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Wolff Trapped

Ben Gabbe/GETTY

Snuffle. Snuffle. Snuffle. The little black nose is cold and wet on my arm. “Gracie, stop that!” media writer Michael Wolff scolds the small, spastic spaniel wriggling next to me on the sofa. Gracie tumbles to the floor, but Trixie the cat soon takes her place and delivers an exploratory head butt. “No. No. No. Come on,” says an embarrassed Wolff, leaning out of his high-backed red chair and waving an arm.

Wolff and I are seated in the living room of his comfy Upper East Side home. The sixth-floor co-op is bright and airy, with buttercream walls, multiple built-ins, and proudly hung rows of black-and-white photos that Wolff has taken of his three kids. Every few minutes, our chat is interrupted by phones ringing, pets prowling, or family members popping in to introduce themselves and see how we’re getting along. (Famously, thank you.) Slouched low in his seat, wearing a dark gray t-shirt, gray cotton pants, and black sneakers, the 50-year-old Wolff has an air of casual domesticity that fits perfectly into this low-key, family circus scene. But, having heard so much about the columnist’s calculating nature--especially his meticulous, leave-nothing-to-chance P.R. skills--I start to feel like the picture is a little too perfect, the casualness too studied. Wolff clearly wants me to see what a charming, regular-guy dad he is, even as he explains what it’s like to be one of the most powerful, most talked about, and most hated figures in New York media.

It’s difficult for non-New Yorkers to fully grasp the Michael Wolff phenomenon. In the most literal terms, Wolff, from 1998 until he decamped for Vanity Fair this winter, wrote the weekly “This Media Life” column for New York magazine, spinning out stylish, pointed observations on everything from Viacom’s power struggles to Rupert Murdoch’s love life. From the start, Wolff was adamant about being neither a media reporter (working the phones isn’t really his style) nor a media critic (“that dour schoolmarm figure”). Instead, he put himself at the center of the story, giving readers a first-person glimpse of the inner workings of the media biz as it happened to, and all around, him. Uninterested in the working press, Wolff’s special focus (fixation, even) has always been on the power players--the moguls--most of whom he has relentlessly and repeatedly skewered, scraping away the sheen of power and money to reveal the warts, flab, and psychic scars plaguing that rarefied breed of (in Wolff’s view) super-wealthy narcissists who buy, run, and ruin media companies for the gratification of their insatiable egos.

But to describe what Wolff does hardly explains what he is. With his wicked rants, Wolff swiftly emerged as the It Boy of New York media. His quick wit, dizzying writing style, and willingness to say absolutely anything about anybody made his column a must-read. Plus, he was writing (gossiping, really) about the New York media’s favorite subject--the New York media--in a catty, caustic way that no one else dared. (Snarky critiques of his subjects’ grooming habits are a Wolff perennial.) Love him or hate him (and many of his colleagues truly despise him), Wolff could not be ignored. And, as the columns sparked ever more buzz, the columnist became nearly ubiquitous: speaking at conferences, hosting conferences, holding forth on American media in the foreign press (the Euros absolutely adore his cheekiness), schmoozing at all the best parties, and grabbing as much airtime as possible on the chat shows. In 2002, Wolff won a National Magazine Award for commentary, followed by a second nomination in 2003 and then a second win in 2004. Meanwhile, his coverage of the media elite was elevating him to the level of bona fide big dog. (Page Six gossiped about him! Mort Zuckerman returned his calls!) Around New York, this status was best manifested by Wolff’s securing his own table--number five--at Michael’s, the Midtown eatery where everyone who’s anyone in media goes to be seen having lunch. A coveted piece of real estate, table five signaled Wolff’s professional dominance far more than any award.

As New York’s marquee name, Wolff was free to write about whatever he wanted. As Wolff defines it, media is an all-encompassing “superstructure,” a refracting lens through which to examine all aspects of American culture. Increasingly over the past couple of years, he has focused this lens on national politics. In early 2003, Wolff traveled to Qatar for a brief stint as war correspondent. (There, he produced a series of columns that won him his second National Magazine Award.) As the presidential race got underway, he frequently held forth on the Democratic primaries. And, all along, the Bush administration has been a favorite whipping boy. Now, in his posh new post at Vanity Fair, Wolff plans to continue this political musing. His July piece for the magazine looked at the media elite’s response to Abu Ghraib. For August, he wrote a profile of Democratic uber-adviser Bob Shrum. And, in light of Editor Graydon Carter’s antipathy toward the current administration, if George W. Bush wins reelection, Wolff will certainly be encouraged to spend the next four years making the president’s life as unpleasant as possible.

