Susan Glasser is editor of Politico. Michael Kruse is a senior staff writer for Politico.

Back in early March, Politico Magazine brought together five Donald Trump biographers for a conversation over lunch at Trump Tower. At the time, the country was just beginning to grapple with the reality that the presidential nominee from one of the two major American political parties stood a good chance of being a real estate mogul and entertainer. Wayne Barrett, Gwenda Blair, Michael D’Antonio, Harry Hurt and Timothy O’Brien knew him better than anybody, had studied him more than anybody, had written an aggregate 2,195 pages in books.

So much has happened over the past seven months: the crackpot conspiracy theories, the rageful late-night Twitter tirades, the surges and slides in the polls, an onslaught of investigative reporting that painted him as a racist, sexist, selfish, uncharitable, lying predator. So we thought it was time, especially in the wake of “grab them by the pussy,” for an emergency reconvening of the Trumpologists.


In a conference call on Monday with Barrett, Blair, D’Antonio and O’Brien, the biographers were unanimous in their assessment of what we are seeing: They are not surprised. Trump is who they thought he was. This, they said, is not a show. It is not an act. This is the man they wrote about. In 1992. In 1993. In 1999. In 2005. In 2015. This is a man who has been one of the most famous people in America for going on 40 years. Only now, though, are many people, finally, really, getting to know Donald John Trump.

He is, the biographers said, “profoundly narcissistic,” “willing to go to lengths we’ve never seen before in order to satisfy his ego”—and “a very dangerous man for the next three or four weeks.” And after that? “This time, it’s going to be a straight‑out loss on the biggest stage he’s ever been on,” one biographer predicted. And yet: “As long as he’s remembered, maybe it won’t matter to him.”

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Susan Glasser: First of all, I’m super grateful to everybody for this, what we’re calling, “The Emergency Session of the Trumpologists.” Not only has a lot gone on since our first conversation back in the spring, but the last three days since the release of the Trump tape, the second debate and the implosion of the campaign has really, I think, led us all to want to talk with the people who spent the most time studying and thinking about Trump. What does he do in his paramount moment of crisis? Help us to make sense of the sort of tumult unfolding around us.

Michael Kruse talked to a few of you for a very good piece he did yesterday, trying to take this into account, and he made the point that, on the one hand, this seems all totally unprecedented in American politics; on the other hand, it seems somehow utterly predictable in the context of the personality of Donald Trump. I thought that was a good starting point for this discussion today. Let the emergency session begin.

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

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

Michael Kruse: So this past Friday when you all heard the hot mic tape from the gossip show bus, were you surprised?

Gwenda Blair: No.

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

Michael D’Antonio: Raise your voice if you were surprised.

Blair: Yeah. I don’t think any of us were surprised.

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

Kruse: Why not?

Wayne Barrett: Well, I would have to say that “grabbing by the pussy” was a little surprising to me. You know, thrusting his tongue down whatever mouth was available wasn’t much of a surprise, but “grabbing by the pussy” was not something I had anticipated.

Timothy O’Brien: I think he’s always been a skirt chaser. I guess, you know, in that context, it didn’t surprise me. I think he’s always boasted about the things that he’s the most insecure about, which is his wealth, his intellect and his sex appeal. And, you know, he’s held James Bond and Hugh Hefner out as role models. And I don’t think that’s evolved for him much since the age of 12.

Glasser: But James Bond didn’t have to force himself on women. So my question for this group is: Is he merely a foul‑mouthed guy, or is it possible that he is acting on these words in some way, that he is somehow aggressive or violent toward women?

Barrett: They talk about this as if this is locker room bragging, and really, I was in a lot of locker rooms and I never heard anything like this. Men don’t brag about forcing themselves on women. They want to paint themselves as desirable, and, you know, he doesn’t look like a stud here. He looks like a predator. I’ve never heard men talk this way. This is boasting of something that shows your own weakness. It shows, you know, that a woman doesn’t want you; whereas, most boasts in these kind of scenarios are about women who do want you.

Blair: I think that’s a super important distinction. I haven’t hung out in locker rooms, guys, so I’ve got to take your word for it. But my impression is it’s more like, “Women, you know, couldn’t wait to have me,” not that “I was able to force myself on her.” But, also, the frame of mind that women are objects, which, I mean—this just in, that’s not new, but the degree to which that permeates everything, I think, is stunning.

O’Brien: And then that they’re objects that are there for his taking because he’s a predatory personality…

Blair: Dominating, an alpha male and having a woman as arm candy. She’s just arm candy.

Glasser: Did any of you spend time actually talking to any of the women who went out with him or had sex with him? I mean, did any of these accounts ring true for any of the actual reporting that any of you have done?

D’Antonio: I didn’t come up with anything that anyone would go on the record. I did interview women who confirmed some pretty aggressive, if not violent—actually, I considered it violent sexual behavior—but no one will go on the record with this.

And the thing that I found consistent where Donald is concerned is that this kind of language and act is in his mind. I mean, that’s the thing that really shocks me is that he’s so predatory and so oriented toward seizing what he wants rather than relating to a person that, you know, it’s pathological. I’ve never heard anyone say this kind of thing ever, and the way that he’s talking about it, as if it’s locker room talk, is just ridiculous.

