Illustration: André Carrilho

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“It’s dreadful,” Anna Wintour said in early October, looking out the south-facing windows of her 25th-floor office in One World Trade Center, which has been home to Vogue and its publisher, Condé Nast, since 2014. It’s the neighborhood she hates — corporate, sterile, and encumbered by security. She preferred the previous headquarters, in Times Square, which offered the ability to pop out for afternoon matinees on Broadway and, more important, the feeling that Condé Nast was at the center of it all. But the landlord had given the world’s glitziest publishing company a deal to move downtown, and Condé built out 23 sleek, futuristic floors as though magazines were thriving. This proved overly optimistic. Three years later, in 2017, Condé lost more than $120 million; Graydon Carter, who relished his life among the moguls and stars, a player among players, announced his departure after 25 years running Vanity Fair; and Si Newhouse, the company’s Medici-like benefactor, died at 89.

Members of the old guard couldn’t help but look around the room during Si’s memorial, at Jazz at Lincoln Center, and see that it was also a funeral for the glory days of the company. As David Remnick, the editor of The New Yorker, put it to a fellow media executive in 2017, Condé was facing the same daunting challenges as the rest of the media business and seemed to be in “a dignified state of panic” as it belatedly adapted to low-margin, constantly pivoting digital realities, closed and sold titles, and underwent a “restacking” — the chosen euphemism for squeezing everyone onto fewer floors so Condé could sublet some of the fancy real estate it now realized it could no longer afford.

“You have to acknowledge it, then move on,” Wintour said from behind her signature sunglasses, when I asked what it was like at the top of a once lavishly well-funded company on an ever-tightening budget. The upside? “How joyous to think about the future and what’s new and what’s next.” Unlike lesser editors in the Condé hierarchy, Wintour has held on to a relatively palatial space, and that morning she had hosted a breakfast for 50 women in her office as part of Vogue100, a $100,000-a-year membership program offering access to Wintour and parties attended by Vogue-adjacent celebrities — one of Condé’s many attempts at monetizing decades of brand prestige (even if the magazine itself was never going to make the money it once did selling ads).

“The print magazine is the runway show for Vogue,” Wintour explained. She meant that Vogue on paper was now the showpiece of Vogue the brand, which includes not only a $100,000 breakfast club but regular “Go Ask Anna” videos on YouTube and 26 different Vogue.coms producing daily content around the world. Wintour was sitting at her desk in front of a copy of the September issue, which remained a door-stopper at 596 pages, although it was smaller by a third than the one that appeared in The September Issue, the documentary shot in 2007, in which Wintour seemed to pull the strings behind the entire fashion industry. When I asked how Instagram and the rise of influencers had changed her job since then, Wintour demurred. “Vogue is the biggest influencer of them all,” she said.

Condé Nast’s future is now being charted by Wintour’s new boss, Roger Lynch, the former CEO of Pandora, the music-streaming service he ran until it was sold to SiriusXM in February. Lynch is Condé’s first outside CEO in its 110-year history, replacing Bob Sauerberg, who’d been at the company since 2005 and was steeped in the genteel-magazine model. Lynch was relocating from San Francisco without any publishing experience, and upon arriving at the end of April, he embarked on a “listening tour” across the company meant to help him discern Condé’s path forward. When we met, he certainly looked the part of a Condé executive: wearing a well-fitted blue suit and a tan, seeming to have gone through the Condé glow-up that others described to me in reference to business-side employees who joined Condé from less glamorous jobs. This is another way of saying Lynch was a long way from donning the MUSIC GEEK T-shirt he wore at Pandora. “What I was hired to do was to create a 21st-century media company,” Lynch told me in his glass-enclosed office on Condé’s new executive floor, once the company’s dedicated gallery space. “Part of that is defining what that means, because they don’t really exist yet.”

Ultimately, the company’s fate is up to the Newhouse family. A new generation has taken over since the death of Si, who loved the magazines, the most glamorous delivery devices for cultural power and advertising revenue for much of the 20th century. The question that lingers is how much the Newhouses value these storied brands and are willing to invest in their continual reinvention. “The family can financially withstand years of losses, but they’re also facing the challenge of Why should they?,” a former executive close to them said. “The family doesn’t view themselves through the lens of Condé Nast, and I don’t think they would suddenly wake up tomorrow and say, Who am I? if Condé Nast wasn’t in their lives.”

While they’ve sold off some magazines — W most recently — that doesn’t mean they’re willing to sell off the top brands piecemeal. Vogue, The New Yorker, GQ, and Vanity Fair currently bring in more than 60 percent of Condé’s total revenue. In 2017, before he left, Carter and Jim Coulter, the co-CEO of TPG, the private-equity firm that ultimately backed his post–Vanity Fair digital-newsletter project, Airmail, met with Sauerberg to discuss investing in Vanity Fair’s efforts to find new revenue streams, according to multiple people with knowledge of the conversation. After those discussions stalled, Carter and TPG floated the idea of buying Vanity Fair outright, but it was rejected.

