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Timothy O’Brien

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Timothy O’Brien

Author, TrumpNation

Timothy O’Brien is a senior executive editor at Bloomberg Opinion. He was previously a reporter and editor at The New York Times and is the author of TrumpNation: The Art of Being the Donald. Donald Trump filed a $5 billion defamation lawsuit after the publication of O’Brien’s book. The suit was later dismissed.

The following interview was conducted by the Kirk Documentary Group’s Mike Wiser for FRONTLINE on November 18, 2024. It has been edited for clarity and length.

This interview appears in:

Trump’s Comeback

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Trump’s Biggest Comeback

What does it mean to Donald Trump to win reelection this time?

Well, it’s a validation, I think.I think most of the things he’s strived for in life are about validation, whether it was in his business life or his personal life, and certainly in his political life.He thrives on being in the spotlight.He thrives on connecting with an audience.And he just had the biggest kind of live polling you could do, which is an election to be president.And he was under existential threat from a series of court cases.He had campaigned as if he didn’t care if he won, but I think he deeply cared.And he’s remade the Republican Party in his image, and he has sold a vision of the U.S. and what it’s about and what its future should entail that reflects a lifelong journey through, I think, resentments and neediness.And I think he feels this deep connection with underdogs.He perceives of himself as an underdog, and I think a lot of his voters who really support him feel seen as underdogs.

Let me just ask about how important his biography is at that moment, because there’s been so many places along the way that we’ll have done where he was written off or seemed like he’d failed in business and in bankruptcies and written off politically after Access Hollywood.How did his life prepare him for this comeback?

I think it’s very important to understand that Donald Trump is an outcome.He didn’t spring, like Athena fully formed from the head of Zeus, onto the American landscape.He is an outcome of things, of wildfires that have been burning through American life for centuries: anti-institutionalism, civil war and civil strife, racism, political polarization, misogyny.

And that’s not to say he wasn’t an accelerant, which he has been, particularly through social media, but everything that—the stars that aligned to create the Donald Trump moment were long in the making, and he filled, I think, a vacuum of leadership from both parties to take advantage of a lot of dislocations in American life that he was offering answers for.So I think anybody who feels surprised by Donald Trump or shocked at how did he suddenly stride across the national stage with such force and determination really wasn’t paying attention to all of the historical roots that gave rise to Trumpism and then his own journey, as someone who is deeply needy and deeply in touch with other people’s neediness, and he knows how to pluck those emotions like guitar strings.

Winners and Losers

How much of it is personal, going back to his dad and winners and losers?I mean, how much of what he has tied up in the election is—

Well, you know, Donald Trump’s gravestone will say, “I won.”He’ll need nothing else on that.That is an organizing principle for his entire life.And I think he grew up with a very demanding and randomly abusive father who had high expectations of all the children, and some of the kids in the Trump family suffered and bent, and some even broke under that pressure.I think [his father] Fred Trump was fortunate in that he found in Donald this mass of clay that he could set in motion.And you can’t explain Donald entirely without Fred.He’s much more important to Donald Trump’s development than Roy Cohn.I think Donald Trump recognized in Roy Cohn a facilitator, but Fred Trump is the person who molded the clay.And it was interesting, in his first term, when Trump moved into the White House, there were no photos on the table behind his desk in the Oval Office but for one, and it was one of Fred.It was a black-and-white photo of Fred that used to be—and that really leapt out at me because I had spent so much time in Trump’s office in Manhattan, and that same photo was very prominent in his office.But there it was, surrounded by the children and his wives and others.

But there was a period of time, and I don’t know how long it lasted, the only photo in the Oval Office was of Fred Trump, and I think that’s because he’s sort of a Svengali figure for Donald.And I think he felt a deep desire to outperform his father, which he did in a lot of ways.I think Fred Trump’s wealth and Fred Trump’s housing developments were the foundation of the Trump family’s wealth.And Fred Trump was an authentically self-made entrepreneur, which Donald Trump was not.Donald Trump was born on third base and spent his whole life telling everyone he hit a triple when in fact his father’s money, his father’s signature, his father’s mentoring gave him this incredible springboard, and he knows that.And I think these dual demands of his father pressuring him to be a certain kind of person and then his own need to accelerate past his father and break out of Brooklyn and Queens into Manhattan, where all of the high-end real estate developers existed and thrived, was incredibly important to him.

It was almost like, you could imagine election night he’s thinking about his dad and proving to his dad.

Well, he said—I can’t recall this year if he said it on the campaign trail, but he certainly said multiple times when he’s been campaigning he speculates about what his parents would think looking down at him from heaven.He tends to say that in front of religious groups.I don’t know how much time Donald Trump actually thinks about heaven, but when it works in front of a crowd, he invokes this idea that his parents wouldn’t believe where he’s gotten, which, of course, they wouldn’t.Whether or not they’re in heaven or whether or not there’s a heaven, I think Donald Trump is right that his parents would be bowled over by the fact that their son successfully ran for the presidency of the United States twice.