Barrett: You know, if you look at the Jill Harth tale that Nick Kristof just recently wrote about in the New York Times and that for some strange reason even now, after the release of this video, still gets no mention in all of these endless discussions on television about the video—they don’t discuss this parallel example that a Pulitzer Prize‑winning columnist from the New York Times took seriously enough to write about. But it’s a very parallel circumstance with the tape because Melania is pregnant at the time of this tape, and Trump is talking about this kind of activity. And Marla Maples was pregnant when this incident, the first incident happened between Ms. Harth and Donald. And so it’s regardless of what his own home circumstances are, regardless of what’s going on in his personal life. In both instances, his wife‑to‑be in one case and actual wife in the other, was pregnant with his child, and he’s walking around either talking this way or actually behaving this way.

Now, of course, he’s denied the Harth charges, but Kristof said he totally believed them. He gives you every reason in the piece to believe that this is a credible allegation, and it’s certainly consistent with the video. You know, Erin Burnett went on CNN and told a very similar story, at least about the kissing part of it and the Tic Tacs, about a friend of hers. So it’s not like we have to search for examples of this behavior. There’s at least two of them staring us in the face.

O’Brien: Graydon Carter in Vanity Fair, in the most recent issue, recounted inviting Trump to one of the Vanity Fair parties in the ’90s and seating him next to Vendela Kirsebom, the Swedish model. And about halfway through the dinner, she comes running up to him quasi-hysterical because she can’t handle sitting next to Trump any longer because of all of his lewd behavior.

But the problem with reporting all of these things is that the women involved often are afraid to go on the record. I know that his ex‑wives, when I was reporting, were very wary of being interviewed and running afoul of him by doing so, at least when they spoke with me.

Blair: Aren’t they nondisclosured up?

O’Brien: Well, I interviewed with Marla, and Donald knew it. And I interviewed with Ivana, and Donald knew it. But, in the course of interviews, they were a lot of things they were nervous about that did involve just a classic, you know, NDA. They were nervous about him.

Kruse: Do you all think he is driven more by lust or by fame?

Barrett: I think this is almost nothing to do with lust. This is subjugation.

O’Brien: Right. It’s acquisition.

Barrett: This has almost nothing to do with sex. This is a total power move if you’re talking about “I can plunge my tongue down any mouth I see. I just make my move quickly.”

O’Brien: After doing a round of power Tic Tacs.

Blair: As we all know, he is popping Tic Tacs all the time, but it’s just the analog behavior to how he is with men in any room—looking to dominate, being competitive, looking for a way to be in charge. And for women, I think for him, there’s really only one way to be in charge, and that is to dominate, and if possible, you know, some physical aggression isn’t off the table.

O’Brien: And, you know, he brought that into this political campaign. He’s really destroyed a sense of decency or boundaries or civic behavior in the course of this election that involved almost polluting everything he’s touched in this process, and this is the sort of apotheosis of all of that, unfortunately.

Glasser: Based on what you know about his personality from having studied it and written about it, how do you see him handling the next three weeks, given that he’s now in this hole? To me, his combative behavior since the release of the tape, his lack of remorse, his going on the offense, his complaining that it’s not fair, essentially, his going to war even against his own party seems very consistent with the person that you all have done such a good job of describing. So what does he do for the next three weeks? Is there a point at which he gives up, stops fighting? How can he be a loser for three weeks before the actual election?

O’Brien: I think he is just going to wage a scorch‑the‑earth campaign for the next three weeks. And if he loses, which I think he’s going to—I think he’s going to lose badly—he’s then going to come up with a scenario in which it was stolen from him, that the election was rigged, because he’s survived by creating alternate realities. And he’ll never say to himself he lost because he had a skeletal campaign operation, which he did; that he lost because he’s unappealing to a large swath of the voters; that he lost because he’s willfully ignorant about public policy; that he lost because he’s a nasty and unappealing bigot. He’ll never, ever acknowledge any of that. He’ll just come up with an alternate reality that said, “It was rigged against me.”

D’Antonio: Well, I think that what Tim is saying is consistent with the guy who would decide to have this campaign in the first place. You know, who would proceed knowing that he has all of these problems in his background, knowing how much audio and video exists, having been on “Howard Stern” and said horrible things? He just doesn’t seem to recognize his own issues and problems and how he’s perceived. So maybe for the next three weeks, he’s going to be trying out, you know, Breitbart TV and proving to the masses that follow him that he’s as red in tooth and claw as he seems to be. And, as Tim said, he’s already laid the groundwork to declare it was rigged in the first place.

Blair: I think that’s so on the mark, and that I was always kind of uncertain that he would really go for it, running for president, because he would have to do financial disclosures. What I didn’t realize was that he wouldn’t do the financial disclosures and would barrel ahead, and at least up until very recently, that he would seem to be getting away with it. So that all those tapes that are out there, he knew that, but he would just barrel over them—I think that has been his M.O. that we’ve seen in every other realm, so why wouldn’t it work in this one?

