At the start of the 1990s, Robert Gottlieb may have been stumbling at The New Yorker, but Tina Brown was riding high. Her Vanity Fair was the red-hot center of the Condé Nast universe, each of its glamour-soaked issues a monthly distillation of the culture. Si had spent the prior decade in acquisition mode. He added Gourmet to the Condé stable in 1983; debuted Condé Nast Traveler, an upscale Baedeker edited by Tina’s husband, Harold Evans, in 1987; and purchased the downtown cult fashion magazine Details in 1988. But it was a blowout party thrown by Tina that captured the raw cultural power of Condé Nast writ large.
Vanity Fair’s fifth anniversary bash in 1988 took place at the Diamond Horseshoe club in the basement of the Paramount Hotel near Times Square, a defunct 1940s-era supper club revived for the night by Tina with the help of Studio 54 impresarios Steve Rubell and Ian Schrager and the go-to event designer of the era, Robert Isabell. Amid an Old Hollywood backdrop of white limos and cigarette girls in Carmen Miranda turbans, celebrities from every sphere waltzed in past the flashbulbs of the paparazzi, like an issue of the magazine come to life: Liza Minnelli, Norman Mailer, Halston, Swifty Lazar, Jacqueline Bisset, Jackie Collins, Kurt Vonnegut, Tom Wolfe, Gloria Vanderbilt, Donald Trump, Ron Perelman, Julian Schnabel, Bianca Jagger, Bill Blass, Barbara Walters, Henry Kissinger, and Reinaldo Herrera, who took charge of a midnight-hour conga line. Like a basketball coach, Tina laid out a man-to-man defense: each of her writers and editors was assigned to look after particular VIPs, with highly specific instructions on flattering their ego or ensuring they did not duck out early. The excess was palpable: gold-painted palm trees flown in from Miami; sixteen female saxophonists dressed head to toe in Calvin Klein. This was the apotheosis of the Condé edict that editors become something more than rearrangers of pretty words and pretty pictures: for Si, the ideal editor in chief was a curator of the culture. Si himself presided and, sloughing off his usual shyness, delivered a speech—“Vanity Fair fever is sweeping the country!”—reveling in the elite stratosphere that Tina had created for him.
The event itself “was a strategic decision to revive the sense of cultural elitism that was part of the premise of Vanity Fair,” an executive later recalled. Si was bankrolling his own version of Condé Montrose Nast’s lavish soirees on Park Avenue: extravaganzas of the good and the great that doubled as highly effective tools to dazzle advertisers and advance the commercial prospects of the publisher’s brand. The party laid bare how the Condé Nast of the 1980s had perfected the art of harnessing glamour as a corporate tool, to be manufactured, marketed, and ruthlessly exploited for its own corporate interests. The fact that Tina commissioned the former proprietors of Studio 54 to design the event—and assigned her celebrity wrangler Jane Sarkin, who started her career as Andy Warhol’s receptionist at Interview, to oversee the guest list—neatly tied this pinnacle of 1980s New York excess to its 1970s antecedent. Schrager and Rubell themselves would go on to popularize the concept of boutique hotels, transposing the tax-evading, coke-bingeing antics of their youth into the legitimate realm of high-priced lodgings, whose swishy bars and dim lighting epitomized the louche decadence of the 1990s and pre-crash 2000s. Condé Nast repaid the favor: when the duo opened the Royalton Hotel on East Forty-fourth Street, Tina and other star editors made it their regular canteen, fueling a happy cycle of hype that benefited all parties.
Vanity Fair’s influence was bending the culture in more profound ways, as well. In the spring of 1989, Tina was invited by Anna Wintour to attend a tribute to her psychiatrist husband, David Shaffer, recognizing his contributions to research on youth suicide. Tina was moved when William Styron, the hugely successful author of Sophie’s Choice, stood up from his seat and spoke about his struggle with clinical depression and suicidal ideation. At the time, depression was not widely understood as an illness, and the act of suicide carried a similar stigma. Tina made a beeline to Styron and asked if he might consider writing about his experience for Vanity Fair, an essay that she imagined “would be news and literature combined.”