Trump After the 2020 Election Loss

So that was a great summary of this guy.So now I want to take you back, especially as you’re thinking in terms of winners and losers and proving himself, to the moment when he leaves Washington in 2021, after Jan. 6, after losing the election, after being impeached a second time, after having a lot of people in the media, in his own party, believe that he has done.Can you help me understand Donald Trump at that point in his life?

One of Donald Trump’s strengths, great strengths, and also one of his great weaknesses is that he lives in a reality distortion field, and he thinks very cinematographically about himself.He wanted to be a Hollywood movie producer when he was in college; his father pulled him back into the business.But he has always thought about himself cinematically, and he is always writing the script of his own life.He is the writer, the director, the producer and the star of this drama that’s always going on in his mind.And I think any time he encounters a setback, he just rewrites it in a way that comports with his own need to see himself as a winner, a survivor, someone with a perfect track record, someone who doesn’t take no for an answer, whether or not that means you lost an election or your business is going bankrupt or your wife is leaving you or you’ve got difficult relationships with your children or Manhattan doesn’t love you anymore.All of those things he finds these little drawers he can put them into in the back of his mind, and he puts them away, and then he comes up with a different version of what’s in front of him, and he’ll resort to any narrative he needs to make that tangible to himself.So in 2021, after he lost the election, it was, of course, the election was stolen; it wasn’t that he lost, because he can never lose.It was that the election was stolen, and he didn’t care if he polluted the foundations of American democracy and brought down longstanding civic and civil norms about the transfer of power.Those things didn’t comport with his understanding of who he was and how he wanted the world to perceive him, so he developed a different story.

And the benefit of that for him as a person is it allows him to survive.The negative of that, obviously, is it comes with burning down the house.

And in that period, as we’ve talked to people who have gone down to Mar-a-Lago, he’s not referred to as the former president; he’s introduced as the 45th president.He has a desk that looks like the Oval Office down in Mar-a-Lago.People said it’s almost like a White House in exile.What is he doing in that period with that?Not opening a presidential library.There’s a lot of examples.

Well, I think he saw the interregnum—and I think he sees it as an interregnum—at Mar-a-Lago as a place where he would lay the groundwork for his comeback.And he wanted anyone who would come down there to know that there would either be retribution or inclusion, depending on how they decided to play it.And most of the leaders of the Republican Party who condemned Donald Trump after the Jan. 6 siege at the U.S. Capitol basically flip-flopped once they started reading the political tea leaves, and Donald Trump was making it very apparent to all of them that he was still a kingmaker.He could be influential in political races.He was, of course, influential on social media, and he could handpick who rose or fell within the party.And I think he saw that period as a training ground and nothing other.

And you’re saying it’s a life method, right?This is the same thing he would have done after bankruptcies, after other setbacks in his life?

Yeah. A very important thing, I think, to remember about him is he has always been surrounded by various sort of rings of fire that have protected him from having to undergo the consequences of his own mistakes.Like, most of the rest of us try to course-correct during our lives as kids or adults when we make mistakes that we want to learn from, he’s never had to do that.The first big insulation he had was he was born into a wealthy family, and his father’s wealth protected him from bad business decisions, being a bad student, getting access to the corridors of financial and business power.And then he becomes a celebrity, and he gets insulated from the real world by all of the things that celebrity convey upon people.It essentially allows him to recreate who he was as a businessman.A guy who had been a serial bankruptcy artist was recreated through The Apprentice as the entrepreneurial guru to the masses.

And then he becomes president, like the biggest insulating force imaginable.It insulates you from the law.It insulates you now, because of the way the Supreme Court looks upon it, it essentially insulates you from criminal conduct.

And so he has never had to really grow up.He’s never had to become more sophisticated.He’s never had to develop empathy.He’s never had to grow as a person.He’s essentially a seven-year-old grown old.

Trump’s Legal Troubles

I mean, there’s a moment, though, where it looks like there’s going to be consequences in that period.There’s a raid at Mar-a-Lago, and the FBI shows up.Help me understand that moment where it looks like, for Donald Trump, who had successfully been investigated for things in the past but had avoided this moment, what does that mean for him?

Well, I think one of the things we’ve learned about American institutions in the Trump era is that when American institutions confront someone like Donald Trump, who doesn’t care about the law or civic norms, morality, and he’s essentially a grifter who won’t stop, and he has power, he can bend a lot of those institutions in directions people didn’t think they would go before.A lot of the prosecutors, Republicans and Democratic prosecutors, lifelong prosecutors, highly skilled—Bob Mueller, a Republican; Merrick Garland, a Democrat—they’re essentially Boy Scouts who believe that the rule of law will triumph, and evidentiary prosecution built on the fact pattern that is thoughtful and patient will win the day.And Donald Trump eats Boy Scouts for breakfast.And they moved along methodically, and he was throwing every bit of sand in the machinery he could.… He misrepresented what he was doing.His own cameras at Mar-a-Lago showed employees moving boxes of documents around.

