So this is the guy who's been terrorizing all those Manhattan media moguls? Over sparkling water at the Madison, he doesn't seem all that intimidating. Doesn't exactly suck the oxygen out of the room. Smart, yes. Blunt, sure. High opinion of himself, definitely. But as we talked -- Michael Wolff is a compact man with a serious air -- it was hard to read his pale blue eyes. He holds back, doesn't tip his hand. Maybe what he says is true: He just doesn't care a whole heck of a lot what people think of him. Which made me wonder . . .

This is how the piece might begin if it were written in the style of Michael Wolff, New York magazine's combative media writer. His column, it seems, is mainly about him. Which is okay, because he has a lot to say. About the Internet, where he once tried to make a fortune. About the strange, relentless, culture-transforming nature of modern media. About the gossip. About the personas of people like Tim Russert and Mort Zuckerman and Michael Eisner, whom he seems to like slapping around.

"People enjoy Michael because he's willing to take on media establishment figures who other people would love to write about but are afraid to," says Caroline Miller, New York's editor. "It's one of the few columns that is aggressively, frankly, unapologetically his opinion. He doesn't pretend to be neutral. That's why it's a great read."

Here, for example, is Wolff on his recent sit-down with New York Times financial columnist Paul Krugman:

"Krugman is your basic academic -- unfriendly, condescending, abrupt. . . . Right away, we get off on a bad foot. . . . I absorb his withering annoyance and condescension."

Says Krugman: "I don't know what he thinks his job is, but it was clearly a mistake to talk to him."

Wolff, 47, describes his style thus: "I like to be honest, to say what I'd say to other people over dinner. I seem to have -- and I don't know exactly where this comes from -- I don't have this gene that most people have that makes them worry about where they're going to get their next job. I have a certain combination of fearlessness and foolishness. I don't really care. I will say anything."

Marion Maneker, Wolff's editor at the magazine, says the columnist enjoys being confrontational. "The idea is to needle people," Maneker says.

Zuckerman didn't enjoy being needled and complained to Miller that her columnist had never called him before writing about his "mercurial nature and his quest for personal stature."

Miller recalls telling him: "Mort, Michael isn't really interested in what you would say about what you're doing. He's writing about the persona of Mort Zuckerman. He's really writing about his theories of what makes Mort run."

Which naturally raises the question: What makes Michael run? Why does this writer, commentator and lecturer keep pushing the journalistic envelope? How is it that HarperCollins has given him a $750,000 advance for a book about the future of the media?

And, even more tantalizing: How can he be riding so high after two spectacular, career-threatening failures?

Chronicling Celebrity

Wolff is spending more time in Washington these days, trying to understand the place, to deconstruct the art of politics as seen through the lens of media mythmaking. He is a Big Bang columnist whose universe is always expanding.

While Wolff is insightful, often authoritative, on media subjects, he seems less sure-footed in the political realm. Sometimes he merely sounds like an Upper East Side liberal.

In New York's Feb. 5 issue, Wolff wrote: "The same fluke that put Bush into office affords Clinton the opportunity to be a character and have a job possibly more distinguished than that of president. . . .

"Celebrity-in-chief is obvious. He will be the finest invite, the ultimate get, the most doggedly pursued person in the social and media firmament. The novelty of his position feeds the celebrity -- along with his hunger for it. . . . All of Manhattan is astir. . . . He will be on television more than Bush; he'll be a part of daily language and reference; hell, he'll be an airborne antigen. This is, potentially, enduring celebrity of the Beatles-Kennedy-pope kind. . . . He may become the first commander-in-chief of pop culture."

A bit over the top for the man then being engulfed by the pardon scandal? "I guess I'd like to take it back," Wolff admits.

After watching President Bush address the American Jewish Committee, Wolff wrote mainly about his "High Wasp" style of "remoteness," likening it to dining "with my in-laws." A few weeks back, he was more critical of Bush on Bill O'Reilly's Fox News Channel show, saying flatly: "The man sounds dumb."

O'Reilly gave him a hard time about pundits labeling conservatives dumb. Wolff retaliated in print, describing the host when the camera isn't on him: "His face goes slack, eyes heavy, and he clearly loses concentration. He looks . . . stupid. Without the anger, he appears mostly brutish and sullen, uninterested in the world. So why, I wondered, would he want to call attention to the stupid issue?"

Wolff has written some favorable pieces about, for example, Tucker Carlson and John Hockenberry. But he got into a dust-up with Russert when the NBC anchor wouldn't grant him an interview.

"I'm going to make a big deal about Russert ducking from the press in next week's column," Wolff told Russert's spokeswoman, Barbara Levin, by e-mail. "At the same time he demands access and accountability from others, he himself stays hidden and unavailable."