Styron had first revealed his thoughts on the subject a few months prior in a New York Times op-ed, but a national magazine represented a much broader platform. When his article ran in VF in December 1989 under the headline “Darkness Visible,” a phrase that Tina borrowed from Paradise Lost, it caused a sensation. Letters poured in from Americans who had struggled to explain similar demons to family members and friends. Clipped, photocopied, and passed around by hand, the essay offered a way for sufferers to articulate what Styron called “the diabolical discomfort of being imprisoned in a fiercely overheated room.” Tina had offered Styron whatever length he needed, and his essay ran at fifteen thousand words. The following year, Styron expanded the article into a short book, a bestseller that prompted a wave of similar memoirs depicting struggles with depression; Elizabeth Wurtzel’s Prozac Nation was published in 1994. It was a signal moment in the mainstreaming of mental health. “Out of a great deal of luck and timing,” Styron recalled, “I was able to be the voice for a lot of people”—a role that Tina and Vanity Fair had instigated.
This was not the first time that Tina had reoriented the conversation around public health. In 1987, she commissioned a story on the lethal toll of AIDS on New York’s creative community. Mainstream publications had been slow to acknowledge why so many young and middle-aged artists, writers, and actors were dying, in part because many of the victims and their families, frightened by the still-potent stigma around homosexuality, had sought to hide their diagnoses until the end. (Vanity Fair itself had done plenty to glamorize Ronald Reagan, who did not deliver a speech about the AIDS epidemic until late in his presidency, by which point nearly twenty-one thousand Americans had died.) Tina decided to publish a gallery of fifty black-and-white photographs, annotated with each victim’s name, profession, and the age they died. “AIDS: In Memoriam” was modeled after a celebrated issue of Life magazine in 1969, “One Week’s Toll,” that included photographs of 242 American soldiers who had died during a recent week in Vietnam. Readers were confronted with the sheer scale of the carnage; Tina’s AIDS gallery had a similarly powerful effect. “It was bringing AIDS out of the closet,” said Michael Shnayerson, who wrote the accompanying article. “There was still no recognition of its impact, or the toll it was taking on people in the arts.”
The feature included the fashion designer Perry Ellis and the decorator Angelo Donghia, whose New York Times obituaries did not mention AIDS as the underlying cause of their deaths. Shnayerson had been tasked with convincing relatives and friends to allow their deceased loved one’s photograph to appear—for some, a terrifying prospect. He spent hours with the celebrity hairdresser Maury Hopson, who recounted the final days of his lover, Way Bandy, a makeup artist to the stars who died at age forty-five. Recalling the interview to me thirty-six years later, Shnayerson began to cry. Hopson’s account was so heartrending that Shnayerson devoted the final portion of his article to it, printing many of his words verbatim. “I wanted to let him speak,” he told me. “There was nothing more powerful than what he was saying. And Tina ran it just like that.”
But arguably Tina’s biggest splash as editor of the magazine came in the summer of 1991, with the publication of a nude photograph of the actress Demi Moore, pregnant, one hand casually draped across her breasts, the other supporting the sphere of her swollen belly. When the image appeared on the cover of the August 1991 issue of Vanity Fair, it caused a national scandal.
Demi, who was fresh off her blockbuster turn in Ghost, was already comfortable with Annie Leibovitz, who had shot her wedding to Bruce Willis in 1987. For the couple’s personal use, Leibovitz also photographed Demi unclothed while she was pregnant with their first child, Rumer. Now Demi was pregnant again, with Scout, and Tina wanted to feature her on the cover. An initial shoot was called off because Demi had dyed her hair blonde for a movie called The Butcher’s Wife, and the VF crew preferred her in her usual guise as a brunette. Later, at the reshoot, Demi posed in a flowing green gown by Isaac Mizrahi. There were no plans for her to pose nude, but Leibovitz asked Demi if, as a gift, she would like a companion set of disrobed photos to go with the earlier ones. The images were not intended to be seen by the public. When Tina saw the contact sheets back in New York, she was mesmerized. Would Demi let them use it? Leibovitz got on the phone and, to Tina’s shock, convinced the actress to say yes. Alex Liberman tried to talk Tina out of it, telling her, “I don’t think so; I think it’s rather too vulgar.” Tina had a great deal of trust in Alex’s instincts, but in this case, she overruled him. (Later, Alex would happily claim the Demi photo as one of his great moments at Condé Nast.) When Tina ran it past Si, he looked pensive for a moment and then acquiesced: “Why not?”