And ultimately, the clock ran out.If those prosecutors both had more time and a better understanding of who Donald Trump was, and the presidency didn’t get in the way, he would have been in trouble.But that’s a big qualifier because he was president, and he’s about to be president again.

You said his dad was more important than Roy Cohn, but did he learn something from Roy Cohn about dealing with the prosecutions and dealing with investigations in the way you’re describing?

Yes, yes.Donald Trump once looked at me in the back of one of his cars, and he said, “The thing I really like about Roy is he would brutalize for you; he would brutalize people for you.”And I think in the way that his father taught him how you could weaponize business relationships and public subsidies and contracts and your own will to forge ahead in business deals, Roy Cohn taught him how to weaponize the legal system, and that the simple filing of a court case, whether or not the case had merit, or whether or not you even intended to see it through to the end, that the mere filing of a complaint in a courtroom freaks out a lot of people, and that could solve a lot of your problems.If you’re unsatisfied with how a business partner treated you, how a romantic partner treated you, how the media treated you, you could just use the court as yet another cannon in your artillery.

… He goes out after being convicted and he says, you know, the voters are going to have the final verdict on this.Donald Trump in that moment, who is he?How is he reacting to it?And we’re looking back now, how did he win the election?What did he understand in that moment?

Well, I think he’s always understood that he has a very loyal base.He said in his first tour of the White House that he could shoot someone on Fifth Avenue and get away with it, and I think he’s felt that way about himself his entire life.And some of that is reality-based.He has the wealth and the resources and the determination to make that real, and he also has the powers of the presidency behind him now.I think he was, during the court cases—I was in court for two of them—and he clearly was under pressure.He was not a happy man, and he was feeling the weight of those prosecutions, and he wasn’t entirely sure whether or not he would skate.And there was a very real possibility that he would get massive financial fines, which he did.There was a very real possibility that he could go to jail.We never know; we won’t know now.But I think those things weighed on him, and he got very angry.And, as he does when he’s in a situation he can’t control, and he’s uncertain of the outcome, and he’s cornered, he lashed out.He went after the judges, he went after the prosecutors, he went after the press, all the while telling his supporters and anyone watching that once again he was the victim; once again, institutions were putting their huge thumbs onto him and what he represented.It wasn’t about wrongdoing; it was about the system.And I think that’s his go-to, and I think he stuck with his script.But he was not, during that period, someone who felt he was definitely going to overcome it.

But it does seem like it was politically successful in some way, that message, that when they’re coming after me, they’re coming after you, and for even other Republicans.

Donald Trump has known for a long time how to make people who are authentic underdogs—they’re either struggling financially, or they’re struggling with their place in the world—feel like he’s with them, even though he is someone who was born into great wealth with every advantage imaginable.The Art of the Deal is a nonfiction work of fiction about what it takes to get ahead in business.The book is largely ridiculous, and a lot of it is mythic and contains Donald Trump’s version of events.But that book became a bestseller because for average folks wanting to figure out how to get ahead in America, it was like a Horatio Alger story to them.He ran casinos, which are these palaces to separate working folks from quarters and dollars on a rapid, nonstop, daily basis with the idea that you might strike it rich and get ahead in life, and “My emporium is the place where that would happen.”The Apprentice was about selling this group of youngsters the idea that Donald Trump would stick his golden finger on your shoulder and you would learn how to be successful by coming into his orbit, even though he had presided over six corporate bankruptcies and almost went personally bankrupt himself and was never a particularly good entrepreneur.He was a very good salesman, but he wasn’t a very good businessman.And ultimately, I think for a lot of his supporters, particularly his male supporters, Donald Trump is the guy you’d want to be if you won the lotto.You could move into this triplex in Manhattan that looked like Louis XIV built it on a bad acid trip, and you could have jets with your name in two-story-high letters across the side of the jet, and you could wear these monochrome ties and suits that look like they haven’t been updated since the 1980s, and you could have Las Vegas babes on your arms and do whatever you wanted.And that is a very attractive outcome for a lot of people, and he never apologized for it.He reveled in it, and he said, “I’m going to take down the institutions that don’t allow you to be here with me sitting happily atop this pile of cash.”

What you’re saying is he built a lifetime brand, and when he goes out in front of the court and he blasts the court, he’s not just doing that— it’s not what he does in that moment.

It’s a lifelong set of approaches and lessons he’s learned that have worked for him, and worked for him repeatedly.That became apparent when he got on the debate stage in 2015 and completely mopped up, in his very first debate appearance, all the other candidates by simply being who he is, which is a force of nature, someone who doesn’t care if the people around him feel insulted, and is willing to look into a camera and say, “I am who I am; love it or leave it.But I’m here, I’m going to stay around for a while, and I will feed every appetite you have.Come along for the ride.”

