In the days immediately after the election that shocked the world, POLITICO Magazine convened the group of people who know Donald J. Trump better than anyone outside his family. We asked his biographers the questions that were on everyone’s mind: What happens next? Will the unabashedly self-promoting and self-obsessed businessman transform himself into a selfless and dignified president of the nation he was elected to lead?
Now, after more than two months of Trump’s norm-shattering transition, we gathered Gwenda Blair, Michael D’Antonio and Tim O’Brien by conference call (Wayne Barrett, the dean of Trump reporters, could not participate because of illness) to assess whether Trump has continued to surprise them. Their collective wisdom? In a word, no.
Story Continued Below
From his pick of nominees for posts in his cabinet to his belligerent use of Twitter (our conversation was a day before he traded barbs with Congressman John Lewis) to his unwillingness to cut ties with his business to avoid conflicts of interest, they see the same person they’ve always seen—the consummate classroom troublemaker; a vain, insecure bully; and an anti-institutional schemer, as adept at “gaming the system” as he is unashamed. As they look ahead to his inauguration speech in two days, and to his administration beyond, they feel confident predicting that he will run the country much as he has run his company. For himself.
“He’s not going to be that concerned with the actual competent administration of the government,” D’Antonio said. “It’s going to be what he seems to be gaining or losing in public esteem. So almost like a monarch. The figurehead who rallies people and gets credit for things.”
Michael Kruse:The last time we talked, we were in the immediate aftermath of the shock of November 8, and now we are days away from the swearing in of Donald Trump as the president of the United States. Has the transition over these last two months gone better than you’ve expected, or worse?
Gwenda Blair: I think it’s gone exactly as I expected. It seems like the exact same M.O. that we saw throughout his career, throughout the campaign, and now. This is all about him completely dominating the news cycles—the use of Twitter to distract from any real questions, emphasis on loyalty, vituperation toward anyone he sees who is disloyal or doesn’t toe his line, and his emphasis on conflict, the notion of setting people against each other. Now it’s countries against each other. It’s news organizations against each other.
Tim O’Brien: I agree with Gwenda that a lot of this has been in keeping with the same guy we’ve known for the last 20 years. But I don’t think we’re really going to know yet about the implications of anything that he’s doing until he has his team in place. I think some of the people he’s brought in have surprised outsiders … people like Rex Tillerson and Gary Cohn and what appears to be an entire fleet of Goldman Sachs alums are joining his administration. And none of those posts, I think, were anticipated prior to him getting elected. We won’t really know what the full scope of his engagement is with the world or with the American public until that team gets rolling. So some of this, I think, is premature, but there’s no question that it would have been in his best interests to sit back from the Twitter show and take a breather. And he couldn’t help himself. And he’s opining on subjects that he knows very little about from national security to healthcare policy and others.
Michael D’Antonio: I also think that he’s the same old Trump and emphasizing this combative quality and wanting to fight with just about everybody. I’ve been asked lately about why he seems to have affection for a guy like Putin. And the thing that I’m afraid of most, based on what I’m seeing, is that he seems to want to be the same style of leader, where he intimidates people. He tries to shame them. The most shocking thing I think he did was note all of his enemies in his New Year’s message. The idea of a president actually having even the thought of all of these enemies in his head as he’s welcoming the new year and greeting the country is almost crazy to me.
Kruse: Michael, in your book, and other places, too, he has talked about how much he enjoys fighting. And he certainly fought a lot of people throughout the campaign, and he hasn’t stopped fighting. From Meryl Streep to the intelligence community, he’s still picking fights. Do you think he is going to pick fights with leaders of other countries? In other words, is there any indication that he would be able to separate the interests of the country now from his own personal pique?
Blair: Zero.
O’Brien: Absolutely not. There will be no divide there. The whole thing has been a vanity show from the second he ran to the Republican Convention. I think we can expect to see the same on Inauguration Day. He’s been unable to find a clean division between his own emotional needs and his own insecurities and simply being a healthy, strategically committed leader who wants to parse through good policy options and a wide series of public statements about the direction in which he’ll take the country.