Throughout all the changes, Wintour has remained a constant, the embodiment of the company’s enduring authority. She took over Vogue in 1988 and became Conde’s artistic director in 2013 with oversight of all its monthly magazines. This summer, she added global content adviser to her list of titles, cementing her claim as the keeper of the company’s values at a moment when, with the arrival of Lynch, Condé was consolidating its American and international businesses. Which makes sense: Vogue alone brings in 28 percent of Condé’s global revenue. Jonathan Newhouse, Si’s cousin, who is now chairman of Condé Nast’s board, has described Condé’s international operation as “The Vogue Company.”

Many of Wintour’s current and former colleagues consider her indispensable, someone whose eventual departure — she turns 70 next month — will spell the company’s doom. Others have watched Condé’s decline since she took over as artistic director and wonder how she’s still in charge. Wintour didn’t have a ready answer when I asked if she recognized any missteps in her tenure — “I’ve made so many mistakes” — nor when I asked about particular successes, other than to say she’s proud of the people she has hired. “So much of it has to do with the talent around you and having talent that’s right for the moment,” she said. That made her think of a recent performance she had seen of The Wrong Man, an Off Broadway musical about someone framed for a murder they didn’t commit. At the show, Wintour sat next to a man whose son was going to the same school the man had attended 30 years earlier. “He was so amazed that the boy had the same school-bus driver,” she said. “I’m sure he’s a wonderful bus driver, but you don’t always want the same driver from 30 years ago.” I gingerly pointed out to Wintour that she had been editing Vogue for longer than that. Wintour laughed, looked back out the window of One World Trade, and said, “I’m a really good bus driver.”

What was Condé Nast? In 1909, Condé Montrose Nast started a company to make magazines — Vogue, House & Garden, Vanity Fair — with the motto “Class Not Mass.” Sam Newhouse Sr., the newspaper magnate, liked to say he bought the company 50 years later as an anniversary gift for his wife, who loved Vogue. Condé was a money-loser, and the deal was dubbed “Sam’s folly,” but his son, Si, helped turn it into America’s second-largest magazine publisher after Time Inc. (an empire that has now crumbled). At its peak in the aughts, Condé published 29 magazines: Gourmet, Allure, Self, Wired, Architectural Digest, Details, and on and on.

But Condé Nast was something else, too: a totem of aspiration, a hub of self-importance, and a place of near-mythic profligacy. “Page Six” and Gawker regularly chronicled its palace intrigues. Annie Leibovitz gave the world a pregnant Demi Moore on the cover of Vanity Fair; Mr. Big, from Sex and the City, was based on the publisher of GQ; and everybody had an opinion about what Tina Brown had done to desecrate The New Yorker after Si bought it and later put her in charge. Meryl Streep got an Academy Award nomination for portraying a Wintour avatar in The Devil Wears Prada and in 2007 went from the ceremony to Vanity Fair’s Oscar Party, as anybody who was anyone would. No expense was spared, from the $30 million cafeteria in Times Square designed by Frank Gehry to extravagant compensation not only for star editors but for marketing employees, too. (It was also a place that seemed to assume low-level staffers didn’t have to live on their salaries: An assistant in the aughts told me that the cost-of-living raise for her magazine’s design director was about what she made in a year.) The party continued through 2007, when Si made what will go down in history as the last great print launch, reportedly spending more than $100 million to start a business magazine called Portfolio on the event horizon of the financial crisis.

Portfolio folded in two years, and the crash trimmed Si’s personal wealth in half to $2 billion. Condé started flying editors business class instead of first, and perks were cut back: The then-CEO, Chuck Townsend, responded to complaints about the newly bare office refrigerators by saying, “You don’t need it! You don’t need the Orangina!” Still, there was a belief within Condé, motivated by self-interest, that the bust was cyclical and print would rise again. “One executive said openly to me, ‘I don’t know what’s going to happen, but let’s ride this out, keep our salaries for another couple years, and then, if it falls apart, fuck it,’ ” a senior editorial employee at the time told me. (I worked as a fact-checker and writer at The New Yorker from 2009 to 2015 and once received a $1,000 fee and a signed thank-you note from Graydon Carter for writing a 148-word review of a tennis documentary — the best rate of my career, but less than what the magazine’s stars were said to make.) An editor who joined GQ a few years after the crash was shocked to find that, even then, nobody talked about budgets, spending whatever was considered necessary just as they always had: “That was my first realization of, How does this business work?”