By the way, I wanted to ask something else about the tax stuff, which is being played as, you know, being a great business man. He lost all this money. You know, what’s so great about that? But I’m wondering if that wasn’t sort of like a strategic belly flop that he did. I’m not sure that he saw that as some kind of string of bad judgment at all. He knew he would be able to write it off against his personal income for 20 years.

O’Brien: Yeah. But I still think that that was really bad, bad decision‑making. I think he didn’t enter into guaranteeing $900 million in personal loans in order to engineer a write‑off six or seven years later. I think he ended up getting a boost from the tax code, but that $916 million write‑off is an emblem of how abysmal his judgment is and what a bad deal‑maker he is.

Barrett: I think we’ve got a very good preview of what the next several weeks will be like in the debate last night. I thought when he literally prowled the platform or the stage last night, we got a picture of what it’s like in his bedroom while he’s tweeting at 3 a.m. He was barking in the ugliest fashion, saying the ugliest things. And from the moment he got out there, he played the role of a victim. He now considers himself a victim of the national media, primarily, and a bit of the Republican establishment that abandoned him overnight, and I think he’s a very dangerous man for the next three or four weeks.

We have seen what kind of polarization he can evoke over the course of 15 or 16 months, but I’m afraid that he’s going to attempt to deepen that in profound ways in the coming weeks. As recently as the convention, he tried to cool down those who said “lock her up,” and now he’s saying he would lock her up and even describing the way in which he would do it.

So I think that what is really dangerous is, over the course of the next few weeks, he’s going to push every button he can, and the primary button that he can push is racism. That’s been the undercurrent of the campaign throughout. Believe it or not, you can be more explicit about it than he has been so far, and he may well go down that path. And it’s a very dangerous time because he has still a substantial number of Americans who support him, and where he takes them is really quite threatening.

O’Brien: And, you know, his danger throughout has been a danger by omission, I think—you know, that he was ill‑informed about policy, that he didn’t care to think things through, that he was shooting from the hip. But, you know, he then starts to crawl into the realm of nuclear weapons and has had off‑the‑cuff statements about re‑arming Japan and South Korea, and China should just go ahead and invade North Korea. And you first had that on the foreign policy front—the actual parameters, how dangerous he could be, took shape there.

And then last night in the debate, on the domestic front, when he said he’s be quite happy to use the Department of Justice to settle scores with Hillary Clinton and, you know, by inference, anyone else who he would regard as a political opponent, and that gets back to an old kind of way of politicking that the country has moved on from a long, long time ago.

D’Antonio: Well, don’t you think this is a kind of thuggery, that this is a guy who is playing to a mob when he talks about how he can say these things, because he goes before crowds and they’re out for blood, and their anger and rage is the justification he has for saying these thuggish things? And now he’s going to plunge the whole country into an authoritarian dynamic because the mob is telling him to do so? This is beyond shocking, and it makes you think that he has no frame of reference other than himself, that the country doesn’t matter, the peace doesn’t matter. Hillary Clinton’s physical survival doesn’t matter to him. You know, he’s going to take it all down, if he’s going to lose.

Blair: Like Tim said: “scorched earth.” That’s on the way to the thing that he started at the very beginning by saying the U.S. was falling apart, on the brink of disaster, inner cities are terrible, unemployment rates are through the roof, all the rest of it. That justifies that strongman thing.

D’Antonio: Well, imagine if this was an African-American leader who is saying these kinds of things. I think that the Republican Party would be screaming for the man or woman’s arrest, but he gets cheered for saying these things.

O’Brien: Well, he gets cheers from his base. And if you look at the electoral map now, he’s dug himself into a pretty big hole. It looks now, if the trend line continues, he’s going to lose North Carolina and Florida. There’s no way he’s going to win without those. Ohio is turning blue. At the end of the day, he’s turned the electoral map solidly against himself, and the kind of rage he’s stoking is regional rage. And I think we’re going to live with that well beyond this election. He’s really served to solidify the divisions regionally and ideologically in the country, and I think he’s blown up the GOP.

Glasser: In many ways, a lot of what Trump has done has been sort of predictable, at least very consistent with his personality and with his past, as you all have documented it. But what has gone on in the last few months since we had our initial conversation, that has actually surprised you about Trump? Michael has posited that the fact that Trump has actually held it together this long, that we’re having the implosion now in October of 2016, might be the surprise.

Kruse: And beyond surprise, what have you learned about him that you didn’t know before this all began?

Barrett: The parallels between the period of time leading up to his downfall in 1990 and the campaign now are striking. And what he did last night in standing up in this moment of crisis and being a victim—he thought of himself as a victim in the downfall of 1990 and playing the victim card and being as angry at others as he was in the ’90s in the way in which he dealt with the bankers. It was very strikingly similar to that period of time. But when you’ve dealt with the bankers in 1990, you could figure out a way where both of you came out with something and lost something. But in this case, there’s going to be a winner and a loser. And so there’s some similarities, but ultimately, he’s going to be a loser. He managed to survive in almost an unbelievable way when his empire collapsed, but managed to survive with the aid of the bankers. But this time, it’s going to be a straight‑out loss on the biggest stage he’s ever been on, and how he handles that—I don’t think we’ve got any precedent for that.

