“Shelby was the Marlboro Man to David’s Pillsbury Doughboy,” maintains a well-placed observer to Anna’s blossoming relationship. “Anna, who is one of the world’s great flirts, and Shelby, who is a skirt chaser extraordinaire, fell for each other the moment they locked eyes at that gala. She was like a schoolgirl, acting sexy with him. And he was smitten. It took a while for them to really get serious—they were both married, for God’s sake!—but their meeting that night sealed the fate of both of their marriages.”
Until she met Bryan, Anna had been viewed as a caring and loving wife, which was quite a feat, especially during the period when she was alone in London running British Vogue and later spending long hours changing HG and American Vogue into her image.
Friends say that, despite her ambition and drive and the demands of her career, Anna had always tried to be compassionate and sensitive to her husband’s needs, as he was to hers. “There was a point about midway through their marriage when David was going through major suffering from ulcers,” says a pal who knew Anna from her days with Jon Bradshaw. “Anna was just so concerned, and I don’t think my wife would be as sensitive and caring to me as Anna was to David. I was there at their house in the Village one day and David had the ulcers and there were tears in Anna’s eyes. She was worried about getting the right doctors for him, and the fact that he couldn’t eat this and couldn’t eat that. And she was hugging him and holding his arm and crying. I was truly moved because in all my years of marriage, I’ve never seen that from my wife.”
Anna and Shaffer were also concerned and loving parents, and would do anything in the world for their children, Charlie and Bee. They were active as much as they could be in their very fancy private schools. They attended parents’ nights and orientations regarding the course curriculums for the year, and Shaffer at one point volunteered to be a safety patrol crossing guard at his son’s school.
But they rarely mingled with the other parents. “Anna always sat by herself at all school functions,” says a parent. “When she and David came together before they broke up, they sat next to each other and apart from everybody else. They were cold and aloof and felt they were above everyone else.”
However, they made at least one halfhearted attempt to be friendly when they invited a group of parents for cocktails and hors d’oeuvres. They’d even hired transportation and bought tickets to treat them all to a Neil Simon play. It was a gracious gesture and an apparent attempt by Anna to be more of a down-to-earth mother. But it turned into a strange scene because the Shaffers at the last minute never joined the others at the theater. Recalls one parent, “We had been rushed in and out of the house, and after they didn’t come with us to the theater, everyone was like, ‘What’s with them?’ That sort of sealed their fate with the parents in the class from then on.”
Not long after Anna met Bryan, he began sending her flowers and little gifts. Once things started heating up, Anna would close the door to her office at Vogue to chat with him on the phone, and she soon began taking long lunches, seeing him secretly. Anna knew the game well; she’d played it when she was with Jon Bradshaw.
Unlike the Euro types Anna had been involved with over the years, Bryan was all-American, his roots buried deep in the oil-rich Texas soil. The man for whom the city of Austin was named, Stephen F. Austin, was his great-great-great-great-uncle, and the town of Bryan, Texas, was named after another ancestor. The man for whom Shelby Bryan was named, Evan Shelby Smith, his maternal grandfather, owned enormous tracts of land in Brazoria County. Bryan’s father, James Perry “J.P.” Bryan, was a lawyer, his employer for many years was Dow Chemical, and he was a regent at the University of Texas. Bryan’s older brother, named after their father and also called J.P., was hugely wealthy, the money flowing in from a Houston oil and gas company he founded called Torch Energy Advisors.
Bryan was something of a jock. At high school in Lamar, Texas, he was a football player. “He also was a pompous ass at fourteen,” recalls a co-ed who became a prominent Houstonian. “Shelby was cocky, self-assured, and very good-looking. He was involved with the most beautiful cheerleader, he was big man on campus, handsome, and muscular—the same as he looks now [2004], but minus thirty or forty pounds. He was very popular and everyone adored him, for the same reason why people like him today. He’s a guy’s guy, a man’s man. Just very macho.”
She could have been talking about Bradshaw.
