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Wolff often says he hasn’t had a boss since he left The New York Times as a copy boy 35 years ago. He cultivates the role of fearless maverick, though as another friend of his pointed out, “New York and Vanity Fair aren’t exactly renegade brands.” But he got there on his own terms. As a 25-year-old magazine writer, he published “White Kids,” a book positioned as the voice of disaffected Seventies youth, but burned out writing a novel. He turned to making media deals with a banker friend and stumbled on the Internet in the Nineties.
Wolff saw its potential, he says, because he was like other Internet pioneers who “tended not to have an anchor somewhere else.” His true entrée to the Establishment came, paradoxically, in 1998 with “Burn Rate,” the flagrantly blunt chronicle of his failed Internet media company.
In the book, Wolff is a keen-eyed observer of what would later be called the Internet bubble, replete with hubris and illusory valuations. “I’ve come to think of Wolff as having presented himself as a kind of ‘Richard III’ character, someone so detestable, so devious, so underhanded and plotting that he becomes attractive,” says Slate editor at large Jack Shafer.
A decade later, Wolff’s hunches about the Internet age well — among them, that content, rather than being “king,” would lose its value once everyone could cheaply create it, or that content on demand would undermine media companies’ authority. “People, perhaps, aren’t waiting to be spoken to anymore,” he wrote. “They want to hold their own conversations.”
Luckily for Wolff, the transformation wasn’t immediate. “Burn Rate” got him his New York magazine column and eventually a table at Michael’s. From both, he got to play both outsider and insider, delighting and often infuriating New York chatterers with his willingness to insult anyone with his elegant, sometimes showily elliptical prose. “Michael was the king of New York when I arrived,” recalls Carr.
He won two National Magazine awards for his columns. In 2003, Wolff assembled a group of investors to buy New York magazine, but lost to Bruce Wasserstein. He landed on his feet at Vanity Fair. “We may not always agree, but I’m usually interested in what he has to say,” Vanity Fair editor in chief Graydon Carter says.
Indeed, if Wolff is fearless, or even reckless, in his behavior, he so far has suffered few consequences. “There is some kind of formula here in this business,” he says. “For every enemy, you make 10 friends.”
Despite his eagerness to predict the future, Wolff has sometimes dragged his feet toward it. In 2005, he quoted Truman Capote — “That’s not writing, that’s typing” — to describe blogs, vowing never to write one and comparing it with “that scene in ‘Doctor Zhivago’ where the professionals and the intelligentsia are reduced to having to walk with the hoi polloi.” But two years later, he cofounded the aggregator Newser.com, his offering for the saving of the news, and the online column helps draw attention. (Former New York editor Caroline Miller runs the site, Wolff having learned to stay away from management.) In June, Newser said it had raised $2.5 million in funding from individual investors.
This time around, the Internet — where anyone can be a troublemaker — has both amplified and diminished Wolff. It’s grown his notoriety on blogs like Gawker, where photos of him and Floethe (who wrote on Slate, perhaps semi-ironically, about her shriveling trust fund and sugar daddy yearnings) are enough to ignite commenters’ snark. The online column has also meant a new crop of outraged readers unaware that “Is Sonia Sotomayor Gay?” is his idea of a puckish joke. Still, it’s harder to shock when you never disappear.
“Michael will always try to push things too far,” Dumenco says. “That was frustrating and thrilling as an editor….Michael’s not only fearless, he’s almost self-destructive.”
Wolff admits he regrets writing on Newser that Post editor Col Allan would be fired for publishing a cartoon that appeared to equate Barack Obama and a rampaging chimpanzee. His theory is that it led Allan to order a hit on Wolff, with Murdoch’s apparent approval. “In print, someone would have said, ‘Be careful,’” Wolff says. “And I wasn’t.” (The Post had no comment.)