The answer, in part, was that it never really had to. For decades, within Advance, the company that houses the broader Newhouse empire, the newspapers were the profit engines: In the ’90s, a Condé executive said that the Staten Island Advance alone probably made more money than all of Condé Nast. “It was such rarefied air they had no idea what was going on in the real world,” an executive who signed on after the recession said. (Many current and former Condé employees requested anonymity to talk about the company, fearing professional consequences.) Even when newspapers began tanking, luxury advertisers were slow to abandon print, which gave Condé undue assurance that the disruption might be only for the little people. Efforts to develop new revenue streams were fitful, and when they produced margins nowhere near print’s, the impulse was to double down and try to sell a few more pages rather than invest more deeply in reimagining the business. Si had wanted little to do with the internet, and under Steven, his nephew, the company launched a series of websites separate from the magazines, like Style.com, to avoid sullying the print brands. An executive who arrived in 2016 was surprised to find how much time was still spent managing whether Estée Lauder or L’Oréal got the first scent strip in a given magazine.

The new (and old) establishment at Condé Nast. Illustration: André Carrilho

And what is Condé Nast today? It’s a company that lost as much in 2017 as it made in profit in 2003. It has two dozen brands, which used to be called “magazines,” nine of which still have print editions in the U.S. Among the departed since 2007: Jane, House & Garden, Men’s Vogue, Golf for Women, Domino, Gourmet, and Details, along with the print versions of several more, including Glamour, which was once the company’s most profitable magazine. (“My LinkedIn is a graveyard of the magazine industry,” one longtime staffer said.) The company has a branded-content studio that used to be called 23 Stories, in reference to the original number of floors Condé occupied in 1WTC, but it changed its name to CNX last year as it became more of an in-house advertising agency. Also, the company doesn’t occupy 23 floors anymore. Condé Nast Entertainment produces 4,000 digital videos a year, plus a few movies and TV shows.

GQ now sells boxes of socks and grooming products for $49.99 and recently launched a line of furniture with CB2. Allure has had success selling subscription makeup boxes. Bon Appétit’s test kitchen is a hit on YouTube, while Self does well on Snapchat. Teen Vogue, which went online-only in 2017, has refocused on fashion; a post-Trump foray into wokeness was hard to monetize. Pitchfork, the music site Condé bought in 2015, hosts festivals in Chicago, Paris, and Berlin, plus another in Queens as part of a sponsorship deal with Anheuser-Busch InBev. Architectural Digest is trying to balance the tradition of documenting the tastes of the rich and famous alongside its business proposition as a trade publication. Digital brand Epicurious aims to be Wirecutter for food, while Them aspires to be a stylish destination for queer young people. Condé Nast Traveler has been offshored, with the American magazine now produced largely by the London-based staff of the U.K. edition.

There have been investments in journalism: Wired and Vanity Fair have built out digital newsrooms and surrounded them with paywalls that new subscribers can reach for under $10 a year. The big success in charging online admission has been The New Yorker, which says it has persuaded 1.3 million people to pay as much as $149 a year for the weekly magazine and online access — a good thing, given that an issue in September had just three full-page ads. The rest of the company still offers most of its digital goods for free.

For years, the Condé magazines operated like warring clans on separate islands in a posh archipelago, all of them firing their golden cannons at each other as often as they aimed them at Hearst or Time Inc. (It was said that Si used to tell his editors not to talk business on the elevator because the others in the building were their rivals.) Competing with each other for cover stars and ad pages worked well enough in an era of plenty, when Condé often owned several magazines in the same category — Details and GQ; Gourmet and Bon Appétit — but things like having each website operate separately, with duplicative teams solving the same problems as technology evolved, meant everybody defended their territory, never mind what was best for the entire company. David Carey, a Condé executive who became Hearst’s CEO in 2010, once explained the difference between the two companies to a Condé executive. “At Hearst, we have a federal system — when I say something, everyone is going to do it,” Carey said, according to the other executive. “Condé is like a states’-rights organization.”

Jokes were made about how we were all bickering while the White Walkers were getting closer.

That attitude made the changes, when they came, all the more painful. In 2017, Condé started “hubbing” into centralized teams various functions traditionally performed at each magazine individually. (Hearst had begun this process years before.) Each title’s photography and design teams were merged into the Creative Group, while the copy editors and fact-checkers became part of the Content Integrity Group, and the tech teams, which made the websites, were folded into something called Co/Lab. On the sales side, magazines were combined into clusters — one includes both Teen Vogue and The New Yorker. A once-cohesive magazine might now have people spread out over three or four floors of the building. It certainly reduced the internecine warfare, but at the price of everyone feeling they were on the same brand team. Shortly after the hubbing, a Creative Group employee tacked a pale-pink Post-it on a wall in the office, summing up their feelings on the situation: WE ARE CREATIVES, NOT 2ND CLASS CITIZENS.

The purpose of the hubbing was to cut costs by sharing resources, but the Creative Group was also asked to attract new revenue by becoming an advertising agency in its spare time: GQ’s team worked on a campaign for Brooks Brothers, while Bon Appétit’s designers produced one for Reynolds Wrap. Many employees initially approached this new function as an opportunity — if nothing else, it would burnish their commercial portfolios — but requests for additional manpower to meet the new workload went unanswered.