At the University of Texas, where he studied history and art, Bryan played some football and at one point was a Golden Gloves boxer. He went on to get a degree in law. A pal, Fred Baron, now a powerful Dallas attorney, called him “the Great Gatsby—you could tell he was going to be successful.” In the early seventies, when Anna was just starting out in the fashion magazine world in London, Bryan worked for Ralph Nader in Washington, D.C., then went to the Harvard Business School, and for a time was at Morgan Stanley. From there he eventually got in on the ground floor of the cellular phone business and made a bundle.
Along with being a macho jock, with a good business head on his broad shoulders, Bryan was “a mama’s boy,” says another Houstonian—and that might have something to do with why he fell for Anna, and she for him.
For the two, mama and Anna, were remarkably alike.
Bryan’s mother, beautiful Gretchen Smith Bryan Chandler Josey, who died of cancer in the early 1990s, was a fashionista par excellence who draped herself in Chanel or mixed and matched it with Yves Saint Laurent. She was a culture maven, involved in the Houston opera and in charity work, and was driven and ambitious.
“Gretchen was very Dina Merrill–ish,” says a friend. “Thin, not tall, she had the look of society, very country club, with a little edge. She had the pretty blond frosted hair, not the cookie-cutter haircut. She had an artistic flair—her clothing, her whole look was different from other Houston women. She was a style setter. If Shelby was looking for a woman like his mother, he couldn’t have chosen anyone more like her than Anna Wintour, in terms of style, glamour, and fashion.”
Shelby Bryan’s mother also was said to have figured in the demise of the marriage of wealthy “old money, old guard” Houston oilman Jack Josey. “Gretchen didn’t come from old money, but she married into Jack’s family and Jack’s reputation and Jack’s social standing,” says a friend, “and then the closets became full of designer names and couture.”
Josey had followed in the tradition of the legendary married Houston oilmen who kept one or more women on the side, and it was rumored that Shelby Bryan’s mother, before Josey married her, might have been one of them. As a friend said of Josey, who died in 2003, “He loved to party. He liked the women. Shelby followed in his footsteps.”
There was one legendary Houston oilman who is said to have built an apartment complex in which he housed all of his ex-mistresses, took good care of them, which kept them from talking. As one knowledgeable Hous-tonian noted, “Jack Josey’s father had mistresses, too, and he also had a very understanding wife. Every time she caught him, she got diamonds. That’s how these rich Houston men grew up. It was a way of life.”
The wealthy Josey was Shelby Bryan’s mother’s third husband. Her second, after she arrived in Houston with Shelby and his brother after her divorce from their father, was to a much younger local TV news personality. That marriage lasted only a year or two, but they remained friends.
During that time she was the proprietress of a chic little antiques shop.
As the friend points out, “Gretchen married well but divorced better. Jack Josey was a great catch with a money-is-meant-to-be-spent-and-have-fun philosophy.”
By the time his always glamorous and chic mother married the millionaire oilman, Shelby Bryan was grown and earning his own fortune.
The Joseys had one of the grandest houses in all of Houston. Though she had decorators, she was very involved in supervising style, design, and theme—just like Anna. The house was filled with antiques that she chose and a world-class art collection that she and her h
usband pulled together. Art and the love and knowledge of it was another interest Shelby’s mother and Anna had in common.
“Gretchen was one of the most beautiful and fashionable women Houston had ever known,” notes her friend Diane Lokey Farb, a powerful Houston real estate agent. “You couldn’t take your eyes off her. Gretchen was always in Chanel. Beyond that she was a very driven, very strong woman. Whatever Gretchen wanted to achieve, she would just go forth and achieve.”
Anna appeared to be a virtual clone of her new lover’s mother.
Shelby Bryan tended to pursue interesting, chic women. Anna wasn’t his first.
At twenty-two, just out of law school, Bryan married Lucia Ann Rawson, a pretty Houston society woman two years older than him whom he had started seeing in college. Like Bryan’s mother, his mother-in-law, Natasha Rawson, said to have been a Russian ballerina in her day, was a fashionista.
