The Perfect Pairing of Subject and Chronicler

Disdain for playing by the rules, delight in shocking their audiences, and hunger for the approval of the elites they mock—there’s a lot that Michael Wolff and Donald Trump share in common.

Carlos Barria / Reuters

Love him or hate him, Michael Wolff, author of the dishy new Trump tell-all, Fire and Fury, is a good sport.

Thirteen years ago, after Wolff won his second National Magazine Award, I wrote a profile of him that was not especially flattering. In addition to deeming Wolff a mediocre political commentator, the piece noted that his journalistic m.o. was … unorthodox. He burned sources, busted embargoes, was less-than-meticulous about details, and had a penchant for gilding his actual reporting with colorful bits of what he imagined had happened in certain situations. He didn’t try to pass fiction off as fact so much as he wove both together in a swirl of style, substance, and snark. (Wolff has always been more about painting entertaining, impressionistic portraits than about sweating the nitty-gritty.) His flagrant disdain for journalistic conventions is a key reason Wolff has long been controversial among, and even loathed by, much of the Fourth Estate.

With the release of Fire and Fury—the gist of which is that even those in Trumpworld consider Trump unfit for office—Wolff is getting hammered by the president’s protectors. They aim to discredit his book by discrediting Wolff himself, and one of their pet tools has been my 2004 profile, which Trump supporters both inside and outside the White House have been peddling to reporters and political types. I have written many critical pieces. None has been half so fiercely weaponized—which is saying a lot, since I mostly cover politicians.

Despite all this, when I reached Wolff via email Saturday evening to ask how he was weathering the madness, he was nice as pie. He had just listened to a CNN podcast I had done about him and kindly observed that I had a “nice voice.” Nor was he crabby about any of my past or current critiques. “As my presumptive biographer, you get it about 55 percent right,” he quipped. “That’s not so bad.”

Wolff was on the Amtrak Acela somewhere between Washington and New York and had time to kill. He wasn’t up for an interview, but he and I spent an hour or so swapping emails (which he later said I could share) about random topics: his gift for wooing media moguls (Wolff rose to fame in the late ‘90s and early ‘00s with wicked profiles of machers like Rupert Murdoch and Conrad Black); his “New Yorker’s view” on politicians (“salesmen”) and other Washington types (he finds operatives and media folks “spectrumy”); his professed allergy to cocktail parties (he insists he rarely gets invited anywhere because he has “no party face,” and when he does go, “I am grumpy.”); and how he really isn’t the calculating suck-up everyone thinks: “You seem to see me as slick flatterer. That's hilarious to friends and family who see me more, with great irritation, as Larry David.” He also sent an “in my defense” link to his recent Q&A with The Hollywood Reporter (for whom he writes), in which he presents himself as the rare journalist to approach Trump with no political agenda, driven only by an earnest quest for insight into “how people relate to one another” and “their ability to do their jobs.”

He was, in short, spinning me.

Even in casual conversation, Wolff is always “on.” Those chatting with him should consider themselves “on” as well—as the Trump folk have so painfully learned. Wolff may well have a David-esque streak of awkward, neurotic misanthropy, but he’s also a seasoned, unabashed manipulator. He is famous for knowing how to read people and how to ingratiate himself with the masters of the universe from whom he seeks access. During his years covering New York moguls, Wolff was roundly mocked for his ass-kissing. Among the less delicate assessments in my 2004 profile was a journalist’s snarking that Wolff had written a fawning column about former CNN-chief Walter Isaacson to “get his hands on Walter’s underwear for his collection.”

Considering how desperate President Trump is for someone—anyone!—to appreciate his greatness, it must have been embarrassingly easy for Wolff to flatter his way into the West Wing. (As Wolff told Today last week, he was “definitely willing to say what was ever necessary to get the story.”) Wolff would have known better than most how to play Trump—and not merely because of his vast experience courting the media’s most overinflated egos.

Wolff, like Trump, is a particular kind of New York creature: obsessed with, but not one of, the Manhattan glitterati. (A Queens native, Trump carries a huge outer-borough chip on his shoulder. Wolff is a born-and-bred Jersey boy who schmoozed and slashed his way to the Upper East Side.) Many of the same desires, anxieties, and obsessions that drive this president shaped Wolff as well—from their disdain for playing by the rules to their delight in saying the shocking thing, from their obsession with buzz to their hunger to be embraced by the elite they so often mock. In many ways, the two men are the perfect pairing of subject and chronicler.

Like Trump, Wolff has long been impressed by money and power, and has on more than one occasion attempted to enter the echelons of moguldom himself. His 1998 book, Burn Rate, tells the story of his failed attempt to become an internet mogul. In 2003, Wolff put together a coterie of media players (including Harvey Weinstein) who launched a failed bid to buy New York magazine. So even as Wolff made wicked observations about the power players he covered, his underlying desire to become one of them was clear.

Both Trump and Wolff have gotten famous by being the rebels of their chosen fields. This goes beyond their reputations for caring less about facts than about the truth as they see it. Just as Trump has no time for the boring conventions or niceties—or democratic norms—observed by most presidents, Wolff will not be bound by the tedious or restrictive aspects of reporting, like fretting overly much about who or what is on or off the record. Neither will he play along for the sake of the broader profession. Several years back, in fact, he was shopping around a reality show aimed at exposing what he saw as some of the more ridiculous sausage-making aspects of journalism—for instance, the weird, arguably empty pageantry of press conferences.

Like Trump, Wolff knows how to thrill his audience by making the sort of cutting personal observations and insults most reporters would consider out of bounds. Musing about people’s neuroses, insulting people’s grooming, tittering about their personal lives—Trump has nothing on Wolff in this department.  (The passage in Fire and Fury about Ivanka’s mocking her dad’s comb-over is at once gratuitously cruel and utterly irresistible.) Few understand the thrill-the-masses power of sex talk, profanity, and ad hominem attacks more than Wolff and Trump.

Then there’s the whole New Yorkers-looking-down-on-Washington thing. How could Trump not love Wolff’s schtick as a political-media outsider who denounces the ridiculousness of journalistic conventions and conventional journalists? And that’s before taking into account all the time that Wolff spent courting Trump by publicly slamming the rest of the media as a bunch of haters.

Perhaps most importantly, Wolff knows that, in modern America, the name of the game is buzz. It’s why he can be reasonably zen—grateful even—in the midst of the current tempest. Whatever anyone is saying about him, good or bad, it all adds up to more book sales. What could possibly be more Trumpian than that?