Blair: How can he pivot from that? I mean, for a little bit there was some thought that they were going to start—he and Roger Ailes—another network, but they don’t seem to have the resources to do that. Whatever resources he has, he’s not going to put into that.

I think Wayne’s point is really well taken, but isn’t part of that—I mean, this is sort of obvious, but during the primaries, with so many different people on the stage, that same M.O. worked. But only one other person on the stage for 90 minutes, it’s a totally different thing. And so I both learned and didn’t learn anything new, I guess. I mean, it is the same M.O. but in a different context and framed differently with only one person, one other opponent, who, by the way, is quite skillful.

O’Brien: Yeah. I don’t feel like I’ve seen or learned anything new about him. I think a lot of the way he’s approached this presidential race parallels all of the strengths and weaknesses of his business career, personally and professionally. He’s a profoundly narcissistic person who has been insulated from the realities of his own bad decision‑making by wealth and other people’s needs to kind of glom onto him, and I think he really did repeat so much of his past mistakes throughout this political season. He came into it with an opportunity and an advantage that he could have really built something on. But because of his myriad flaws—you know, he’s financially undisciplined, he’s emotionally and intellectually undisciplined, and he’s incapable of building teams and leading other people, profoundly incapable of those things—he blew those opportunities.

And I don’t think he really cares. I think he’s been more than satisfied to be on a big global stage and have everybody paying attention to him, and he’ll never characterize himself as a loser in this process, even if he ends up one.

I feel like I’ve learned more about the country by virtue of this exposure to the Trump virus than I’ve learned about Trump himself.

D’Antonio: About the country, Tim is touching on something that’s really disturbing to me: I don’t think I knew that the country would be this receptive to his message, but among the things that I think I’ve learned is that he’s truly the offspring of Roy Cohn and Joe McCarthy. He’s more violent in his way of thinking than I understood him to be. He’s less attached to reality than I thought he was.

But the real thing that I’m taking away is that he’s actually been telling us the truth about himself all along, and that this is not a character he’s been playing. It’s the real Trump. And I think a lot of times, people have wasted lots of effort trying to figure out: Is he serious, does he really mean this, is this all just one big joke? And I don’t think it’s a big joke. I think that he really is this horrible creature, and he has no regard for anything but himself, and he’s willing to go to lengths we’ve never seen before in order to satisfy his ego. And now we know.

O’Brien: Yeah. I think the things we’ve learned about the country are that racism is still a deeply troubling and embedded feature of American life, and he’s exploited that. I think we’ve learned that American voters don’t really care if they have a leader who is wildly ignorant about foreign affairs and spins tales about foreign policy that don’t correlate with facts or reality. I think we’ve learned that sexism and chauvinism are alive and well in the United States, and in institutional ways that are going to take a lot of work for the country to overcome.

I think we’ve learned that the leadership of the GOP lacks courage, that their party’s internal division triumphed over any adherence to conservative values, classic conservative values, and that the leadership of that party waited until the eleventh hour to distance itself from Trump and still hasn’t completely, that there’s a complete lack of political courage in this country.

Kruse: What does this next not-quite-a-month look like? What does he do? What is best‑case scenario, or what is worst‑case scenario?

Blair: About what Michael D’Antonio was saying—the whole kind of exercise of “who is the real Trump?” and that what we see really is the real him. It’s not Stephen Colbert. This is not a persona that’s adopted for a performance. That’s really him. He thinks that’s still a winning possibility for him, that he is a success. I think he deeply believes that. He can’t countenance—you know, his brain won’t take in that there’s like another possibility. He will continue to call it a success, and at the same time pursue this scorched‑earth approach that we’ve now seen on full display.

Kruse: So you think this is what he was expecting? There is a school of thought that this all began as sort of an opportunity to enhance his brand, and it was only going to go so far or could go so far. And here he is, less than a month away from Election Day, with not a good chance to win but a chance. Do you think this is a—I’m struggling here. I mean, is this a branding exercise that almost went too well, and now he’s so far down the road that he is where he is and we are where we are as a country?

Blair: After the birther controversy, after he went after Mexico and Mexicans in his announcement speech and he didn’t get called on it, he only heard cheers—I think that was the, you know, that was the liftoff.

D’Antonio: I don’t think he thinks. I don’t think that he is a guy who reflects on a long‑term goal. As Tim was saying, he doesn’t lead groups of people. He doesn’t know how to organize something complex. If you look at some things that he says, a lot of them are the same things he said in the 1980s, and there’s this crazy language about race and “they’re laughing at us.” He’s used these terms since 1987, and he just gets out there and acts and does what Donald Trump thinks Donald Trump wants to do. And there’s no concept of where do I want to lead the country or what’s good for anything—anyone else but him.

Glasser: I have one question I’ve been dying to ask that’s a little bit—well, it is related to this, which is the Putin affinity, obsession. This weird theme of this campaign is not something that had really fully emerged when we initially talked. And it gets to this question: Does Trump see himself as a dictator? Is that why he is expressing this fellow-feeling with Putin and others like him? What do you make of that subplot of this campaign?

