Michael Kruse is a senior staff writer for Politico.

There’s a tiny handful of people who know the story of Donald J. Trump better than anyone outside his family, and never at any point in their long observation of his life did any of them think this was a man who one day would be president. Back in March, when POLITICO Magazine first convened Trump’s biographers at Trump Grill in Trump Tower, they all agreed: There was no way he would win. The second time we convened them, in a conference call last month after the release of the damning Access Hollywood tape, they figured the most likely scenario was that he would wreak havoc in the weeks leading up to what they expected to be a resounding Election Day repudiation. Now, though, they are being forced along with everybody else in America to reckon with the implications of a victory they never saw coming. The biggest questions now for Wayne Barrett, Gwenda Blair, Michael D’Antonio and Tim O’Brien are totally different.

What happens next?


Can the proudly, unabashedly, defiantly self-obsessed and self-interested businessman they wrote about now find it in himself to act more selflessly, benevolently, on behalf of the people, all the people, of the nation he has been elected to lead?

What will Trump, the owner of golf courses and luxury apartments, a former reality television celebrity, a master marketer and brand builder extraordinaire, do with the far-reaching authority of the office of the leader of the most influential country in the world?

What will he do with the kind of profound power and prestige he has so craved for so long?

“He’s gotten where he wanted to go,” Barrett, the dean of the Trump biographers, told us. “He can’t get any bigger. This endless search that he has had all his life to get to the top put him at the top, and maybe that has a sobering impact on him.”

Barrett and the others, though, are not sure it will turn out that way.

Michael Kruse: He won. And we can talk about numbers and who voted and who didn’t. We can talk about Hillary Clinton and what she did or didn’t do. But, you know, what he accomplished last night is amazing. Is there something about Donald Trump that you, in all of your reporting on him, didn’t give him enough credit for that enabled him to pull this off?

Gwenda Blair, author of "The Trumps: Three Generations That Built an Empire" (2000). | Photo by Jesse Dittmar for Politico Magazine

Gwenda Blair: He came across as sincere and authentic, I think. The rambling, the incomplete sentences, all those things that seemed proof of incompetence and inability to deal with the complicated, sophisticated issues that were going to come up for a president—not to mention all of the negative, disparaging, crude and vulgar remarks— were reframed as sincerity, authenticity, what he’s really thinking, versus thoughtfulness. On her part, being focus-grouped, being careful with what she said, saying she was careful with what she said, I think we’ve all commented on it at various points, but didn’t really grasp how strong that is. Especially in a world where reality TV has played such a role … the usual metrics of reality like actual truth just don’t matter. It’s how it makes you feel when you’re listening. And that’s what he really was very, very strong at.

Michael D'Antonio, author of "Never Enough: Donald Trump and the Pursuit of Success" (2015). | Photo by Jesse Dittmar for Politico Magazine

Michael D’Antonio: That’s what Scott Adams, who is the Dilbert cartoonist, was going around predicting, that Trump would win based on his evaluation on his kind of hypnotic appeal to people. And there is something really compelling about that hyperemotional presentation where it doesn’t matter that these aren’t complete sentences, and that he has no policy. And what’s so strange to me, and also reassuring, is he is a demagogue, but really only on behalf of himself. And I don’t know what he’s going to pursue, and he, if he had an agenda that was firm, we could identify it and predict something. But I’m not sure he’s going to hold to anything that he promised. He could change direction tomorrow and say, “I see victory in this, along this avenue, and not the one that I set out to follow, so I’m going to change course.”

Wayne Barrett, author of "Trump: The Deals and the Downfall" (1992). | Photo by Jesse Dittmar for Politico Magazine

Blair: Not only did those things didn’t turn out to be considered flaws—they were considered strengths.

D’Antonio: Well, right. I had a Trump voter say to me, on Tuesday, “I know he’s a total asshole, and I can’t stand his personality, but I know who he is, and I don’t believe I know who Hillary Clinton is.” So that message—that she was a liar and two-faced and all of those things that people hung around her neck—obviously got through.

Wayne Barrett: Michael, I would say that the thing that I missed was—I don’t know if I missed it because he wasn’t the big public personality, but I missed his ability to connect. I missed his humor. You watch these rallies—and yes, he has times of incoherence. But especially as time went on, he was making a real connection with audiences that surprised me. I think I said in our earlier conversations, how engaging he could be on a one-to-one level when he was—you know, in my earliest dealings with him, way back in the ’70s, when we were both young men, but I didn’t think he could translate that to a platform like this, in front of 20,000 people, day after day. And the stamina was just enormous. He has no attention span and a great deal of stamina. So long as he’s talking, he can pay attention.

