Donald Trump Biographer Maggie Haberman On How ‘Apprentice’ Put Mogul In The White House, Those Outtakes, & 2024

SPOILER ALERT: This post contain details about Maggie Haberman’s Confidence Man: The Making of Donald Trump and the Breaking of America, which was published today. 

“Trump’s not an actor,” says Maggie Haberman of the man who once fronted The Apprentice and occupied the Oval Office. “He just happened to be in this role on television playing himself,” the New York Times reporter often called the Trump whisperer adds of her primary subject for nearly the past decade. “He is a former real estate executive who ran a relatively small firm, who constantly was trying to make himself look much bigger so people didn’t see, in various ways, how small he was. And that I think is problematic for the presidency, because he’s really incurious.”

The former Apprentice host may be incurious, but many are very curious what Haberman has unearthed about one of the most examined men on the planet in her new book Confidence Man: The Making of Donald Trump and the Breaking of America.

Out today, the well-excerpted and teased 608-page tome is unsurprisingly full of deranged details and salvos that have characterized many books on the 45th POTUS. More than most and better than many, Haberman has specialized in such finer points for years. However, if you are looking for Trump trivia to feed your political ravenousness for Red Meat or Blue Delicacies, and confirm your assumptions, Confidence Man might not be the meal you’re looking for.

Now, already No. 1 on Amazon’s bestseller list, Confidence Man certainly does have lots of insider anecdotes and accounts of Trump’s reign of error and terror in and out of the White House. Yet, unlike many of its printed predecessors, this book is as much about the New York and the New Yorkers that created Trump, as it is about his presidency.

Focusing in on the final component that made Trump a true winner among Republican voters, Confidence Man is also A Face in the Crowd cautionary tale about how the almost bankrupt executive who always wanted to be in front of the cameras used the small screen to make it to the biggest stage in the world.

DEADLINE: At the end of the final chapter of the book, you detail Trump’s departure from D.C. on the morning of January 20, 2021, as he snubbed Joe Biden’s inauguration, You write: “As the plane taxed down the runway, a recording of Frank Sinatra’s “My Way” blasted over the speaker system, like a movie finale.”  Reading that, reading your coverage of him over the years, and some others who stepped out of political norms, it reinforced the impression that Trump was a movie, a horror movie but a movie nonetheless that played out in real life. Fundamentally, is that your take?

MAGGIE HABERMAN: There is something to that. Look, I write, and I explore just how much of his driving impetus is about being famous and is about being a star, down to toying with the idea of going to USC Film School once upon a time. Obviously, he didn’t do that, but he would talk later about how he had found a way to bring show business into the real estate business.

That really was what he was doing, and he was just constantly scripting this movie out of his life. It culminated, for him, initially, in this moment when he becomes a reality television star. The Apprentice opened up a whole new world financially for him, but it also took him to a different level of stardom. He was actually part of the entertainment industry in a way he hadn’t been before, and then the presidency was just something utterly different.

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DEADLINE: His lack of self-awareness is always striking, even over the decades. How do you think he saw himself?  

HABERMAN: It’s interesting, one of the things he said to me in our interviews was he said, “before I did the presidency,” as if it was some kind of a show he was doing. I don’t think I’ve ever heard a former elected official refer to holding office as, before I did the governorship or before I did the mayoralty, and this is just fundamentally what he has been doing his entire life.

DEADLINE: Do you think that he sees this, fundamentally, as a role, or does he somewhere see this as a responsibility?

HABERMAN: Which? The presidency?

DEADLINE: The presidency.

HABERMAN: I think he sees it as a role. I think so.

DEADLINE: So, with all the legal issues, the January 6th committee, the midterms, and more now on his plate, do you think he’s running for president again?

HABERMAN: I think he’s backed himself into a corner where he has to.

DEADLINE: In that dual context, for you as his chief chronicler, how does that affect your approach to covering Trump?

HABERMAN: There’s two answers to that question. One is trying to make sure that we were not simply amplifying things, and I think that we had mixed success at it, the collective we. Not simply amplifying things because the president was doing them. That having been said, he was a president, and I think that was something that people really struggled to understand when they would say why are you covering him?