Barrett: I think we saw the power of this last night in the debate. He openly contradicted his own running mate about Putin. It’s the only issue on which he would do that, and it has everything to do with the WikiLeaks revelations, which is still, in my judgment, his hope for the remaining several weeks, that there is more power in that.

You know, you got to follow very bizarre people to diagnose this, but follow Alex Jones, Roger Stone’s sidekick. Roger had predicted that the WikiLeaks stuff would come out last Wednesday, and when it didn’t, Alex Jones went on his show and absolutely denounced WikiLeaks and Assange in the vilest terms. And then the next day, he went out—and you can see the video—and apologized profoundly to Assange and said Assange was a hero to all of the world. And voila! What happens? Suddenly, WikiLeaks is dropping its stuff.

And I think the way in which Donald has approached Putin in recent times—and again in the debate last night—is all about the WikiLeaks revelations and trying to induce them and induce even more of them, and Pence just didn’t get the message. He didn’t get the memo, and he was out there actually saying what made sense from a Republican standpoint. He was basically opening the door to a war against Putin and Syria, and Trump just openly contradicts that because Trump is playing the Putin card to get the WikiLeaks revelations injected into the body politic before Election Day. And we still don’t know whether or not there’s some good bombs in there. So far, I don’t think it’s added up to much, but there’s been some interesting stuff in there. And I think that’s what it’s all about.

D’Antonio: I think that that’s a really fascinating element to this, especially when you consider Alex Jones. I’ve been wondering who Trump’s brain is, whether it’s Roger Stone or Alex Jones, but it’s a pretty dark personality that’s driving all of this.

Barrett: It’s Roger. I mean, the interesting thing is when you saw him do the number with the four Clinton‑associated women last night, that is Roy Cohn orchestrated through Roger. Roger has been talking about this forever. What is so interesting about what happened in the debate last night with these women is that Roger is back running the show in the person of those four women, and this is exactly what Roger has wanted him to do. You know, Susan was talking about the origins of the campaign. Well, you know, I’m always very upset about the fact that the television people allow Rudy Giuliani and others to say, “Well, you know, in 2005 [the date of the hot-mic tape], Trump wasn’t running for president.” Well, as a matter of fact, he did run for president for about four months in 2000, and Roger was running the show. And so this has been a constant theme of the Roger‑Donald relationship.

Look at Roger’s own statements. The night that Donald was nominated, he said it was the culmination of—I think he said 36 years of his life, the night that Donald was nominated, and so they’ve been cooking this and working this for decades and decades between the two of them.

D’Antonio: And Stone does represent one of the most distorted aspects of American political life. He’s so far out.

Blair: He’s a protégé of Roy Cohn, isn’t he?

Barrett: Yeah, they’re evil incarnate. The two of them are evil incarnate.

Blair: Yeah, the two of them together. Whoa!

Barrett: Yeah. I mean, just the fact that Donald Trump—with these two people as a young man—that he bonded with them…

O’Brien: I don’t think you can discount Ann Coulter’s role as an influence on his thinking in this either. You know, his language when he rolled down the escalator at Trump Tower, when he first announced, and his descriptions of the evils of immigration closely paralleled things Ann Coulter had written in the past. I think she had a big influence on themes and images that he used.

But I think this stuff with Putin has been wildly overblown. He’s always bragged about his relationship with Putin and his business dealings in Russia. The reality is he was never able to get anything done in Russia. He went over there on little speculative ventures.

I think he, in years past, talked up Putin when it was to his advantage to make it look like he was getting things done in Moscow, but he never had a real relationship with him. And the people in the Kremlin are laughing at this guy because all of them are far more sophisticated and shrewd than he is, and they would love for him to become president, not because they have deep lending relationships with him and not because he’s got a deep relationship with Putin, but because they know that he could be their sock puppet because he’s ignorant and overconfident. So I think that’s one part of this election that got a little bit overblown.

Blair: One more piece out of last night: I wondered what people’s responses were when he called Hillary Clinton the devil. What was that?

O’Brien: Well, again, he’s using it as another alt‑right thing. He’s appealing to the evangelical conservatives.

Blair: That was a real shout-out, wasn’t it?

O’Brien: You know, that she’s the devil, that wasn’t an accident. You know, he hit millions of themes in that thing last night that appealed to the Breitbart coalition, and I think it’s a measure of what you’re going to see in months and years to come from him and that part of the Republican populous faction, that he’s channeling their anger and their imagery.

Kruse: This question that has existed for months at this point—“is this the media’s fault,” quote/unquote—always sort of avoided the reality that Alex Jones is the media, Ann Coulter is the media—for some just as much as the New York Times, the Washington Post, Politico is the media. Over these last seven months since we first talked, how have you assessed—at the risk of sort of making this unbelievably broad—how have you assessed the role of the media in helping, hurting, influencing how the American public has met the presidential candidate Donald Trump?

