The debut cover of Condé Nast Portfolio, the blockbuster new business magazine that Si brought to market in May 2007 at a cost estimated between $100 and $150 million, was a nighttime aerial photograph of the Manhattan skyline, skyscrapers aglow with electric light, a romantic vision of American power and hegemony. The lead headline touted an essay by Tom Wolfe, the country’s foremost chronicler of status, on “The New Masters of the Universe,” the hedge fund kings who had succeeded 1980s corporate specialists as the national avatars of wealth. The issue was a 332-page behemoth, with 185 pages of high-priced ads, the heft itself a conspicuous argument by Condé Nast that, no matter where the magazine industry was headed in the digital age, print remained supreme.
It was the wrong idea at the exact wrong time.
Even before it hit newsstands, Portfolio, whose tumultuous and expensive run lasted only two years, had been described as perhaps “the most counterintuitive (not to say craziest) media venture of the decade.” Just as online news was devouring the advertising base for print media, and rival magazine publishers were shifting resources to the web, Si decided to bet on the sort of luscious, big-budget print product that, since his father’s death in 1979, had driven the growth of his family’s influence. He had faced naysayers before: the critics who denounced his revival of Vanity Fair as overpriced and superficial, who assumed Tina would be exiled back to London and Si exposed as another failed striver. Now, as Si neared eighty, Portfolio offered him a chance to prove the doubters wrong, one more time—maybe the last time before he would be forced to relinquish control of his kingdom to the next generation. After all, hadn’t Condé Nast always given readers what they wanted, before they knew they wanted it?
Si had reasons beyond ego to invest in this new venture. When he conceived of Portfolio, in 2005, business magazines like Fortune and Forbes were still posting healthy ad revenues. A new era of Wall Street hedonism was underway, fueled by record banking profits. Ivy League graduates and other rising elites—the core Condé demographic—were choosing Goldman Sachs and Lehman Brothers over law school. And if Tina Brown had managed to sex up suits like Barry Diller and Michael Ovitz, why couldn’t another talented young editor do the same for Ken Griffin and Jamie Dimon? Si also believed deeply that luxury advertisers would never accept the gimcrack world of digital banner ads, that they needed the thick pages of a glossy magazine to appropriately showcase their wares. “There was a sense that Condé Nast was in such a unique position that it wouldn’t be as vulnerable to the market changes that were coming,” Tom Florio recalled.
To enact his vision, Si again turned to an outsider: Joanne Lipman, a financial journalist who had spent her entire twenty-two-year career at The Wall Street Journal. She created a pair of lifestyle sections, Weekend Journal and Personal Journal, that modernized the paper’s stippled pages and succeeded with readers and advertisers. Lipman was in contention to replace the longtime Journal editor Paul Steiger when, in 2005, Si invited her to lunch at his East Side apartment and asked if she thought it was a good idea for Condé Nast to start a business magazine. “Oh my god, yes!” Lipman replied. Later, she said she felt so elated by their discussion that if she had been hit by a truck on the way out, she would have died happy. When she got back to her office, there was an email waiting for her from Si: “Let’s do it.”
True to his word, Si spared no expense. Lipman was able to hire more than seventy-five journalists, lure stars with salaries in the mid-six figures, and give her team more than a year to develop the magazine without having to produce a single issue. Internet aside, this was still the peak era of Condé, and the staff acted accordingly. “All I did for a year was go to extremely expensive restaurants and woo people to write for us,” recalled Jim Impoco, a deputy editor who was eventually ousted after clashing with Lipman. “I put on twenty-five pounds from my expense account.” Ambitious cover ideas were commissioned, executed, and abandoned. One early concept involved photographing the Brooklyn Bridge from a helicopter, with the Portfolio team arranging for a container ship and a water taxi to sail under the bridge at the exact moment that a fleet of cars crossed its span. The staff pulled it off—but never used the resulting image, which was deemed not dramatic enough for the debut issue. Tom Wolfe’s essay was rumored to have cost twelve dollars a word. Its first sentence was a signature Wolfean onomatopoeia—“Not bam bam bam bam bam bam, but bama bampa barama bam bammity bam bam bammity barampa”—and a joke flew around the office that the nonsense opening sentence “was two hundred bucks right there.” (The full piece ran 7,400 words, netting Wolfe twice the average newspaper reporter’s annual salary.) The day that the first issue was published, every staff member received a bottle of Perrier-Jouët Champagne, and Lipman went to the Nasdaq to ring the closing bell.