Blair: There’s a fusion, I think, of his childhood, an emphasis on being combative, being killers—as his dad famously instructed his boys to be—but also, I think, his own competitive nature, and then his grasp in early adulthood that being a bully and really putting it to other people and not backing down often works. He also had his church background telling him that being a success was the most important thing and that got fused with the sort of ‘You want a crowd to show up, start a fight,’ P.T. Barnum-type thing early on in his career. And then Roy Cohn as a mentor, a guy who stood for cold-eye calculus about how bullying people works. And you put all of those pieces together, that he’s been doing this his whole life, and I don’t see a single reason for him to back down. He’s going to go full blast ahead with that.
O’Brien: His father and Roy Cohn, those are the two most singular influences on his whole life, and they provided him with a militarized, transactional view of human relationships, business dealings and the law. And he’s going to carry all of that stuff and all of that baggage with him into the White House.
D’Antonio: Those early influences are essential, and I also think it’s correct that he has been conducting his entire life as a vanity show, and he’s been rewarded, most recently since his reality TV show, by ever-greater public interest in him. This is a guy who is a president-elect who describes himself as a ratings machine, which is an absolutely absurd thing for a president to be reflecting on, but that matters to him.
But one thing I think that we have overlooked as we see Trump trying to delegitimize others is what I suspect is a feeling he has inside that nothing he’s ever achieved himself has ever been legitimate. This is a person who has never known whether anybody wants to be around him because he’s a person they want to be around or they want to be around his money. And since he’s promoted himself as this glamorous, incredibly wealthy person, that’s the draw he’s always given. So he doesn’t know if he has any legitimate relationships outside of his family, and that’s why he emphasizes family. … He’s always kind of gaming the system—not, in my view, winning on the merits. And even his election was with almost 3 million fewer votes than his opponent. So he has this deep fear that he is himself not a legitimate president, and I think that’s why he goes to such great lengths to delegitimize even the intelligence community, which is the president’s key resource in security, and he’s going to do this demeaning and delegitimizing behavior rather than accept what they have to tell him.
Blair: I wanted to go back to one of the words that Michael used, which was “gaming the system,” which is so much a part of his dad’s—what Fred Trump did, what Donald has done. Looking for the loophole, pushing it as wide as possible, going through it. Donald did it through his whole career. His dad did it through his whole career with his use of federal subsidies and tax abatements. And now we’re seeing that he’s gaming the White House. He’s gaming, looking for the loopholes. The president is exempt from these conflict of interest laws. There’s an awful lot, it turns out, that are matters of tradition, of habit, of what we expect. But they’re not actually legally required—the tax returns, all of that. He’s gaming all of that. All of the things that people thought had to be done, don’t have to be done.
D’Antonio: I think Donald Trump measures himself by the number of norms that he can violate. The more he can get away with, the more he can thumb his nose at convention, the more powerful he feels.
O’Brien: He’s a profoundly anti-institutional person, and I think that’s part of his great appeal to voters. Voters right now are sick of institutions, and he’s got no problem railing against them. I think the danger here is he’s completely ill-informed and lacks, I think, the generosity of public spirit to think about what the right replacements should be for the same institutions that he’s railing against.
Blair: He’s the kid in the back of the class who is taunting the teacher, who is taking over, who has pushed the principal out of the principal’s office, and he’s appealing to that instinct that everyone has at some point in their lives to overthrow everything.
O’Brien: I remember one thing in Palm Beach at a party there. I had dinner with him and Melania, and afterwards he was cranking music up around his swimming pool as loud as he possibly could and he leaned over to me and he said, “All these stuffy so-and-so’s here in Palm Beach hate how loud my music is, so I want to turn it up as loud as I possibly can, so they can hear it everywhere—and I don’t care if they don’t like it.” That’s more or less what he said to me, and that’s fun and funny that he’s taking on the Palm Beach establishment. But the reality, too, is that he chose to move to Palm Beach and tried to become part of the community there at the same time. So at the very moment he hates the establishment, he also desperately wants to be approved by it.
D’Antonio: You know what I think is really odd about this is that this sort of makes him the classic ‘60s, early-‘70s baby-boomer, anti-establishment ruffian. Everybody talks about how it was, this cliché version of the anti-war hippie person that represents the ‘60s, but I think this narcissistic, anti-establishment tenor of his personality and what he’s doing now makes him the inheritor of all of that chaos. He just never outgrew it.