Blair: When he held up that mask of himself. I’ll resist calling him brilliant, but it was pretty darn terrific as a spectacle, you know?

Tim O’Brien: Well, we know from The Apprentice that he’s able to captivate the attention of a large audience. I think that was one of the reasons I did my book at the time I did it—was the traction he had gotten in the American imagination as sort of America’s favorite entrepreneur. So I don’t feel like that side of him was overlooked at the time I did my book. I also sort of get why he and Wayne didn’t have a lot of humorous exchanges of when he was calling up and saying, “Now, why did you kick all those black people out of your projects in Queens?” And Donald didn’t laugh.

Barrett: He didn’t get the joke.

Timothy L. O'Brien, author of "TrumpNation: The Art of Being the Donald" (2005). | Photo by Jesse Dittmar for Politico Magazine

O’Brien: Yeah, he didn’t get the joke. But I feel like I got that side of him. I traveled with him a lot, when I worked on the book, and at his home, had meals with him. And you know, as Wayne mentioned, he’s personally charming. I think that puts a little bit of a rosy gloss on the fact that I actually think he ended up appealing to people’s worst instincts in his campaign. And I really think, as I mentioned in the last round table, that the Trump virus infected the body politic in a way that we’re going to have to spend a lot of time recovering from because he surfaced and condoned bigotry, locker room talk about assaulting women, paranoia of immigrants, a really coarse dialogue about his political opponents, about any huge number of people’s physical features. And the people who voted for him overlooked all of those things. They just want a Rottweiler to go to Washington and rip the face off Congress. That is all they want out of this guy.

Kruse: Let’s say he did appeal to people’s worst instincts and did that consciously. And I just pulled my copy of The Art of the Deal from my Trump shelf, and there’s a part in this book when he talks about Sylvester Stallone, who created two all-time great characters, as he calls them, Rocky and Rambo, and he commends Stallone: “He knows what the public wants and he delivers it. I like to think I have that instinct.” What is that instinct? And the second part of that question is: Where does it come from?

Blair: His family. Big part. His grandpa, his dad. They’re just as sharp as he is about what people really want, and what they want to hear, and not what they say they might want.

Kruse: So his grandfather thought people wanted women out west?

Blair: Yeah. Women, alcohol, liquor. That’s what he delivered in his restaurants out west and got that original nest egg going. Dad had these thousands of units of middle-income housing and each unit had a little extra closet. He also was very shrewd about the financing end of things, as I think Wayne is particularly well aware of—how to make those mortgage guarantees, and various kinds of federal support for housing; how to absolutely push them to the limit, which we’ve now seen a latter-day version of with Donald, with his tax returns and losing other people’s money, and then using that to offset his own income 20 years into the future. That particular shrewdness and attention to what his own advantage is going to be. And actually it’s kind of a remarkable flexibility in a way. You could call that the principles, you could call it being able to see the advantage. But the family, there’s been a century of that. That’s the family culture.

Kruse: The most charitable interpretation of this is that he has some kind of genius-level ability to intuit what people want.

Barrett: Shamelessness is a skill. A lot of people, a lot of Republican politicians, knew where this nerve was, and knew what they had to say to hit it, but they didn’t do it. You know what I mean? I mean, he was willing to be much more explicit. What’s the difference between Romney and Donald Trump? What is the difference between them? One is a winner, and one is a loser. And what is the fundamental difference between them? In many respects, they were talking about big tax cuts; in policy terms, there were stark similarities. There were differences on trade and so forth. But what is the fundamental difference that explains their success and failure is how the language was the language of anger and revolt that Romney is just personally incapable of. And the language of racism, the explicitness of it, the willingness to do it in so many different forms, to be outrageous, to keep the camera on you. You know, so that’s a skill.

Blair: Raised to be a killer by his dad.

O’Brien: I agree completely that shamelessness is one of his key traits. I wouldn’t call it a skill, though, as much as a malady, and I think that—I think Donald lacks any kind of sophisticated strategic planning. I think he’s simply a force of nature. He’s Mr. Id, and he just plows forward into any situation in which he can get attention. And he soaks it up and he performs.

And I think he stumbled onto this national stage without a lot of long-term plans about what he was going to do when he began running. I think he was surprised as anyone else that he got as much pull with the voters as he did. And I think even if you look at some of the photos from him as the vote tallies came in, some of the photos of him he looks a little surprised and stunned himself that all of this is suddenly upon him. It’s like Robert Redford at the end of The Candidate, “Now what do we do?”