Inside 4 Times Square, though, there were signs of unease. Lipman had trouble fitting in with the Condé milieu. Part of this was her background in newspapers, which left her unfamiliar with the expectations of a glossy magazine. She turned down a wardrobe allowance—standard-issue for Condé editors in chief—and some of her styling choices raised eyebrows among the staff. “She was a fish out of water,” recalled one former colleague. “I don’t think she quite understood what the Condé culture was, or what the vibe should be, because it wasn’t really her.” The notion of Lipman, an accomplished journalist, being judged for her clothes and makeup would be repellent at many professional organizations. And yet Condé Nast was all about perception, and the success of Portfolio—its ability to attract high-end readers and high-spending advertisers—hinged in part on Lipman projecting a high-status image. Ugly bits of gossip soon turned up in the trade press, painting Lipman as a rube; The New York Observer reported that after being urged to assign an article to the five-time National Magazine Award finalist James Fallows, she had asked to see his clips. (Lipman told me this anecdote “is laughable and invented.”)
Then the high-flying economy, the basis of Portfolio’s business model, began to collapse. Bear Stearns was sold for a paltry two dollars a share in March 2008; advertising began to dry up. Confident Condé Nast kept spending. In the summer of 2008, the writer Jesse Eisinger filed a story about the credit derivatives desk at JPMorgan Chase. Presciently, Eisinger identified the bank’s mutant securities as a lurking risk to the global economy. The Portfolio editors settled on a headline—“The $58 Trillion Elephant in the Room”—and commissioned a photograph of a live elephant inside an office building, “to illustrate the notion that these credit derivatives are the huge problem in the room that people are trying to ignore.”
It would have been easier and cheaper to create this scene with a stock image of a pachyderm and the magic of Photoshop. But this was Condé Nast. “There wasn’t really any hesitation,” the photographer, Phillip Toledano, said about the pitch from the editors. “It just made sense. Of course it’s going to be an elephant.”
The shoot at the Brooklyn Navy Yard happened in early September—days before Lehman Brothers collapsed. An elephant was trucked in from Connecticut and led by handlers into the studio through a massive garage door. “I’m just standing there fucking amazed,” Toledano recalled. The result was a dramatic and arresting visual, the sort of manufactured fantasy that had long been a Condé calling card: an elephant bellowing beside a water cooler as a white-collar worker cowers in fear. Between the star photographer, studio fees, and rental of a gigantic exotic animal, the image was exorbitantly expensive to produce—$30,000 for the elephant alone, a staffer later told The New York Times. And yet the photograph was buried inside the November 2008 issue, the cover of which instead featured Dov Charney, the founder of American Apparel, reclining on a bed and flashing a come-hither look. (Lipman told me that she did not authorize the elephant shoot and was alarmed by the cost. “I assumed it was Photoshop—and was stunned when I found out they hired an elephant!” she wrote in an email. “This was a real ‘not in Kansas anymore’ moment for me. We never did anything like that again.”)
The collapse of Wall Street and the ensuing economic downturn seemed expressly, almost perversely, designed to hurt Portfolio. Financial firms, whose advertising was expected to provide a healthy chunk of revenue, pulled their ads en masse; luxury, automotive, and travel advertisers retrenched, too. Portfolio reportedly lost close to $35 million in 2008; by the first quarter of 2009, its ad pages were down 40 percent. Lipman had leaned into an elevated form of service journalism, publishing explanatory articles on the basics of fractional private jet ownership and useful tips for truffle hunting. (“Make sure your truffle feels heavy for its size; that means it’s fresher, because its natural moisture hasn’t yet evaporated.”) Such features now looked risibly out of touch.