The First Assassination Attempt

That first assassination attempt, what did you see when you watched the video of him?

Well, I think he had incredible presence of mind.He, I think, again, Donald Trump, the student of performance art, Donald Trump, the man who always thinks about himself cinematically, I think knew as he was going down that he had a moment in which he could show himself as a heroic survivor and as someone who wasn’t going to be put down, even by an assassin’s bullet.And you can see in the tape he’s pushing away at his Secret Service guards.He doesn’t want them to keep him down.He doesn’t want them to contain him from putting his fist up.He knows he needs to play to the audience.And that’s an unusual presence of mind in a moment like that.And that was baked into him from decades of practice about what to do when the spotlight is on you and how to take advantage of it to its greatest extent.

… I mean, and thinking about that moment, too, it seems like he is—in some ways, is he more comfortable in that mode, “Fight, fight, fight,” than just winning the election, having just beaten Joe Biden in the debate?Does the fight give him something?

Yeah. I think it gives him a sense of being, and I think fighting gives him a connection to reality.Donald Trump has the attention span of a gnat.He doesn’t read.He doesn’t really absorb other people’s conversations unless he needs something from them.He loves golf, cheeseburgers, women, the media and power.And he’s bored—and money.And he is bored when those things aren’t in the mix, which is a lot of time, as it is for most of us.And he loves the idea that there’s an enemy that is coming at him that he can take down and prove that he was right all along and that he’s a survivor.It explains his fascination with boxing and wrestling.He loves the idea of people in the ring who are uncompromising and are willing to bloody themselves in this overt macho display of force that an audience is there to witness.

Support from Elon Musk

He struggled over his life to get acceptance from other real estate developers, from others in Washington.… What does it mean for him in that period, do you think, to have the support of somebody like Elon Musk?

Well, Elon Musk is an authentically seismic entrepreneur.He put the United States back into the commercial rocket business.He invented—well, he didn’t invent, but he capitalized on an electric vehicle maker, Tesla, that reordered the automotive landscape.He put his money at risk.It was money he made on his own.He came from an affluent family, but the money that he put into play in the United States was very much of his own making.And he’s now the richest man in the world.He’s a cult figure for the digital age and for digital entrepreneurs.And for Donald Trump to have someone like him not only kiss the ring but essentially work for him on the campaign and camp out in Pennsylvania and rally voters on his behalf is the ultimate validation.And anybody who survives in Trump’s orbit understands that you only last there if you’re validating him.He won’t validate you.Loyalty is a one-way street.If you’re in the spotlight too long, you won’t be in his orbit much longer.As Steve Bannon found out after appearing on the cover of Time, I think he was out of Trumpland a few weeks after that.And Elon Musk will remain in Trump’s orbit for as long as he understands that Trump comes first, and that the second he starts putting his own interests ahead of Trump or Trump sees other people paying more attention to Elon Musk than him, the timer will start ticking.

Running Against Harris

… What do you think, when Biden drops out and Harris becomes the nominee, who is the Donald Trump that responds to that moment?

I think it’s Donald Trump who recognizes the power of celebrity, the power of a kinetic connection with an audience, which Kamala Harris authentically had, and I think he was very nervous when she was anointed to succeed Biden in the race.And everything he said about her conveyed that he was assessing her, as he does everyone physically—he talked about how attractive she was; he immediately went to, "How big are her crowd sizes compared to his;" "What kind of real traction does she have with voters," because he was worried.I think they knew that Trump was ahead of Biden in the polls and that the fact that Biden had become so infirm put Trump’s own age by the wayside, even though Trump himself was an old man who had visibly and objectively aged quite a bit and had been much more diminished than he was in either 2020 or 2016.

And Harris coming into the race, you have a younger, vital, energetic woman who is authentically self-made, who is smart and purposeful, had been a prosecutor.And there are an array of female prosecutors of color at this moment who are also on Trump’s back in the courtroom, and now he’s campaigning against another version of “that woman” on the campaign trail, and I think it discombobulated him to the point that everyone in his camp came up with these ridiculous criticisms that somehow the Democrats had subverted democracy by deciding they wanted a candidate who could actually win as opposed to the candidate who had come through the primary season and hadn’t actually been candid with the American public about how viable he was physically, mentally and spiritually.And the Democrats engaged in a bit of realpolitik, replaced him, as they’re allowed to, perfectly legal because Joe Biden stepped aside.And Trump wanted to create this idea, again, that it was poisoned and fraudulent and unfair when he would have done that himself in a nanosecond.

And it seems like a crisis going into the fall.A lot of people say he lost the debate, that she had the mysterious momentum, whatever that is.Was there a sense of crisis, and what does Donald Trump that you know do in a moment of crisis where he thought he was winning and now he’s worried that maybe he isn’t?

