Moss, who is stepping down after 15 years as editor, reflects on the ‘child-like wonder’ of journalism, publishing against the grain and, of course, Trump

In December 2013 David Carr, the revered media columnist, defined in five words the unmistakable, intimate New York sensibility of one of the city’s cultural behemoths, New York magazine. He called it “lippy, smart and regally provincial”.

When Carr’s phrase is read back to the individual who, more than any other, has honed that voice over the last 15 years, it elicits a lippy chuckle. “Regally provincial, what does that mean?”

Well, Adam Moss, if you think you’re so smart, how would you describe the magazine of which you have been editor-in-chief since 2004?

He thinks for a while, then says: “Jaded, a little world weary, and yet extremely curious. Skeptical, sometimes cynical yet wildly generous. Funny yet serious. A set of contradictions that somehow adds up to a point of view our readers recognize as their own.”

The magazine business is doing fine. Speaking for New York alone, our journalism is richer, better in many ways Adam Moss

Then he adds, a little wistfully: “That’s how I see it. How it continues to be seen, that’s not something I will be able to control.”

Last week Moss, 61, announced that he would be stepping down almost 15 years to the day since he took over the reins of New York. News of his willing handover to a younger generation shot through New York’s media world with a shudder, as jolting in its way as Carr’s death in 2015.

It added to the looming sense of the end of an era, that the golden period of New York magazines, the heyday of modern literary journalism in its Manhattan crucible, was now officially over. Coming after the departure of Graydon Carter at Vanity Fair, and the financial struggles of the big powerhouses Hearst and Condé Nast, Moss’s exit felt more like a wake than a new beginning.

So is that how he sees it? Is it really the end for the magazine business?

“No it isn’t,” he replies emphatically. “The magazine business is doing fine. Speaking for New York alone, our journalism is richer, is better in many ways, we are publishing more of it to more people. This magazine is as strong as it’s ever been. Stronger.”

Facebook Twitter Pinterest New York Magazine, featuring 35 women who have accused Bill Crosby of sexual assault. Photograph: AMANDA DEMME / HANDOUT/EPA

Though he is too old – born in 1957 – to have digital as his first media language, he wholeheartedly embraced its potential from day one, helping New York steer a more successful path into the modern world than many of its rivals.

Under Moss, the magazine retains its print edition and has added five digital verticals – Intelligencer (news), the Cut (aimed at women), Vulture (entertainment), Grub Street (food), Strategist (e-shopping) – each of which is growing into a powerhouse of its own within the extended New York family. Between them they reach almost 50 million users a month.

Moss made sure to immerse himself in each vertical, taking a three-month “residency” with each in turn to learn the digital craft. “Over time I began to love what digital could do. I began to love the speed of it, the looser, more colloquial and playful voice you could deploy, how you could make it interactive, animate it, apply audio to it, change narrative structure.”

Of all the adjectives that can be applied to Moss’s editing style, “playful” is key. In his note to the magazine’s staff explaining his decision to quit on 31 March, he said the best thing about magazines is that they are “more like a kindergarten project than anything else, and that’s what I am saddest about giving up. I’ll miss playing with you all.”

Moss says that play, closely aligned with curiosity, is at the core of his editing style. “There is a child-like wonder to the journalism I’ve always loved, long before I was in this business.”

Growing up in the 60s and 70s on Long Island, he was awed by the stable of writers assembled by Milton Glaser and Clay Felker when they founded New York in 1968. Among the stars they cultivated were Tom Wolfe, Nora Ephron, Jimmy Breslin and Gloria Steinem. Moss was drawn to what he calls the “boundless playfulness” of the writing and editing, as well as a “kind of confidence which journalism later lost some of. It was a powerful medium, taken very seriously.”

Under Moss, New York has continued to pull off the same complex, exhilarating notes – playful, serious, both. One minute he will be publishing a piece on the gynecological perils of emulating the uses of ice cream in Fifty Shades of Grey, the next he will be revealing the prison life of Bernie Madoff or adding rocket fuel to the #MeToo movement with astounding work on Bill Cosby’s accusers.

There is a child-like wonder to the journalism I’ve always loved, long before I was in this business Adam Moss

But Moss is not without his apprehensions about the state of modern magazine journalism. As someone who fell in love with narrative storytelling as a teen, he is fearful that some of the energy, some of the confidence of the form has slipped.