Something deeper, too, was turning in the culture, a change that boded poorly for Si Newhouse and the elite society his kingdom presided over. It wasn’t just consumption that was losing its luster. The Great Recession, and the ensuing bailout for Wall Street’s wealthiest, had signaled a larger shift in societal attitudes toward the establishment. The carefree capitalism that had buttressed Condé Nast’s fortunes all these years was yielding to wariness, suspicion, even disgust and anger toward the elite. On April 27, 2009, two years after its debut, Si told Lipman that he was shutting down Portfolio. The Last Great Magazine Launch had failed.
At the time, Lipman defended her creation as “the right magazine at a very unfortunate time.” “Si was generous, and he was truly heartbroken when the magazine closed,” she wrote to me sixteen years later. “He loved Portfolio. So did readers—our renewal rates were among the best in the building. Condé Nast for me was an entirely different world. I’m a subway girl, so entering a world of car service and first-class travel and wardrobe allowances (which I turned down!) was an eye-opener. Elephant aside, we were not big spenders, especially compared with other magazines in the company.”
But in the immediate wake of the closure, it was Tina Brown who grasped the existential significance of the magazine’s demise. “All this is so unlike Si,” Tina wrote in a post for her relatively new web publication, The Daily Beast. “Until now, he was always the media emperor who could live and do as he chose.” As familiar as she was with Si’s caprice, Tina knew that he loved magazines, relished doting on them, and was willing to sustain enormous losses to preserve them. The death of Portfolio, she concluded, amounted to an “unprecedented sight”: “The magazine world’s last big believer, Si Newhouse, exhibiting what looks like signs of throwing in the towel.”
THE SPENDTHRIFT CULTURE OF CONDÉ NAST could not remain immune from the Great Recession. In October 2008, editors were asked to reduce their budgets by 5 percent; five months later, word came down that another 10 percent had to go. The New York Post reported that several top editors and executives had even relinquished their chauffeured Mercedes in favor of the subway; among the straphangers were David Remnick and Ruth Reichl of Gourmet. “When they gave up the town cars, that was a moment,” recalled Jim Impoco. “That was like Marie Antoinette saying, ‘No croissants for me this morning!’ ”
Part of the problem was the erosion of other branches of the Newhouse empire. The family’s regional newspapers had once functioned as financial buffers for the big spenders at the magazines; one executive claimed that in the 1990s, The Staten Island Advance netted more money than all of the Condé titles combined. The digital revolution had steadily worn away those revenues—and then, in June 2007, the iPhone went on sale. Here was all the power of the internet, with its myriad platforms for information and lifestyle journalism, placed directly in the consumer’s pocket. In the ensuing years, billions would be sold. Being privately held, Condé Nast refused to disclose the extent of its pecuniary plight. But while Condé was spared the two-week furloughs that were imposed at the Newhouse newspapers in the spring of 2009, the company’s chief executive, Chuck Townsend, was forced to issue an all-staff memo expressing a very un-Condé sentiment: “We’ll all have to do more with less.”
Townsend was a genteel, mid-Atlantic lockjaw type who favored elegant suits and once served as commodore of the New York Yacht Club. He had climbed the Condé ranks as a salesman and ascended to the top job in 2004 after Steve Florio stepped down with health issues. (Florio died in 2007.) In an earlier era, Townsend might have been an ideal steward for Condé, adept at glad-handing advertisers and working a cocktail hour. “What Si saw in Chuck was someone who had really good breeding,” recalled a person who worked under him. But Townsend had the misfortune to reach the summit just as the mountain began to melt. In July 2009, he hired McKinsey, the white-shoe management consulting firm, to conduct a top-to-bottom review of Condé Nast business practices. The company that once spared no expense in the pursuit of creative excellence was capitulating to cost-cutters who wanted several magazines to slash a quarter of their budgets. And Alex Liberman was no longer around to tear up the budget sheets and banish the suits from his office.