Co/Lab was among the biggest shocks to the old hierarchy, because the company was woefully underinvested. An employee who joined the company in 2017, having worked previously at Gawker Media, told me Condé’s back-end technology was about as robust as Gawker’s had been a decade earlier. “I always felt of two bodies: totally in awe of the editors in all their brilliance but also trying to say, ‘You don’t understand the technical realities of this world that’s going to gobble you up,’ ” one Co/Lab employee told me. “Many jokes were made about how we were all bickering among ourselves while the White Walkers were getting closer.” The Co/Lab team was meant to solve problems across the sites, and employees there spent much of its early days getting ad pages to load faster — 30 percent of ads weren’t being viewed because consumers clicked off the site before they even appeared, according to two former employees. But this task left little time to fix problems specific to various brands, like how The New Yorker’s and Vanity Fair’s paywalled websites had an infuriating habit of requiring subscribers to repeatedly log in.

In an attempt to compete with tech-company perks, the 33rd floor, home to Co/Lab, had couches, Ping-Pong tables, and excellent snacks. “Word got out,” one employee told me. “They had seltzer, string cheese, good beer, packets of hummus and guacamole, Chex Mix. There were containers of walnuts and almonds and those really good pretzel chips.” Editorial employees started making their way from other floors “like ants marching up and down.” One Co/Lab staffer told me New Yorker fact-checkers often appeared on Friday afternoons to stuff their backpacks with beer. It created a new social dynamic in which certain developers now identified themselves as a higher caste in much the same way Vanity Fair and Vogue staff used to look down at their counterparts at Details and Brides. Some developers started to complain about the encroachment by the proletariat. “It turned into this weird French Revolution vibe where everyone in tech was allowed to have Cheetos but editorial assistants weren’t,” one Co/Lab employee told me.

Late last year, the company’s chief digital officer resigned, and the class-warfare-tainted Co/Lab name was discarded. To boost morale on the team after a round of layoffs, Bob Sauerberg, the then-CEO, put on a hot-dog costume at an all-hands meeting in front of the snack dispensary. (His departure from the company was announced a month later.) The snack bounty was replaced with a more equitable but cheaper selection on every floor. “Condé somehow found singles of Nature Valley granola bars,” an exasperated employee said. “I’ve never seen that. Single packs of Nature Valley granola bars!”

Anna Wintour at the Condé Nast offices. Photo: Evan Bryson

After taking over as artistic director in 2013, Wintour began gathering top editors from every magazine in a corporate boardroom for regular off-the-record chats with notable people: Hillary Clinton, Tim Cook, Lena Dunham talking about the newsletter business. (Condé had an ad partnership with Dunham’s Lenny Letter.) Wintour was trying to navigate a shifting landscape along with everyone else, and in 2017, she invited the group to meet an undisclosed guest, which was unusual. The editors were taken aback when Ivanka Trump walked in, and even more so when Wintour, a major Democratic fund-raiser, introduced her by saying it was “brave” of Trump to come before the editors and walked her around the room to shake everyone’s hand. “The message was: Be polite,” an editor in the room said.

The more general message was that Wintour was in charge, and she had begun remaking some of the magazines since taking on her new job. A certain sameness seemed to prevail thereafter, a reduction in whatever individual identity and voice the brands had developed to appeal directly to their audiences. Many of the newly hubbed groups, including the creative teams, were being led by former Vogue people. Some staffers joked that Self had become “Sweaty Vogue.” In 2015, a former editor at Allure walked into a conference room where the magazine’s art director had turned one wall into a giant mood board. “Every image was a page from Vogue,” the editor said. “She said, ‘I know this is ridiculous, but I’m trying to think this way because it’s the only stuff that gets approved.’ ” Vogue is a huge success, of course, but it wasn’t clear that the same haute aesthetic worked elsewhere. Among some of the magazines Wintour became most involved with — Self, Glamour, and Brides — the first two no longer publish print editions, and the other has been sold.

In the early years of her artistic directorate, Wintour meddled far and wide but was careful to respect the independence of a few titles, including GQ and Vanity Fair. Now both of their long-standing editors were out. Jim Nelson, at GQ, was replaced in January by Will Welch, who had been at the magazine since 2007 and spent much of the past decade pushing it to target a more fashion-obsessed demographic, a vision that had been embraced enthusiastically by the company’s sales side and Wintour. When we met in his office, Welch wore all black — glasses, denim jacket, pants cropped above his ankle — with a gold watch, a pinkie ring, two earrings, and multiple visible tattoos. (One on his left hand said WANT NOTHING.) A photo of the Grateful Dead hung above his desk. “It’s a long story, but zero while Jerry was alive,” he said, when I asked how many concerts he had seen. “But Dead & Company I’ve seen probably eight times.” At a toast for Welch at Frenchette this spring, Wintour mentioned the time he and Adam Rapoport, the editor of Bon Appétit, played basketball with LeBron James, until Welch “removed himself from the court because of a seriously damaged fingernail,” Wintour said, joking that Welch “was ahead of the curve in knowing that grooming was going to come first in the men’s world.” She offered only one editorial note on his first few issues: “I wouldn’t have predicted that there would ever be quite so much tie-dye.”

