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For Michael Wolff, the best thing about moving to the East Village from the Upper East Side may be the chance to fight with a whole new set of people: the neighborhood’s restaurant staff. Since arriving in April, the Vanity Fair columnist has tussled with several, and been asked to leave at least one place. (Telling one unsatisfactory server, “Oh? Possibly you’re on drugs?” led to his ejection, Wolff says.)

When Wolff complained bitterly to his daughter about all this, “She went on to tick off 10 restaurants on the Upper East Side that I’d been asked to leave,” he says.

This story first appeared in the July 2, 2009 issue of WWD. Subscribe Today.

Another problem with the East Village is that, for the first time in 30 years, he doesn’t have a doorman, which makes newspaper delivery difficult. (He has been told homeless people steal the papers.) Though Wolff has lately been publicly gleeful in predicting the death of newspapers (arguing not only that newspapers will die, but also that they deserve to), he cannot do without them. Most mornings he throws his overcoat over pajamas and trudges down to the gas station for The New York Times (which he loves to hate), The Wall Street Journal, the Daily News and the New York Post (which, of late, loves to hate him).

Wolff, who published a biography of Rupert Murdoch in December with his cooperation, has always expressed fondness for the mogul’s down-and-dirty tabloid. And Wolff loves a brawl, having transparently started several himself, often when he has a project to promote, and historically in the pages of the Post. “I don’t mind getting in fights,” he says. “Do I like it? Well, sometimes I like it. You get in fights because there’s something to fight about.”

The last few months have been different. In the spring, the Post ran a series of items and a cartoon about Wolff’s affair with fellow East Village resident Victoria Floethe, a former Vanity Fair temp half his age, his subsequent divorce proceedings, and a messy lawsuit involving his mother-in-law.

“Pretty brutal” is how he describes all this. He adds, somewhat unconvincingly for someone who has artfully skewered the extramarital dealings of politicians and moguls, “The scandalous elements of a man having an affair seem to escape me.”

For now, though, the Page Six glare has faded. “You start getting used to it,” he says of the attention. “And then you pick up the paper and you’re not there and you think, ‘Well, what am I, chopped liver?’”

Wolff denies he is having a midlife crisis, which is what people who talk about Michael Wolff think. The term, he says, “implies a dysfunction or a profound turnaround or something that has gone off track, and what I’m saying is that it hasn’t. It actually proceeds apace.”

Still, downtown is not the only new frontier for Wolff. Lately he has been doing what he says he would never do — blog, which he does once a day for Newser. His disagreeableness can distract from the astuteness of his assessments. But whereas once his columns earned him Manhattan media prominence, even his admirers complain that daily traffic bait for Newser ill-suits his talents. He has tested the limits of his bomb-throwing schtick, bewildering even his friends by repeatedly going after New York Times media columnist David Carr, whom he called a “nitwit” and “semi-retarded” on his blog, and by cheering on the death of traditional media. “I don’t even want to do this,” blurts a friend asked to comment on him. “He gets harder and harder to defend.” (Not everyone agrees. “Say what you want about Michael — that he’s a self-promoter, that he’s an a–hole, but he’s my favorite a–hole,” says Simon Dumenco, the Advertising Age columnist and his longtime editor at New York magazine.)

His credo of acerbic truth-telling and calculated artifice, which in print so sharply reflected New York and its media class, is arguably the same. What’s changed the most, though, is the media landscape itself — and the medium he’s trying to master.

Decades uptown have not erased the hint of New Jerseyese in Wolff’s voice — yuge for huge. In person, he is deliberate and controlled, taking pauses, which recall the commas and parentheticals he favors in writing, and alternating between a half-exaggerated courtliness and spittle-spraying indignation.

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, 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.)

But he regrets nothing he said about Carr, who reviewed the Murdoch book in the Times. (“Historically, one of the problems with Wolff’s omniscience is that while he may know all,” Carr wrote, “he gets some of it wrong.”) In May, after Carr worried in his column about what might be lost without newspapers, Wolff insulted him on Newser and added, “It is really worth remembering that most newspapers are rubbish and that even the Times itself is quite often pretty dim. It won’t be hard for the future to be better.”