If one had to pinpoint the end of Condé’s halcyon era, it might be August 11, 2009, when The New York Observer, the paper of record for Manhattan’s shapers of the monoculture, ran a devastating story declaring that “the enchanting, mystical era of Condé Nast is pretty much over.” Weekly flower deliveries and complimentary Oranginas were gone. The receptionists who greeted guests at each magazine’s office—a tradition dating to Vogue’s gold-and-lapis antechamber in the Graybar Building—were laid off (although The New Yorker managed to transfer its receptionist to the fiction department). Graydon Carter had been spotted waiting in line with the plebes at the Gehry cafeteria’s stir-fry station, sending chills through the lower ranks. Condé’s zephyrs of old-school civility were wafting into the past.
“In the old days, everyone sent gifts to everyone else,” one editor recalled. “If someone had a baby, they might get eight deliveries of flowers from the office. And everyone would expense it…. There would be lots of flowers and all sorts of gift bags and you’d try to look at the name tags of the people getting them. But there’s not many of those rides on the elevators these days.” All these subtle indignities were encapsulated in a detail that could only have mattered in Condé’s rigidly hierarchical world. Before 2008, mini-fridges at 4 Times Square were fully stocked with bottles of Fiji water. After the crash, the Fiji turned into Poland Spring. Then, in 2009, the Poland Spring supply dwindled, too.
“We won’t have any more after this,” an employee complained. “We have to start drinking tap water.”
Chuck Townsend took exception to all the focus on potables. “The Red Bulls and Oranginas are maybe no longer there, but what’s the difference?” he told the Observer. “I don’t want to lose the specialty or the quirkiness, but a lot of this stuff that has been part and parcel of it is just meaningless.” He added, “You don’t need it! You don’t need the Orangina!” But Condé did need the Orangina, and all the other little luxuries that had made the company a byword for sumptuousness. Without the decadence and the perks, the smugness and the swagger, the entire edifice of Si’s creation—the illusion that sustained its excesses all those years—came crashing down.
In October 2009, Condé announced it was closing Gourmet, its venerable food magazine, along with three other titles. “In the economics of the ’80s, ’90s and early 2000s, this would be a business decision balanced by the cultural reticence to part with iconic brands,” Townsend said. “This economy is a completely different bag.” These concessions may have seemed seismic within 4 Times Square. But in other ways, Condé exceptionalism endured. One marketing executive who joined Condé well after the crash expected to find an organization grudgingly coming to terms with financial reality. Instead, they were shocked by how little seemed to have changed. “All the publishers had car services with a driver that was their driver 100 percent of the time,” the executive recalled. “Most of them had clothing budgets.” Tom Florio’s idea of saving money was to reserve a room at the Paris Ritz that was less expensive than his typical 2,100-euro-a-night suite.
Few on the company’s publishing side were incentivized to bet on digital expansion. Internet ads paid pennies on the dollar compared to print ads; the commissions and bonuses that paid for private school and summer homes were not going to materialize from the web. And the executives could scrape together just enough evidence to convince themselves, and persuade their bosses, that the print business remained viable. Vogue, for instance, recorded its biggest-ever issue in September 2012: 916 pages, weighing in around five pounds. Even as once-mighty Time Inc. stumbled toward oblivion—it would eventually be sold, in 2017, to a second-tier publisher based in Iowa—Condé Nast, fueled by residual prestige and institutional intransigence, tried to carry on.
In this environment, the act of spending itself took on an elegiac air, as if the denizens of a crumbling palace were throwing a final bacchanalia before the coup. Editors took themselves out for elaborate steakhouse dinners, figuring they should take advantage of expense accounts before they were vaporized. In 2016, well after Condé’s fortunes had turned, mid-level New York–based staffers were still flying out to California for ten-day work trips, with rooms booked at luxe hotels in Beverly Hills. In 2017, Condé Nast was reported to have lost more than $120 million.