And I think we now have somebody who’s going to sit in the Oval Office who is lacking in a lot of adult restraints and in mature emotions. And America’s going to get a front-row seat to watching what that means.

Blair: It sounds like part of what it means is the people around him—who are they going to be?

I think when the advisors need him, they’re going to find him in the Rose Garden on a pogo stick, bouncing around, watching CNN on a flat panel.

O’Brien: Yeah, I think it’s really disturbing to think about who might be Trump’s brain in the way the Rove was Bush’s brain or Cheney was the guy who many people thought was in charge in the Bush White House. Who are we talking about? Is it Steve Bannon or Roger Stone or Rudy Giuliani? There might be a role for Newt Gingrich. I think Donald will let them have independent portfolios, but I also don’t think he’s a guy who’s ever taken counsel from anybody else. I think he may have them all filter their points of view through Jared Kushner and his daughter Ivanka, who are two people he listens to maybe a third of the time. But, by and large, Donald has never listened to anybody his whole life, and I don’t think that’s going to start changing now.

Kruse: I think Trump’s brain in the White House is Trump’s brain.

O’Brien: Yes, agreed.

Barrett: Well, you know, there’s too much day-to-day work for that. He doesn’t have the attention span for that.

Blair: He has said that he’s going to delegate stuff that’s boring.

Barrett: I think Rudy, if he stays in the government, and my inclination is that he may just stay with Greenberg, the law firm that Jack Abramoff turned into such a lobbying power, and they’ll become the biggest lobbyist in Trump’s White House. I think—look, he’s already held the number two and number three jobs in the justice department. He may prefer to be chief of staff in the White House. Whoever is chief of staff in the White House is going to have an enormous portfolio, and they always do. But this guy—look, Tony Schwartz [co-author of The Art of the Deal] wrote the book with him. He spent more time with him than we have. And Tony Schwartz, I think, said back in ’87 that he had no attention span. So he’s not going to—he’s going to want to talk about big issues, and there’s so many day-to-day decisions in a White House that have enormous impact that he’s not going to want to be bothered with. His management skills are extremely limited.

O’Brien: That’s right. I think when the advisors need him, they’re going to find him in the Rose Garden on a pogo stick, bouncing around, watching CNN on a flat panel.

D’Antonio: Well, he’s going to be very frustrated with the flow of information if they try to press it upon him in the way that staff would press information upon a normal president. And I could see him lashing out and sending people out of his office because he doesn’t want to deal with data. He’ll want to gossip about Angela Merkel or somebody else. This guy lives on gossip. And that may be what drives his decision, is who gets his intel on the juiciest story.

O’Brien: He’s going to do rallies. I guarantee you we haven’t seen the end of the rallies.

Blair: Isn’t there also a not-small matter of his own business interests? How are those going to figure in there?

He’ll want to gossip about Angela Merkel or somebody else. This guy lives on gossip.

O’Brien: Remember, the president isn’t governed by any conflict-of-interest laws. And it was designed that way, and he’s got a latitude to wheel and deal as he sees fit, and there’s not going to be any built-in trust that’s a band-aid around that because he said he’s going to live his kids running the Trump Organization, so that’s presumably Ivanka, Eric, Don Junior. And I would find it highly curious if he didn’t have regular phone calls with them about how the business was doing and didn’t have, in the back of his mind, things he could do in the White House that would benefit his businesses.

Wayne just shrewdly alluded to Rudy Giuliani and lobbying. I think that there’s going to be a lot of feathering of nests around that kind of stuff.

Blair: I don’t think he has ever made a decision that wasn’t to further his own interests. When has he made a disinterested decision about anything?

O’Brien: Never. Right.

Blair: Never. And he says, “Oh, it’s not going to be a problem. The kids are going to run it,” and the kids say, “Oh, no, it’ll be fine. We’ll be separate.” What? How are they going to be separate?

D’Antonio: What happens when Judge Curiel convenes the trial of Trump University in San Diego? I wonder what kind of scandals await Trump and what we’ll be treated to if the Democrats decide to get together in January and say they’ll obstruct him in the way that the Republicans obstructed Obama. I think there’s a lot of game left to be played, and I wonder if Donald is up to what’s going to face him once he’s actually in office.

Kruse: I’m wondering if you all think there’s any possibility that he will govern in a different way than he campaigned. Is there a part of him, from your reporting, that will be more measured, more responsible, as chief executive of the country?

Barrett: I don’t think he wants to prosecute Hillary Clinton, which is another reason why Rudy can’t wind up as attorney general, because Rudy has said many, many times, “Oh, I could put her away in two months.” He can’t go in as AG and not prosecute Hillary Clinton after saying it as many times as he’s said it. So I don’t think he really wants to do that.