So should Washington’s political chieftains be concerned that the scourge of New York’s mogul class--the man who claims partial credit for Michael Eisner’s current job crisis--has them in his sights? Not really. Whatever his gifts in chronicling the follies and foibles of the Manhattan media elite, Wolff is neither as insightful nor as entertaining when dissecting politics. As New York journalists are the first to acknowledge, Wolff is the quintessential New York creation, fixated on culture, style, buzz, and money, money, money. (For Wolff, nothing is more erotic than a multibillionaire.) Though not of the mogul class, he arguably understands the culture and mindset in which it thrives better than almost anyone. The same cannot be said of politics, which Wolff approaches from the perspective of your garden-variety Upper East Side liberal. “I don’t think he’s anywhere near as sharp on politics,” says one Washington press eminence (and Wolff admirer). “He’s basically a conventional liberal with a Manhattan-centric view of the world.” Indeed, much of what enabled him to pull back the curtain on the Manhattan media scene--his New York-centrism, his obsession with (and proximity to) the city’s power players--is precisely what makes him poorly qualified to comment on much else.

Barry Diller, chairman and CEO of InterActiveCorp, is on the line waxing rhapsodic about what a “damn interesting writer” Wolff is. “He has lots of ideas,” growls the megamogul. “His columns are filled with ideas and concepts.” Fans and detractors alike talk about the big ideas and theories Wolff likes to spin out. Sometimes he’s right. (From the start, he saw the AOL-Time Warner merger for the synergistic stink bomb it was.) Sometimes he’s not. (In 1998, he predicted Conde Nast would jettison the post-Tina Brown New Yorker.) And sometimes he sounds downright nutty. (He posits that the media backed the Iraq war because the moguls hoped to win a favorable ruling from the Federal Communications Commission on media-ownership limits.) But he has never been one to dull things up with cover-your-ass qualifiers or small-scale thinking. “He did get a lot of things majorly wrong, but he never was just pedestrian,” says a former New York colleague. “You have to admire his balls.”

In presenting his theories, Wolff takes readers inside the psyches of the media bigwigs involved, understanding that even arcane theories can be entertaining when explained in terms of the personal quirks of the rich and famous. This allows Wolff to deploy his sharp (and scathing) eye for detail. Of Steve Rattner’s wife, Maureen White, he observes: “She had something more like a Beverly Hills than Manhattan coif and whitish makeup (her lips were exceptionally shiny and pale). There was no expense spared here, no detail untended, no consideration unthought of--but nevertheless (and unlike Beverly Hills) she presented herself with a certain austerity and sexlessness.” Give Wolff five minutes in a room with someone, and he can get to “the nut of something,” says a friend and former colleague. “What Michael is really good at doing is reading people. He’s a psychiatrist on paper.” Think of him as a Gail Sheehy for the mogul class--but dispensing scorching derision instead of faux empathy. As Wolff explains it, disgraced Hollinger CEO Conrad Black has done what he’s done because of his need to be seen as a Great Man (“Stature is what he’s sought: standing, significance, importance”). Maureen Dowd writes the way she does because she can’t get a man. (“That would certainly explain her anger--it’s at her own women-who-love-too-much weakness.”) And “control freak” Rupert Murdoch’s 1998 marital troubles signaled that “the most elemental part not only of Murdoch’s personal life but of his business empire may have spun out of control.” Part gossip columnist, part psychotherapist, part social anthropologist, Wolff invites readers to be a fly on the wall of the moguls’ inner sanctum. Chronicling Steve Rattner’s rise from ink-stained wretch to investment fund manager, Wolff writes: “How to be a dealmaker--a deal macher--without doing any deals? That was the question. How to be out there is the way it would have been put. We have to be out there, Steve, someone would have said.”

Much to the annoyance of Wolff’s critics, the scenes in his columns aren’t recreated so much as created--springing from Wolff’s imagination rather than from actual knowledge of events. Even Wolff acknowledges that conventional reporting isn’t his bag. Rather, he absorbs the atmosphere and gossip swirling around him at cocktail parties, on the street, and especially during those long lunches at Michael’s. “He’s around town enough to have those insights, to spot people, to come across [pieces of information],” says a friend. He also has a talent for making the most of even the briefest encounters. “His great gift is the appearance of intimate access,” says an editor who has worked with Wolff. “He is adroit at making the reader think that he has spent hours and days with his subject, when in fact he may have spent no time at all.” More than one chapter of Wolff’s 2003 book, Autumn of the Moguls, spotlights anecdotes about random mogul sightings in his neighborhood. In contrast to The New Yorker’s Ken Auletta, whose sympathetic portrayals of media moguls have allowed him to enter their inner sanctums, Wolff does not confer with the titans he covers. He channels them.