Leibovitz’s portrait was unadorned and unashamed, a riposte to an emerging 1990s pop culture awash in sex, but uncomfortable with its potential consequences. Several major supermarket chains balked at carrying the issue on their newsstands. So Ron Galotti, Tina’s macho publisher at Vanity Fair, dreamed up the idea of shrink-wrapping the magazine in white plastic that cropped Demi’s body below the head. It looked like a peekaboo issue of Penthouse, which only fueled the runaway sales. Within days, it had sold out across the country. One magazine store in Ottawa, Canada, received a thousand calls from customers asking if its shipment had arrived. “I guess they want to be first on their block to own it,” an employee mused. Phyllis Schlafly denounced it as “sickening, cheap sensationalism.” At least fifty-nine American newspapers ran stories about it. The cover turned up on network television shows for eight days in a row, and ABC News named Leibovitz its “person of the week.”
The New York Times ran an assessment by its art critic, Roberta Smith, who called Demi “the ultimate yuppie madonna”—and observed that Leibovitz’s career arc from counterculture icon Rolling Stone to the materialist glitz of Vanity Fair reflected the embrace of popular culture “by the American corporate structure.” Indeed, Leibovitz had in recent years created a series of advertisements for American Express, perhaps the ultimate status symbol of American yuppie splendor. (In a neat corporate ouroboros, Leibovitz’s Amex ads sometimes appeared alongside her editorial work in Condé magazines.) The Condé Nast alchemy had struck again, merging a cultural cause—in this case, female empowerment—with pecuniary reward, a feat that the firebrand intellectual Camille Paglia found both revealing and delightful.
“Isn’t it ironic that capitalism, not feminism, brought this one about?” Paglia quipped at the time. “There is no benevolence here. There’s sheer manipulation and salesmanship. And, again, I’m for it!”
Crassly motivated or not, the uproar sparked by Demi’s naked body busted old taboos. A glossy magazine had managed to open the door for a more frank cultural conversation about pregnancy. Every subsequent People and Us Weekly headline celebrating an actress’s baby bump owes it a debt. Demi later wrote that she found the accompanying article, by Nancy Collins, demeaning, given its focus on her diva-like demands for private jets and on-set psychics. (The piece also included a quote from the director Joel Schumacher comparing Demi to “a young Arabian racehorse.”) But for Tina, the fallout of the cover image was a kind of culmination, perhaps even a vindication, of the philosophy of celebrity and provocation that she had infused into American media, and the brickbats she had endured because of it. In a triumphant staff memo—“Demi Does a Million”—Tina congratulated her Vanity Fair team on the stupendous newsstand sales, up 77.6 percent from the year prior. The number of issues sold by then: 1,087,000.
“Any ideas for next August?” Tina asked, puckishly.
THINGS WERE GOING A LITTLE more quietly at The New Yorker.
Gottlieb had made improvements on the margins, but the consensus was that his magazine was still mostly a snooze. “A piece on a collection of plastic guitar picks?” E. J. Kahn Jr., a contributor since 1937, remarked after happening on a Gottlieb-approved “Talk of the Town” item about the subject. “I don’t know. Then you read it, and you find out that it wasn’t even the world’s best collection of plastic guitar picks. It was the second best collection. Mr. Shawn would never have approved of that.” One columnist observed that Gottlieb’s magazine “doesn’t do celebrities, it doesn’t do sound bites. Like Custer’s troops at the Little Big Horn, it stands proudly, and perhaps vaingloriously and foolishly, trying to fight off the utterly relative and transitory ‘values’ of our age, which circle it howling like Red Indians.” Famously, it didn’t end well for Custer.