In his piece -- which said of Russert that "sometimes he's oily, other times a pit bull" -- Wolff chided Levin by name, adding: "Would Russert himself be less interested in a story if the subject's flack called his boss?"

Levin says she explained that Russert had to honor previous interview commitments first, but that "Wolff was very unprofessional and threw a fit rather than wait his turn. But then, too, he is getting the attention he craves, isn't he?"

Wolff insists that Russert's refusal to speak to him was "a creepy thing."

Not surprisingly, some of Wolff's subjects fight back. That's what New Republic columnist Andrew Sullivan did after Wolff described him as an ambitious man with no sense of humor. "Certainly," Wolff wrote, "he sees himself as an important entity; he believes that he is the most significant gay public intellectual in America today -- and he may well be."

Sullivan fired off an e-mail (and a milder letter to the editor) accusing Wolff of putting words in his mouth, saying he never uttered a word about considering himself the leading gay intellectual.

Such sniping pales beside Wolff's 1999 column on HarperCollins's hotshot editor Judith Regan, who was a classmate of Wolff's at Vassar College. It was excruciatingly personal:

"She fought pitched battles at Simon & Schuster. Ranted. Raved. Attacked. The penalty of not loving her enough (and it is doubtful anyone can) is that she will punish you without remission. She always wins, because life is too short. . . .

"I have never heard anyone talk about sex the way Judy does. I have never heard anyone talk about their sexual partners the way Judy does. I have never heard anyone analyze individual motivations, the workings of the marketplace, and politics, too, in such precisely sexual terms. . . . A conversation with her is about only her goals, her agendas, her beliefs."

Any reaction from Regan?

"She doesn't speak to me."

Wolff pauses.

"I suppose the world is full of people who no longer speak to me."

Regan calls the piece "vicious" and disputes almost every paragraph, saying she hasn't had a personal conversation with Wolff in 30 years. She even says Wolff had a thing for her college boyfriend.

"He's a nasty guy," says Regan. "He's so pathetic. . . . He hates my guts." While Wolff was the rising star in college -- "obsessed," she says, with "money and position and success" -- her future was hardly bright. "I kind of caught up and surpassed him, made more money, had more success, and I think he deeply, deeply resented it. He has no hair and looks a lot older than I do."

What's more, Regan says, she fired his wife, Alison, and her law firm in her divorce case. (Wolff mentioned the representation in the column and says his wife, a corporate lawyer, merely introduced Regan to another attorney at the firm.)

Wolff is unperturbed. "She is weird," he says.

No wonder Wolff is considered a must read in New York.

"Michael gets a lot of hate mail," Maneker observes.

Randall Rothenberg, an Advertising Age columnist and a friend, says: "I think of his column as taking people, holding them by the ankles and shaking stuff out of their intellectual pockets. Most media reporters don't have a clue how these companies make money, and Michael does. He was a magnet drawing the chattering classes back to New York magazine."

Says another friend, Wall Street Journal columnist Kara Swisher: "He's a beautiful and angelic writer, and he can be devilish. Michael can be terribly tough, but I also think he can be really dead-on. He likes to be a bad boy, and I like to read what bad boys write."

The bad boy reaches for a literary metaphor: "It's almost as if I'm treating these people as a book and I'm the book reviewer."

Colleagues say Wolff is tough to edit because he is very particular about his language. "Like many people who can be difficult, he can also be very charming," Miller says. "I feel comfortable when I have to tell him the column has a fairness problem."

Wolff will undoubtedly bring his stiletto style to his new book, "Autumn of the Moguls," which will track the czars of old media as they grapple with the lightning-quick world of new media. He has been typically outspoken on this score, declaring many Internet content sites dead and the revolution all but over.

"I suppose I have a point of view that lends itself to being provocative," Wolff allows. "If you're trying to bust balloons, the media business is largely founded on hype and selling and image. Most of the people I'm writing about are very good at their jobs. That doesn't mean they're not disingenuous and over-inflated and pompous asses in many ways."

Bound for the Internet

Everyone at Vassar knew Michael Wolff was ticketed for success -- and not just because he was one of the few men at an all-girls school that had just gone coed.

It wasn't his lineage -- Wolff grew up in New Jersey, the son of an advertising man and a mother who reported for the old Paterson Evening News -- as much as his persona.

"He's been driven since the day I met him," says Jason Isaacson, a classmate now with the American Jewish Committee. He describes the young Wolff as "acerbic and cynical," "intellectually impressive," "a prolific writer" and "a little bit of a smartass."

While in school, Wolff became a New York Times copy boy -- a thoroughly "horrible" experience -- and managed to publish a big piece in the Times Magazine in 1974. After college, he freelanced for such magazines as Rolling Stone and New Times, published a well-received book called "White Kids," got a lot of money from Simon & Schuster to write a novel and moved with his future wife to Rome.