Grand “ideas and concepts” notwithstanding, Wolff is a successful columnist because he is an entertaining columnist. “He’s a superb writer,” raves Mort Zuckerman, overlord of the New York Daily News and U.S. News & World Report. “One of the things you look for in the publishing world is the whole notion of voice. It’s a very difficult thing to come by.” Without question, Wolff’s writing is distinctive--glorious or ghastly, depending on whom you ask. His prose is a whirlwind of flourishes and tangents and asides that often stray so far from the central point that you begin to wonder whether there is a central point. (“I find it nearly impossible to read his columns,” says a columnist at one of the dailies. “They’re flabby. I don’t know what the fuck he’s trying to say.”) Wolff’s language and references are both erudite and lowbrow, cultured and crude. (In analyzing Martha Stewart’s trial, Wolff dubs Doug Faneuil, ex-assistant of stockbroker Peter Bacanovic, “the Whitaker Chambers [sic] of Martha’s circle,” then shifts gears to describe “this sense of a lackey culture--the dominants and the submissives. Bacanovic as Martha’s bitch. Faneuil as Bacanovic’s bitch.”) The tone is chatty and gossipy and catty-shading-into-bitchy. Opining about Arnold Schwarzenegger’s sex life, Wolff pauses to marvel at wife Maria Shriver’s freakishness--”The jaw planes, the cheekbone ridges. The porno-star hairdo”--and sum up a 1980 interview with her that he did for Life magazine: “She was over-vivid. On. Crystal-clear. Fabulous. Carpe diem-ish. She frightened me.” If Wolff’s psychoanalytic schtick evokes Sheehy, his voice smacks of the cheeky, exuberantly gay Brit talk show host Graham Norton.

But, above all, Wolff has excelled by saying the unsayable, taking shots both serious and petty at the media gods. And, truth be told, it’s the petty shots that thrill the masses. It’s one thing to trash Harvey Weinstein’s business acumen; it’s quite another to call him fat. “Michael will say anything about anybody,” says New York Times media reporter David Carr (one of the few journalists who asked to be wholly on the record). “He’s fearless in a way that people attribute to sociopathology but that I always thought was a business strategy.” “Michael Wolff grabs people’s attention because he can be brutal--and I mean that as a compliment,” says Howard Kurtz, Carr’s counterpart at The Washington Post. “He delights in ripping to shreds the various media hotshots and potentates who most journalists might trash in a bar but never in print.” But, even as he’s gigging the moguls, Wolff is openly in awe of them, frequently bemoaning (with a knowing wink) his helpless adoration. (“It is hard to escape the thrall.”) Shrewder than a mere hatchet man, Wolff is perhaps best captured by the headline of Eric Alterman’s Atlantic Monthly review of Autumn of the Moguls: “a portraitist who has mastered the art of the suck-up putdown.”

It’s unsurprising that, as a former colleague delicately puts it, “people really can’t stand Michael.” What is surprising is how much of the animus seems unrelated to the content of his commentary. On a meta level, Wolff is resented for not playing by the rules of his chosen profession. He has a reputation for busting embargoes and burning sources by putting off-the-record comments on the record. (A reputation cemented by his using an off-the-record conference as the basis for Autumn.) Half the New York-area media is still aghast at Wolff boasting in print about enlisting his son to serve as a spy while on a play date at Steve Rattner’s home. (“What kind of person uses his child like that?” asked one outraged editor.) “Everything’s a transaction with him,” says Carr (who, after writing a positive piece about Wolff, found himself the subject of a self-congratulatory Wolff column about how he had spun Carr). “There’s no unalloyed moment with Michael. You’re always on the record and performing. I think people don’t like him because they have to be careful around him.” Says an editor close to Wolff, “There’s a certain amount of fear, because people have been burnt so many times.”

Much of the hostility, however, seems purely personal. While perfectly pleasant, Wolff’s demeanor is reserved and a little cool (maybe it’s the ice-blue eyes and the close-cropped white hair). “’Graciousness’ isn’t a word you would attach to him,” says an ex-colleague. A few people chalk it up to social awkwardness, the insecurity of a Jersey kid made good; most write it off as arrogance. At New York, Wolff earned a reputation as a prima donna, where he was known for, as one ex-staffer put it, “strutting around like a little peacock” and requiring much hand-holding. The increasingly self-referential nature of his columns fueled the perception that he is overly impressed with himself. A friend of Wolff’s recalls hearing a “very senior official at The New York Times” snipe that “if Wolff were any further up his own ass, he’d be a colonoscopy.” And his weird love-hate relationship with the moguls gives some people the creeps. (One media wag jokes that a fawning column Wolff wrote about Walter Isaacson was a ploy to help him “get his hands on Walter’s underwear for his collection.”)