In public, Si studiously backed the soft-spoken Gottlieb, praising his preservationist instincts and dismissing the critics who, Si believed, wanted the magazine to “run pictures and run color and run stories on Harry Helmsley,” the scandal-tarred real estate magnate. Privately, though, he was worried. Si was something of a gambler: in his twenties, a friend recalled, he learned Yiddish phrases so he could play games of chance with the Seventh Avenue garmentos he’d met through Vogue. Now Si had invested much of the Newhouse legacy in the wager that he could prove himself a capable steward of a literary treasure. Steve Florio had channeled his inner Barnum to improve the magazine’s advertising and marketing effort, but by the start of 1992, The New Yorker was still in the red. Worse yet, it had little cut-through in the national conversation. Si didn’t really mind losing the money: between the local newspapers, with their fat margins, and his brother Donald’s shrewd investments in the bustling cable industry, the family business was doing gangbusters. But the losses from its magazines were only worth it if the editors achieved the right level of renown, if the articles received notice on the morning shows and in gossip pages—if the glossies functioned as a highly tangible reminder of Si Newhouse’s ringmaster role in the culture. And plastic guitar picks weren’t going to cut it.I
Si raised the subject with Tina in January 1992, in his usual sidelong manner. “How much do you read The New Yorker?” he asked, somewhat to her bewilderment, during a meeting in his spare executive office at 350 Madison. Tina was well acquainted with Si’s sphinxlike utterances. Not quite knowing where he was going, she hedged: “Not much lately.” The seconds ticked by. Finally, Si asked how she might go about editing it. For Tina, the timing was apt and inapt at once. Her son, Georgie, who had been born two months premature, had learning disabilities and would later be diagnosed with Asperger’s; Isabel, her daughter, was not yet two. The notion of spending less time with her young offspring immediately struck her as painful. But professionally, Tina was also feeling antsy. Over the years, she had been tempted by opportunities elsewhere: Condé’s great rival Hearst hoped to put her in charge of Harper’s Bazaar, and Barry Diller had mused about putting her in charge of a Hollywood movie studio.
She’d turned them both down. Condé Nast was the closest that the late twentieth century had come to reassembling the great Old Hollywood culture factories of the 1930s. Overseen by a Jewish outsider, employing the finest artisans and visual technicians of its day, the company generated a voluminous output of entertainment products celebrating the wit and manner of upper-class splendor that were then transmitted to the hinterlands, where the masses could marvel at and consecrate the most beautiful women and men of the day. In 1992, Condé Nast was MGM and RKO rolled into one. And Tina, for all her discomfort with Si’s defenestrations of Grace Mirabella and William Shawn—her awareness that her mercurial Medici could withdraw his patronage, with little warning, at any time—still appreciated the freedoms and benefits that only the Newhouses could provide. Condé Nast, for all its growth in the 1980s, was still run like a mom-and-pop—or, rather, a bro-and-bro, with siblings Si and Donald in charge of every aspect of its privately held operations and accountable to no one besides themselves. This was why, when Si wanted to stop Tina from leaving for Bazaar, he offered to pay in perpetuity the long-term medical expenses of her aging parents in Europe; why he threw in a five-digit annual clothing allowance. Plus, as the Demi Moore cover proved, Americans were talking about Vanity Fair, not a lesser title at Hearst.
Still, Tina was stirring for a new challenge, something more intellectually stimulating than the world of Hollywood that she and Vanity Fair increasingly inhabited. Seated beside Richard Gere at a gala dinner, Tina had struggled to muster the energy for small talk, finally asking the actor, “What are you working on?”
“My spiritual life,” Gere replied.
Gottlieb, meanwhile, had an inkling that his close friend Si was not entirely happy with his tenure. But he liked his version of The New Yorker: the Jane and Michael Stern exegeses on chilies, John McPhee’s novella-length meditations on geology. Years later, in his memoir, Gottlieb bragged about publishing “a piece that had a radical influence on the way bats were perceived and treated in America.” (He meant nocturnal mammals, not Louisville Sluggers.) Confirming the qualms of people like Calvin Trillin, who questioned Gottlieb’s lack of interest in topical journalism, he continued to edit the full-length books of favored authors like Robert Caro while putting out a weekly magazine.