Blair: The sleeper anti-establishment figure—because at the time, of course, he was going to class in a coat and tie and preparing for a completely straight-ahead business future. He had no interest in the counterculture.
O’Brien: Except where it concerns doing what you want to do to the exclusion of all norms. It’s a case of people who were very liberal and idealistic. It was in the pursuit of something for the community and maybe for yourself. And in Donald’s case, there is no other thing than himself.
Kruse: So if he is ill-informed, is he, in your estimation, putting people into place who are informed? His hiring M.O. has been to go with his gut and prioritize “the look” and loyalty or potential loyalty over experience and credentials.
Blair: The cabinet appointments seem to me to be people who have been successful in some realm, so he takes that as proof of their abilities. But he’s also looking for people that will be in conflict with everyone in that department. Down the line, it’s the same kind of sowing-conflict mode that he’s used throughout his career of setting people against each other so that they’re not going to be loyal to each other and they’re going to be loyal to him.
O’Brien: Don’t you think it’s kind of ironic that the one person who might be more a defender of democratic institutions is a general that he’s putting in charge of the Pentagon?
Blair: Who’d have thought?
O’Brien: General [James] Mattis is the one person who seems extremely well-read and committed to a sort of well-rounded view of power and how the country works and he could impose some moderating influence on Trump. I think that’s amazing to think that we’re all hoping for that to happen in the person of a general who had to get a waiver to serve in the post.
Kruse: These are people who have been successful in their areas. They have also giant egos. They know a lot, more than he does. Do you think he is going to take their advice?
O’Brien: At the end of the day, the two most powerful people in his White House, other than him, are going to be Jared Kushner and Ivanka Trump, and they’re going to have the final say on everything. And whatever Gary Cohn or Rex Tillerson or General Mattis or Jeff Sessions or Steve Bannon has to say, it will all end up getting filtered through Javanka.
Kruse: Did you just say “Javanka”?
O’Brien: Yeah. Other than those two, he won’t listen to anyone in a meaningful way, and he never has listened to anyone outside of his core group and family at the Trump Organization for decades, and that’s not going to change.
Kruse: Can any of you think of one time that a subordinate had to tell him something bad, something he wasn’t going to like? And what were the consequences?
O’Brien: You know Jack O’Donnell is a case study of that in the casino business. He routinely brought Donald bad news, but Donald either ignored it or pretended it didn’t exist. Any number of people who have worked with him in his real estate dealings in New York will tell similar stories. News that contradicts his worldview gets flushed down the sort of emotional and intellectual dispose-all that I think he carries around with him from the second he gets out of bed to the minute he goes to sleep each night. He is the master of counter-reality programming, and it makes him uniquely insusceptible to advice and creative thinking.
Kruse: My read, based on reporting over the course of the last year, has often been that he is simultaneously this utter terror of a micromanager and a “don’t-bother-me,” “hands-off” delegater—depending on the moment, the task, and how he’s feeling. So my question is: What makes him jerk the leash? What makes him become the micromanager?
Blair: If he perceives that there’s the tiniest threat to his authority, that there’s any ripple of disloyalty, as he would think of it—then he’s on it. Whether it’s, like, a cigarette butt in the corner of the parking lot, it doesn’t matter—he’s got to show that he’s on top of everything and that he’s got eyes in the back of his head. And at the same time, in his own organization, the Trump Organization—he would hand off authority on things. He didn’t have to manage everything, but if there was any hint that anybody was doing anything other than paying 24-7 attention to his needs, then he would discover that something was a 32nd of an inch off or a second late or whatever. And that person would be cowering, and he would lash out.
With the cabinet, of course, as Tim was saying, we have to wait and see, but I think he’s appointing people who, in many, if not most cases, have the exact opposite point of view from everyone in that department, and they’re just going to thrash it all out, and he’s going to be listening to Jared and Ivanka and sailing ahead.
