The move bewildered Andersen. "Before Graydon transformed and reinvented the Observer," he explains, "it was kind of a dopey thing. I mean, it wasn't like, 'Whoa, the brass ring!' It wasn't, 'Do you want to be editor of The New Yorker?' Not remotely."
He smiles. "So at least whatever sense of surprise I had was not compounded by great jealousy.
"It's funny," continues Andersen, now a co-founder of Inside.com. "On the one hand, you could say Graydon's temperamentally a conservative, kind of a Tory in his bones. On the other hand, he does make these radical breaks in his life, whether it's leaving Canada, starting Spy, leaving Spy, living on the Upper West Side, living in the Village, all these things. And at the moment Graydon's doing whatever he's doing, it is the greatest thing in the world. He can't imagine living any other way."
Carter transformed the Observer almost overnight. Founded in 1987, the paper started as a sleepy little attempt to cover local community-board meetings; Carter turned it into a gossipy, characterful rag about Manhattan's defining professions: the media, the law, real estate, entertainment, Wall Street. "He was a story-generating machine in those days," says Helen Thorpe, the writer who did the paper's media column at the time. "I got a lot of credit for 'Off the Record.' But what no one realized is that I got only half the items myself. Basically, Graydon would go out for these long lunches, and he'd come back slightly flushed, and then he'd dump in my lap the most unbelievable media gossip I'd ever heard."
Carter was thriving. Before even the first year of his tenure was up, S. I. Newhouse called to invite him by for a little talk. He revealed that Tina Brown wanted to leave Vanity Fair. Then he mentioned that he was also thinking of making a change at The New Yorker.
Carter jumped. The prospect of editing The New Yorker got him so excited he went home and drew up a plan to reinvent the weekly, then stuck in a murky, post-William Shawn amber. But it was not to be. Newhouse wanted Brown for the job. And when she finally said yes, he offered Carter second prize -- Brown's vacated Vanity Fair post. Carter accepted. Privately, he was crestfallen.
"I blew my relationship with Tina," Carter says. What I should have done was ask her advice more."
Newhouse insists he wasn't trying to use Carter to leverage Brown's interest in the job. "I talked about both jobs being open," he now admits, sitting in his spare, lunar office in the Condé Nast building. "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."
Graydon Carter announced he was leaving the Observer. Arthur Carter was furious. A decade later, he's still furious. "I was surprised," he says. "But, uh, it might have happened anyway. Truthfully, I found him to be homophobic and anti-Semitic."
He can think of only one example.
"He would use the expression, over and over again, 'Oh, he's just an old fruit,' or 'He's just an old Jewish fruit,' " he explains. "The first few instances, I thought it was just a bit of a joke, but when it was repeated over a period of time, I saw it was beyond that."
When I tell Graydon Carter about this at Da Silvano, he seems perplexed. At this point in our conversation, he has just named Arthur Carter as one of his seven or so major professional influences. "Well," he says, "I can easily see calling someone that as a joke. That's a holdover from Spy." He doesn't sound particularly defensive. "I'd say most of my friends are Jewish," he adds. "I don't know. I have no idea. I never even think about it."
"I'm sorry that Arthur feels upset," he says, a few minutes later, as the bitterness of the accusation sets in. "Because I have nothing but warm feelings for him."
The former editor of slash-and-burn Spy and the cheeky New York Observer at the helm of the celebrity-worshiping Vanity Fair? It was like the fox taking over the henhouse. Why did Newhouse do it? "Any editor is a gamble," he explains today, "but I think that between Spy and the Observer, Graydon had a flair for a kind of journalism that was important to Vanity Fair. Vanity Fair is a strange animal. It's popular, yet it appeals to a very cultivated taste."
And Newhouse seemed to understand something else. Carter was ready for the change. He wanted it. As soon as he accepted Newhouse's offer, he began frantically distancing himself from his past. "Spy is long behind me," he told USA Today. "Spy was a day job."
His former colleagues didn't appreciate it. "Given that I was still at Spy," says Andersen, "I felt as though he sort of defined Spy as a youthful indiscretion, which didn't particularly please me."
"Let me tell you something," Carter says now. "No one at Spy had three kids and a fourth on the way. That's the basis for almost all of it -- I had to make a living. If I'd been hired by National Geographic, I'd have learned about science and nature."
Even as Carter was airbrushing his years at Spy out of the picture, he was hastening to mend fences with the magazine's victims. He called Donald Trump, whom Spy relentlessly referred to as a "short-fingered vulgarian," and later became so friendly with him he attended his wedding to Marla Maples. At a party at Barbetta, Carter also sheepishly extended his hand to Liz Smith. She graciously accepted his apologies. "I admire him for it," she says in a drawl thick as soup. "Why should he go on being a professional shit if he could get out from under it?"
Ironically, Carter was also now the target of media coverage himself, and often it was his former colleagues who were writing about him. He hated it. Every item, no matter how trivial, was viewed as a betrayal. "I think he wished that the Observer wouldn't cover Vanity Fair at all," says Susan Morrison, who started with Carter at Spy and took over the Observer when he left. "But because of Graydon's own innovations at the paper, the Observer was fueled by media stories, and the credo of Spy had always been 'no sacred cows.' "