Welch’s argument for the new GQ is that niche is what works in 2019. “It’s people who see the world through the prism of stylishness and taste,” he said of his GQ reader. “That’s not everyone, and I’m completely at peace with that.” The magazine’s covers and photo spreads were now being targeted less at a man looking for help picking out an outfit from J.Crew than at someone interested in the latest Supreme drop. Tips on tie width and face lotions would be relegated to the web. “That is a core GQ story, and we’ll do it until the world stops spinning, but I just can’t see any reason to print it in a magazine,” Welch said. He believed the narrow focus would lead to growth. “There was an era when GQ could legitimately claim to speak to ‘American Men,’ ” he said. “Now you can get a huge audience by being very focused.” A men’s-fashion rep told me he likes it: “GQ is cool now, which is the first time that sentence has ever been true in 30 years.”

What has been de-prioritized in the process of becoming cool: as much investment in deep-dive journalism. Last summer, Nelson, Welch’s predecessor, had a meeting with Wintour and Sauerberg during which Nelson excitedly reported that Julia Ioffe, a recently hired political reporter, had just broken a big story on Russiagate for GQ.com and was making the rounds on cable news. According to multiple people familiar with the conversation, Sauerberg got red in the face and replied, “I just don’t see how that’s going to make me any money.”

This approach requires fewer editors, too. One told me that he wasn’t sure how many people still worked there after many rounds of layoffs in recent years but that GQ hadn’t been able to field a softball team this summer. Others said they felt a sense of renewed purpose after the constant cutting. GQ’s focus, however, not only risked alienating a huge chunk of its readership, which is roughly 40 percent female, but also brought with it the dangers of myopia. In the December 2018 issue, Serena Williams was included as one of four honorees for its Man of the Year Award. Shortly before the print deadline, Welch took a copy of the cover to Virgil Abloh, the streetwear designer, and had him cross out MAN and write WOMAN. Abloh puts quotation marks around words for emphasis, a fact known to every kid standing on a street corner in Soho but almost no one else. The word WOMAN appeared in quotes next to a photo of Williams, causing an uproar online. Williams didn’t put the cover on her social media.

One afternoon in September, I met Radhika Jones, who is almost two years into her job as Vanity Fair editor-in-chief, on the floor the magazine shares with Pitchfork, Wired, and the Content Integrity Group. (A floor below, on 26, six brands are now very cozy new roommates.) In a company meeting last year, David Geithner, Condé’s CFO — and the former Treasury secretary’s brother — broke news of the restacking of all the magazines within the building and responded to objections from several editors by nodding to Jones and saying, “Some of us have said they have too much space,” according to a person in the room. This was apparently in reference to Graydon Carter’s massive office, which had two sitting zones and a CinemaScope view of the Hudson River over the domed roof of the office building to the west. “I actually thought a workable revenue stream would have been to Airbnb it,” Jones, who now has a much smaller space, said of Carter’s office. “I didn’t get any traction. Maybe I didn’t take it to the right people.”

As Jones gently needled her predecessor — “I felt that Vanity Fair had become preoccupied with the past. I wanted it to be obsessed with the present” — she wore a sly grin. Jones said she had spent much of her first year trying to figure out “what is the right story for Vanity Fair right now.” Tina Brown had given Vanity Fair “immediate relevance,” Jones said, while Carter added “top notes of nostalgia.” But the nostalgia of today, Jones thought, was less for the Kennedys than for the ’80s and ’90s and noted the magazine had recently done a piece about Lorena Bobbitt. When I asked Jones what she was looking forward to at Fashion Week in Europe (she was going to Paris but skipped Milan, in part because her son was starting kindergarten), she cited the sustainability and diversity conversations that were bubbling up in the fashion world — which might be relevant but certainly sounded less delicious than, say, Ingrid Sischy’s exclusive 2013 interview with the fallen John Galliano.

From the beginning, Jones was seen as an odd choice for a magazine fixated on Hollywood celebrity, wealth, royalty, and scandal. She came from The New York Times Book Review and didn’t seem to have the swashbuckling, name-dropping social panache embodied by her predecessors. The critiques of Jones’s Vanity Fair came hard and fast: She’d sucked the glamour and mischief out of it and replaced it with bland, earnest celebrity virtue signaling. The magazine’s stories rarely seem to break through the noise.

Jones wasn’t oblivious to the expectations for the magazine. “At a base level, there’s a reason our trademark event is a party,” she said. Every new editor, Brown and Carter included, had suffered an early adjustment period, and Jones wasn’t able to throw money at the problem as they could. Jones had to cut at least $14 million from Vanity Fair’s 2018 budget, according to several employees. She had to lay off editors who had been with the magazine for years, along with some of its biggest writers, including a particularly gruesome culling on Valentine’s Day 2018, which left the offices littered with bouquets of flowers. “One thing that helps is that was never my money,” Jones said, when I asked if the cuts had made her job difficult.

