Anna Wintour and Tina Brown: Inside their Condé Nast rivalry

At the Royalton, Anna Wintour and Tina Brown could be found at different tables like queens on their own separate thrones.

Other editors, writers, models, and famous faces might mill about at this hotel’s posh restaurant, known humorously as “the Condé Nast café.” But the two star editors, with very different styles and tastes, attracted the most attention.

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In the early 1990s, the seemingly limitless largesse of Si Newhouse’s media empire was on full display during breakfasts and “power lunches” at this upscale hangout in midtown Manhattan.

During this era, much of the Royalton chatter, often tinged with a British accent, involved Wintour and Brown, who were quickly becoming celebrities in their own right.

“All of a sudden, Anna walked in,” recalled modeling agency exec Ivan Bart, about the first time he spotted Wintour on the runway-like entrance to the Royalton’s restaurant. “She had such an aura, a presence. I couldn’t believe it. I was like, ‘Oh my God, there’s Anna!’”

At the Royalton, more than 25 percent of the restaurant receipts were paid from Newhouse’s billionaire coffers. Hefty bills were signed by a phalanx of editors, writers, and business executives in his employ. Along the restaurant’s back wall, there was a row of “power booths,” half-moon-shaped seats in green velvet, where the Condé Nast people socialized with name-brand advertisers like Calvin Klein or other fashionable celebrities.

Tucked behind the reservation desk, the maître d’ kept a book containing Condé Nast mastheads so the appropriate seating could be found. One newspaper, the New York Observer, actually printed a map of the seating plan. It identified each booth and table with the editors who sat in them, deciphering their meaning in the overall scheme of Newhouse’s world. The best seats were reserved for Wintour and Brown.

“The celadon banquettes in the restaurant were gorgeously lit,” recalled Candy Pratts Price, a former Vogue editor. “Anna had the first banquette. Tina had a round table [around] which she could almost pull the curtain, like a medical room.”

The Royalton’s management “takes wonderful care of me,” explained Wintour, breezing in for lunch of mashed potato and a very rare hamburger sans the fattening bun. “I can be in and out in less than an hour.” Anna’s cool, thin never-changing appearance—with the same bobbed hair and trademark sunglasses—pleased the fashionistas, usually insistent on the latest look. They viewed Vogue as their bible and Wintour as its high priestess.

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The meteoric trajectory of Brown and Wintour’s careers at Condé Nast seemed like two parallel lines destined to collide someday as they came closer to the top. In this rivalrous atmosphere at the Royalton, many nibbled on little bits of gossips. They wondered which editor might be more in Si’s good graces—Tina or Anna? Whom between the two women did longtime editorial director Alex Liberman prefer as his eventual replacement?

Among the “Condé Nasties”—the media’s nickname for Newhouse’s whispering employees—there seemed a yearning for some bloody confrontation between the two editors, like something out of a Mafia movie. Or at least something very public like Newhouse’s televised “off with their heads” firing at Vogue, replacing Grace Mirabella with Wintour, a shock still fresh in everyone’s memory.

“The magazine mavens and gossip columnists who have speculated so relentlessly about Wintour’s designs on Mirabella’s job have made even more of her supposed rivalry with Tina Brown, a fellow Briton,” explained theWashington Post. It seemed only a matter of time until one woman knocked off the other.

Yet, direct confrontations between Brown and Wintour—like their early battle over the services of fashion editor Andre Leon Talley—were relatively rare. Publicly, they eschewed talk of any rivalry in their carefully prepared chats with the Washington Post and other sober-minded publications.

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“The press is already hoping for a rivalry between us,” Tina observed privately, early in her relationship with Wintour at Condé Nast. “Anna is too frontal for feuds and Vogue has never interested me. I suppose catfights are the cliché that always dog (as it were) powerful women working in the same business. Actually, her presence upstairs is a bit like suddenly having a sleek-haired race-horse pawing the other side of the fence.”

For these two ambitious editors, better to keep their hands clean and avoid the bloody chum thrown out anonymously to the press sharks at the gossip columns. They would outflank and out-flatter those inside Condé Nast. Being too obvious, too ambitious, not Miss Congeniality, was considered bad form for a female candidate seeking someday to run the billion-dollar Newhouse conglomerate, still very much a male-dominated domain.

So instead, the differences between Brown and Wintour were most apparent in their clashing styles and different tastes, their hard-driving approach to their jobs, and how they were personally perceived by higher-ups who would decide their fate should a final confrontation between them ever take place. For those caught in their fast-paced world, Anna and Tina seemed like two media superpowers, constantly upping the ante, trying to out-do the other, while their minions struggled to keep up.

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“I was trapped in an ecology of splendor,” recalled Joan Juliet Buck, a writer and editor who worked at various times for both magazines. “Most of what I earned…went on clothes to wear to parties for Vogue and Vanity Fair that Anna Wintour and Tina Brown threw in an arms-race escalation of launches, celebrations and landmark events.”

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Wintour and Brown appeared almost analogous as young British female editors only a few years apart. In an era when society still debated whether women could “have it all” in the workplace, both seemed modern exemplars—married to older men and mothers of young children yet deeply devoted to their high-profile jobs.

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“It’s very important to me to have my balance,” explained Wintour, with two children, a boy and girl, born in the mid-1980s. “You can do both—it’s just working out the priorities. To me, it’s unthinkable not to work. It’s unthinkable not to be a mother. Every time there’s a choice where I can put the children first, I’ll do that.”

While at Condé Nast, Tina also gave birth to two children, including a son with Asperger’s Syndrome. “George is a challenged boy,” she later explained of her oldest child. “There are a lot of issues that have been very demanding for us as parents. But when you have a kid that has a disability, you are so thrilled by the small triumphs.” Finding a balance between professional duties and home life was always a challenge. “It’s so damn tough to make the power women-to-mommy switch,” she explained.

