Michael Wolff on Trump Presidency, How Hollywood & Democrats Messed Up

With the possible exception of Melania, few people have a better bead on Donald Trump than Michael Wolff, the veteran journalist and author who spent much of 2017 quietly embedded in the White House, a fly on the wall during the chaotic first year of Trump’s tumultuous first term. Wolff’s book about that period, Fire and Fury, was an immediate smash hit, selling almost 2 million copies at last count. (He followed it up with two other popular books on the Trump presidency, Siege and Landslide.)

So, last Thursday, shortly after the 45th president became the 47th, Wolff was naturally our first call. What does he predict for the next four years? Who will be in Trump’s new inner circle? How will his second reign upend life in Hollywood and the world beyond? Is it time to jump on a jet to New Zealand? (Not just yet, Wolff says.)

When we talked just before the election, you were really convinced it could go either way. Turns out it wasn’t really even close. 

It wasn’t just me!  Everybody thought it would be close. Including the Trump campaign. I was speaking on election night pretty much up to the minute to people inside the campaign, and they were all worried sick. They had no clue which way this was going to go. So this came as a total shock to almost everyone. One of the lessons from this campaign, as it should have been from prior campaigns, is kill all the pollsters. 

I guess you can blame the pollsters, except Trump’s victory came as no surprise to the betting markets. And if you closely parsed some media accounts, there was a palpable sense that Trump was probably going to take it. 

I don’t know. Maybe that was true a couple of weeks ago. But just before the vote, the smart money I spoke with was very clear that Trump had peaked even before his Madison Square Garden rally. And after that, he just kept damaging himself. That was a very cogent theory of the case. And I’m not just talking about Democrats who believed that. That theory had quite a lot of traction inside Trump world. Even they were kind of shocked that he won so much of this country over.

This sounds achingly similar to the narrative the last time he was elected: Trump, the accidental president. Except he has a popular mandate this time. Where did the Democrats go wrong?

Well, virtually everything went wrong with them. I mean, to start with, the Biden administration utterly failed to make a case for itself. It was unsuccessful at managing the factions, particularly the loonier left factions in the Democratic coalition. The Biden age thing was a disaster — there’s just no way around it. The Democrats asked you not to believe your lying eyes, and then finally they couldn’t ask that anymore so that they had to switch out and find somebody else, and ultimately they selected a kind of mediocre candidate. So I think a whole lot of blame is going to be passed around in the next days and months. It’s like the whole party is being transported against its will back to 2016. 

But with profoundly different implications this time around. 

Maybe? Who knows. We don’t know if there will be different implications. One of the things about Donald Trump is that he doesn’t change. He just does the same thing over and over and over again. People are always asking me, “Well, what’s this time going to be like?” And the obvious answer is, we know what it’s going to be like because we’ve already lived through it before. 

Isn’t that a little easy? Trump might not change, but he now has a coterie of people around him who have been avidly preparing for this moment for the past four years, and who are determined to do it right this time. 

Total bullshit, complete bullshit, bullshit, bullshit. That’s just their press. That’s just what they put out! He doesn’t listen to them. He doesn’t listen to anybody. There’s always people in Trump’s wake whispering to him about one thing or another. But since he doesn’t listen to anyone, getting anything done will be a very difficult proposition. The Project 2025 people shot themselves in the foot by getting all that bad press. And now they’ve kind of been pushed aside by the America First Policy people — Linda McMahon and her group. So you have a bunch of rabid ideologues on one side, but at the same time, he’s also surrounded by this small group of insiders who ran his campaign who are not very ideological at all, but very disciplined, political, just get-it-done people like Susie Wiles. So which side prevails in the end? We don’t know. But the truth is, when Trump is involved, nobody ever wins. Donald is always at the center. It’s always about what he wants, which changes every moment, so it’s incredibly difficult to influence him. He doesn’t listen, he doesn’t hear, he just does what he wants to do. 

But I imagine Trump is a very different person now. He isn’t as cowed and awed by that office as he was the last time. You don’t think his defeat in the last election, narrowly escaping prosecution, surviving an assassination, has impacted him in any significant way?