People still thought there was blood in the water. Last year, Bryan Lourd, a partner at CAA and a friend of Carter’s, was overheard referring to Jones in Hollywood, the magazine’s most important market, as “the interim editor-in-chief of Vanity Fair.” (Lourd denies this, adding, “I did say she was an all-star in the Condé Nast company and that I wouldn’t be surprised if she moved in the future to other titles.”) At the end of Jones’s first year on the job, a Vanity Fair editor, acting on the encouragement of a Condé executive frustrated with the magazine, emailed Wintour asking for a meeting, but Wintour replied by simply cc’ing Jones, according to multiple people with knowledge of the exchange. (Several told me this was a classic Wintour managerial tactic, meant to force colleagues to confront issues head-on.) The collection of writers Carter had hired to populate the magazine with their expensive words and to break news on its website seem less beholden to the low-key Jones, who in turn, they sometimes feel, seems less interested in them. Recently, several considered leaving all at once to join a competitor, according to one of the people involved.

“One thing that helps is that was never my money,” Vanity Fair’s Jones said.

The fashion world had been especially dubious about the new direction. Revenue from fashion advertisers has plunged. Estée Lauder alone has moved $2.5 million in print advertising from Vanity Fair to other Condé titles over the past few years, although the cutbacks began under Carter.

Jones’s first cover, featuring screenwriter-actress Lena Waithe, had surprised readers who didn’t know who she was and elicited some of the uglier responses to Jones’s regime. (A prominent publicist went up to a Vanity Fair editor at a party after Jones took over and asked, regarding its diverse cover stars, “What is this, Ebony Fair?”) But some in the fashion world were fixated on the simple fact that Waithe was wearing a T-shirt. “That could have been an incredibly powerful moment — changing the culture, upending Hollywood. But did she have to wear a T-shirt?,” a Condé salesperson told me. “It felt like they were completely walking away from fashion.”

Jones’s Vanity Fair is trying to embrace a more progressive future — a recurring theme at the new Condé is trying to monetize stylish wokeness — but the company’s appeal had always been about speaking less from a place of hipness than authority. Executives on the business side eventually confronted Jones in a meeting this year, pointing out that her vision for the magazine was making their lives difficult. When I brought up that meeting to Pam Drucker Mann, Condé Nast’s chief revenue officer, who had been there, she insisted it wasn’t different from meetings pressing other magazines on their commercial prospects. She used an analogy for thinking about the old Vanity Fair versus the new: “There’s a song Bill Withers may have written and sung that people of his time are like, ‘This is the best,’ and then Drake might remake it, and the people that love Drake will be like, ‘This song is amazing.’ ” I took the point, then asked if there actually was a Drake remix of a Bill Withers song that I had missed; she said it was a hypothetical but would get back to me with a real example. An hour later, a Condé Nast spokesperson emailed me Drucker Mann’s revised answer: “‘Old Town Road,’ original by Billy Ray Cyrus. Remix by Lil Nas X.”

The company’s biggest bet is Condé Nast Entertainment, a video-production company launched in 2011 after several articles from Condé titles had been optioned to become movies — Brokeback Mountain originally appeared in The New Yorker, and Argo was a Wired feature — without the company receiving any money. But after eight years, it has made only a handful of movies and TV shows, none of which were hits, and has turned much of its attention from Hollywood to digital video, specifically YouTube.

CNE’s early days were a struggle. The money spent on videos was enormous, and not enough people watched. One CNE executive recalled a meeting with Vogue about a video series interviewing models at the Plaza Athénée in Paris. “It cost $250,000, and I went on YouTube and they had 200 views each,” the executive said. According to multiple CNE executives, its early viewership was hugely inflated by an arbitrage in which Condé bought ads on lowbrow websites to redirect viewers to its videos.

Eventually, the company leaned into a series of repeatable formats, most notably “73 Questions,” a Vogue feature in which celebrities walk around answering rapid-fire queries. “It was supposed to be high-end, expensive-looking content, but eventually the whole model changed and it became BuzzFeed Lite,” a former CNE employee said. During press junkets, they now grab celebrities for a few minutes and have them sit for video interviews: Vanity Fair has celebs take a lie-detector test, Wired has them answer questions people frequently Google about them, and GQ asks about their tattoos.

Condé has become one of YouTube’s top premium publishers, but the margins are slim. “I tell my team, ‘Guys, I went to the bank the other day and tried to deposit some views, but they told me they only take revenue,’ ” Oren Katzeff, the head of CNE, told me, repeating a dad joke well-worn enough that another Condé executive already knew it before I repeated it. His path to success for CNE? “Practicing extreme business discipline.”