Poetically, the things about Wolff that his colleagues seem to hate the most--his ambition, his social climbing, his worship of status and buzz and money, his self-referentiality and solipsism--are seen by some as the perfect reflection of the world he covers (and thus the key to his success). New York is utterly obsessed “with success, competition, schadenfreude, and public failure,” says one Wolff friend. “And I think most people felt Michael chronicled all that with absolute precision.” “I find the Michael Wolff phenomenon so New York,” says a veteran New York-area journalist who knows Wolff casually. “If he lived anywhere but in the middle of the New York media world, they would say the emperor has no clothes. He can’t write. He doesn’t report. But Graydon Carter doesn’t give a shit. He only cares that he has buzz. … This could only happen among the delusional New York chattering classes.”

If so, Wolff may have a tough time maintaining his buzz at Vanity Fair--where he landed after a failed attempt to buy New York along with a coterie of mogul moneymen (including Zuckerman, Harvey Weinstein, and Donny Deutsch) that he had assembled. (Financier Bruce Wasserstein placed the winning bid, and, when the new management came in, Wolff was stunned to realize that “I was supposed to fall on my sword.” Although, he muses, “If you pay fifty-five million dollars for a magazine, you don’t want a competing power center, I suppose.”) Though catering to an upscale, cosmopolitan sensibility, Vanity Fair isn’t the Manhattan-centered vehicle that New York is. And, as a monthly, the magazine doesn’t allow Wolff to play off the topic du jour. The pieces he’s done so far are quite good, says Caroline Miller, who was editor of New York during Wolff’s tenure (and to whom people think he showed disgraceful disloyalty by maneuvering to buy the magazine and, presumably, establish himself as editor).

“They’re just not … they’re going to be bigger and not so much intimately part of the conversation.” What do the extra time and space provided by Vanity Fair give Wolff? asks Carr. “The luxury of many phone calls and doing a lot of reporting. But that isn’t really in Michael’s wheelhouse, is it?”

But, more than the format, Wolff’s growing political focus may prove a poor fit. At New York, in between jabs at the likes of Steve Case and Sumner Redstone, Wolff made the occasional foray into politics. The results were typically unremarkable. The pieces were stylish and fast-paced but, on the whole, showcased the sort of conventional thinking and predictable observations that Wolff avoids in his mogul pocket-portraits. The topics were old standards: The pro-business, yuppie-ish, Clintonian Dems and the more economically lefty, antiwar types are in a fight for the party’s soul; the Bush White House is manipulating the media; the “pageant-size fantasy” of certain starry-eyed Dems is of a last-minute Hillary run. His pensées tended toward the obvious: “My hunch is that the lower regard we have for you, the easier it is to pick yourself up from the trough. For George Bush, people’s expectations have always been naturally low.” None of his stuff was terrible. (He even had some nice takes on the Dean Internet phenomenon.) But it was decidedly unfresh. Even the pieces for which he won his 2004 National Magazine Award were based more on a p.r. stunt than on any sharp insights: At a press briefing in Doha, Qatar, Wolff stood up and asked General Vincent Brooks why it was worth the media’s time to show up for such highly orchestrated, unnewsworthy events. Overnight, Wolff became a darling of the press and the left. “But what was that about really?” asks Carr (among others). “Was there some huge intellectual scoop driving that? No. He just had the stones to say what was on everybody’s mind.” (Wolff, meanwhile, took a different lesson from his “Doha moment.” He’s currently shopping around the idea for a TV series that would turn the cameras on the media, exposing the odd, occasionally absurd standards and practices of the business.)

