He has led an Internet venture, chronicled the New York media world and told the "inside story" of moguls like Rupert Murdoch — all the while making bold claims that, whether embraced or rejected, were impossible to ignore.
So it was little surprise that magazine columnist and author Michael Wolff sparked a media storm this week with the publication of leaked excerpts of his forthcoming book, "Fire and Fury: Inside the Trump White House."
The book, for which Wolff reportedly secured access to the White House and conducted more than 200 interviews, quotes former Trump advisor Stephen K. Bannon as saying a meeting between Trump's confidants and Kremlin-linked Russians was "treasonous," and Katie Walsh, the former deputy chief of staff, as saying that working with Trump was like "trying to figure out what a child wants."
Trump cut ties to Bannon on Wednesday, saying he had "lost his mind," and unleashed lawyers to stop the book's release.
Meanwhile, it seemed Wolff was enjoying the spotlight, gloating on Twitter that "Fire and Fury" was No. 1 on Amazon and praising journalists who offered positive reviews.
Wolff, 64, has never been afraid of the limelight, establishing himself as a controversial critic of a media culture that he also seemed to relish being part of.
He grew up in New Jersey and got his start as a copy boy at the New York Times. But he moved back and forth between the worlds of media and business.
In the early 1990s he launched a company that provided guides to the internet, first in book form and later online. He resigned over disputes with his investors, Wired reported at the time.
In the two decades since, Wolff has written about the intersection of media, money and power, especially among New York's elite, in four books and as a columnist for New York magazine, Vanity Fair, the Hollywood Reporter and Newser, the news aggregator site he founded.
At one point he tried, unsuccessfully, to buy New York magazine — a failure over which he later felt "immense relief," he said in a video interview on the forum Big Think. In that same interview, Wolff said he no longer read New York, likening his response to that of "a lover spurned."
Wolff's portraits of media titans have been unflinching. He described News Corp.'s Murdoch as a "coldhearted realist" who looked forward to "a media business full of his competing children," and he said New York Times columnist Maureen Dowd was an "angry" writer whose tone might be explained by anger at "her own women-who-love-too-much-weakness." And when Newsweek was sputtering in 2012, Wolff wrote of its chief, "What will happen to Tina Brown? And should we care?"
His subjects have often disputed the facts in his reporting: Murdoch, who cooperated with Wolff for a 2008 biography, quibbled with the way he described Murdoch's relationship with two top executives. The magazine Brill's Content found 13 people who said Wolff inaccurately portrayed people and events in "Burn Rate," his well-known book about his time as an internet entrepreneur. (The title refers to the rate at which a company spends money in excess of its income.)
Wolff peppered his next book, "Autumn of the Moguls: My Misadventures with the Titans, Poseurs, and Money Guys Who Mastered and Messed Up Big Media," with sightings of famous media figures around New York, leading the Guardian to describe him as a media critic turned "mogul-stalker." But Wolff himself denied being a critic, which he called a "dour, school-marm figure."
Nor was Wolff a traditional journalist.
"Wolff has never distinguished himself as a reporter," the late media critic David Carr wrote in a 2008 review of Wolff's biography of Murdoch, "The Man Who Owns the News: Inside the Secret World of Rupert Murdoch."
Carr went on: "One of the problems with Wolff's omniscience is that, while he may know all, he gets some of it wrong." Carr pointed out an error in the chronology and a false statement about his own newspaper.
And in a 2004 profile of Wolff for the New Republic, Michelle Cottle said Wolff didn't follow the standards of journalism.
"The scenes in his columns aren't recreated so much as created — springing from Wolff's imagination rather than from actual knowledge of events," she wrote. "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 times, Wolff has himself been the subject of New York gossip, with tabloids eager to cover his relationship with writer Victoria Floethe, who is nearly 30 years his junior and worked at Vanity Fair when he did.
Wolff and his then-wife, attorney Alison Anthoine, were also involved in litigation against Anthoine's mother over an Upper East Side apartment where she lived. According to court records, the pair sought to evict Anthoine's mother from the apartment; she said they wanted to sell it. The case was ultimately settled, and Wolff and Anthoine divorced in 2016.
Now Wolff is back in the news with reports of his upcoming book — which as he pointed out is already a success on Amazon.