Eventually, the bottom dropped out. Having moved to sleek new offices at 1 World Trade Center, Condé began squeezing its magazines onto fewer floors, freeing up commercial space that it could sublet. Vogue resorted to gimmicky tactics like “Vogue100,” where members paid $100,000 a year for perks like breakfasts with Anna and invitations to sponsored parties. In a cost-saving measure that rivals like Hearst had instituted years earlier, Condé consolidated its copy desks, fact-checkers, and photo researchers into a central operation, stripping individual magazines of their proprietary teams. (Si’s favorite, The New Yorker, was exempt, and its editing staff allowed to continue using Microsoft Word when other magazines were required to switch to Google Docs.) These efficiencies were ultimately not enough to offset the accelerating collapse of the print advertising market. In 2017, Self—the magazine that in 1979 had kicked off Si’s ambitious reinvention of the company—ended its print edition. Teen Vogue went next, followed by the company’s onetime revenue leader, Glamour, and three years later by the once-innovative Allure. Editors who once sweated over typefaces and photo crops were now urged to focus on raising their web traffic and making “snackable” online videos go viral.
In September 2017, Graydon Carter announced that he would leave Vanity Fair after twenty-five years at its helm. The digital revolution, he believed, was sapping the magazine business of its old romance. In 2015, though, he pulled off one final print triumph, landing the first photographs of Caitlyn Jenner, formerly Bruce, who had recently revealed her new identity as a woman. The arresting cover—Jenner in a stylish corset, shot by Annie Leibovitz and accompanied by the cheeky headline “Call Me Caitlyn”—was in its own way a milestone, a transgender celebrity looking as glamorous and confident as any Hollywood star. President Barack Obama issued a statement, posting on Twitter that “it takes courage to share your story.” Vanity Fair published the story on its website well before the physical magazine appeared on newsstands, and the online traffic numbers broke the magazine’s prior record. But the success of the Jenner cover masked Graydon’s growing discontent. His relationship with Anna, a one-time friend and champion, had soured, particularly after she was promoted in 2013 to the newly created role of artistic director, which granted her Alex Liberman’s old powers to oversee nearly every title at Condé Nast. Anna refrained from meddling with The New Yorker and Vanity Fair, but at one point, over lunch, she told Graydon that she had some advice about the fashion choices in Vanity Fair’s photo shoots.
“Can I offer you some advice on Vogue’s writing?” Graydon replied. The one-time friends fell into a new period of froideur.
For a while, Graydon staved off the budget and staff cuts that Condé was imposing on other magazines, but in late 2016, Anna conveyed to him that Vanity Fair had to acquiesce to the newly centralized structure and give up its longtime fact-checkers, designers, and photo editors. Graydon balked and was granted a reprieve, but he knew it was a matter of time before he could no longer protect Vanity Fair from what he believed would be a damaging retrenchment. The following year, Graydon put into motion a plan that his aides wryly dubbed “London Bridge,” Buckingham Palace’s code word for its playbook in the event of Queen Elizabeth II’s death. Not one to wait for a corporate permission slip, he arranged to break the news of his departure with a journalist at The New York Times (me) and choreographed the announcement down to the minute to avoid any leaks. Even the Newhouses would be left in the dark. Steven Newhouse, by then a top executive at Advance, was standing in an Apple store on the Upper East Side when he learned of Graydon’s exit via a Times alert on his iPhone. “You had the scoop before me,” he said when we spoke later that day. Steven was quick to say that he had previously scheduled plans to dine that evening with Graydon and his wife, and that he had no interest in missing their date. In fact, he was looking forward to it: “We’ll have more to talk about than we had anticipated.”
ONE DAY IN THE MID-2010s, Condé Nast staffers were summoned to a series of company-wide seminars on diversity, held by an outside firm. The watchword for the event was inclusiveness. During one meeting, an attendee piped up to point out that the entire company had been founded on, and sustained for decades by, the celebration and fostering of exclusivity. An awkward silence filled the room.
The economic damage wrought by the 2008 market crash was one thing; Condé’s magazines had weathered recessions in the past. But the company now faced a more existential threat: Condé’s métier was privilege, and privilege had become a dirty word. The elites whose lives were romanticized, packaged, and sold to the masses by Condé as exemplars of American success were suddenly being recast as villains amid a populist surge. Wealth porn, long a core appeal of the Condé stable, was no longer sexy—in the immediate aftermath of the crash, it could even be seen as borderline obscene. College students who graduated into the 2008 meltdown had struggled to find work, and economists predicted this early setback would significantly curtail their lifetime earnings. The totems of American success that were fetishized by Condé Nast—designer clothes, beautiful houses—appeared increasingly unobtainable. “America is an aspirational country, and up until recently, when people who were living affluent lives were displayed in magazines, the country was fine with that, because readers had a chance at those lives,” reflected Graydon Carter. “The financial crisis in 2008 changed the rules dramatically. The aspirational aspect of American culture has diminished because chances are, you can’t achieve affluence the way you could’ve 25 or 30 years ago.”