The most promising stars in Condé’s video universe are the cast of Bon Appétit employees who have successfully turned the company’s test kitchen into a film set. Its chefs are easier to wrangle than celebrities, offering ways to make more money than publishers can by simply selling ads on YouTube; Condé can more easily integrate brands into the test kitchen than it can with celebrity videos, which require sharing a cut, for example, with Gigi Hadid to get her to use a Google Home device in a “73 Questions” segment.

According to a former executive who worked on a five-year plan developed last year to guide the company back to profitability, Condé explored dozens of potential paths for growth — a Pitchfork vinyl club, more branded content, a Vogue business offering — but the numbers were so heavily dependent on video that they worked only if CNE increased its revenue fourfold. “In a way, everything other than video was irrelevant,” the former executive said. A current executive told me Condé was on its way to becoming “a video-first company.”

Things could be worse: RIP, Time Inc. Five years ago, Condé made 80 percent of its revenue from print advertising but now makes more than 60 percent in other ways. “It’s weird what we’re doing for money,” one GQ employee said. Condé Nast is currently in a monthlong stretch of events that includes Vogue’s Forces of Fashion, The New Yorker Festival, Bon Appétit’s Hot 10 Party, Vanity Fair’s New Establishment Summit, Condé Nast Traveler’s annual summit, and a four-day Wired event in San Francisco. The company’s employees were getting so many offers to post sponsored content on their Instagram pages that this year Condé held a meeting in which it told employees that it needed to broker such deals and would keep a cut. The things Condé Nast was now doing for money might be weird, but newer employees who didn’t know the glory of living off print pages weren’t complaining. A young employee with a large Instagram following recently told a group of colleagues, “Once I decided this was my year of selling out, I’ll do anything.”

If there is a financial bright spot among Condé’s legacy brands, it is, to pretty much everyone’s surprise, The New Yorker. Over the years, the magazine has often been a venerable money pit, but thanks to a concerted effort to boost its subscription price, a loyal readership, a Trump bump, and investment in its digital offering — plus the tote bag — the magazine was now making more than 70 percent of its revenue from subscriptions. Condé Nast says The New Yorker is profitable.

But it wasn’t clear what lessons other Condé magazines could take from The New Yorker’s success. The title had been exempt from Wintour’s involvement, along with the worst of the cutting and hubbing that had depleted the others’ abilities to put out the best possible product. (The New Yorker is the only magazine with its own floor in 1WTC, its editors were allowed to keep Microsoft Word while the rest of Condé switched to Google Docs, and it is exempt from the Content Integrity Unit’s Condé-wide style guide.)

Which brings us back to the Newhouses. Today, the family is richer than it’s ever been, with a net worth well above $18 billion. They have since been exploring new industries, investing in Stealth Space Co., which plans to launch low-orbit satellites, and they bought Turnitin, the plagiarism software, for $1.7 billion. They have also been off-loading parts of the empire. In 2016, they sold a cable company for more than $10 billion. That made the amount they earned selling Brides, W, and Golf Digest, the last of which went to Discovery for just $35 million — $400 million less than what Condé had paid for it in 2001 and $24 million less than the Newhouses received that week for selling a single Cézanne at Sotheby’s — seem like a rounding error. (In a public pissing match reminiscent of Condé’s golden age, the W sale has dissolved into a mess of tabloid recriminations: Stefano Tonchi, the magazine’s editor, was forced out, after which he sued Condé, which countersued Tonchi for “all monies paid to him during his period of disloyalty, as a faithless servant.”)

Within the Newhouse clan, the future of Condé largely rests with Si’s nephew Steven and his cousin Jonathan, both of whom are in their 60s. Jonathan, who became chairman of the board after Si’s death, moved to Paris in the late ’80s and has led Condé Nast International ever since. Steven is the head of Advance and has been stationed in New York for years, where he led much of the company’s early digital efforts. (In 2006, he pushed Condé’s $20 million purchase of Reddit, perhaps the ultimate mass-not-class outlet, which the Newhouses have since spun out into its own company; Reddit was most recently valued at $3 billion.) There are other Newhouses sprinkled throughout, most of them paid from a separate family budget; Jonathan’s daughter writes about astrology for Allure, while Si’s grandson, Si IV, has been on staff in various ways.

Wondering how much the Newhouses still love the magazines keeps some Condé staffers up at night. Last May, the Newhouses hosted a private dinner at Little Park in Tribeca honoring their three Pulitzer Prize winners: John Archibald, an op-ed columnist for several Newhouse papers in Alabama; Ronan Farrow, who reported on Harvey Weinstein for The New Yorker; and Rachel Kaadzi Ghansah, who wrote about the Charleston, South Carolina, shooter for GQ. A GQ editor at the time found himself seated next to Steven Newhouse and took the opportunity to express hope that Ghansah’s win would encourage the family to continue funding such work. He got a dispiriting response. “That’s not how we think of GQ,” Newhouse said, according to the editor.