“I always confused Natasha with Gretchen,” notes a Houston socialite friend. “Natasha was divine, glamorous, a natural and great beauty. Lucia looked nothing like her mother. Lucia’s a nice, cute, lovely, and charming gal—quiet and low-key. But her mother looked just like Shelby’s mother—breathtaking, with fine bone structure and clear transluscent porcelain skin. I would see her and I would think, ‘Why are you in Houston? You belong in Paris.’”
Shelby and Lucia Ann Bryan had two children, Ashley, who was born in Boston in 1973, and Alexis, born in New York, in 1976.
Four years after the second child, the marriage fell apart, and the couple separated on November 1, 1980. Bryan filed for divorce on the grounds that his marriage “had become insupportable because of discord or conflict of personalities.”
The divorce was final on August 6, 1981, a few weeks before what would have been the Bryans’ thirteenth wedding anniversary, and she got a nice settlement that continues to the end of 2024. From their house in exclusive River Oaks, Bryan was permitted to take a punching bag. But he also kept property the couple owned in the tony Wainscott area of East Hampton, a condominium in Houston, some fifty-six acres of land in Brazoria County, Texas, along with the Porsche, the Jaguar, and the Pontiac, and stock in a number of companies.
He wasted no time in remarrying, tying the knot for the second time some seven months after the divorce. On March 12, 1982, he married his girlfriend, Katherine Gurley, a brunette Kansas beauty with a young son—but not before she signed a prenuptial agreement. Some six months after the Bryans’ wedding, their first son, John Austin Bryan, was born. A second son, James Alexander, was born in 1985.
Anna and Bryan tried to keep their affair a secret, but they were reportedly spotted early one morning leaving an elegant Manhattan apartment building, Anna draped in a chinchilla coat meant for evening wear. The sighting reached the media, and in 1999 the scandal broke. At home, David Shaffer learned of the affair when he found a message Bryan had left for Anna on their answering machine.
The psychiatrist called Katherine Bryan, the psychologist. “Your husband and my wife,” he is said to have told her, “are fucking each other.”
The gossip press was all over the story like Chanel on Anna. The outrageous Internet fashion industry Web site Chic Happens, overseen by Ben Widdicombe and Horacio Silva, two thirty-something Australians working in New York, was the first to break the story based on an anonymous e-mail. Chic Happens was designed for fashionistas and people within the industry who wanted to drop a dime on their colleagues and bosses. Where else could one find items such as “Which aging glossy editrix dyes her pubic hair to cover the grey?” Because Anna was at the summit, she was a particular target of Chic Happens, and the Web site ran bitchy items about her. But the story about Anna’s adulterous affair was the biggest. Widdicome, who later became a gossip columnist at the New York Daily News, and Silva, an editor at The New York Times, never revealed their Deep Throat but noted that most fashion magazines “treat their staff like dirt . . . if you screw someone they get on the phone. They want revenge.” The pair believed that Anna had subsequently attempted to censor their appearances on cable TV; they were told by station executives they could not mention her name, or any of Condé Nast’s magazines, on camera.
“Page Six,” the must-read gossip column in Rupert Murdoch’s tabloid New York Post, was running neck and neck with Chic Happens, and ran a blind item in February 1999 asking, “Which fashion oracle—who appears to have an ideal home with a loving husband and kids—has been having a yearlong affair with a telecommunications titan who also appears to have a wonderful marriage?”
By mid-June, the “Intelligencer” gossip column of New York magazine, Anna’s alma mater, reported under the headline “Wintour of Discontent?” that after a “series of teasing half-blind items in the tabs” Anna’s “love life is fast becoming a public drama.” The item didn’t mention her lover by name but described him as a “millionaire Democratic fund-raiser” and said that they’d been involved “for more than seven months, in a none-too-secret dalliance that has raised eyebrows all over town.”
Asked for comment, David Shaffer stated, “I have no plans to get divorced, and I hope Anna has no plans to get divorced.”