Moreover, as a denizen of one of the bluest areas of blue-state America, Wolff’s political perspective is not exactly nuanced. He is liberal (in a striving, aspirational, Clintonian new-Dem way); the Manhattan media universe in which he operates is overwhelmingly liberal; and, since he eschews traditional reporting, his opportunities for exposure to the non-liberal mindset may well be limited to his chat-show encounters on Fox News. It’s hardly surprising, then, that Wolff’s columns tended to line up along the basic Republicans-bad-but-effective/Dems-well-intentioned-if-often-bumbling axis. (Not to mention that only a hardcore Upper East Sider would see Wesley Clark’s lack of warmth--his “austerity” and “precision”--as political advantages.) Bush (like so many conservatives) is portrayed as dumb but crafty, especially when it comes to Iraq. A virulent opponent of the war, Wolff cannot imagine any legitimate reason to have backed it. In one pre-invasion column, he suggested Bush was trying to relive Poppy’s glory days. In another, he suggested the war was a product of Bush’s quest to drag U.S. foreign policy down to his unthinking, unreflective level--and that the folks who supported it must have been in on the joke: “I think many people, perhaps most, if pressed, might suspect that the president has a screw loose about Iraq (which actually gives him an odd kind of idiot-savant nobility). That it’s all too obsessional. That his view is too simple. (Not, however, that this in any way compromises the virtues of keeping it simple.) It’s foot-stamping. He tried to kill my daddy.” This may have been the calculation of Wolff’s cocktail party pals, but it almost certainly was not the case for the bulk of the 70 percent of Americans who supported the war at its outset. Then there’s Wolff’s bizarre, totally unsubstantiated conspiracy theory that the media hawked the war because its executives hoped that, if they didn’t antagonize the administration, the FCC would loosen the limits on media ownership: “But conspiracy wouldn’t quite be the right word. Negotiation, however, would be the right one. An appreciation of the whole environment, the careful balancing of interests, the subtleties of the trade (at this point, the ritual denial: ‘There was no quid pro quo.’)“ It seems that even Wolff’s mogul savvy abandons him when politics are involved.

Thus far, Wolff’s political columns at Vanity Fair have been equally disappointing. When the Abu Ghraib story broke, he wrote a piece (which, to be fair, he banged out in something like 48 hours) about the reaction to the scandal at a swank book party Diller threw for Senator John McCain. The piece begins as a strange, vapid, inappropriate exercise in navel-gazing and name-dropping before morphing into an uncomfortably (if self-consciously) classist antiwar screed (“So, once again we’ve exported the troubled American underbelly, our scary, marginal, unsocialized, backwoods economic refugees, to another country”) with weird asides about the “complexly layered eroticism” of battle and the “aesthetic” offensiveness of the photos. (“[T]he reaction, I’ll bet, is not just revulsion at the pictures, but an even more devastating sense of a thing on your shoe.”) Maybe this creepy indulgence could have worked as a shortish New York column with a shelf life of one week, but it may also be that war doesn’t lend itself to Wolff’s brand of frothy, isn’t-it-all-so-amusing commentary.

Wolff’s August profile of Democratic eminence Shrum also missed the mark, though for different reasons. If his Abu Ghraib musing is a technicolor vulgarity, his Shrum portrait is a gray, pedestrian primer. In a straightforward look at Shrummy’s position as the dean of Democratic advisers, Wolff rehashes all the basics: his paleoliberal populism, his tendency to “captur[e] the candidate” and “shrumify” him, his formidable infighting skills, his abysmal track record in presidential races. But, with virtually no reporting, without access to his profile subject, and without the fundamental instinct for the world he’s writing about, the piece feels flat. (Sadder still for Wolff fans, it’s largely toothless, perhaps because he’s writing about a fellow liberal in the pages of a sympathetic magazine.) There are a few nice observations about the political world (Republicans do tend to have more efficient press ops than Dems), and Wolff even takes a stab at analyzing the essence of a consultant “as exemplified by Shrum.” (“His is a career not just of endless travel, terrible accommodations, incredible sleep deprivation, and ghastly food, but also of submission to the vastly inferior, albeit more socially presentable, front man.”) But Wolff’s Shrum riff (like many of his political riffs) lacks the insiderishness and juicy details to give it the authoritative feel of his mogul writing. And, in the end, you get the sense that his heart isn’t really in it--that, all things considered, he’d rather be kicking it at Michael’s, giggling with Harvey Weinstein about the heartburn Eisner’s suffering over Fahrenheit 9/11. (“If only Michael Moore weren’t such a sartorial nightmare,” you can almost hear him sigh.)

Of the new job, Wolff admits, “I’m not sure I exactly know how to do this yet.” But, as he adjusts to the longer lead times and the higher word counts, New York’s mogul-slayer may want to consider whether--with only twelve columns a year--he wants to waste his time on political commentary that is unlikely ever to be buzzworthy. From the tall, lovely windows of his dining room/home office, Wolff has an enviable view of the daily hustle and bustle of Lexington Avenue. The action way down on Pennsylvania Avenue, however, is much tougher to see.

This article originally ran in the August 30, 2004, issue of the magazine.