D’Antonio: Well, don’t you kind of think that the media promoted this for ratings, especially—I mean, I’m talking almost exclusively about broadcasts and almost exclusively about CNN, that Jeff Zucker made a ton of money putting this guy on the air. And I actually think that people scared themselves, that at some point, they said, “Oh, wait a minute. We’re journalists. We better start reporting on this guy.” And that’s what’s happened since the convention is that there’s been some serious reporting on him. Trump has been exposed and revealed for what he is, but prior to that it was almost entertainment-driven and with the journalism, especially on television, really on the backburner.

O’Brien: I think broadcast media was, for the most part, an enabler for most of his run, and I think early on, both broadcast and print didn’t know how to handle him. I think they mistakenly took him for a zoo curiosity when the campaign began last year. I think by the time—it took almost him getting nominated for most of the media to take him seriously.

I think print took a little while to get rolling, but once big institutions like the Times and the Washington Post got their engines going, they really brought a lot of force to bear on him. And even within broadcast and even within CNN, there were people like Brian Stelter and Jake Tapper and Chris Cuomo and Anderson Cooper who took strong shots and strong looks at him, even if CNN was an enabler, you know, and that went along with, I think, a really egregious mistake on CNN’s part to bring Corey Lewandowski in as a quote/unquote, you know, “political analyst.”

But I think TV really gave Trump an early lift and that he was able to capitalize on what other candidates didn’t get.

Blair: Wait. What about Twitter in here? I mean, that’s hugely important, I think, in the driving force fueling all of this that he was out there even, you know, ahead of the media. The media kept always feeling like it had to catch up to him, and Twitter was such an important tool and he used it really so well. I think his ability to harness attention through Twitter is a big piece.

O’Brien: And not just harness attention but demolish his opponents. He really used Twitter much more effectively during the primary season, I think, than he has during the general election. But he’s certainly used it during the primary season to label, diminish and then expel political opponents like Jeb Bush and then Ted Cruz and Marco Rubio with labeling and name‑calling. And he dropped that into the Twitter echo chamber to great effect.

Blair: It’s a perfect format for name‑calling.

Barrett: Maybe I’m completely out of touch with technology, but I believe that television news is still the canvas on which these campaigns are painted. And I think that the broadcast news media—you know, I’m a big sports nut, and they basically have covered the campaign the same way they cover the NFL season, you know, promoting the game at all times to encourage ratings and advertisers. I think they have not really, until very recently—they had a moment there in August when they were covering him pretty tough—but, you know, especially when you get around the debate period, you got to build up to the debate. You’ve got to have a close contest to get the tens of millions of people you want watching it.

Mike McIntire wrote an unbelievably brilliant story on the front page of the New York Times that laid out the Trump SoHo [a Trump-developed building in Manhattan] and even showed that the district attorney of Manhattan had conducted a criminal investigation that included Ivanka and Donald Jr., who made all kinds of false claims about how many units had been sold, and, you know, that Trump had worked out a settlement that included a specific provision with the depositors who bought units in Trump’s SoHo. He had worked out a settlement in which they agreed that they wouldn’t cooperate with the district attorney, which sounds like obstruction of justice to, I think, anyone who read the story. And it couldn’t get a minute of airtime. It never has gotten a minute of airtime, and so you would have, I think, some outstanding pieces of print journalism.

Michael Kruse just wrote one about how Trump on 9/11, 15 years ago, started talking about how he now had the biggest building in downtown Manhattan, the very day that the bodies were still lying in the streets, and no one on television even mentioned the story. And so these great pieces of print journalism got no airtime and died, and I think that was a conscious decision at the highest levels of the television news networks. And they kept this narrative alive of a real campaign and a real competitive race, and they kept it alive by not telling voters what voters should have been told on this medium that I think still controls presidential campaigns.

Kruse: So let’s say he loses, and let’s say he loses even by a lot. What is the next act of Trump? Is he still a businessman in the way he’s been a businessman? Is he now some sort of much more active politician? Is he a politician by that name? And he himself said it last night, said it during the debate. He called himself a politician, I think, for the first time. If he’s a politician now for the first time, I’m wondering—where to from here for him, assuming he loses and potentially loses badly?

O’Brien: I mean, I think he’s going to start a media company, despite the fact that he said he won’t. I think he and Sean Hannity and the Breitbart crew and Roger Ailes will figure in that in some way, although Ailes has a non‑compete with Fox. But I think Trump is going to try to start a media company. I think it’s going to be impossible for him to get advertising for it, except for maybe Viagra ads, and he’ll just take this movement that he’s fomented on to digital and broadcast media and build up, or try to build, a media movement around it.

D’Antonio: I think he’s addicted to this kind of attention and addicted to being taken seriously, or at least in his own estimation being taken seriously. So whatever he does, it will be devoted more to politics and media than what he’s done so far, and the kids are going to pick up the pieces of the real estate and branding empire. I’m working on a piece with some people who are evaluating his business, and he’s really suffered an erosion of his brand, even among the people who supported it. So the kids may have seen some of their inheritance go down the drain here.

Barrett: He’s had an incredible tax loss on this campaign, Michael. [Laughter.]

Blair: Right, going forward.