Brown and Wintour were part of a group of British literary and media types living in Manhattan in the 1980s, both devoted workaholics swept up in the city’s hard-charging atmosphere. They shared a few mutual friends such as Gabé Doppelt, a staffer at various times for both of them, and jointly threw a book party for British writer Nigel Dempster. “She can come off as chilly but when the dark glasses come off she’s candid and confiding,” Brown noticed of Wintour. When her young son first showed signs of developmental problems, Brown asked Wintour’s husband, Dr. David Shaffer, a child psychiatrist, to meet him and Shaffer recommend more medical follow-up.

Yet a sense of competition always seemed present between the two, even when they were pregnant at the same time in 1985. As Tina confided in her diary: “I am now the size of a tank. How can it be that also pregnant Anna Wintour seems to have only a neat couture bulge under a long Chanel jacket while I am now the size of a helium balloon? She’s due two months before me, too—in January!”

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Inside Condé Nast’s headquarters, both Brown and Wintour were prized by Newhouse as decisive leaders, known for brilliant snap judgments and a keen sense of what was right for their respective publications. However, beyond their appearance and British heritage, plenty of differences existed between them, the kind that defined their opposite styles.

For example, though Wintour was the editor of a major magazine, she generally didn’t write anything. Her editorial strengths were expressed in the visual presentation and overall contemporary concepts found in Vogue. By contrast, Brown’s sharply-honed skills as a feature writer was evident throughout Vanity Fair, right down to her willingness to pay top dollar for staffers who got into the best parties and shared her vision.

In dealing with employees, Anna preferred a more hierarchical approach, like the post-war Fleet Street newsrooms once run by her father Charles. Everyone at Vogue seemed to know their place in the social pecking order. Like their austere leader, many Vogue staffers were bone-thin women who favored the finest clothes.

Meanwhile, at Vanity Fair, Tina acted as the impresario for a wide-ranging cast of characters, as if mirroring the theater experience of her parents. Rather than by fiat, she seemed inclined to convince with a good idea or a creative suggestion. Words rather than haute couture appeared her obsession. “I guess my style secret is that I like uniforms,” Brown later explained in denying any friction with Wintour. “I like white shirts in the summer and black shirts in the winter.”

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During these early years at Condé Nast, Tina clearly enjoyed the limelight more than Anna. When interviewed by the press, Brown took pride in coming up with pithy quotes, knowing from first-hand experience how a writer delights in an amusing comment or memorable insight. Certainly, Brown reaped the rewards of her good PR.

Wintour steered clear of inquiring questions by journalists or dutifully put up with them with polite rote answers and a guarded mien. Indeed, Wintour’s most memorable public expression was her cool stoic look exiting a limo or along the runaway in Paris, Milan, or New York. She left an impression rather than words. In the fashion world, Anna created a persona for herself, the way Americans once projected their fanciful dreams onto a silent Greta Garbo.

Perhaps Anna wouldn’t need publicity in the long run. Wintour’s taciturn style, far different than Tina’s constant fireworks sparking “buzz,” suggested there might be other factors at play in deciding who would run Condé Nast.

To borrow the well-worn metaphor of another Briton, philosopher Isaiah Berlin, Brown was the fox and Wintour was the hedgehog in their slow march to the top. Brown embraced America in all its glory and crazy experiences, while Wintour ultimately viewed it through the singular lens of fashion.

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In the early 1990s, Brown’s great success at Vanity Fair made her seem a natural choice someday to replace Alex Liberman—far more so than Wintour, still only a few years into her tenure at Vogue. The smart money, especially among those journalists outside Condé Nast, predicted Brown would be running the whole place in the not too distant future.

But Tina, as vainglorious as she was independent-minded, didn’t seem to understand Alex’s psyche—his underlying need to be deferred to, rather than challenged. This paradox was illustrated in April 1991, during Liberman’s fiftieth anniversary at Condé Nast, when Newsweek ran a revealing profile of the 78-year-old master.

“Some former high-level employees say that disagreeing with Liberman can prove fatal,” Newsweek reported. “Others, like Vanity Fair’s editor Tina Brown, argue that he appreciates intelligent disagreement; he simply has no patience for mediocrity.”

The Newsweek story’s implications were telling, like foreshadowing in some Russian novel. How many times did Brown engage in “intelligent disagreement” with Liberman? And did Alex really “appreciate” such conversations with a woman half his age, the same kind of female magazine editor that he had patronized for a half century—even if Tina considered herself less “mediocre” than the others?

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Touted as Si Newhouse’s whiz kid, Brown always seemed convinced that her talents and wit would win the day. She didn’t seem to appreciate fully how her considerable achievements in reviving Vanity Fair would be received warily by such an aging delicate egotist as Liberman. Tina failed to heed the lessons learned by her predecessor, Leo Lerman, who eventually concluded “Alex is evil—a dreadful being, a wretched murderous Russian of the blackest blood.”

Anna took a very different approach inside Condé Nast. Like Brown, Wintour’s name was also touted as a possible Liberman replacement. As early as 1988, the Los Angeles Times reported that “stories have been printed that Wintour wants Liberman’s post once he retires.”

But rather than outshine the old master, Anna seemed more intent on courting him. Far more than Tina, Wintour went out of her way to seek out Liberman’s advice, to make sure her vision for Vogue coincided with his own.

This stealth approach seemed the only way to overcome Brown’s celebrity and the speculation that she was the certain choice to lead Condé Nast someday. Instead, when the time came to choose his replacement, perhaps Alex would suggest her name to Si rather than Tina, who seemed her only other competitor on the horizon.

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