"That was a disaster," Wolff says. "I sat there with this thing I just couldn't write. I probably spent the better part of five years not writing this book. It was a life and career calamity. I was so embarrassed."

A series of business debacles followed. Wolff tried to take over the National Lampoon. He lined up backing for a travel magazine, but his investors backed out. (He turned that effort into a book and PBS series.)

In 1992 Wolff formed a small company that published a guide to the then-fledgling Internet. The book included an 800 number that drew 40,000 calls. Other guides followed. Suddenly Wolff had 90 employees, the Wall Street Journal was taking notice and he was swept into the breathless world of cyberhustlers and venture capitalists.

Says Jay Sears, an employee at Wolff New Media: "He had many traits of a classic entrepreneur: driven, ambitious, wanting everything yesterday. . . . An almost evangelical point of view about what you're doing. If it was necessary to take the gloves off, he took the gloves off."

At one point, facing the loss of his company when he could no longer meet payroll, Wolff staved off the bankers by fabricating a tale (complete with a staged phone call) about his wife's father having open-heart surgery.

"How many fairly grievous lies had I told?" he would write. "How many moral lapses had I committed? How many ethical breaches had I fallen into? . . . Like many another financial conniver, I was in a short-term mode."

There were meetings, calls, trips to Silicon Valley as Wolff and his financial backers explored one scheme after another to sell the venture to other firms (including The Washington Post Co.) or otherwise open the Wall Street spigot. In the tumultuous period when Wired and Yahoo were ramping up and Amazon was but a gleam in Jeff Bezos's eye, Wolff believed he was on the verge of something big.

"There was a moment in which I was theoretically worth $100 million," he says. "But in truth, for the most part, I never saw the logic of how this was going to work out. There was no money coming in."

The venture collapsed in 1997. Wolff was in a state of "complete emotional and physical exhaustion," Sears says. He needed to make some bucks. So he decided to do a book on the fiasco. Failure had led him back to writing.

"It was the best thing that could ever have possibly happened to me," Wolff says.

While some critics challenged the credibility of "Burn Rate" -- there were long, verbatim conversations even though Wolff took sketchy notes -- its scathing, score-settling portrait of people screwing over one another landed it on the bestseller lists. Brill's Content found a dozen people disputing quotes in the book. Wolff responded by writing a column about the magazine investigating him and chiding Brill as a "holier than thou" figure.

Controversy, of course, sells. The 1998 splash caused by "Burn Rate" prompted New York magazine to run a long, puffy profile of Wolff, which led to Miller offering him a job. "I thought, I could do this," Wolff says.

Conference Guru "So I organized this conference about old media and new media, and Kurt Andersen didn't show up. Arthur Sulzberger, Norm Pearlstine, and CNBC.com's Pamela Thomas-Graham were on the stage at the Museum of Modern Art, where the conference was held, but Kurt's chair was empty. . . .

"I got angrier throughout the day that he hadn't said a word about this when I'd seen him the day before and that he'd give some greater deference to people he didn't know . . . than to a friend (me). When I got home and found the e-mail he'd sent at 9:40 that morning (obviously knowing I wouldn't see it before the conference), I shot off a [expletive] e-mail to him, which he returned immediately professing innocence, with me responding that this was a personal betrayal, then his saying he didn't realize it meant so much to me and apologizing profusely, until, shortly, we were (mostly) friends again."

There are two conclusions to draw from this New York piece last May:

Michael Wolff's column is mostly about himself.

Michael Wolff goes to an awful lot of conferences. (At least 200, by his count, from Monterey, Calif., to Davos, Switzerland.)

He is also in the conference business, organizing and moderating them. He ran a media summit for New York magazine and the Industry Standard, a Comedy Arts Festival in Aspen, has one this fall on e-books. And they become his subjects.

With a weekly deadline, says Wolff, "if you go, you damn well are going to have to write about it."

With this kind of rising profile, Wolff might be expected to take his act national. But he turned down an attractive offer last summer to move his column to Newsweek, and his agonizing reveals something interesting. Turns out Wolff loves the hundreds of e-mails he gets from the Manhattan cognoscenti, even those who denounce what he writes.

"New York is a terrific place to write for," he says. "Everyone I know reads it. I don't know who reads Newsweek. Three and a half million people do, but I don't really know them."

One might think that Wolff's frequent skewering of the city's power brokers would make him a bit of an outcast on the Manhattan social circuit. Wolff insists he has no interest in that scene, "but I have never been invited to so many parties since I started this column."

New York magazine columnist Michael Wolff: "I suppose I have a point of view that lends itself to being provocative. If you're trying to bust balloons, the media business is largely founded on hype and selling and image.""I like to be honest, to say what I'd say to other people over dinner," says Michael Wolff. His targets call him "vicious," "nasty" and "pathetic."