One weekend in Palm Beach, in early 1992, Si and Gottlieb took a walk along the sand. Si made clear that he needed to make a change; according to Gottlieb, Newhouse said the magazine was everything he had hoped for, “but he didn’t like the demographics.” Privately, Gottlieb wondered if Si was under pressure from his more cost-conscious brother, Donald, who had never been keen on the New Yorker purchase in the first place. But blithe as ever, the editor took it in stride. “I’m good at putting out the magazine the way it is,” Gottlieb declared later that year. “I didn’t want, nor was I really equipped, to rethink the magazine to the extent that Si came to want.”
Newhouse could be ruthless in cutting down his editors, but when it came time to formally dismiss Gottlieb, he felt racked with guilt. In 1971, after he fired Diana Vreeland, a vivid nightmare jolted him awake; in 1992, Si suffered through a sleepless night before he sat down with Gottlieb one day in June for their usual lunchtime sandwiches. (Gottlieb was not a Four Seasons guy, which in Condé world was part of the problem.) After delivering the news, Si immediately offered a consolation prize—and here was where the singularity of the Newhouse empire came into play. For his five years of service at the magazine, the company would pay Gottlieb roughly $350,000 a year for the rest of his life. Gottlieb died thirty-one years later, in 2023, at age ninety-two. By a conservative estimate, Advance Publications paid him about $10 million over three decades to not work at its magazines. No wonder that Gottlieb, after being fired from the most prestigious job in literary journalism, denied any rancor. Asked by a reporter how he was feeling, he invoked the title of a campy country song about a lovestruck newlywed: “I’m the happiest girl in the whole U.S.A.”
Gottlieb would later claim that at the time of his firing, Si had not yet made up his mind about a replacement. Was this true? Tina Brown said that Si’s official job offer arrived in the middle of June 1992; startled, she asked if she could take the summer to consider. The next day, Si showed up in her office and asked, “Did you make up your mind yet?” Gottlieb, meanwhile, had flown to Japan with Ingrid Sischy to judge a literary translation contest. Si planned to reveal everything upon Gottlieb’s return in July. This, in hindsight, was laughably optimistic, given the speed at which gossip traveled inside Condé Nast. When the news started to leak, during the last weekend in June, Si moved up his big announcement. A sleep-deprived Gottlieb found himself fielding reporters’ phone calls from his hotel room in Tokyo. Tina’s accession was seismic enough to merit the front page of The New York Times, although it was widely assumed that the woman who turned the flailing Vanity Fair into a global phenomenon had always been at the top of Si’s wish list of candidates he wanted to take charge of the jewel in his magazine crown.
But as Graydon Carter tells it, he had The New Yorker before Tina did.
BEYOND THE FACT THAT HIS byline was hard to forget, E. Graydon Carter would have come to Si Newhouse’s attention by 1984 at the latest, when he wrote the Donald Trump profile for GQ that generated the idea for The Art of the Deal. In 1986, he and a former Time colleague, Kurt Andersen, founded a new monthly called Spy. Plucky and scathing in its satire, Spy combined investigative reporting, inventively droll prose, and visual pizzazz to lay bare the foibles and excesses of status-crazed 1980s Manhattan. Among the magazine’s pranks was to mail checks of smaller and smaller quantities to wealthy celebrities and wait to see who was avaricious enough to cash them; Trump redeemed a check for thirteen cents.
Two years into Spy’s run, Si approached Graydon and Kurt about acquiring a 25 percent stake in the magazine. This was somewhat surprising, since Condé Nast—and, in particular, Tina Brown and Vanity Fair—was among Spy’s favorite targets. Si himself would be cited in its pages for “his famous aversions to leisure and interaction with other human beings”; he also fell for the check prank, cashing one worth sixty-four cents. Perhaps Si wanted to use his money to neutralize a threat. Or, as a magazine enthusiast, he may have simply been impressed by the quality of the product. (Likely a bit of both.) In any case, the deal was never consummated, though the possibility prompted a spirited discussion in the Spy offices about what Si might choose for his first cover. The consensus: “Those Nasty Men at the IRS,” a joke about Si and Donald’s epic, years-long tax dispute over their father’s estate, which they eventually won.