I think we know he’s going to do these things: One is he’s going to tear up the climate accords and he’s going to defund the UN global warming program, and he’s going to promote the coal industry, and he’s going to be a complete captive of the oil and energy companies.

O’Brien: He’s also going to get a number of Supreme Court appointments. He’s got the Scalia vacancy. There’s a good chance that Clarence Thomas leaves the Court. Ruth Bader Ginsburg is aging; how much longer does she have on the Court? Conceivably, he may get three Supreme Court appointments that the country is going to live with for a generation.

Barrett: Yeah. And I think he’s going to do a lot of deportations and he’s going to tear up a lot of families.

O’Brien: And he’s got the nuclear codes and access to the biggest nuclear arsenal on the planet. And that’s one of my biggest fears as a citizen and as a journalist. It’s a concern because he doesn’t regulate his own emotions, he’s not a disciplined thinker, and I could see him surrounding himself with people that say to him, “Oh, North Korea just got a little bit out of the cage there. Let’s just drop a tactical nuclear weapon on them.” I think that kind of thinking could be very present in his White House, and I think that that’s another huge policy concern with him.

Blair: Wasn’t he kind of casual about the idea that we’re going to—one way to lower our defense budget is to give nukes to Japan and South Korea?

O’Brien: Yes, and allow China to invade North Korea and just deal with it that way.

Blair: Yeah.

O’Brien: And turn our backs on NATO. Save some money by turning our backs on NATO. Sort of budget cutting through reduced support for our strategic allies abroad.

D’Antonio: You have to also think about what he would do with the national security apparatus. Imagine that he’s getting the morning briefing from our overnight monitoring of what’s going on in the world or is aware of what’s going on domestically, and how tempting it will be for him to meddle. And if he’s willing to go to the low level he was willing to go to in the campaign, what crazy idea will he resist and which ones would he embrace just because he sees them as being unconventional, out-of-the-box thinking and this is how you shake things up? Are we going to have assassinations? Are we going to have black ops in places we shouldn’t go? And what happens if something like that blows up? I think this is more likely than a nuclear attack, but—

Blair: Isn’t there kind of a disconnect for him, that he wants the strongest country on the planet, but, at the same time, withdraw behind our borders? I don’t see how those two fit together.

Kruse: What is the best-case scenario? Could he rise to the occasion?

Blair: He’s capable of being flexible … to get a deal, and he does sometimes see an opportunity and he does go outside the box. That can be a good thing.

O’Brien: I mean, I think it would be good, obviously, for the country that he discovers his hidden resource in the back of his brain and rises to the occasion. I am inclined to think, from the way he’s behaved during the campaign and over the last five decades of his public life, that he’s not that person. But I think we should at least give him the benefit of the doubt for a period of time and see what he does.

Barrett: Well, I think he wants to be admired. I think he does want to be admired, if not beloved, so I think that’s part of him. No one has any idea of the enormity of this office and what kind of impact it can have on him. It could—I doubt it seriously—but it could make him a more serious person. The obligations here, the responsibilities here are so enormous. He’s not a fool, and he has to be aware of them.

And we know that he did not make it this far alone. We know that the RNC played an enormous role in his election yesterday. It’s possible that he will be restrained by the party itself and, in some ways, he will mature with this awesome responsibility that the people of this country have given him and not be the person that we’ve known, this group of us, all these years. He’s certainly going to have many of the negative policies that he’s talked about. He’s going to try to implement some of those policies, many of them, I think, but there may be some restraint that begins to sink in.

He’s gotten where he wanted to go. He can’t get any bigger. This endless search that he has had all of his life to get to the top put him at the top, and maybe that has a sobering impact on him.

D’Antonio: I sort of take some comfort from what Tim may have seen in the photograph of Donald when it was dawning him that he was winning, and he probably was a little bit shocked and taken aback. And it would be a sobering thing because it’d be the showman who mounts this campaign and does it in such an extreme and outrageous way and suddenly finds that he won. That’s comforting to me, to know that it’s possible that he is awed by what has happened to him.

He also, I know, has studied what worked for other presidents. And he, I think, looked to Reagan. He talked to me about that—but also admired certain things about Obama and his mastery of communicating with the public, especially in his more successful first-term moments and campaign moments. So he wants to be adored. I think he understands what the public wants, and he’ll be sensitive, if they turn against him, to try and scramble to please them again.

So maybe he’ll be reactive in a way that is better, not worse, and reassuring and not disturbing.