Vanity Fair’s Todd Purdum detected this shift in the early 2010s, when he pitched Betsy Bloomingdale, an LA socialite and Nancy Reagan confidante, on a profile depicting her as the last great hostess-with-the-mostest in Hollywood. Bloomingdale readily agreed; to be profiled in Vanity Fair was a kind of lifetime achievement award within her milieu. “Then she called back,” Purdum remembered, “and said her son had told her she couldn’t do it in the wake of Occupy Wall Street, and that she’d be absolutely pilloried.”
Soon, the company ran into another cultural sea change: the rise of identity politics. Too often, Condé’s magazines had showcased a thin, white, heteronormative Anglo-American ideal. As heated debates over racial equity coursed through corporate America, employees who felt excluded from or forced to conform with this vision were no longer willing to stay quiet. By decade’s end, complaints had grown inside 1 World Trade Center about microaggressions, pay disparities, and a workplace culture that some nonwhite staff members said could be intimidating at best and discriminatory at worst. When the socialite and Vanity Fair contributor Reinaldo Herrera visited VF’s web department one day in 2013, he noticed several employees of Asian descent. “It’s like a visit to the Orient in here!” Herrera mused aloud, according to several people who witnessed or overheard his remark. In June 2020, the editor of Bon Appétit, Adam Rapoport, resigned amid accusations of racial insensitivity, prompted in part by the resurfacing of a photograph from years earlier in which Rapoport, who is white, was shown dressed up as Puerto Rican for a Halloween party. Bon Appétit had been a digital success story for Condé, thanks to its popular cooking videos featuring a multiethnic group of millennial staffers, but several of them had complained about pay disparities and feeling tokenized, and some later quit.
The history of race and exclusion at Condé Nast was complex and fraught—regressive and progressive by turns. In 1938, Condé Montrose Nast fired Cecil Beaton, the celebrated society photographer, after Beaton smuggled anti-Semitic remarks into an illustration for Vogue; hidden in his drawing was the phrase “all the damn kikes in town.” After the offending language was highlighted in Walter Winchell’s gossip column, Beaton was summoned to Nast’s penthouse. “My periodicals have been free of attacks on race and creed and I am determined that they must remain free from such attacks,” Nast told the press. “I was particularly distressed that these slurring comments should have been printed in Vogue, especially during these days of cruel, vicious, and unreasoning persecution of Jews.” At a cost of roughly $800,000 in today’s dollars, Nast paid to reprint the offending page in a portion of the month’s print run to excise the anti-Semitic language.
Gordon Parks, a Black photographer, was almost broke and living in a YMCA in Harlem in the mid-1940s when his portfolio was sent to the art director of Harper’s Bazaar, Alexey Brodovitch. When they met, Brodovitch praised Parks’s work, but he apologetically explained that the Hearst Corporation forbid the hiring of Black employees, “not even for sweeping floors.” Parks recounted the exchange a few days later to Edward Steichen, who nearly choked on his corned beef sandwich. “That son-of-a-bitch,” Steichen muttered, and then scrawled a name and address on a sheet of paper. “Go see this man,” he instructed Parks. “Tell him I sent you.” The address was the Condé Nast office, and the man was Alex Liberman, who told Parks, “We must give you a chance.” Soon, Parks was shooting for Glamour. Alex became a mentor to Parks, gradually increasing the prestige of his assignments and the size of his paychecks. After six months, Parks received a commission to shoot women’s evening wear for Vogue—the beginning of a wider recognition of his talents. Parks shot for Vogue for five years and went on to a celebrated career at Life magazine and in Hollywood, where he directed Shaft.