Well, he goes to his comfort zone.There had been a lot of pressure, I think, even from Republicans when he was campaigning against Biden and especially after the failed assassination attempt going into the Republican National Convention in Milwaukee.And I was there.I was by the stage watching Trump’s speech in Milwaukee.And at that point, they had had a very vivacious, kinetic convention, and the polling was on their side; momentum was on their side.He had this aura of a hero because of the assassination attempt.And they wanted him to talk about unity, and he could not.He talked about unity for about 30 seconds, and then he got back to “But they’re loathsome people, and I want to stick my boot heel into their faces and grill them into the ground.”And this is after a convention in which everyone had come out on the stage and bent the knee.Then he encounters Harris, and there’s this sudden twist in the script, and he can’t bear it, and I think he was panicked.And I think it wasn’t just that Harris had an aura of magic about her, which she did.It was also that she polled very well.She completely overcame the polling gap that existed between Biden and Trump, at least in the polls that we were looking at at that time, and he was aware of those.And in the swing states, she not only closed it, she appeared to be inching ahead, and I think that worried him, and I think it worried people in his camp.The Democrats had a better ground game, by far.They had had field offices in states since January.Trump, in states like North Carolina, only began opening field offices with Elon Musk’s money in August.That’s usually in a close race the kiss of death, because it comes down to what are you doing, daily door-knocking, emailing, texting, direct mail to get in touch with people.I think the thing that everyone missed, and it’s been true in every campaign that he’s run, is there are these silent Trump supporters who don’t respond to polls.And in part, I think it’s they don’t want their neighbors to know they’re kind of OK with him being an authoritarian and stepping on every form of civility and tolerance imaginable.They don’t really want to say they’re OK with that.But there’s a lot of people who want other changes in American society, and they’re willing to accept that in order to get these changes affected, and they weren’t being captured by polls.And Trump, I think, was saying at different points, he said at the Madison Square Garden rally, “I’m going to win by a landslide.”I don’t think at that time he authentically believed he would.But again, it’s the bravado that he puts out in front.

The other interesting thing is, if he’s at this moment of crisis, is that if you’re reading what people are writing in newspapers, they’re saying things like the campaign is saying he needs to define Harris; the campaign is saying he needs to stay on message on inflation.But it doesn’t seem to be what he’s doing when he’s out at his rallies.What does he do in response to this crisis?

He goes to the worst place possible.He preys upon people’s racism, and he preys upon people’s sense of outrage, and he assembles casts of characters around him who are bit players in that same bit of very ugly and divisive performance art because that’s where he’s the most comfortable, and it’s where he goes when he’s desperate.It’s what he did in the courtroom when he felt cornered, and it’s what he did on the campaign trail when he felt cornered.And I think that it is an indicator that he wasn’t sure he was going to win.But again, he is the luckiest person in human history because he had a number of things going for him in this election.But one of them was that the Republican Party has always been branded and perceived by voters as the best stewards of the U.S. economy, even though the data doesn’t show that.The economy has performed, since the 1960s, better when a Democrat has been in the White House than a Republican.¹

Economic Policy Institute: New report finds that the economy performs better under Democratic presidential administrations

That’s just in the numbers.But there’s a perception that Republicans are better stewards of the economy, and then Trump himself, even though he had all of this wreckage behind him as a businessman, was still perceived as a can-do businessman who could solve people’s problems.And that’s playing out at a time when a lot of working- and middle-class Americans had been overlooked by both parties, and they felt like the American dream was eluding them.They couldn’t afford housing.They couldn’t afford college.They couldn’t save for retirement.They weren’t sure that their children would enjoy a better life than they had.And that group of voters has bounced around between both parties for quite some time.And Donald Trump enters that vacuum and says, “I’ll save you, and I will provide solutions.”He did very little for those people, that group of voters during his first term.But on this campaign trail, he simply said, “I am who I am.I’m going to take the man down.I’m going to take institutions down.And you know I can do better in the economy than my opponent.”And I think that was enough to get him over the top.

Donald Trump, whose life includes mastering the tabloids, becoming a reality TV star, really harnessing something called Twitter when that arrives, and then in this campaign is on podcasts, these sort of male podcasts.Where does that part of him fit into his life story?Is that part of his just innate media savvy?

Well, I mean, he’s a student of celebrity.When The Apprentice was soaring in the ratings, he had a conversation with Lorne Michaels, the producer of Saturday Night Live, and he said, “Is it better to be a movie celebrity or a TV celebrity?I really want to know.”And Lorne Michaels said to him, "Oh, undoubtedly a TV celebrity because you’re in front of an audience much more of the time, and you should just be very thankful that you’ve got a hit TV show, because it will do more for your celebrity than anything else can do."And Lorne Michaels was right, and Trump took that to heart.