Kruse: So do you think he expected any of this? Do you think—in his discussion with himself way back when about whether to do this—do you think he envisioned this scenario as it has played out, where he almost does so well that his brand, his name, his ability to turn his name into money has been sullied and compromised with not everybody, certainly, but a wide variety of people, a good portion of the electorate?

Blair: Well, 40 percent doesn’t get you to the White House—or whatever, 35 percent—but it gets you a lot of customers in the future.

Barrett: Well, nobody who is going to vote for him can afford to go to one of his places, you know? I mean, I shouldn’t say nobody, but his base is a high school‑educated, white, working-class base.

Blair: They watch TV. They buy wallets and ties and shoelaces and all the rest.

Barrett: Oh, yeah. I’m talking about his current businesses. They certainly can’t buy a unit in one of his buildings, or they can’t go to his hotels. The remarkable thing is that the people who are his customers have been so turned off by so much of what he’s done.

D’Antonio: But business people do not want to stay in a hotel and have someone call and hear the word “Trump” when they answer the phone. It’s really poisonous right now.

Kruse: Is there any scenario in which he does, in fact, win on November 8?

Barrett: No. I think I just mentioned it. The WikiLeaks scenario, revelations through WikiLeaks, I think, are his only hope, and we don’t know what those could be. But we know they’re flowing, and I think that that’s why he’s played such a strong Putin game. I think that’s what he’s counting on.

O’Brien: I think he’s done. I think it’s over. I think even if there are WikiLeaks photos of Clinton with horns and a tail, the states that have allied with her aren’t going to change because of that, and I think as much damaging information about her that might sway voters is already out there. You know, unless there’s WikiLeaks of her and Bill taking huge bribes from the Saudis and other dictators that affect State Department policy, I think short of that, I don’t think anything WikiLeaks has is going to change anything in this election. And I think she’s already got it nailed down, the Electoral College.

Barrett: I don’t disagree with that, Tim. I was just answering if there’s anything that could possibly change the numbers, and that’s the only thing I can think of. I agree with you that I doubt that it would change. I mean, so far, as I said, the WikiLeaks revelations have not been seriously damaging, and I don’t expect them to be.

D’Antonio: It might be more likely that another horrible thing is going to happen for Trump. There’s got to be more video and audio out there.

O’Brien: Yeah. I guess I sort of think that the danger of leaked material now, it feels to me like it’s a little more in his camp than hers, but I could be wrong.

Kruse: So what would his legacy—I’m not sure that’s quite the right word—but what would his legacy have been had he not run for president and run for president in this way, and what will it be now?

D’Antonio: I would say that if he hadn’t run, he would have had a legacy of master promoter and a guy who pioneered publicity and converting publicity into cash. But now he may go down as the thing that he doesn’t want to be remembered for at all, and that is as a loser in a landslide election.

Blair: Yeah. From a pioneer celebrity brand guy, I mean, he sure ran a good race with that, and from that to the asterisk in the list of people who ran for president and lost. And that’s a pretty big shift.

O’Brien: I think he was somebody who would have been remembered as this curiosity of reality television and casino gambling and real estate to somebody who is likely to go down in history as having unleashed some very hateful forces in American life, and I think that’s what’s going to end up defining him.

Kruse: Is there any part of him that knows this and that is embarrassed by it or ashamed by it?

Blair: Not yet, but—

Barrett: He was a blowhard in business and then a blowhard in politics. You know, I mean, there isn’t much difference. The Times [Trump Soho] story is, certainly, just as one example, and I think Tim has written about this too. It shows what a minor Manhattan developer he is in the total context of things. So he was a blowhard as a developer too, and he’s a blowhard as a politician. You know, I think if he had not run, he would be an inconsequential developer who did a project or two in Manhattan that seemed to matter for a moment, and maybe at some level, he understood that and thought he wasn’t big enough to go out. You know, he wanted to be bigger, so he went down this trail to see what it would do. I think it was part grudge, part, you know, him and Roger talking and taking a shot, and now it’s grown into this giant thing.

I think Tim has it perfectly correct that he would go down now as the man who embodied more than he did in evoking the racism that Barack Obama’s election and two terms of Obama conspired to bring to the surface in America.

As long as he’s remembered, maybe it won’t matter to him.

Kruse: That is what I was thinking as you just said that, that he’s always had the opinion that even bad publicity is publicity and, therefore, good publicity, and that he has had, over these last six months especially, just an incredible onslaught, such intensity of negative publicity. But perhaps that doesn’t matter, and the fact that he will go down in history is what he was after all along.

O’Brien: You know, I think he has stumbled into this whole event. I don’t think he contemplated being the nominee. I don’t think he thought he could be the nominee. I think he just thought it was a moment of, you know, put on a show, and then he got carried along by events. And I think those events are far larger and more momentous than who he is as a person, and he has not been able to rise to the occasion because he lacks the skill and character to do that and instead has made the worst sort of thing that he could out of this, which is, again, unleash these forces of hatred and opposition. And I don’t think he realizes probably how badly it taints him and his family—I mean legacy. I think if he did realize it, he still wouldn’t feel ashamed of it because I think he’s incapable of feeling shame.