Trust me, he was never awed by that office. He is not a different person! He was no different in the White House than he was in Trump Tower. He was not different in Mar-a-Lago than he was in the White House. He lives in his own exclusive bubble, so his environment doesn’t really impact him. He is his own environment. Also, never underestimate how short an attention span he has, because in Donald Trump, it is the shortest it can be. He is always on to the next rhetorical gesture. He exists wholly in a rhetorical world — doing things, getting things done, follow through, all of that normal business discipline doesn’t exist for him. 

You had a birds-eye view of Trump’s early days in office and got an unprecedented look at his team and how he interacted with them. Are any of his old minders still on board? Does your pal Steve Bannon still have a voice?

Bannon has a voice in the outer orbit, but Trump can’t stand Bannon and doesn’t listen to him. Steve can influence people who call up Trump and try to lobby him, but Bannon himself is pretty much banished to the sidelines. Trump now has a close campaign staff that knows how to manage him, relatively speaking. But their secret to managing him is not trying to manage him. Instead, they have been able to carve some influence by doing the kinds of things he’s not interested in, which is always the way to get things done in Trump world. You just focus on the stuff that he couldn’t care less about, which as it happens, is a lot of things. That was Jared’s secret. 

Jared and Ivanka [Trump’s son-in-law and daughter] kept a really low profile in this campaign, and they’ve both ruled out a return to Washington. In fact, two days before the election, Ivanka was tweeting Torah verses and talking about about her spiritual transformation. Do you think they can really resist the proximity to so much power?

No. I think it’s very, very likely that both will be back. These are power-mad people! Jared and Ivanka are opportunists in the purest, ultimate sense. You know, the Trump campaign always kind of regarded Jared as a barometer of how well they were doing. In the early days of the campaign, after Trump announced at Mar-a-Lago, Jared wasn’t at all interested. He was nowhere to be found! But as they became more successful, as Trump’s numbers improved, Jared’s appearances would increase. He’s all in now. And I think there’s a good chance, with Republicans running the Senate, that Jared may be the Secretary of State. [Editor’s note: He won’t be.]

So one thing we’ve covered a lot here during this election is the intersection of celebrity and politics — which seemed to reach a fever pitch this year. Kamala Harris was able to draw a team of all-star A-listers to her cause — De Niro to Taylor Swift, Bad Bunny to Springsteen. But none of it seemed to have made a difference. What’s the lesson in all of this? Do people no longer give a shit what celebrities have to say?

Hollywood clearly had no impact whatsoever on this election. And arguably Hollywood no longer has much impact on anything, but especially on politics. Maybe when the dust settles, there’ll be some self-scrutiny that will go on. But since Hollywood folks aren’t given to introspection, everyone will sulk for a bit and then go on their way. But there will be some Hollywood powers who will be thinking opportunistically, like, how do we make a buck off this? And looking at how [Warner Bros. Discovery CEO David] Zaslav and some others have been responding, I think that’s already starting to happen.

What does that look like? Given the impact that podcasts and other alternative media had on this election, there has been speculation that Murdoch will go on a buying spree to bring these right-wing voices together under the Fox banner.  Do you think other media companies will pursue a similar strategy?

I do, actually. But I would put Murdoch off to the side, since he’s 93 years old now and non compos mentis half the time, and also embroiled in a lawsuit with his children, the majority of which clearly want to do something entirely different with this company. I wouldn’t really look at Rupert as any kind of bellwether, but I think other media companies, and certainly their leading shareholders, are paying rapt attention to this major shift in consumption and habits. The day after the election a lot of them probably woke up and said, “OK, Donald Trump is the president. We got to figure this out. We got to adapt. We got to make our peace.” 

Do you think this will have an impact on programming? In 2016, we saw a lot of shows about the heartland and about steelworkers and veterans — Hollywood’s idea of real people.

Yeah, well, they’ll try to figure that out. Hollywood will, as it always does, try to read the zeitgeist. But the challenge is getting the zeitgeist right, which they do only occasionally. Maybe they get lucky 20 percent of the time. 

I was just looking at a piece that you wrote for THR after Trump first got elected where you wrote about this bizarre paradox of Trump being alternately besotted with the media and at war with it. You pointed out that despite his bluster, he had close ties to people across the media and Hollywood establishment. People forget that he dreamed of becoming a Hollywood mogul himself years ago. 

