The past is another country. Want proof? Between 1953 and 1970, United Airlines offered a flight called the Executive that flew between New York and Chicago on the East Coast and between Los Angeles and San Francisco on the West Coast at five p.m. weekdays. Weekdays because, once upon a time, Saturdays and Sundays found every businessman successful enough to fly the Executive in a hammock in New Rochelle or Wilmette, just as far from an airport as a man can possibly get. Rush hour—after the deals have been negotiated and the contracts inked, after the junior managers have been scolded and the secretaries goosed: that’s when the Executive took flight.
The selling feature of the Executive, which would not stand up to Supreme Court scrutiny even with Gorsuch and Kavanaugh on the bench, was not who flew but who was prohibited from flying: kids and women. Or, as Frank Sinatra, who, had he not owned a plane, would surely have flown the Executive, might have put it: No punks, no dames. In fact, the only women allowed on board were the flight attendants, every one of whom, per unwritten rule, was good-looking and single. You were to notify your airline boss the moment you put that ring on your finger.
I found out about all this from my father. He is 90 years old. Now and then, when he says something, especially about the past, I think, “That can’t possibly be true,” but later, when I look it up, it turns out it is. “Of course it’s true,” he said when I returned to him like a dog with a bone. “Why would I tell you about it if it wasn’t true? What do you think I am, crazy?”
In its first years, the Executive fleet was made exclusively of Douglas DC-6s, a prop-driven workhorse of the postwar, Mad Men–era commuter boom, when it suddenly made sense to have lunch at Stouffer’s Top of the Sixes in Midtown Manhattan and dinner later that day at the Walnut Room in Chicago.
This was before the self-check-in, the moving walkway, the jet bridge. You crossed the tarmac on foot. You stood in the wash of steely propellers that came to life with a cough then spun into a void. The engines were loud, the planes big and maddeningly slow. It took more than three hours to get from Idlewild to O’Hare. For those unmoored by turbulence, which was more common and more furious in that antique age, the preferred in-air state was a two-drink drunk, which is why, on the Executive, passengers were offered free cocktails, most of which were gin martinis.
The only women allowed on board were the flight attendants, every one of whom was good-looking and single.
Think about the army of insurance men, bank managers, literary agents, magazine and book editors, jingle writers, pro quarterbacks, and political bosses waiting in line to board the five p.m. Executive to LAX or San Francisco Municipal. The Executive, where all seats were first class, where a table—a desk in the sky—was available to those who needed to sign a multi-million-dollar deal, stock-market quotes were on tap—By God, I just got even richer!—and a call could be made to the office from the runway.
Here’s something totally American.
The Executive probably began with a complaint. Some passenger was told he couldn’t smoke his cigar on the plane. The rule was industry-wide. Unless you smoke them yourself, and maybe even if you do, you will find a cabin filled with cigar smoke at 30,000 feet intolerable. The Executive was proposed as a solution—a flight set aside just for cigar and pipe smokers, which could even entice the Beat poets and professors. The flight would become something grander still—the romance of the old rail-service smoking car reborn at altitude.
In an ad that ran in newspapers in the early 1960s, which showed a man in a gray suit and a fedora crossing a tarmac with briefcase in hand, the route is advertised as “The Chicago Executive: A Club in the Sky for Men Only.”
“Relax after a busy day on this special DC-6 Mainliner flight. You’ll enjoy the informal, club-like atmosphere. Smoke your pipe or cigar, if you wish, and make yourself most comfortable by using the pair of slippers provided.”
It was not the absence of women that drew most of the customers, nor even the cigars and other freebies—a parting gift, cuff links or an ashtray, was handed to every passenger on his (yes, his!) way out. It was the ban on children, because, well, you know what kids can be like on a plane.
Passengers were offered free cocktails, most of which were gin martinis.
The service was a big hit in the 1950s. Nearly 20,000 men—some big and strapping, some mousy and small; some in it for the cigars, some to get loaded away from the admonishing looks of ladies—took the Executive in its first years. The price was $67 round trip, every passenger given a stogie before takeoff and served a medium-rare filet on real china after. Cocktails, meat, and laughter while the DC-6 cast its shadow on the sun-dappled waters of Lake Michigan—it never got better for the American man who needed to travel for business.
My father says he flew it for the cigar. “I took it even when I had no reason to be in New York just to get that free cigar,” he told me. When I protested—“But, Dad, that’s a $67 cigar”—he cut me off, saying, “You’re not listening. They gave you a free cigar.”
It ended just as it probably began—with a complaint. The National Organization for Women, which was founded by Betty Friedan in 1966 and was soon on the march, knocking down barrier after barrier, picketed the United Airlines headquarters in Chicago in 1969, then filed a complaint with the Civil Aeronautics Board. The protesters were, in a sense, pushing against an open door. The Executive, which already seemed like a relic, had been steadily losing customers. In the Age of Aquarius, it was the only thing worse than evil: uncool.
It made its final trips in the winter of 1970. The cabins were half empty by then, the steaks tough, the cigars cheap, the flight attendants mostly annoyed. When the last Executive left O’Hare, it was like the last square-rigged caravel leaving Spain in 1690. Or the last Saturn V rocket ascending from the pad in Florida in 1972. An entire era dissolved in its wake. And now no one, not even a Betty Friedan, is allowed to smoke a cigar in the sky.
Rich Cohen is an Editor at Large for AIR MAIL and the author of The Adventures of Herbie Cohen: World’s Greatest Negotiator