Well, because he’s the president of the United States, and everything the president does is not objectively, newsworthy, but much of it is. So, I think it became much more challenging because people in Washington were often confused and interpreted his actions as he’s doing this because he sees this as what a leader should do or a leader does, or this is part of his ideology.

DEADLINE: Why was he so frenzied, so crazed, so uncouth and so unconventional?

HABERMAN: Realistically, he was doing things because he wanted to see how they were going to play in the media.

DEADLINE: Really?

HABERMAN: Yes, and because it was part of the role he was engaged with.

It doesn’t mean he didn’t get things done that he wanted to get done, in some cases. It doesn’t mean that he didn’t have what he would point to as accomplishments, but it does mean that his objectives were not the same as how Washington was interpreting them.

DEADLINE: That impulse has deep roots, as you point out repeatedly in Confidence Man. But there was also the cash. You say early in the book that it’s impossible “to separate out Trump: The Potential Political Candi­dacy from Trump: The Established Brand.” Now, that was in reference to his 1999 exploratory presidential run, but it seems to hold pretty true through all of his political career, don’t you think?  

HABERMAN: What I mean is that, particularly at that moment, although, certainly, it continued into 2015 and 2016, and we saw numerous examples of it, he was aware of a business enhancement by running for president. He would talk openly about how he could be the first person running for president to make money, because he was talking about doing paid speeches in various cities during the 1999 New York campaign. Yet I would point to the fact that he was on the ballot in a small handful of states, and he won a few primaries by not doing anything. Now, these were third-party nominations. These were not major parties, but nonetheless, it really taught a lesson about how inextricable the political brand was becoming for him, that he was forming from his business brand.

DEADLINE: To pivot on the branding principle, there’s a moment of revelation for you in January 2016 just before the Iowa caucuses and after Trump has been on The Apprentice for 14 seasons, where you talk about a “spectacle that would soon come to an end.” Then you meet a voter, who you describe a “middle-aged man,” who informs you that he will be voting for Trump because “I watched him run his business.” A lightbulb of sorts goes off for you. So, let me ask you, could there have been a President Trump without The Apprentice?

HABERMAN: There could not have been. There is almost no doubt in my mind.

Now, he could’ve gotten close. He was certainly a brand name. The Art of the Deal book and success made him pretty well known, but there’s an exponential difference between being on television and being seen sitting in a leatherback chair. It was actually Roger Stone who had said to me years ago during an interview about Trump, just how the line between news and entertainment is much thinner for people watching it than people working in the news industry, and I don’t think we understand that all the time.

DEADLINE: To flip it, do you think Trump sees The Apprentice as fundamental to his ascension to the White House?

HABERMAN: Well, this was something fundamentally different for him, and you know, he was playing this character that was created by The Art of the Deal. Mark Burnett was an Art of the Deal fan, but that was how the public interpreted him. I don’t think he would’ve been the president without The Apprentice. I asked him that question in one of our interviews, and he didn’t…if memory serves, he didn’t take an opinion on it, but I just don’t see how it would’ve happened, based on my interviews with people.

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DEADLINE: What was the role Burnett, then NBC boss and later CNN chief Jeff Zucker, and his WME agent Ari Emanuel played in sealing that deal, so to speak?

HABERMAN: I mean, Zucker and Mark Burnett helped guide Trump onto The Apprentice. Ari Emanuel helped keep him there, in some respects, right? I think all three played a role in creating Donald Trump, the reality television star, and as I said before, I think that without Donald Trump, the reality television star, there is not a Donald Trump president.

DEADLINE: Burnett is a figure who appears kind of time and time again, The Apprentice, the 2017 Inaugural Gala, prayer breakfasts, and more. Yet he never took on a formal role in the White House. Why do you think that was?

HABERMAN: I don’t think that Mark Burnett ever had a clear lane that he would be occupying in the White House, and I’m not, frankly, sure that that was something he would ever want. You know, he was one of the many phone-a-friends who Donald Trump had, outside of the White House, who he relied on for counsel and advice, but I can’t even imagine…it would be so minimizing for somebody of his experience. What he would…was he going to run the video section? I just can’t imagine what it would’ve been.