He stresses that in his view New York has continued to create high-quality storytelling, pointing to the magazine’s success in occupying three of the top 10 positions in the Chartbeat list of the most engaging articles of 2018 – all for glorious narrative reads. “If there’s one thing I’ve been haranguing my staff about it is that we need to get back to the business of telling stories.”

But he is anxious for the industry as a whole about a new cadre of writers emerging with much less grounding in the shoe-leather craft of reporting. “It’s not their fault. Having grown up in a commentary-soaked internet and absent of things like small newspapers where they could get proper training, reporting is not something they do. They don’t pick up the phone or think to go out and find stuff out. That’s frustrating.”

His other preoccupation relates to the ceaseless onslaught of social media, and the way it acts as a giant focus group which he fears is sapping the risk-taking energy and creativity of editors and writers by making them hyper-aware of popular reaction. You can see just how worried he is about this by turning to his Twitter feed. Correction. He doesn’t have one.

Facebook Twitter Pinterest New York magazine cover election issue featuring Donald Trump. Photograph: Mark Peterson / Redux

(His successor as editor-in-chief, whose promotion to the top job was also announced last week, David Haskell, 39, does have a Twitter feed but has tweeted only once. So much for the shift to a younger generation. “He’s pretty active on Instagram,” Moss protests hurriedly.)

Moss sees it as a real problem that journalists have come to feel dependent on the approval of the Twittersphere. “People are afraid to make enemies. They don’t want to encounter hostility. Some people are very courageous, but I’ve had situations where I’ve asked writers to do a story that make some trouble and they shrug and say they’re not comfortable with it. That’s a danger.”

Moss has felt that wind of change blow in his own face in recent years. Though the magazine retains a “great deal of confidence in what we publish, even swagger”, he says, “it is harder to publish against the grain. That’s important to me, because challenging people’s thinking is our fundamental role, it’s what we’re in business to do – intelligently to force people to think. Sometimes that view is not shared by younger journalists who believe journalism should validate a point of view rather than challenge it.”

Which brings us, with heavy heart, to Donald Trump. As Moss points out, throughout the entirety of his life in magazines – from Esquire where he cut his teeth as an editor, through the short-lived 7 Days and the New York Times magazine to New York – he has been followed around by one character: Trump.

“I’ve lived with him for years. I’ve actually banned him any number of times and said we are not going to publish another word on Donald Trump. And then, frustratingly, I’ve had to row back and start talking about him again.”

It is harder to publish against the grain. That’s important to me, because challenging people’s thinking is our fundamental role Adam Moss

Trump is splattered disconcertingly around Moss’s office in Lower Manhattan. There’s a blow-up of a 2013 Trump tweet on the wall in which the then Apprentice reality TV star dismissed the magazine as “boring and irrelevant” after it published a photo of him speaking before a half-empty ballroom at a conservative conference.

There’s also on Moss’s magazine stand a back-copy of New York dating from September 2015, early on in Trump’s presidential campaign, which has a cover of the candidate mocked up as George Washington. It related to a piece by Frank Rich that argued that by tearing up antiquated norms, Trump was acting as a positive force, with the cover line: “Donald Trump is saving our democracy.”

Ouch. Do you remind Rich of that article often, I ask. “He reminds himself all the time,” Moss fires back.

So what does he think is at stake for magazines like New York amid the Trump insurgency? “There’s so much at stake, our relationship to truth, to our values – all these things are truly up for grabs. As a citizen I find that very scary, as a journalist it’s fantastic. The ideas that are in play make this an amazingly interesting time to be a journalist.”

He thinks Trump, and the political period leading up to him, has allowed New York to put some of its finest writing on display, from Rich to Rebecca Traister and Jonathan Chait. It has also pushed the magazine to the left, the result of “the Trump administration forcing you to pick sides”.

But there’s also a sense of impotency amid the tussle between journalism and the current White House. “On the one hand, journalism matters now more than it has ever mattered, and publications including ours are better than they have ever been. Yet there’s a frustration that we can’t matter as much as we need to, that when everybody is in their own self-contained world it’s hard to break through and say something with consequence.”

He speaks like a person with unfinished business. Though he insists he has no idea what he’ll do next, one thing is certain: Adam Moss hasn’t finished playing yet.