34 West Ninth Street, Air Mail

I think the best word to sum up the office of Air Mail would be an Italian one: sprezzatura. It means the art of making hard work appear effortless. The word originated in Baldassare Castiglione’s 1528 The Book of the Courtier, but I was introduced to it by Peter Eisenman, who was running his own Renaissance court in my architecture graduate program.

The sense of ease, bordering on whimsy, starts at the front door of Air Mail’s building, where the buzzer has five entries:

The publication occupies only Unit 2, but when it moved in the rest of the apartments were empty, so the editors took the liberty of filling in all the names on the buzzer. Though the other units are now all full, no one has revisited that decision.

Inside, Air Mail coeditor Alessandra Stanley sits in front of a bookshelf stuffed full of picturesque boxes labeled “letters,” apparently all empty. “It’s fitting because we are digital, to have no paper,” she says. What is the ideal Air Mail story? “One that people read,” is her answer. “Murder, scandal, any story that surprises.” Stanley parries my question as to whether she would ever take Air Mail into print: “Does anyone read magazines anymore?”

Air Mail is an email—Stanley prefers the term “digital weekly”—that goes out each Saturday morning at 6:00 a.m. The tagline is “The Best of News from Abroad,” the mood nostalgic, and the intended audience cosmopolitan. The subject line is always the same: “Graydon Carter here…”

Graydon Carter is the other coeditor. He answered my questions for this piece by email, but when I visited the office, he was not in fact there. As the cofounder of the insurgent Spy Magazine in 1986 and then the editor in chief of Vanity Fair from 1992 until 2017, he presided over the pinnacle of publishing for nearly three decades. Air Mail, founded in 2019, is sort of his retirement project.

When he dispatched his then-assistant and now-deputy editor, Nathan King, to find a location for the office, Carter—whose previous office at Vanity Fair was inside the vertiginous glass box that is the Freedom Tower—stipulated King eschew anything that might register as “Class A” office space: “No building with a swipe card. No elevator.” Also: “Within a short walking distance of my apartment.” Using StreetEasy, King found a parlor floor of a West Village town house. Carter approved. “High ceilings, French doors, three fireplaces, and a terrace out back,” he wrote me. “It’s heaven.”

Indeed, it feels like a home. Specifically, Graydon Carter’s home. His belongings populate the walls and shelves. On one wall is portraitist Daniel Adel’s painting of Carter in a military uniform—“Qaddafi spring/summer,” said King. Apparently, each time a new employee started at Vanity Fair, the portrait would appear behind their desk. On a mantle are cups of pencils, per Carter’s instructions kept very sharp, as Carolina de Armas—another former assistant–turned–editor—explained. Above another fireplace sits a portrait, depicting a couple and their dog now referred to as the magazine’s founders, that Carter found at a flea market. In one bathroom there is a calendar Carter has kept since working at the first magazine he cofounded, The Canadian Review, which grew to be the third largest magazine in Canada before going bankrupt in 1978. His current assistant, Victoria Herman, updates it each day. Leaning against the wall in the shower of the other bathroom there is a pencil about five feet tall, a gift from Louise Grunwald, whose husband, Henry Grunwald, was the editor in chief of Time Inc. and Carter’s first boss in New York. Carter explained: “They took me in. When Henry died, we sort of took Louise in at Vanity Fair, and we’ve been together ever since.”

One day, a package arrived from Air Mail’s landlord: swipe cards, complete with a name and photo for each employee. They were updating the security system. Carter despaired and declared that they would have to move. Then they discovered it was all a practical joke orchestrated by their chief operating officer, Bill Keenan.