Graydon had also developed a powerful friend inside Condé Nast: Anna Wintour. In later years, long after both editors ascended to imperial status, the Anna–Graydon alliance would sour, and in 2016 it was Anna, by then Condé’s artistic director, who informed Graydon of the budget reductions that partially prompted him to quit. But in the 1980s, the two admired one another, a Canadian Anglophile and a Brit bonding over their emerging success in Manhattan media. “We were friends,” Graydon recalled to me. “We’d have dinner and things like that. She was really cozy and conspiratorial. I had great affection for Anna.”
Graydon wrote for House & Garden prior to Anna’s takeover of the design magazine in 1987. Impressed by his work, she brought Graydon along with her to Vogue the following year, awarding him a contract to write features. The notion that the chief Spy man, who had made his reputation scorching the ruling class, would accept a side hustle at Vogue raised some eyebrows. Graydon acknowledged that while there was a conflict of interest, he would not modify Spy’s approach toward covering Condé Nast. Besides, he told a reporter, he needed the gig “to stave off poverty, make a car loan, and pay for my kids’ school.”
In truth, it was a shrewd move by both. Graydon, who may have suspected that Spy’s flame would burn brightly but quickly, burnished his journalistic reputation and laid some groundwork for a future career move. Anna, meanwhile, could brag to Si that she had successfully coaxed the city’s most scathing satirist into the Condé tent. (“I figured it was a protection racket situation,” Graydon told me, “but I was fine with it.”) Spy tended to give friends a pass from the usual acid bath treatment, and indeed, Anna, despite her notoriety and sway in late 1980s New York City, was conspicuously absent from the magazine’s pages. Si also got off relatively easily: In a 1987 Spy feature about New York’s vertically challenged power players—“Little Men: How the Runts Have Taken Over”—the diminutive Newhouse was mentioned only in passing, whereas Lawrence Tisch was labeled a “dwarf billionaire” and Henry Kissinger a “socialite–war criminal.” At one point, Susan Morrison, Spy’s executive editor (and a former Vanity Fair staffer), pitched Graydon on a regular gossip column about goings-on at Condé Nast. It would be called “The Women,” a nod to the Clare Boothe Luce play from 1936 about the lives of pampered Manhattan socialites. Graydon nixed the idea, although he did not prevaricate about the reason: he didn’t want to offend Si, whose paychecks from Vogue helped cover his children’s tuition. (Actually, Si may not have minded: years later, over dinner at the Connaught in London, Si told Graydon that he’d always wanted Spy to run a Condé gossip column, “so I would have known what was going on.”)
By 1992, Anna would have been aware that Si was seriously considering a change at The New Yorker. It is likely that she recommended Graydon, if not for The New Yorker per se, then as a potential editor in chief. At Condé, Si acted as an emperor: his whims alone determined the fate of even the most powerful editors. (The brutal backstory of Anna’s own accession was proof enough of that.) Elevating Graydon would gain Anna another ally at the top ranks of the company—one who owed his career at Condé to her. The move would also prevent Si from appointing a new, unknown rival who might threaten Anna’s status in the Newhouses’ court. No slouch himself, Graydon had also taken steps to attract Si’s attention. In 1991, Spy was sold off to outside investors, and Graydon left to assume the editorship of The New York Observer, a weekly that chronicled the city’s power elite. Although the paper was mainly read in pockets of the Upper East Side, Graydon sent copies to friends at the Condé Nast offices in London and Paris. When Si toured his European outposts, he kept spotting the pink-hued Observer on his editors’ desks. As Graydon put it later, “He thinks this is a fucking international hit!”
The call finally came. Si wanted to meet.
“I’ve got two things, and I wonder if you would be interested,” Si said, after he and Graydon sat down inside his apartment overlooking the East River. “The New Yorker or Vanity Fair.”
For once, Graydon was speechless. Two thoughts flashed through his head. The first was how far the boy from Ottawa had come. Here he was, on the cusp of taking over the magazine he had worshiped for much of his life, that had fired his youthful desire to attain the heights of urban sophistication. The second was: “Jesus Christ. Vanity Fair?” Thanks to all the nasty things Spy had written, half the staff probably wanted him dead. And now he was supposed to be the editor? How the hell was that going to work?
“You know, to be honest,” Graydon began, “we’ve made fun of Vanity Fair for the last five years…”
Si cut him off. “Okay. The New Yorker.”