Well, that’s textbook Trump. He loves to scream and yell and threaten the media — “The press is garbage! The enemy of the people!” But the truth is, anybody who runs the media, anybody who has an audience, Trump is going to embrace. He’s always been like that. And anybody who has money, he also embraces. Publicity and money are the two things that most move him.

But the third thing that moves him is power. And the establishment media today is obviously a lot less powerful than it was even four years ago. 

Well, he doesn’t know that. I mean, he lives in a world where the old rules still apply. Everything he does from a political point of view is media-directed. The one strategic view he has had from the beginning of this campaign and from the beginning of his entire career, actually, is if you own the news cycle, you win. You just have to own the cycle. And it doesn’t matter if the attention is good or bad. 

How do you think this plays out? After Trump won in 2016,  there was this shock and horror that soon morphed into “the resistance” —  this mobilized sense of speaking truth to power. This time around, it just feels like dark despair. How does the media come out of it? 

I cynically think that, despite their protestations, the media will come out of this election better than they would have if Kamala had won. Trump will be a net positive for the media, at least on a short-term basis. The guy is about one thing, and that is ratings. He’s always good for ratings. So now the media actually gets to live for a few more years. Courtesy of Donald Trump. 

But outlets like The Washington Post and MSNBC and The New York Times previously did well because they were considered checks on Trump. The perception among journalists was that if they exposed who Trump really was, people would reject him. Obviously, they were wrong. 

I don’t think it’s just about Donald Trump. It’s just that sense of watching a car crash. It’s that sense of conflict. You don’t have to go further than that. What does the media thrive on? What gets clicks and sells papers? The same thing that Donald Trump thrives on. Conflict, conflict, conflict. The more conflict, the more eyeballs. Simple. 

Do you foresee the media rethinking the way it will cover this second administration? I’ve seen a lot of think pieces in the last two days, wondering how the media got so isolated from the public. Do you think that portends real changes ahead or just jittery day-after recriminations?

No, it’s all just blah, blah, blah. The media is incapable of rethinking anything except where there is a short-term opportunity for it. 

After the first Trump victory, you wrote about certain Hollywood fixtures like Ari Emanuel, Bob Iger or Jeff Zucker who were unofficial conduits to the White House. Are there still people in Hollywood that can pick up the phone and get through to him? Are there any new names on that list? 

Yes. I’m not sure about Zucker these days, but I think that are certainly a bunch of people in Hollywood who have relationships with either Trump directly or with people around him. Ari or Zaslav or people like that. They’ll make what hay they can make on that. But the real center of power and the difference from the previous administration will be the tech people, who will play a much bigger role in his administration this time around. 

The tech bros made an all-out multibillion-dollar bet on Trump, and it paid off. But how will that play out for Elon Musk or Peter Thiel, or even Bobby Kennedy.  What kind of role do you see them playing in this new White House?

There’s a couple of ways that this can play out. I mean, we don’t really know what Elon particularly wants, other than getting on the phone with world leaders. I don’t know what Musk thinks his end game is. Obviously he has a particular, and maybe extraordinary, opportunity here, and lots of big social and economic ambitions, but maybe his play is more long-term. And having JD Vance in that position [as vice president] is obviously very wise and very meaningful to the tech people who installed him there. Vance will be there long after Trump is gone.

Kennedy, however, is a different matter. He’s in that classic position where he has loudly announced that Trump has offered him a job. Now, the unfortunate thing for Bobby is that Trump offers everybody a job. But what Trump has offered Kennedy is a job that does not exist — some kind of healthcare post that doesn’t appear on a government org chart. And that’s a typical Trump move: He gives you something which doesn’t cost him anything, but also doesn’t really accomplish anything. And then you get sort of lost in the morass, which I would suspect is what’s going to happen to poor Bobby. 

Elon in particular seems bound to play an outsized role in all this — which is a little scary, because he seems as grandiose and intemperate as Trump is.  But he’s the kingmaker in a certain way. And there are many people who think that he’ll now have the ability to implement a whole host of ideological and economic changes that go well beyond the usual Trumpian dogma.