William Norwich, a former Vogue editor, recalled his awe at Vogue’s decision, in March 1966, to put Barbra Streisand on its cover. “She had been called basically a singing anteater,” said Norwich, who grew up Jewish, referring to anti-Semitic comments about the size of Streisand’s nose. “Can you imagine the revelation it was for people to see Barbra Streisand? Down in the South, or in Westport, Connecticut, WASP-land? ‘Barbra Streisand, that Jewess?’ I found that Vogue, in its gentle way, declared moments that moved people culturally. It would behoove some people to have a sense of history and of what Vogue has contributed.”
March 1966 was also the month when Donyale Luna, a Detroit-born model and a member of Andy Warhol’s Factory crowd, appeared on the cover of British Vogue, becoming the first Black cover model on any version of Vogue around the world. Luna almost made the cover of Vogue Paris in 1966, too—but according to Alex Liberman’s stepdaughter, Francine du Plessix Gray, Sam Newhouse intervened. In her memoir, du Plessix Gray wrote that Sam caught wind of the idea and insisted that Alex arrange for the image of Luna to be replaced. Vogue Paris’s editor, Edmonde Charles-Roux, refused to accede, and she was quickly fired. Du Plessix Gray did not speculate on Sam’s motivation, only that he was “cautiously conservative.” It’s possible that Charles-Roux was already on the outs with the powers at Condé Nast, who viewed her edgy version of Vogue Paris as too avant-garde for the commercial market. One biographer speculated that Charles-Roux seized on the pretext of American racism as a useful public rationale for her firing.
There is ample evidence, however, that Luna was blocked again at Condé Nast later that year, this time from appearing in American Vogue. Richard Avedon had photographed Luna in April 1965 for his previous employer, Harper’s Bazaar, and the pictures prompted objections from readers and advertisers in the American South and, reportedly, William Randolph Hearst Jr. himself. Avedon later said that “for reasons of racial prejudice and the economics of the fashion business,” he “was never permitted to photograph” Luna for Bazaar again. The backlash had led, in part, to Avedon’s move to Condé Nast in 1966, and the photographer was now planning “The Great Fur Caravan,” a lavish fashion shoot in Japan, for Vogue. Avedon wanted to cast Luna as the lead model, but he encountered resistance. Alex Liberman called and recommended that he cast Veruschka instead; next was talk of bringing both models on the shoot. Then, as the departure date neared, Diana Vreeland called Avedon into her scarlet office.
“Dick, you can’t take Luna to Japan. She’s nobody’s idea of what anybody wants to look like,” Vreeland said, according to Avedon, who described the conversation to the journalist Doon Arbus in 1972.
The photographer recalled feeling sick to his stomach. “Diana, she’s extraordinary,” Avedon said.
“So was King Kong,” Vreeland replied.
Recalling their exchange six years afterward, Avedon said, “That’s when I knew I had to get out of that room.” Nearly another decade would pass before a Black model, Beverly Johnson, finally made the cover of American Vogue.
ANNA WINTOUR’S TRACK RECORD on inclusivity was mixed. In 1989, for her first September issue as editor, Anna insisted on putting Naomi Campbell on the cover. She did so despite the skepticism of Si Newhouse, who had sighed and asked her, “You’re going to put an African American model on the September cover of American Vogue?” Recalling the experience years later, Anna said that “it never crossed my mind to think that way. I just thought, ‘This is a fantastic girl, this is the model of the moment, this is a great image.’ ” In a July 1997 editor’s letter, Anna acknowledged that “black models appear less often than I, and many of you, would like on Vogue’s covers,” and offered this explanation: “It is a fact of life that the color of a cover model’s skin (or hair, for that matter) dramatically affects newsstand sales.” Still, the following year, Vogue put Oprah Winfrey on its October cover, a decision that generated enormous publicity and newsstand sales. If Winfrey had qualms about appearing in a magazine that historically featured white women, she did not publicly express them. In the Vogue article, she conveyed her excitement at receiving the ultimate Condé honor: “I’m a Black woman from Mississippi. Why would I be thinking I was gonna be in Vogue? I would never have even thought of it as a possibility. That’s why it’s so extraordinary.”