D’Antonio: I think the key thing that you said, Gwenda, was that he expects people to pay attention to his needs, and the job, seems to me, when you’re dealing with him, it should be about focusing on imagining what his ego requires and not contradicting him publicly. Maybe not even contradicting him one-on-one. I wonder if he’ll give orders and they may not be followed and he wouldn’t care if he doesn’t find out about it. He’s not going to be that concerned with the actual competent administration of the government. It’s going to be what he seems to be gaining or losing in public esteem. So almost like a monarch. Like a modern monarch. The figurehead who rallies people and gets credit for things.
Kruse: Some of the things that his nominees have said over the last couple of sessions have contradicted him—aren’t they being disloyal already, in some sense? Do you think he sees it that way?
O’Brien: Well, it depends. If what Jeff Sessions and Rex Tillerson, for example, have said thus far in the confirmation hearings are completely in keeping with how they actually see things—absolutely, yes. If part of it is simply a confirmation strategy, then we won’t know. But I think we owe it to both of them, at least now, to take it at face value that both of those men are being completely candid and honest about how they see things and they’ve already come out on very important points with contradictory viewpoints from Trump on things like water boarding and civil rights. And interactions with Russia. However, they work for him. And at the end of the day, he’s going to be telling them what to do. They could offer him contradictory advice in keeping with their own values and not in keeping with his—but, again, at the end of the day, he’s the president.
D’Antonio: Do you think, though, that he would allow that kind of thing to maybe be worked out publicly in these hearings, so that, for example, on the matter of torture, he could then say, “Well, I prefer it, but my cabinet members remind me that it’s against the law and as long as that’s what the law is, we’ll just have to go along with their advice. I’m the really tough guy. I want to do it, but my hands are tied right now.”
Blair: You know he’s going to use them to give himself cover.
O’Brien: He always has an escape hatch. He always builds in some way of justifying not doing the things he’s promised to do on the basis of what someone else has done to him. In this case, it could be Congress, or, “We’re required by the Army manual that governs interrogations to not do this torture. I wish it wasn’t so but, you know, we’re stuck.”
Blair: He’s the master of saying one thing, and then, 10 minutes later, you’re seeing the opposite. What is it that he stands for? He’s a moving target, and you never exactly know. So he’s able to move around the landscape and never exactly be on point. So using these folks as cover? Sure. Why not?
D’Antonio: He stands for what he can get away with, and if he can’t get away with it, but he made a promise on a ceremonial basis, he’ll figure out a way to blame it on someone else that he can’t fulfill a policy promise.
Kruse: He couldn’t let go of his company, obviously. I’m wondering if he thinks Don Jr. and Eric are going to be able to run the company without him. And will he even expect them to, or is he still going to be sort of the president of the Trump Organization, in essence?
Blair: Totally. What was in those manila folders? What was in the stack of papers that was flourished at the press conference?
O’Brien: That reminded me of after, I think, he won the South Carolina primary, and at this press conference he had a table stacked high with Trump steaks and Trump water and other Trump goodies from some businesses that already were defunct.
Blair: Yeah, he’s big on props, and that was a pretty good prop and his lawyer talked with a bunch of legalese and so, “Okay, that’s out of the way.” It’s not out of the way at all. Not in the slightest and he doesn’t exactly—and the idea that they’re not going to do any new deals internationally. How is that defined? They’re going to continue to do domestic deals? That’s a pretty darn big market. There was a lot of smoke and not even any mirrors.
O’Brien: Most of what the Trump Organization does, anyways, is domestic—overseas is primarily licensing deals and three golf courses. So the idea that they’re walking away from something significant by declining to do overseas deals is irrelevant in terms of the current mix of business they have. And I guess I sound like a broken record on this issue because I first wrote about his need to release his tax returns in the fall of 2015 and I first wrote about conflicts of interest last June. But conflicts of interest are going to haunt his administration if he doesn’t take a clean and consistent approach towards creating a real barrier between White House policymaking and Trump Tower deal-making. And nothing he’s done, including the fig leaf that he rolled out on Wednesday, is going to cure that problem. It could create real ethical lapses that tarnish the White House and the legacy and dignity of the office he’s about to inhabit. And he’s done nothing, including the plan he rolled out on Wednesday, to make people think he takes these kinds of ethical responsibilities seriously.