He’s also watched, to the extent that he pays attention to history, he watched how his predecessors used different media to reach an audience and to create a connection with an audience and, in some cases, I think, to brainwash an audience.That’s also not new.You had Father Coughlin in the 1930s use radio in a way other political demagogues hadn’t, and used it to great effect and to sow antisemitism and a lot of other hateful thoughts.In the 1950s, you had Joe McCarthy use the new medium of television to amass power for himself briefly in the Senate.JFK [John F. Kennedy] famously used television positively.FDR [Franklin D. Roosevelt] used radio positively.Donald Trump used social media in its various forms and in this new era positively and in his own interest.

And he had a lot of practice at that before social media came along.He had always cultivated the tabloids in New York.He knew the power of giving tips to the gossip pages because he could call on them to do a favor for him and go after one of his enemies if he needed it.He was a fixture on the morning TV shows, the Today show.He was on TV shows, Lifestyles of the Rich and Famous, all of these different venues where he knew it would create an image of him that was at odds with who he was in reality but that people tuning in thought of him as the great American entrepreneur.

This is so amazing.There’s so many examples of these things of being able to call into cable news when he’s in 2016, and then these podcasts where he goes on and does these three-hour, four-hour interviews.

Because he loves it.Like people are like, “Gosh, it’s amazing he could sit for three hours.”For him, it’s like being in a warm bath with a movie and a cheeseburger.Like, of course, he’s going to sit there forever.It’s nirvana to him.Someone talking to him, focusing on him, just wanting him to talk about himself, that’s what he’s looking for every single day.And he loves to hold court.It’s why he likes doing press conferences.It’s why he’s fascinated by TV.So I don’t think it’s extraordinary that he was willing to sit with anybody like Joe Rogan, who had a 20 million-or-so-sized audience.That’s like catnip to him.I think he probably would have sat there for 12 hours if Rogan would have let him.Can I tell you one other story?

Yes.

You may not want this.At one point, when we were in his apartment once—this is in like the mid-aughts—and he said, “I really don’t care what kind of a book you write.”And I said, “Well, then why did you participate?”And he said, “Well, three reasons.”He said, “One, I really like you.”I don’t think that was true.I was at the New York Times.I think he what he cared about was the New York Times’s Good Housekeeping Seal of Approval.And then he said, “Secondly, I thought this was a challenge, and I really wanted to convince you that I’m successful, and I wanted you to like me.”I think that was true.And then the third thing he said is, “And I don’t really need the media anyway.If you people do something I don’t like, I can go right over your head.I can call Page Six.I can go on the Today show.I can go on the Today show and say, ‘Timothy O'Brien’s a whack job.He’s not a good guy.’I’ll just savage you.So I really don’t care.”

And he’s saying that before Facebook, before Twitter, before podcasts, before the advent of this whole other media environment that he was going to exploit tremendously because he always had this—he knew he could go around the media.He was a creature of the media.He couldn’t get away from the media, but he also had the power to go around it when it suited him.

Trump’s 2024 Election Victory

… Everything about his story is amazing.And then there is election night, which clearly he’s worried about.He’s got the criminal trials pending.He’s planted the seeds of saying that he didn’t really lose, that it was stolen from him.But then he gets the news that he did win the election and that it’s even more resounding than it was in 2016.What does that mean to Donald Trump?

Well, victory to him is everything.It’s well beyond a nourishing meal.It represents, for him, that he has arrived on the biggest stage in the world, and it’s a vindication of who he is as a politician, as a man, as a businessperson and as a cultivator of public regard.And I think that it’s, that neediness comes from a whole mass of insecurities.He’s insecure about his intellect.He’s insecure about whether or not he’s physically attractive.He’s insecure about his business prowess.He’s insecure about his wealth.He’s insecure about how good of an athlete he is.And he’s actually like a naturally very good athlete, and he was born wealthy.But he has this deep vacuum inside of him that is insatiable.It’s this hole that will never be filled.And it is so deep, and the need is so strong, that he’s constantly pursuing all these new forms of validation, and each one’s larger than the next until you get to the presidency.And then he’s been validated.He’s now a historic figure.He’s not just an oddity who found a moment in U.S. politics and exploited it, as many have before him and have amassed temporal power.He’s somebody who has recreated a party, has changed people’s perceptions about what the U.S. character and destiny is, and he’s bent a lot of public forces to his will.But I would say that’s more by accident than design.He is not a strategic thinker; he is not a planner.He is just the luckiest man on the face of the earth.

But this is interesting, this question of the hole that he has.And here he is at this moment where, unlike 2016 when they said maybe Russia was involved or Jim Comey, where he has won a decisive victory.In fact, he cannot lose in the sense that he can’t run again, presumably—

“Presumably” is doing a lot of heavy lifting there.

—and lose, again.He has come back.He’s got the world’s richest man.It would seem like, if you could ever achieve validation and satisfaction and prove to his dad that he was a winner, that it would be that moment.But I mean, does it do that for him?