Kurt Andersen calls the two columnists “two alpha dogs in that little part of the dog run…circling each other and sort of snarling.” Beyond competitiveness, it’s a case study in Wolff’s dislike for others’ sacred cows, chief among them the Times. Wolff now argues that Carr, as an employee, can only defend the interests of his employer (Wolff’s words: “the in-house flack”). The salty, idiosyncratic Carr has mostly refused to take the bait. He does liken the Newser posts to “staring into a furnace.” Wolff, he tells WWD, “has credibility. I just don’t think he’s spending it very well.”

Wolff sees all of old media’s woes as vindication for his predictions. “It’s not a bad time to be a bear now that chunks of the sky are really falling,” concedes Carr. “But I’ve never understood the glee of it.”

“I like being engaged or at risk,” Wolff says. “What’s the level of excitement? How do you make something meaningful? If you’re at risk….I put my money and time at risk [with Newser]. I am trying to figure out what happens in this business.”

As for proclaiming the death of magazines, Wolff concedes he does it less often because he still gets paid by one, but also because “other than a very select few, they have died.” Crucially, the ones that have survived, including the ones he has written for, were subsidized in recent years by a luxury economy that has since proven ephemeral.

If that period was to be short-lived, it treated him well. By now, he’s living closer than most to the mogul life, and not just because he has a younger girlfriend: he is a businessman insulated from startup instability by what looks like the last generation of fat magazine contracts and possibly the last million dollar media book advance (for his Murdoch tome).

Much of the media world has been remade in Wolff’s image, more than even he might have expected. As his friend and New Yorker financial columnist James Surowiecki notes, whether out of choice or necessity, more journalists are now interested, as Wolff has long been, in being both “capital and labor,” and in trying to find a new business model to replace the old, broken one. And there are fewer employees.

Writing online, says Wolff, is closer to doing television (which he has long done at CNBC) — more news-pegged, less information required to assume authority.

For him, grabbing eyeballs in an accelerated, competitive news cycle has meant the cheap high of a provocative headline and choosing a hot-button subject based on its momentary buzz, not on whether he has an argument about it. And if he lacks the command he had when opining on New York power players, well, the old days of cocktail party chatter as feedback are mostly gone. The noisy post on David Carr got 1,000 pageviews, but “Is Barack Obama a Bore?” got 80,000. That few care as much about the media as it cares about itself is now measurable.

Newser has old-fashioned elements, assuming people want professionally sourced news digests. The business model is ad driven (Wolff says the site will be profitable this year, his chief executive told PaidContent it would soon break even), and its success depends on drawing a wide audience rather than a deep one. (It gets 2 million monthly visitors; he wants 20 million.) “I don’t really want to replace The New York Times. I want to replace the network news,” Wolff says.

While media behavior is changing, Wolff argues that “establishing a daily baseline of news” will remain a constant. Critics point out that even as Wolff is dancing on newspapers’ graves, Newser relies on their content. He responds the site is increasingly relying on native online sources like Politico, though it overwhelmingly features newspaper content summarized by paid writers.

And for all the entrepreneurial self-styling, Wolff says he cares more about being a good writer than anything else. (He is, a friend remarks, a creature of old New York, mud-throwing and all.) “The thing I do, and the only thing I do, is write the damn sentences,” he says. “So whether or not it falls apart, I am blissful to have someone pay me to write the sentences.”

Wolff’s online presence seems to be talking at people, indifferent to the conversational or interactive aspects that define Internet media. He says in his own defense, though, he responds to reader comments and e-mails. But when pressed, he shrugs and concedes he thinks all this social media and tech stuff is “talking, not writing.”

But what if that’s what the Internet is good for? What if, this time, he just doesn’t get it?

“This is what I do, whether it works or not,” he says finally. “And it may be that no one is interested in sentences anymore.”

What then?

“Then I go down with the ship.”


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