O’Brien: Let’s also hope that he and Melania rise to the occasion when it comes to redecorating the White House, because I’m completely freaked out that we are going to get Las Vegas East as the décor and stylistic sensibility in the White House. So brace yourself for that and a possible 30-story extension in the air rights over the White House.

So he wants to be adored. I think he understands what the public wants, and he’ll be sensitive, if they turn against him, to try and scramble to please them again.

Blair: The ever-present air rights.

O’Brien: You know he’s already thinking about how he can get those air rights.

Kruse: Is there anything else that you think we should be thinking about?

Blair: Is he going to have a Twitter account when he’s in the White House? What happens to that Twitter account?

Kruse: I think he takes over @POTUS, does he not?

O’Brien: He already changed his personal Twitter account. He’s already changed his personal description to “President-elect of the United States.” So Donald Trump is on it. This presidency is not going to get in the way of his ability to be a mad DJ on social media.

Blair: Yeah, and that unfiltered presence, that direct connection to the electorate that he used so deftly, he will be continuing to use.

O’Brien: “Angela Merkel doesn’t know what she’s doing. Pathetic! Sad!” That’s how foreign diplomacy will be conducted in the White House.

Elizabeth Ralph, POLITICO Magazine deputy editor: There’s a big question out here in Congress: Do you think he has the potential to work with Congress? Do you think he will be successful in that? Or is he too much of a boss? You know, he’s used to running his own thing. But as a president he’s pretty constrained in a lot of ways.

Barrett: With a Republican Congress, they agree on tax cuts for rich people and just crush every program for the poor that they possibly can. On trade policy there might be conflicting points of view, and he might actually think that the kinds of policies Republicans have rejected, which is no cushion, no retraining programs, nothing for people who are affected by trade policy, there could actually be a Trump interest in doing something for people who are affected by bad trade policy or trade policy itself. And so on there I think it’s going to go from issue to issue. I certainly think that, as they control every lever of government—and they will soon control the [Supreme] Court—that they’ll be able to work together, especially when they have basically common economic perspectives. I don’t think that’s going to be a big issue.

Ralph: Is it possible they know more about legislating than he does and he’ll get pushed around?

O’Brien: Well, I think he would defer to them. I don’t think he cares that they know more. I think he would say, “Fine”—because I don’t think he has an interest at all in policy. I think he’ll want to do something, at a minimum, that’s symbolic on Obamacare and find some way to say, “I have a replacement,” and he’s got to do something on immigration. But beyond those two things domestically—and then some of the regulations that Wayne mentioned earlier—lifting a lot of the regs on energy and financial services industries—I think he doesn’t care a bit about domestic policy and I wouldn’t be surprised if there was a deal cut a month or two ago between Trump and some of the other GOP leaders in Congress, like Kevin McCarthy or others, where he said, “I don’t have a ground operation and I don’t have any money and if you guys give me a ground operation and if you give me money, I will turn domestic policy over to you whole-stock if I get in the White House.”

And I think he’d be happy to do that. It’s less work for him. He says he’s a hard worker, but he really prefers to watch a lot of TV and eat hamburgers. And I don’t think this is going to be an energetic presidency where he’s getting his fingers deep into the minutia of policy details. So I think he’d happily defer to the Congress.

Blair: He will be looking at—let’s see, what is it—435 people who have not small egos because they wouldn’t have run for election if they did, not modest types, who might have their own idea about things. And he’s not used to working with 435 egos that are pretty darn strong, so it could be interesting.

Kruse: Let me just ask you this to end. When you were working on your books, was there any part of you that thought he could take it to this point?

O’Brien: Absolutely not in my case, no.

Barrett: I thought it was more likely that they would lock him up. You know, I thought he was on the edge all of his business career, and that he was destined for trouble—I mean, big-time trouble. I certainly wrote way back in my book that this notion of the presidency was very much on his mind. And I wrote about various ways in which he thought about it and acted on it. But to think that he would actually get there? Incomprehensible to me.

Blair: Sort of yes and no. It was maybe our last roundtable, where someone, perhaps it was Wayne, said that maybe the surprising thing isn’t how he’s conducted himself as how the American people were willing to overlook so much because he hit a nerve with his appeal to the idea that there’s an elite establishment in Washington or in the country that’s getting all the benefits, you’re getting screwed, and to make that override all of the things, including the lack of disclosure of his financials, which I always thought was going to be the deal breaker. I think that’s kind of the big surprise. So that I’m surprised about—not so much that he would continue an MO that works for him, but that it worked very well.

This conversation has been lightly edited and condensed.