Kruse: What about his kids?

Blair: They seem to be all in. I mean, they’re—that’s all we see. But I’m not exactly sure if he unleashed those forces so much as became this visible center for them to coalesce around. I mean, they were there. Maybe that’s what you mean by “unleashed.” They were there, but he became this visible, you know, central hub for all of that, and that has been super dangerous. And her has whipped it into just an astonishingly dangerous force.

Kruse: So this sounds like his legacy. This is what it is.

Blair: Yeah. And I also think it’s absolutely spot on that if it’s negative, I’m not sure he cares. In fact, I’m sort of sure that he doesn’t care because it’s big—or as he would say, “yuge.”

Barrett: Yeah. I mean, in his eyes, he is larger than he has ever been.

O’Brien: And he’ll go on to have influence through his kids. You know, Don Jr. is an aggressive extremist, I think, who sees political aspirations of his own, and Ivanka is a budding entrepreneur and has her own businesses. So the kids are going to remain active in American life to some extent. Whether he’s going to be happy living them is another thing.

Barrett: Well, let’s not forget Jared Kushner. I think Kushner has launched on what is going to be a life worth tracking. News accounts from yesterday indicate that he helped put together the Clinton women thing last night, so he’s way out there. He’s just way out there. He’s got a great deal of money of his own. He’s polished. He’s driven, and, you know, I think he’s a serious player. At least in a New York level, I think he will be a serious player going deep into the future.

O’Brien: And I think that Jared will be part of any media thing that Donald does. He’ll be a key part of that, obviously.

Kruse: Is there anything else before I let you all go—and I appreciate all your time—but is there anything else that you think we should cover, that we should put on this transcript that we haven’t touched on at this point?

Barrett: I was just not sure whether or not, when Tim was talking about Putin, whether he was disagreeing with my assessment of it. You know, I think the two things that we said could simultaneously be true, but Tim was saying he thought the whole Putin thing had been overplayed in terms of Donald’s real business interests in that part of the world. And I defer to him on that, but I’m not sure whether he was saying that he disagreed with my suggestion that Donald’s Putin strategy is connected directly to WikiLeaks releases and that that was evident in the debate last night.

O’Brien: Oh, yeah. I mean, I wasn’t disagreeing with that. I think in and of itself, Wayne, I was thinking more about, you know, all the stuff that came up around Paul Manafort and whether or not the Kremlin was bankrolling Donald’s business operations and, therefore, was going to control in his president. That stuff, I think, got way overblown into kind of a conspiracy theory that I think didn’t have a lot of traction in reality. I meant that piece of it.

Blair: I think we sort of said this, but just to be a little more explicit about it, the through-line between that Department of Justice action against the Trump organization in 1973 about not renting to African Americans, Roy Cohn filing the $100 million lawsuit the next day? I mean that aggressive counterpunch—all about racism. The through-line between—and that was really Donald’s, pretty much his debut in larger New York City to now—I think is just worth underlining. We know that, but just to underscore that through-line is kind of stunning.

Barrett: Well, and then, you know, simultaneous almost with the hot-mic video, I think, in the same day on Friday, he reaffirmed, as we all know, the guilt of the Central Park Five. So talk about a through-line, yes.

Blair: Yes. Which, of course, also got not much attention.

Barrett: Right. Now that what little I’ve been able to read about what is supposedly in the Apprentice tapes is that, supposedly, he uses the N-word. You know, that’s been hinted at in stories.

You know, David Letterman, I think, said in the last few days, “I was wrong. I said I thought he was too smart to be a racist, and I was wrong. He is a racist.” So there’s this racial undercurrent to everything that the man has done in this campaign, and it’s been one of the hardest things. It’s not only that the television news industry has, you know, for business reasons and commercial reasons helped promote this candidacy. They have refused to acknowledge the racial underpinnings of this candidacy. They want to attribute it to everything but that. It’s not like there’s been no illusions to it. There have been some, but it is really a story of American racism. And I think that’s understood in every newsroom, and yet it’s almost never presented that way because it’s thought of as an insult to part of the audience that they want to keep. So it’s like a commentary on part of the audience that they’re trying to attract and retain, and so the racial nature of this candidacy, which I think is so apparent, almost axiomatic—it’s not like it’s never commented on. It is sometimes lightly touched on.

Blair: I think that’s called normalization.

Barrett: Yeah. It’s not really examined.

Blair: Minimalized.

Kruse: Given that, given that assessment—and this is something, Wayne, that you said very explicitly the first time we got together—given that, where do we go? Where do we, this country, go from here? Something ends on November 8, but what begins on November 9, or what continues on November 9, really?

Barrett: Well, if it’s a substantial margin, it will be a repudiation, just as the last two presidential elections have been a repudiation of racism in America. This will be in some ways, strangely enough, without an African-American candidate on the ballot. If Trump loses badly, it will be a repudiation by maybe even the majority of white Americans of that strategy. It could be a good day in America.

O’Brien: And that the better angels of American society triumphed in this one.

Barrett: And it can happen.

Blair: Let’s hope.

This conversation has been lightly edited and condensed.