I don’t know that Donald Trump is somebody who will ever be satisfied and will feel like he’s arrived.I think he has a chip on his shoulder the size of Mount Everest, and almost no form of validation will get him to a place where he finally says to himself, “You’re really good,” and he believes it.I think he says to people, “I’m the best”; I think he says to people, “I’m the greatest.”But the reason he says it so frequently and with such energy is because he doesn’t fully feel it inside.We’ll see, right?We now have a real-world case study of whether or not being elected president twice and being elected the second time when you’ve been convicted of fraud, you’ve been impeached twice, you're a documented sexual predator, and you’ve poisoned the public dialogue in the ugliest way possible, and everyone forgives that and says, “You should be president anyway,” we’ll see if that makes him feel good.²

AP: Jury finds Trump liable for sexual abuse, awards accuser $5M

… I guess the question is, as he goes into this term, where he’s going to have power that he didn’t have the first term before, I mean, is he just as susceptible to the slights?Because that was a pattern in the first term, of responding to everybody who seemed to be questioning him.

Well, I think he’s more than susceptible to the slights.I think he’s ingested them.I think his second presidential campaign was a revenge tour.And I think he’s angry at law enforcement for trying to corral him.He’s angry at the media for trying to tell the truth about him.He’s angry at Democrats for running against him.He’s angry at certain members of the Republican Party for not embracing him.He’s mad at life for not seeing Donald Trump the way that Donald Trump sees himself.

And he is going to want to exact a certain amount of vengeance on all of those camps.And he has now the power and the authority to do that.And he has a party that, thus far, has been very pliant and hasn’t been willing, in the name of the Constitution or civil discourse or the future of the country, to stand up against some of this stuff, because Trump has identified real fault lines in American life around issues that are very real for people and things that need to get fixed, that should be fixed.He’s just actually not offering real solutions.He’s offering these seismic disruptions that are out of proportion to the nature of the problem because it serves his own ego and his own desire to set a bonfire beneath the foundations of the house.

I mean, as somebody who came up against him when he didn’t have that power, when he could file lawsuits but was a private citizen and when he didn’t like what was reported, what does that experience make you feel when you look at him coming in with the power that he will have?³

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Well, he’s a profound bully.My experience of him was that if you stayed the course and you worked hard and you made sure there were no gaps—in my case, in the reporting—and didn’t back down when he got on his high horse and rattled his sabre, everything would be OK.And I think Americans should latch on to the idea that there is immense good in our society and that some of the institutions that we are uncomfortable with have existed for a long time because they do help society move forward, warts and all.And Donald Trump doesn’t have construction in mind, even though he was a builder.He has destruction in mind, and I think it’s going to test people’s values, and it’s going to test what people want to stand up for, because if there’s a virtue to the Trump moment as he’s stripped this Band-Aid off of this myth, a variety of myths that Americans tell themselves what the country’s about, and he’s forcing everyone in American society to look at what we’re about, what we value, what we’ll stand for, what we think democracy and opportunity and tolerance entail.And I think it’s a time for people to simply stand up.And I think we’ll find out, if they stand up, that things may not be as bad as they think they will be, though there will be some very bad things happening.

Trump’s Second Term

What are the challenges that he faces in his second term, especially thinking in terms of him and who he is and the challenges he might bring to bear on himself?

Well, again, he’s a very impatient man.He’s not a process guy.He is not a manager.He’s whipping through his current crop of senior advisers and Cabinet appointments because I think he can’t wait to get through it.And what happens when you do that?Sometimes you appoint rodeo clowns to very important positions, and that’s what he’s been doing.And those are the people who are going to actually have to manage things to realize the vision he has.And there’s a few big things he’s focused on.

He’s clearly focused on a massive deportation program, and I think he’s deadly serious about wanting to execute against that.Reality will intrude.A lot of the undocumented immigrants in the United States are central to the U.S. economy, and if major swaths of them are randomly deported, you’re going to find construction, the service trades, hotels, restaurants, yard work, all sorts of things are going to come to a grinding halt, and people won’t be happy about that.And then the logistics of moving that many people out of the country and into camps—the reality of actually trying to do what he says he’s going to do is going to depend on overcoming a lot of hurdles.

He wants to institute a massive tariffs program to combat China, but tariffs are inflationary, and the costs of tariffs get passed along to consumers.And one of the reasons he just won an election was because people were freaked out about inflation.So now he’s going to make things even more inflationary?So it sounds good to say, yes, I have this bat that I will hit China over the head with, and it’s called a tariff, but he actually doesn’t understand how tariffs work, and I don’t think he’s thought through the real-world impact of what would happen if he puts 20% tariffs on Mexican goods, our second biggest trading partner, and 50% tariffs on China, our third biggest trading partner.And it all goes south.