“Graydon has a very keen design sense. He likes the combination of clean and messy—clean lines in furniture and then a lot of stuff,” Basil Walter, his architect, told me. The design of the Air Mail office began with an object Carter had long ago given Walter: an old model biplane. (Both Carter and Walter are collectors, which is to say they are fond of flea markets and storage units. King said Carter recently consolidated his storage units into a single facility in Connecticut, which King likened to an airplane hangar.) Carter knew they wanted to hang the toy aircraft over the table in front of the empty letter boxes, and the design unfolded from there. This was at least the fourth office and, Walter guesses, the fiftieth project he has designed for Carter since they first worked together in 1992 to renovate the editor’s new apartment in the Dakota. Most of those projects have been parties—most famously the Vanity Fair party at the Oscars, for which they erect a temporary structure that encloses a street in Beverly Hills. Walter has put his event-design expertise to good use for Air Mail as well. In 2023, the publication cohosted a blowout with Warner Bros. as part of the Cannes Film Festival at the Hôtel du Cap-Eden-Roc, where movies by the studio were projected onto a swimming pool.

When Air Mail moved into the town house in 2020, it had a staff of about five. They threw a housewarming party. Then, “the next day, Covid happened,” remembers Stanley. After the pandemic, most of the staff maintained primarily remote schedules, but that was already baked into the office’s design: It has just two big tables and no assigned seats. Even at Vanity Fair, Carter’s inclination was to edit at home, going into the office only for meetings and socializing.

The junior staff all tap away at laptops at a large table overlooked by analog clocks for Moscow, Paris, and New York. Only the New York clock actually tells the time. Which is fitting, because though the emphasis is international, Air Mail is in fact very much rooted in New York—and the West Village in particular. Carter’s home is just a two-and-a-half-minute walk away. Every month or two the publication hosts a book party nearby, often at the Waverly Inn, which Carter owns. Armas shared the guest list for a recent one, which celebrated a new collection from Gay Talese. The invitees included Barry Blitt, Sofia Coppola, Maureen Dowd, Naomi Fry, Megyn Kelly, and Salman Rushdie. In 2022 Air Mail assembled a special issue on the “Downtown Set” featuring, per King’s introduction to the issue, fifty “echt downtowners.” When I asked Carter about Air Mail’s vantage, he replied, “Well, I suppose you could call it a view of the world from Greenwich Village…. The thing is, you’ve got to edit from somewhere. And where better than the Village?”

The objective of Castiglione’s courtier was power. Sprezzatura was a helpful tool because to project ease is to project power—the prerogative to pursue the finer things in life and the finesse to accomplish a great deal without breaking a sweat. As Jon Kelly, the cofounder of Puck and yet another former assistant to Carter, put it to the Columbia Journalism Review, Air Mail is “aimed at an incredibly influential, massively powerful, and wealthy audience.” Though it presents as a personal project, at this point the publication has a staff of about fifty-five, an email list of at least half a million, and is backed with at least $32 million of funding from investors including Warner Bros. chief executive David Zaslav and the private-equity firm TPG. The masthead includes twenty-four people with the word editor in their title, and they close a 25,000-word issue each Friday night.

Its advertisers include brands like Prada, Tiffany, and Hermes, and a growing source of revenue is its own curated shop, Air Supply, whose offerings (sold via affiliate links) range from a $1.99 tube of cherry lip balm to a $450,000 Iso Grifo sports car. Air Supply has a physical outpost, the Air Mail Newsstand, also designed by Walter, also in the West Village.

Carter made his reputation at Spy by being a contrarian who ridicules the rich and powerful, foremost among them Donald Trump, repeatedly referred to on its pages as “the Short-Fingered Vulgarian.” At the top of its menu, Carter’s restaurant still features a testimonial from those days: “‘Waverly Inn: Worst food in the city’ — Donald J. Trump.” The prodding continues in Air Mail, where recent pieces include a scathing profile of acting deputy attorney Emil Bove and a send-up of Tesla’s newfound “Swasticar” reputation. Carter’s nemesis figures heavily among the office memorabilia, too, which include a Trump bobblehead and a letter from the playboy developer congratulating Carter on his ascent to the head of Vanity Fair.

That said, King still believes the publication is at its best when it is more culturally oriented. In fact: “When Carter conceived it, we were not going to cover politics at all.” In these earnest and urgent times, such an approach might still be the most contrarian of all.