In London, Anna’s father’s former newspaper, The Evening Standard, quoted an anonymous “close family friend” as saying, “I think for the first time in her life, she is madly in love with someone and she finds the whole experience totally overwhelming.”
When Texas Monthly did a small profile on Bryan in the wake of the breaking scandal, he confirmed that he and his wife had separated. But regarding Anna he stated, “There’s an old-fashioned view that your personal life should be kept private, and that’s my view.”
In her syndicated column in Newsday, Liz Smith called Bryan “the romantic fly in the sticky ointment of Anna Wintour’s marriage. . . . And let me add this, I have heard only the most unsettling things about Mr. Bryan, all about how ‘fascinating, naughty, thrilling, exciting, and bad-boyish’ he is said to be. Conversation about this tycoon makes him a cross between a movie star and Lord Byron. And I am told by everyone observing that the delectable Wintour is over the moon in love with him, more excited and happier than she has ever been in her formidable and controlled life. It isn’t just his money, either, although, of course, money is always in vogue.”
While Anna refused to talk to the press about the scandal, her and Shaffer’s high-powered New York lawyer and spokesman, Ed Hayes, put up a smoke screen. “I promise you that I’m not doing a divorce. They’re together, they love their children, and they’re going to stay together,” he said.
Every September, the world’s fashion press descends on New York for the annual rag trade bacchanal called Fashion Week, when the beautiful models strut their stuff, when fortunes and reputations of designers and manufacturers are won or lost, depending usually on how Anna reacts to what she sees and what Vogue subsequently features in its glossy pages.
But all the attention for the 1999 Fashion Week was on Anna herself, seated, as usual, front row center. Her marital scandal was on everyone’s glossy lips.
As the fashion reporter of London’s Daily Telegraph, pointed out, “the fashionistas loved it. After all, this is an industry that thrives on celebrity gossip at the best of times, and when the target is one of its own—indeed the widely feared queen of them all—you can virtually hear the shears being sharpened.”
That week, the September 20 issue of New York magazine, with every fashion person in the world in town, chose to make Anna its cover girl. The story was headlined “The Summer of Her Discontent,” and it went into gossipy detail about Anna’s extramarital relationship. The article called Bryan “a flashy extrovert . . . with a notoriously roving eye.”
On the outside, Anna was very British stiff upper lip, but on the inside, according to a close source, “She was embarrassed and devastated. For someone like Anna, who is so private and secretive, to have her dirty laundry strutted down the runway for the world to see, to have the biggest skeleton in her closet on di
splay, it was the worst. She railed against the press, against her competitors at other magazines who were gloating. Anna’s never been much for introspection, but she suddenly was doing a whole lot of soul-searching. She felt guilty. She felt sick. She didn’t know which way to turn.”
And, indeed, there was great schadenfreude in the bitchy, wicked world of fashion.
Despite her disgust at all the horrendous gossip, the media-savvy, tight-lipped, ultraprivate Anna actually cooperated somewhat with New York magazine as it was preparing its story and gathering photos. Surely she must have realized that the weekly was rubbing its hands together and was going to do a number on her. But she agreed to be interviewed, to a point. The article quoted her as saying just forty-two words regarding the scandal. Over lunch at her favorite table at the Four Seasons with the writer she said, “There are certain things that no one wants to read about in the tabloid press.” She added, “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 don’t focus on.” She also acknowledged that there was nothing in any of the reports that she wanted to correct.
However, Anna’s involvement with the photographs that ran with the article was an entirely different story. While she agreed to the brief interview, she refused at first to pose for an exclusive photo and instead sent over to cover editor Jordan Schaps, her longtime friend at the magazine, a box containing pictures she was authorizing the magazine to use.
“One was in black and white taken by [Vogue fashion photographer] Mario Testino,” says Schaps, “and it had Anna with bangs down to her eyebrows, big sunglasses, and a fur coat pulled up so you barely saw her. It could have been Audrey Hepburn or Greta Garbo. She looked to be concealed, hiding, and very removed.”
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