Graydon staggered out of Si’s apartment barely believing what had happened. He’d been sworn to secrecy, but Si said the announcement would come soon. “One hundred percent,” Graydon told me, when I pressed him on whether Si had explicitly offered him the job. “We had a salary—everything.” Graydon told only his wife, children, his agent, and his best friend. In the evenings, he sketched out his plans for the magazine, using a code name: “The Pencil.” Then, shortly before he was expecting the news to become public, his phone rang. He picked up and immediately recognized the voice of Anna Wintour.
“It’s the other one,” she said.
Graydon froze. “I don’t know what you mean.”
“It’s the other one,” Anna said again. “Act surprised.” Click.
About an hour later, the phone rang again. “It’s not going to be The New Yorker,” Si Newhouse told Graydon. “It’s going to be Vanity Fair.”
Recounting the story to me thirty-one years later in his Greenwich Village apartment, Graydon showed no sign of bitterness. “I have no idea what happened,” he said. “My guess is, Tina probably thought, you know, ‘If anybody’s going to have The New Yorker, it’s going to be me.’ ”
He added, “I don’t blame her.”
AFTER MY CONVERSATION WITH GRAYDON, I contacted Tina Brown. I told her I was hoping to get to the bottom of what I called an “enduring mystery,” the precise sequence of events that led to her selection as editor in chief of The New Yorker.
“It’s one of the enduring mysteries to me, too,” Tina replied, “and sadly so entrenched in Graydon’s head, it has led to decades of unfounded bitterness towards me.”
Tina cited her 2017 book, The Vanity Fair Diaries, which dates her first discussion with Si about The New Yorker to a lunch at the Four Seasons on July 12, 1988, when he asked her opinion of the magazine’s performance. She wrote that Si brought up The New Yorker again three months later, but, Hamlet-like, did not seem sure if he wanted to offer it to her or not. Tina said she encouraged Si to keep Gottlieb in place for the time being, in part because of her ambivalence about the strain on her family of running a weekly magazine. More explicit discussions followed in January 1992.
“Si first talked to me about editing TNY as early as 1988, and far from grabbing it out of Graydon’s clutches, I was ambivalent about it all the way through to 1992, when he conclusively and directly offered it to me,” Tina told me. “I was very attracted to it creatively, but with two small children, one of them with special needs, I was concerned it would add impossible strains to family life. I also felt that Gottlieb should be given more time, or it would be impossible to step into the roiling TNY office still furious about the firing of Shawn.
“By 1992, I was beginning to feel ready to make the change and was being courted by several other media companies, but I still felt I couldn’t do the TNY job unless I could persuade my mother to move to the US and help with the kids. She did and I accepted. Never at any time throughout all this did Graydon’s name come up to me as a possible alternate candidate.”
Tina described herself as “bedeviled by Graydon’s angry recollection.”
“Clearly, Graydon wouldn’t make up his version,” she said, “so I am perfectly willing to believe that Si was also talking to him in the early nineties. I know he did talk to Ed KosnerII about TNY at some point in the late eighties, but went off the idea.
“By the way,” Tina added, “Si never asked me whether I thought Graydon would be a good editor of Vanity Fair! Again, you might think my opinion, as essentially its founder editor, would have been useful. Most people thought that if I left, I would be succeeded by Adam Moss,III and I was surprised by the Graydon pick as he had no experience with glossies, but he turned out wonderfully well. So all I can think of is this is how it went down: Si talked to Graydon about the job—perhaps as a backup, given my own hesitancy for so long—and then simply went off the idea. Why, I don’t know. Perhaps Alex was against it.
“It was classic Si MO,” Tina added. “BUT IT HAD NOTHING TO DO WITH ME!”
Si, for his part, publicly addressed the rumor in 2000, telling a journalist that he was not attempting to leverage Graydon’s interest to entice Tina to take on the role. “I talked about both jobs being open,” Si said of his conversations with Graydon. “At the time, it was not clear that Tina felt she could handle The New Yorker, that she was ready to deal with a weekly, so there was some uncertainty. However, my feeling at the time was that Tina would accept The New Yorker, as she did, and I was thinking of Graydon more in terms of Vanity Fair.”
However it happened, it was Tina’s magazine now.