And yet, over the years, Anna made mistakes. Her editor’s letter in the Winfrey issue revealed that the talk-show host had “promised she would lose twenty pounds by our deadline,” a comment that would likely be criticized as fat-shaming today. Anna’s biographer, Amy Odell, reported an ugly incident from the early 2000s involving André Leon Talley, the gay Black fashion editor who was Anna’s longtime consigliere—and, toward the end of his life, would deride her as “a colonial broad.” Talley often wrote memos to Anna urging her to feature more Black models in the magazine. According to Odell, after receiving one such missive, Anna said to another editor, “Could somebody tell André that not every month is Black History Month?” (A person close to Anna told me: “Anna does not recall saying that, nor is it language she’d ever use.”) A notorious cover shoot in 2008 featured LeBron James, dribbling a basketball and baring his teeth as the model Gisele Bündchen, clad in a slinky dress, holds on to him. This was the first time that a Black man was featured on a Vogue cover, and several editors were alarmed: the composition of the image strikingly evoked the classic movie poster of King Kong, with James as the ape and Gisele as Fay Wray, the damsel in distress. “There was a lot of, ‘Anna, this is not going to go over well,’ but she was dismissive,” Anna’s longtime managing editor Laurie Jones told Odell. “She just didn’t see it.” The backlash was immediate, with critics accusing Vogue of trafficking in ugly stereotypes. Anna was bewildered by the reaction. (A confidant of hers later told me that she had received positive feedback about the image from people who were involved with the shoot.)
In 2016, Anna appointed a Black woman, Elaine Welteroth, as editor in chief of Teen Vogue—sort of. Welteroth had made a name for herself as a beauty editor at Glamour and Teen Vogue, where she advocated for Black representation in the magazine. According to Welteroth, Anna offered her a co-editor-in-chief role where she would split leadership duties with two other editors; the position came with a measly $10,000 raise, and Welteroth was given less than an hour to decide whether to accept. One year later, after Welteroth told Anna that she felt tokenized and disempowered in her role, Condé increased her salary, gave her a corner office, and appointed her sole editor in chief of Teen Vogue. (She was only the second Black person to hold the title at Condé, after Keija Minor at Brides in 2012.) Within a year, Teen Vogue’s print edition was shuttered, and Welteroth left the company.
In 2016, after Graydon announced his plans to depart Vanity Fair, Anna made clear that she wanted a new direction for the magazine that wasn’t “pale, stale, and male,” according to a person who spoke with her at the time. She and David Remnick ultimately urged Condé to hire Radhika Jones as Graydon’s successor. Jones was an Indian American journalist with a doctorate in English and comparative literature from Columbia, who had held top editing roles at The Paris Review and Time, where she oversaw the Time 100 Gala. For her debut issue, Jones chose as her cover star Lena Waithe, a queer Black actress and screenwriter; the accompanying profile opened with a sentence that read like a challenge: “If you haven’t heard of Lena Waithe, check yourself for a pulse.” Many readers hadn’t; Waithe had played a breakout role on the Netflix show Master of None, but she was still a relatively niche celebrity at the time. Jones later pointed out that between 1983 and 2017, Vanity Fair had featured just seventeen Black people on its covers. Her supporters applauded Jones for elevating a different kind of celebrity than VF had promoted in the past, but her choices would also prompt objections from some senior Condé leaders. At a company brand strategy meeting in April 2019, Jones laid out her plans for VF’s second half of the year. Two senior executives questioned her editorial vision and declared that advertisers were befuddled by it. Anna, irritated, banged her hand on the conference table to cut the tension and defended Jones, instructing the executives “to get your advertisers to follow along.”
By decade’s end, the Black Lives Matter movement had reached a crescendo, and the outside pressure on Condé to reckon with its own history regarding race and inequality became too great to ignore. In June 2020, Anna issued an apology for Vogue’s past treatment of Black staffers. “I want to say plainly that I know Vogue has not found enough ways to elevate and give space to Black editors, writers, photographers, designers and other creators,” she wrote to her staff. “We have made mistakes, too, publishing images or stories that have been hurtful or intolerant. I take full responsibility for those mistakes.”