That’s very possible, but I can also see their happy union ending very, very unhappily. Having two kings of the world in the same room is really difficult, and neither of theses guys likes to share a stage. And again, Trump is possibly so narcissistic that he is not influenced by anyone, even the richest man in the world. He just can’t listen to anyone. But because he’s that way, even Elon Musk has his work cut out for him.

Knowing how reactive Hollywood and the media tend to be, do you foresee media entertainment companies maybe tamping down on culture war or identity-politics stuff to placate the new regime in D.C.?  

I think everybody is going to have to suddenly react to the political and ideological signals here. I mean, we know the Democrats did not sell their case — in fact, quite the opposite. So perhaps rethinking some of their strategy isn’t the worst idea.  

We haven’t heard much from Melania [Trump’s wife] in this campaign. Do you think she’ll be any more visible than she was the last time around? 

Well, remember, the Madison Square Garden rally was the only campaign appearance she made in the past couple years. During all of his courtroom appearances, she never bothered to show up even once. I mean, I think you can read the obvious statement here. She wants distance between herself and her husband. I mean, she didn’t spend all that much time in the White House during the first administration. I would expect that she will spend even less now. And so to what extent is this a real marriage, anyway? Well, let me put it this way. It’s certainly not a middle-class marriage.  

Just ask Laura Loomer! [laughter]

Yes! Another scandal that just passed over. Why doesn’t the country, this theoretically middle-class country with its traditional values, why don’t they notice all this stuff and take exception to it? 

You could say that about a whole host of his shortcomings. Why does he have this magical ability to survive circumstances that would be poison for any other politician?

Many have speculated about this, and I don’t think that there’s a clear answer, but some things are obvious. I think, at his essence, Trump is the “fuck you” candidate, and people are willing to tolerate a lot of awfulness because they see him as authentic and unscripted and unafraid. Few other candidates can pull that off. Kamala certainly couldn’t. If Kamala said she was a middle-class person one more time, I was going to shoot myself! I mean, that woman has not been a middle-class person for 30 years. And her whole reason for being — and I don’t say this with any condemnation, just what is obvious and true — her reason for being is not to be a middle-class person. Whereas with Trump, there’s no cover. It’s like, “I’m the most ambitious person in the world. I want whatever I can get, I want whatever I can take. I’m Donald Trump!” And everybody says, yeah, well, that’s just what those people are like. At least Trump admits it. 

I know Trumpland was not a fan of your last two books. Do you still have contacts in that world? Have you spoken with Trump since Fire and Fury came out? 

Let me not say whether I have spoken to him. But I still have a whole lot of contacts throughout his company and his political operation and even his family. I’ve been doing this now for more than eight years. I mean, it’s a kind of weird that so many of these people have become, dare I say, my friends, 

He does seem to have this bizarre, almost masochistic tendency to keep courting the very journalists who’ve been most disdainful of him. 

Well, just remember, Trump’s a salesman. Give him the opportunity to sell you. Or give ’em the opportunity to screw you too. That’s a salesman! 

Even before he was elected, he was running around promising to yank the licenses of critical networks like ABC and CBS. Whether he can legally do so is highly doubtful, but he can certainly make life harder for them, right? Do you think media outlets will start pulling their punches to avoid his wrath? 

Well, I think that there is a possibility that might happen, but for all his bluster I don’t think he’ll ultimately do that. And again, that’s not because he doesn’t want to, but because that will take effort and strategy and follow through, which is not his strong suit. Will he condemn and demonize the media? Yes! I mean, that’s the thing he really loves to do. But the media is also a super convenient foil for him. 

Who will be calling the shots in this new administration?  I suspect there will be veterans like Jason Miller and Stephen Miller and Kash Patel who stuck with him through the insurrection. And new people like Susie Wiles and Chris LaCivita and Elon that we’ve already mentioned. Are there other players we should be paying attention to? 

Well, there are definitely some new people. And a whole crew of old ones. It’s a mixture. And I think what everyone is trying to figure that out is who ends up on top. So a lot the calls that I’ve had today are asking exactly that question. “Who do I call?” “Do you know anyone who you can introduce me to?”

And what’s your answer? 

The answer is, I do. [Laughs]

Name three things that we should be prepared for in the next hundred days. 

Chaos, chaos, chaos. 

Sounds fun!

I don’t know about fun. It may well be the start of a real national nightmare. But at least nobody will be bored.