D.R.: When we were talking about Donald Trump, incessantly, in the eighties and nineties, when he was a figure of Spy magazine and the tabloids, you didn’t have to pay that much attention. You didn’t have to care that much. He was an amusement. But, if you look back on it now, there are a lot of people around him, from the very start, not just Roy Cohn, not just his own family but all kinds of sleazy characters, money launderers abroad and at home. He has been surrounded by some awful people, people with serious criminal records. If they ever came close to Hillary Clinton or Barack Obama or many other politicians you could name, they’d be finished. How does it shape him, and how does he survive it?
M.H.: I think that people don’t know the extent of it. One of the things that I was really shocked by, covering him in 2015, was the disparity between the five-borough view—or four-borough; take out Staten Island, where he did very well—but the view of him, certainly in Brooklyn, Queens, and Manhattan, was that he was not a real businessman. And he, at that point, had been bankrupted several times, and he had gone on to licensing businesses and becoming a reality-TV star.
D.R.: Not just licensing businesses but doing deals with people abroad who were uniquely corrupt in their various countries, like Azerbaijan, or Georgia, or what have you.
M.H.: Correct. I mean, but I think that, if you can point to where we did poorly—we, not the Times but the collective media—in the 2016 campaign, I think that pointing to the company he kept was where we messed up. We didn’t do enough of that.
D.R.: That the proliferation of sleazy people didn’t come to light enough.
M.H.: Well, it’s just one after the other. There’s that Felix Sater character, who was arrested and, I think, did time, for shoving a broken Martini glass in someone’s face—
D.R.: Well, who hasn’t had a bad night?
M.H.: Right! Just last night, even.
D.R.: [Laughs.]
M.H.: No, in no way. But it’s not just people with questionable business practices—it’s people with a history of violence. Or some combo. And you tie that with the fact that, throughout the campaign, he evinced some authoritarian impulses. One of the things that was striking about him, and it increased right after he won the New Hampshire primary, was, in the G.O.P. campaign, he kept praising dictators. And then you’d report that he praised them and he’d say, “No, I didn’t.” I mean, one of the things that’s really challenging about covering him is he refuses to agree with the basic fact of what he just said, when you point it out.
D.R.: That we live in Alice in Wonderland.
M.H.: Right. There is no basic agreement on a set of facts, right? So I think that that becomes challenging. And that ties back to your question about the company he keeps. A lot of this, even when we report on it, people don’t believe it. So, I don’t know what you do with that.