DEADLINE: Certainly, part of The Apprentice’s legacy is the much mythologized and never released tapes of the show. Specifically, the outtakes and behind the scenes footage that some have said depict a distinctly more vulgar and racist Trump than ever. Lots of claims, lots of smoke – have you seen the outtakes and why do you think so many feel they could be the true smoking gun?   

HABERMAN: I’m one of many people who would like to see the outtakes from The Apprentice. Like you, I have heard all kinds of rumors about what’s there. I have no idea what’s actually there. What I do know, and that is what I tried doing with this portrait, the outtakes matter significantly more with Donald Trump than what you see on camera.

DEADLINE: How do you mean?

HABERMAN: One of the smartest things, I thought, that the House Select Committee investigating the Capitol Riot did was getting hold of that video of Trump trying to film, you know, a snippet where he was talking after the riot, and he kept saying…you saw the outtakes where he says I don’t think the election is over.

That’s him.

One of the things that we found in the 2016 campaign was how often, his daughter Ivanka would assure people that he was going to stay on message and start following scripts and start following teleprompters and so forth. That was just never who he was and was never going to happen because the outtakes are him.

DEADLINE: At another point, and I am paraphrasing, you call Trump a genius of the digital media landscape. What do you mean by that, and what does it reveal of his depths?

HABERMAN: Look, he spent a lot of time, and I show this in the writing, studying what worked and what didn’t on Twitter.

I was really surprised to learn how much time he was spending on that himself.

Over time, he went from having aides tweet for him to tweeting himself. Which, the person who had been working his Twitter feed, the son of an executive, once described as like the scene in Jurassic Park when the Velociraptor learned how to open doors. You know, there’s no going back. He did understand that everything looks flat and the same on Twitter. In Donald Trump’s life, making everything look flat and the same, because Donald Trump is utterly devoid of context and tends to treat many different situations as if they’re all of a piece, is kind of how he bluffs his way through things. Twitter was ideal for him.

I think there’s a different scenario, which is in the reality television realm, where understanding what plays grandly on a big screen could be advantageous to a president. Trump’s not an actor. He just happened to be in this role on television playing himself. He is a former real estate executive who ran a relatively small firm, who constantly was trying to make himself look much bigger so people didn’t see, in various ways, how small he was. And that, I think, is problematic for the presidency, because he’s really incurious.

DEADLINE: You have been praised and pillared for how close you have been able to get over the years to Trump and Trumpworld. It was always expected you would do a book, to add to the canon. But there has also been criticism that details and information you had, some of which hits its sell-by date by the end of the news cycle, that you held on to for Confidence Man could have been vital, especially in regard to the violence of January 6 at the Capital. How do you respond to that perspective?

HABERMAN: I wanted to do a fuller story than I can do in daily news accounts, and anecdotes that appear in books might not make for a full news story …

DEADLINE: Some would say Trump telling you after the 2020 election that he would refuse to leave was more than an anecdote…

HABERMAN: Ultimately, the process of writing a book and writing a fuller picture takes time. It’s a process of going back and revisiting scenes and incidents with sources and officials and learning who was in rooms and what was there. It takes a while, and I think this is a fuller portrait of him than you can necessarily get from the daily news report. You know, when I have information that is confirmed and ready to be reported, my goal is always to report it, but books take time.

DEADLINE: So now that it’s all done and coming out, Trump is unsurprisingly attacking and denigrating you, as he has done for years. At the same time, he flatters you, he sits down with you over and over, even calls you his “psychiatrist,” as he has others. What’s your side of the relationship?

HABERMAN: Well, I mean, you know, he’s been attacking me, and I expect that he will continue to for some time. I don’t know what happens after that, but you know, Donald Trump is in a perpetual state of punch and then pull, and we’ll see where this goes.

DEADLINE: In true Hollywood ending, are we going to see a movie of Confidence Man?

HABERMAN: (LAUGHS) I don’t know. Stay tuned.


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