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The Summer of Her Discontent

As she fought off a barrage of bad press over staff defections and her affair with a married man, a funny thing happened to Vogue's famously frosty Anna Wintour. She began to seem, well . . . human.


Anna Wintour, the most powerful woman in fashion, is curled behind a sleek wooden desk in her vast corner office in the new Condé Nast building, a phone tucked beneath her Louise Brooks bob, forehead buried in her hand. Behind her, the crisp September sunlight is stained blue by a twenty-story Times Square movie poster for Deep Blue Sea: a tidal wave bearing the devouring jaws of a shark, an image that fills her entire wall of windows.

"Oh, that," says the Vogue editor-in-chief, in a distracted tone, when I note the presence of this oversize predator. "I try not to notice it." But in a world dominated by symbol and gesture, Wintour's new view is too delicious a metaphor to ignore.

These have been unsettling days indeed for Anna Wintour, the British-born editor who has ruled over the world's preeminent (and most profitable) fashion magazine for the past eleven years. Hidden behind a pair of glued-on Chanel sunglasses, she transformed Vogue from a lackluster legend into a blockbuster that generated $149 million in ad revenues last year. A notorious workaholic with a cool, imperious manner, Wintour has as many enemies in the fashion set as admirers. "She's the scariest woman in the whole wide world," said one designer. "Not the kind of gal you'd want to cross."

But in the past few months, her flinty ice-queen facade has begun to melt. Last February, her affair with married Texas cell-phone millionaire Shelby Bryan made tabloid news, wrecking her fifteen-year marriage to child psychiatrist David Shaffer and frequently reducing her to tears. While she and Bryan are now both separated from their spouses and happily together, friends say she's obsessed over her failed marriage and worried about the impact a nasty divorce will have on her children, a girl and a boy aged 11 and 13. As the city's gossip columnists circled -- feeding on rumors of Parisian trysts, gifts of fat emeralds, and even marriage proposals -- Wintour dug in her spiked Manolo Blahniks and declined to comment, directing all inquiries to her attorney, Edward Hayes.

Then, in June, came another burst of unwanted publicity: Wintour's top lieutenant at Vogue, Kate Betts, bolted for the editor-in-chief's job at rival Harper's Bazaar, an All About Eve scenario that the catty fashion world lapped up with delight. Smart and driven, the 35-year-old Betts played a vital role at Vogue, where she was responsible for the magazine's fashion news and many other features. Her departure -- accompanied by several writers and followed by that of fashion director Paul Cavaco -- left Wintour reeling to find replacements.

With pushy newcomers like InStyle and Marie Claire gaining momentum and stealing Vogue's buzz, there was talk that Condé Nast chairman Si Newhouse was losing confidence in his golden girl. Friends whispered that Wintour was burned out, bored with fashion and more interested in joining society than covering it. "The general feeling is that people are abandoning Anna," says one Vogue editor. "And that her heart isn't in it anymore." In November, she will turn 50.

Inside Vogue, "it's really weird," an editor tells me later. "It's like, we all know about the affair, and every time there's something on 'Page Six,' it's all you talk about. It's kind of chipped away at her whole persona. Like she's been caught in the act of doing something . . . human."

Such humanness has made Wintour vulnerable for perhaps the first time in her professional life. "What I feel bad about is people trying to use whatever situation is going on in her life to attack her professionally," says Wintour's close friend Oscar de la Renta. "Is she giving up her job? Is she not doing as good a job? It's easy to try to beat someone down," he continues. "But anyone who'd try to do that to her would be a fool."

Indeed, Wintour dodged the arrows and soldiered on through August, lunching at her usual haunts and maintaining a high profile. On the week of August 16, she headed to The Four Seasons for a long tête-à-tête with her friend Patrick McCarthy, Fairchild Publications' chairman. Friday's Times revealed a surprise: Newhouse had agreed to buy Fairchild from the Walt Disney Company for $650 million, merging two of fashion's biggest publishers. Wintour had agitated for the move for years. The deal potentially gives her control over a vast fashion-publishing empire that includes Women's Wear Daily and W magazine. The timing may have been coincidental, but it looked enough like a masterful counterstroke to a season of bad publicity.

This week, as the world's fashion press gathers in New York for Fashion Week, Wintour is sure to be the prime topic of discussion. For the first time, Vogue's Website will feature live video reports from the Bryant Park catwalks. But the most interesting spectacle, Wintour knows, will be sitting front row and center. "It's like an accident," snipes a rival editor. "You can't help but look."

Though she resolutely refuses to discuss the affair, Wintour acknowledges that all the attention has come with a price. "There are certain things that no one wants to read about in the tabloid press," she says haltingly. We are installed at Wintour's table at The Four Seasons, deposited there by her driver. Tanned from a recent Greek vacation, she is dressed casually in a tight Calvin Klein shirt and a floral Gucci skirt, her sunglasses tucked safely out of sight. She is picking at a rare burger, sans bun, and a baked potato, her regular lunchtime meal. I ask her how it feels to read about her private life in the papers. "You know that your friends and your family have one vision, and if the outside world has another, then that's just something that you just don't focus on."

But the subject seems to unnerve her. Not long ago, when animal-rights activists dumped a dead raccoon on her plate in this very room, Wintour coolly ordered a waiter to remove the offending animal and continued with her meal. Today, however, she seems battle weary and nervous.

I ask if there are press inaccuracies she'd like to address. "No," she says brusquely, and returns to her meal. Suddenly, she shakes the bangs from her green eyes and looks up with a warm smile. "But thank you for asking," she says.

The first installment in fashion's latest drama began last winter with a series of teasing blind items that finally exploded in June, when the press outed Wintour's paramour. J. Shelby Bryan, 53, was a telecommunications millionaire, a well-connected Houston native with rugged good looks and a wife of seventeen years.

He and Wintour met when they were seated next to each other at socialite Anne Bass's table in November 1997, during a New York City Ballet gala at Lincoln Center. Bryan, head of half-billion-dollar ICG Communications, is a Democratic rainmaker who raised $1.5 million for Democratic candidates, including Al Gore, during two 1997 fund-raisers at his posh Upper East Side home. To observers, the chemistry seemed obvious. Friends of Wintour's had long remarked on the disparity between the glamorous editor and her bookish husband, a respected child therapist. But friends say that for many years they were genuinely close. "His friends in Britain all marveled at how these two got together," says one British pal. "But David is a brilliant man, quite charming, and they love playing these word games. Anna is a big fan of all kinds of game books."

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