults, and added a few more illustrations by the noted artist Saul Steinberg depicting the town’s ugliness, just in case anyone had missed it in the magazine.
Chicago’s ugliness was hardly news. No one has been able to glamorize a conglomeration of rail yards, stockyards and steel mills. They have to be put somewhere, and the depressing panorama had been thoroughly aired by an earlier generation of writers. When he did Chicago, Liebling was an established writer and bon vivant. A native of Manhattan, he had been a war correspondent for the New Yorker, and if he had a spiritual home it was probably Paris, where he had spent happy student days and returned with the liberators. He was a tremendous feeder and gourmet which may have killed him early, and his biography was written by Raymond Sokolov, a writer on food (Wayward Reporter: The Life of A.J. Liebling, New York, 1980).
Chicago starts with Liebling’s description of Chicagoans trekking to the lakefront beaches. It tells a good deal about his outlook. His strength is his robust, mocking style, mixing classical literary and street argot, and his expertise on the urban underside. He thought that as a rule, citizens everywhere were being had, and found that the Chicagoans agreed with him. He convicted them out of their mouths. There was a general air of lawlessness about the place, and the inhabitants for want of any other source of civic pride, were rather proud of it. Even the community leaders agreed that the great times were past, that the businessmen had become passive and that the poets and writers had fled. For theatre and style they looked to New York.
A veteran pub-crawler, Liebling found Chicago saloons with their dice girls to be unrestful—he calculated the odds on winning drinks. He visited Sportsman’s Park and pronounced it a second-rate converted dog track. He went out to the great university John D. Rockefeller had founded, and stopped by the bars the undergraduates frequented to learn from them that the touted Robert Hutchins curriculum was a piece of cake.
Bit by bit, bending things here and there, he worked his way through the Second City. He noted that its drama critics visited New York to see the new shows. Even though the fashionable New York stores had branches in Chicago, the local ladies believed that they were sent out only inferior goods. Here Liebling had the help of his wife, or so he said. He reported that New York ladies made their Chicago counterparts feel awkward, just as English ladies felt in the presence of Parisiennes. There was little in the way of book publishing beyond such items as telephone directories. This brought him to a subject he knew: the newspapers. He prepared by attending a broadcast of the Chicago Theater of the Air on Station WGN featuring the musical The Vagabond King and a reading by Colonel Robert R. McCormick, the eccentric press lord who owned the whole shebang. Liebling claimed that McCormick was an embarrassment to most literate Chicagoans. If anything, his description of the elderly colonel reading a piece on the United States Navy while sniffling with a cold should have made the reader feel sorry for him.
The Tribune was the leading isolationist paper in the United States and McCormick reportedly considered himself greatest threat to the British Empire, which at the time was having serious internal problems on its own. Considering that he had been hired to expose the Tribune Liebling contented himself with a fairly mild survey of the Chicago news scene, only observing that anyone condemned to the insular Chicago papers for a few months would find the New York Times or Herald Tribune a breath of fresh air.
He commented that the Tribune, a Republican paper, went easy on the corrupt Democratic city bosses. He omitted any mention of the Tribune’s recent gaffe in headlining a Dewey presidential victory or of the famous leak of an American war plan a few days before Pearl Harbor. In those days it was possible for hog to travel between the East and West Coasts without being disturbed, but humans had to change trains in Chicago. Movie and stage actors shuttling between New York and Hollywood and in need of publicity often overnighted long enough to be interviewed at the Hotel Ambassador East’s Pump Room, and Liebling claimed that when it was proposed to establish through passenger service a hotel man feared that nobody of prominence would stop off in Chicago.
Liebling rounded off his bombardment with serious allegations that the City failed to support its sports figures and get fully behind its major league baseball teams. He dutifully surveyed the strip-tease joints, and the known perils for visiting conventioneers. He interviewed ward leaders, and devoted much space to the way the city responded to gangland’s St. Valentine’s Day “Massacree” [sic]. The recent plague of faked news stories in major American media has led to the realization that revered figures such as H.L. Mencken sometimes made things up, maybe even Liebling. Liebling would admit only to one inaccuracy in his book: he misplaced the Bahai temple in Evanston when it actually was in Wilmette.