When I relayed the story to Steven, he said he didn’t recall saying this and doesn’t get involved in editorial matters. He explained that he and others in the family “admire the incredible journalism and creativity” of the company’s editorial teams but that Condé wasn’t a vanity project. “We’re not in the media business to enjoy it like owners of sports teams,” he said. “We’re in the media business because we’ve been in the media business for 100 years, and we take it seriously.”

The recent losses at Condé won’t sink the Newhouses, but rumors have persisted of a potential sale — to Hearst, Apple, Google. “Condé Nast has not been, is not, and will not be for sale,” Steven told me.

When I asked where he saw the most promise in Condé’s business, he said this was now Roger Lynch’s call. “In the history of Condé Nast, it represents an important change that the CEO is fully empowered to deliver on a vision,” Steven said. The family, more specifically Si, had made most every major decision in the company’s past, but Steven said they now saw the value of ceding things to an outsider and rejected a rumor I’d heard about an intrafamily power struggle. “One of the things that we’ve worked on is to treat Condé a little more seriously versus more of a gossipy approach,” he said. “While it’s a lot more boring, and removed from that kind of royal-family type of intrigue, we have a very stable governance structure now.”

The focus, then, is on Lynch. When I met him, I asked several times what made him the right person for the job, which he didn’t quite answer. “When they first approached me, that was my question. It just seemed out of left field,” he said, before adding he had chosen the Condé job over three others he was considering. Lynch said that after running companies that delivered content made by other people, he now believed the only way to compete with the major tech companies was by producing exclusive content. Condé employees were encouraged by Lynch’s tech background, even if he was coming from the music-streaming service preferred by their parents; they hoped this would allow him to approach each of the brands and their teams dispassionately. (The fact that he sold Pandora 18 months after becoming CEO has done little to dispel the rumors of the company’s impending sale.) Lynch admitted during his listening tour that the only Condé magazine he consistently read was The New Yorker, and in a meeting with The New Yorker’s staff, he spitballed whether, in the spirit of collaboration, the magazine might ship its cast-off articles to, say, Vanity Fair.

After six months of listening-touring, Lynch has settled on a vision for the future of Condé Nast. Lynch told me he had big hopes for video, especially having run Sling TV prior to Pandora. He is convinced there are savings to be found in geographic efficiencies. Sorting out the complicated international merger is among his first major tasks: Bob Sauerberg’s assistant had stayed on to help with the transition, but the international division was so separate that she couldn’t name a single person Lynch should talk to abroad.

Condé Nast was, for a long time, a place where people simply felt lucky to get in the door. But Condé expats have left in recent years to found Glossier, become the “chief content officer” of Goop, and work at Instagram, Snapchat, YouTube, and Victoria Beckham’s clothing line. Last year, The New Yorker’s editorial staff unionized, followed by Pitchfork and Ars Technica, a tech-news site. The New Yorker’s union did not include the magazine’s writers, who are technically independent contractors, and the process revealed the fact that some writers received health benefits while most didn’t. A group of the magazine’s writers met at Soda Bar in Prospect Heights earlier this month to discuss a proposal in which Condé would offer some writers health insurance in exchange for a take in any film and TV projects that result from their articles. “Condé Nast was the publishing company of the one percent, and now suddenly class-consciousness dialectics have come to Condé,” one writer says.

The one employee who is most consistently beset by departure rumors is perhaps the least likely to leave: Wintour almost certainly has the largest remaining editorial salary at Condé, and no one is likely to kick her out. She is worth millions to the company simply by being in the building, forcing the fashion world to continue kissing Condé’s ring. “The higher-ups at Condé are like the DNC, and Anna Wintour is their Joe Biden,” one well-connected fashion publicist told me.

After years of drama, downsizing, and intrigue, what seems to be happening most with Condé is that it is becoming — normal. Just another media company trying to get by. It’s spent the past decade battling Facebook and Google and hordes of venture-capital-funded media start-ups bent on disruption that dragged everyone down in a race to the bottom while readers stopped subscribing to magazines and turned their faces toward their phones. Throughout the industry, profits have been elusive; scale is now the buzzword. Last month, New York Media, the company that publishes New York, announced it will be merging with Vox Media; Soon after, Vice and Refinery29 announced a merger. Everyone worries whether digital-subscription fatigue will settle in, whether digital advertising can withstand a recession, whether even the most clever exploitation of legacy titles will bleed out what was valuable about them to begin with.

“Five years ago,” Remnick told me, “the big conversation at the Times, for instance, was, Can the Sulzberger family, with its great journalistic values, keep the paper and avoid selling to Carlos Slim or Michael Bloomberg? And remember all the drama? Thank God they got through it. They figured it out, and they are succeeding. The crisis hit the magazine world later than the newspaper world. And so the debate for some time now is familiar: It’s about culture and technology and many other things. And getting it right, figuring out the business, and continuing to publish things that matter — that’s at the center of things. It’s a tough trick.”

*This article appears in the October 28, 2019, issue of New York Magazine. Subscribe Now!