Found Inside The Iron Gate (First in a Series)

The Air Force Association (AFA) was founded in 1945 when the head of the Army Air Forces, General Hap Arnold, campaigned for the creation of a veterans group that would support establishing the Air Force as a separate branch of the military. Chapters of the AFA blossomed in major cities coast to coast, and when its initial mission was successfully accomplished the organization shifted its emphasis to fundraising for charitable causes (often targeting the Air Force Aid Society, the official charity of the U.S.A.F.) or educational pursuits in the areas of aviation.

By the early 1960s a New York branch of the Association opened called The Iron Gate Squadron. Aside from, sounding strong and distinctive, that name had specific significance: it referred to the imposing entrance of the high-toned Manhattan restaurant sometimes referred to as “Jack & Charlie’s 21,” or simply as “21.”

The brainchild of two cousins named Jack (“The Baron”) Kreindler and Charlie Berns, “21” had humble beginnings as a Greenwich Village bootlegging operation during Prohibition, changing locations and names three times before settling in with its current name and address, at 21 West 52nd Street. In its heyday the restaurant and its lively bar section were a Must Visit spot for the famous and powerful — Ernest Hemingway, Mae West, Humphrey Bogart, Ed Sullivan, William Saroyan, Clark Gable, Sinatra and his Rat Pack, comedian “Bugs” Baer, Presidents Truman, Kennedy, and Ford, Elizabeth Taylor, Judy Garland, and Gene Kelly are only a small segment of the parade of glitterati who graced the tables at “21.” The restaurant, to steal a line from Doc Savage writer Lester Dent, “charged its patrons outrageous prices and made them like it.”

High-rolling cartoonists were also prominent among “21’s” clientele for the better part of a half-century. Milton Caniff, of Terry and the Pirates and Steve Canyon fame, not only frequented the place when he was in the city during the 1950s and ’60s, he struck up a friendly relationship with Maxwell “Mac” Kreindler, who had become president of the establishment following Jack’s passing in 1947. It was Mac, himself an Air Force veteran, who reached out to a circle of like-minded friends and patrons and founded the Iron Gate Squadron of the AFA; Caniff was one of those founding members, and soon followed Kreindler as the Squadron’s leader (dubbed the “commander” of the group).

During Milt’s tenure as commander, he presided over the second annual charitable Air Force Salute Ball, held at the Waldorf-Astoria’s Grand Ballroom. The hugely-successful, hundred dollars a plate event attracted over a thousand persons, including military representatives from eighteen countries, assembled to honor retiring Air Force Chief of Staff General Curtis LeMay. Caniff’s social nature once again served him in good stead — LeMay was a lock to attend the event in his name, since he and Milton were classmates at The Ohio State University in the 1920s.

Fifteen years before Milt’s grand soiree, a privately-produced salute to “21” was released in hardcover, designed to raise money for the New York Heart Foundation. Its two hundred eighteen pages mingle articles by the likes of John Steinbeck, Westbrook Pegler, Ben Hecht, and Damon Runyon, advertising from Ford, American Airlines, Philip Morris, Warner Bros., and a variety of liquor companies … and a wide range of cartoons by names familiar to many Library of American Comics readers. In this and future postings, we’ll share some of these rare pieces with you.