D’Antonio: This ridiculous reference he made to, “I turned down a $2 billion deal in Dubai just recently.” Why is he even in a meeting with a person who is going to do that?
O’Brien: If it even happened as he said it did. He said he was offered $2 billion in that conversation. I doubt he has ever in his life been offered a $2-billion deal. Maybe that suddenly happened over the weekend right before he had a press conference so he could brag about it. But it’s one of those things, I’ll believe it when I see it. But even more importantly, as Michael points out, he shouldn’t be having those conversations anymore, as he’s about to go into the White House.
D’Antonio: He has no concern for how any of these things look because he’s always gotten away with it and you can only really be sure of anything he says when you have independent paperwork or witnesses to consult. So I think that when I met with him, he told me he had zero debt—and then, more recently, it was pegged at in the hundreds of millions, and I think in the last week or so, there has been reporting that it’s $1.5 billion. So that’s why he doesn’t want to release his tax returns. That’s actual hard data and he’s allergic to hard data. He doesn’t want anything out there.
Blair: I think that it’s not quite that he doesn’t care how this stuff looks. I think he does care, but he sees it as a show of strength that he can do this. He sees that he can get away with it, that he can say these contradictory things, that he can say, “I turned down a $2-billion deal,” that with half a second of reflection anyone knows that’s ridiculous. That never happened and if it did happen, it shouldn’t have. It’s not that he doesn’t care about it. It’s that he’s boasting and bragging about it and saying, “Look, I can do this. I can get away with this and nobody can do anything about it.” That’s what he sees as his strength.
Kruse: He’s also always been a believer in bad publicity, and that bad publicity is, in fact, good. Publicity means people are talking about him. It worked through his breakup with Ivana and his affair with Marla Maples. It worked through the casino bankruptcies. It worked certainly throughout the campaign. Can that work—bad publicity is good publicity—when you’re president?
O’Brien: No, it can’t. It can’t be. The Trump Organization is this mom-and-pop boutique. It’s got less than 100 people, I think, working for it, and he’s about to take the reins of a portion of the federal government that employs over 2 million people, is global, touches on every key policy in American life, and in our overseas profile and he knows very little about most of all of that and papering that over with any kind of publicity or the good publicity, is in a strategy that’s a Hail Mary. And I think he’s going to be in for a rude awakening if that’s how he’s going to approach things, what his day-to-day life might become.
D’Antonio: I think that he’s sort of playing to the kids in the classroom who hate the teacher too and really love it when someone disrupts things or maybe the person who resents the elites. He’s always had a good sense of where those resentments lie because I think he feels them personally. But we need people who are gifted and intelligent to manage our affairs. And I think it’s going to become evident that he’s not up to it.
Kruse: So, last question. At night, when it’s dark and it’s quiet and he’s not sleeping at the top of Trump Tower, do you think Donald Trump is worried that he’s in over his head?
Blair: Not in the least. No.
D’Antonio: I would say not in the least.
Blair: No, no. He’s like, “This is the best thing that’s ever happened.” He’s won the biggest contest there is. He’s got the world’s attention solid for the next four years.
D’Antonio: I think about how Obama has talked about the problem in Syria being one that made it hard for him to sleep and was something he considered every night and every morning. I don’t know that Trump has the ability to think that way. He’s focused on his performance as a ratings machine. So if he gets more Twitter followers and imagines himself to be a star when he takes the stage at press briefings or appears in ceremonial events, that will be enough for him. He’ll think that he’s a success.
Blair: When he’s awake at night, I don’t think it’s because he’s awed or concerned about the responsibilities on his shoulders. It’s because there’s somebody he wants to get even with and how are you going to do it.
O’Brien: The only things that have kept him awake at night historically are money, sex, food, and revenge. And if you take those things out of the mix, it’s not like he ponders the deeper meaning of life. I don’t think he feels that he’s not up to this task. I think he did at different points during the campaign, and I certainly think on election night, and the first few days after that, you could see a kind of a watering down of his bravado. But that seems to have lasted for about a millisecond. Because I think he now feels like he’s fully in charge and has all the aptitude he needs for the office.
This conversation has been edited for clarity and length.
Michael Kruse is a senior staff writer forPolitico.