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Why Our Monsters Talk to Michael Wolff

I couldn’t write about these kind of blurred journalistic lines, of course, without disclosing my largely friendly relationship with Mr. Wolff. I first encountered him in 2009, when he profiled my then-employer, Politico, and wrote in passing that I was a “total dweeb” who was “the only one as interested in what his sources are doing as they themselves are.” I felt both insulted and pretty much seen.

After that, I sought him out for occasional career advice, which he gave generously. In 2014, he invited me to a dinner with executives at Uber, and neglected to ask me to agree that it was off the record. When I published one executive’s explosive suggestion to me that the company dig up dirt on the journalists who had been covering the company, Mr. Wolff, then a columnist for USA Today, blasted me in print as “a gotcha political blogger” who had grown “censorious and moralistic.” (Fair.) A couple of weeks later, he took further revenge by publishing an indiscreet comment I had made to him in private. I was furious. I also figured we were even. And when I was thinking last year about writing a book, I asked him how to do it. He told me, You start with a blank piece of paper, and on the top, you write the amount of money you want.

Mr. Wolff seems to be following his own advice as he cashes in on the success of “Fire and Fury” with his third book in four years. But he offers a scarce commodity in a media market that has moved away from his kind of journalism. A hot political environment has taught many reporters to see their work in moral, even didactic, terms. Magazine writers are out looking for heroes, not villains, and they appear to have little interest in understanding why our bad men do the things they do.

But monsters are fascinating. And Mr. Wolff “doesn’t have that sort of natural recoil to some of the more odious people in the world,” said Janice Min, his former editor at The Hollywood Reporter.

After we parted, he emailed me that he would prefer that his beat not be described as “elderly sex abusers.” It has simply turned out that the class of media moguls he covers “has turned out to, disproportionately, include many sex abusers,” he said.

That generation may, at last, be aging out, meaning Mr. Wolff risks running out of subjects. When I asked who will hold his interest in the years to come, he said he was “scouting the next generation” of powerful media figures.

“Too Famous” includes a few of them — Jared Kushner, Tucker Carlson and Ronan Farrow. And Mr. Carlson, for one, was happy to sit down with Mr. Wolff. “He is one of the last interesting people in American media,” Mr. Carlson texted me. “Anyone who doubts that should have lunch with him.”

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