He’s going to have a lasting imprint on the courts, and there is a chance in this term that he’ll get some more Supreme Court appointments, and you’re going to have, if that’s the case, a court that will be decidedly—I wouldn’t even say conservative, I would say decidedly opportunistic, because the court has been cherry-picking moments of history instead of legal precedent to achieve a vision that in some cases is at odds with the rule of law and American legal traditions.That’s a very real possibility.

I think he’s going to take a sledgehammer to a lot of federal agencies.And part of that might be healthy.Like, an accounting for whether or not taxpayer dollars are really being well spent in Washington has eluded most presidents of both parties, and I think he’s just going to come in here and say, “To the extent I can, I’m just going to pull the plug on this agency,” like the Department of Education or maybe the Centers for Disease Control, which on the face of it sound great, but if there’s another pandemic and he’s neutered the CDC, the American public is going to start to ask, as they do every time there’s a disaster, whether it’s a hurricane or COVID, “Who’s helping me?”And if he’s just taking the roots out of agencies that do that, people in the long run may not be happy with it.He may pay a price, an electoral price for that.

And as far as whether he’s changed, because he was the guy who came in and seems like maybe he didn’t even expect to win, he brings in a lot of people who are sometimes referred to as the adults in the room, who sort of constrained him the first time.Now he has survived … being shot at, the list of things that—

Voted out of office.

—and also then not pulling back who he was at the end of the campaign and winning.How is he different this time for having experienced all that and having seen himself prevail despite all of that?

Well, I think he’s fundamentally who he has always been.He’s just older and angrier and more powerful.But I don’t think he’s ever been anything other than who he is, and I think that’s actually one of the things that his supporters love about him.They think he’s authentic.One politician in Kentucky said to me, “Who do you think the two most popular political candidates ever to campaign in Appalachia were?”And I figured one of them had to be Trump because he was asking me that question.And I said, “Well, Trump must be one of them.”He said, “Yeah,” and he said, “The other one was Bobby Kennedy.”

And he said these were two guys who were rich and couldn’t have been further removed from the conditions of Appalachia than these two.And Bobby Kennedy was in his shirtsleeves, and Donald Trump was in a monochrome tie, but the voters thought they were there for them and that they were authentic and they weren’t lying to them.And I personally don’t think Bobby Kennedy was lying to them.I think Donald Trump was selling them snake oil.But one of his superpowers is the people who love him don’t think he’s selling them snake oil.They think of him as a redeemer and as a guardian angel.And he’s held on to that core attachment to the persona of Donald Trump, and that’s never wavered.

If you look on election night in 2016, there’s this amazing photo in Trump Tower of the Trump family—Jared, Ivanka, I think maybe Eric is there; Lara Trump is there—and they’re all, like, seeing the returns, and they’re elated.And Trump is sitting at the table with his head in his hands looking like the weight of the world has just descended upon him, because I don’t think he thought he was going to win.And the gravity now of, “Oh, you’re president.What are you going to do next?,”was rushing at him like a train.It’s like the end of the movie, The Candidate, where Robert Redford wins, and then he looks at his adviser, he goes, “What do we do now?”

And he learned on the job in his first term.And he had not a lot of interest in public service or policy.He had an interest in golf; he was on the golf course a lot.He liked being able to hit a buzzer on his desk and get a Diet Coke and a cheeseburger.I don’t think he really cared about foreign policy or working with Congress on effecting change that was good for the American people.And he left that to the people around him.

And he had a grab bag of people.He had hangers-on.He had people who saw themselves as safety valves because he was unhinged.And then there were other people who were true believers, but it was a mixed bag.And I think he came out of his first term believing that he hadn’t paid enough attention to who he could trust and who would be loyal.And I think he’s coming into his second term having gone to school, and he knows how all the locks on the safes work, and he knows the kind of people he needs to have around him who will do what he wants, not what they want.

So first and foremost, you’re going to see in every person he’s picking, which he’s already demonstrated so far, is loyalty.The second, because he’s bonkers and shallow, is he wants to think they look good on a movie poster—again, the guy who thinks cinematically.He wants them to look like Marvel superheroes.So there is this Avengers Assemble moment with Donald Trump that is nuts, but that’s also happening.And then the third is a willingness to plow ahead without regard for the public.And those three things are present in every pick he’s made so far.And some of them have the résumé and the bona fides to be good at their job, in spite of those things, but a lot of them don’t.

Can we project where this will end, or is it unknown?To have a Republican Party now that is very much loyal to him, to have installed a lot of people in the courts, to have a staff that isn’t trying to pull papers off of his desk so that he doesn’t see them but is really responding to him—do we have any sense of how it would play out?

That’s such a good question.I think that there’s going to be this tension in the early days between classic conservative Republicans and MAGA Republicans, and the classic Republicans, I think, do, in their heart of hearts, believe in institutions, and they believe in process, and they don’t want to have someone in the White House who is essentially like a teenager in the garage with a matchbook standing next to the gas tank.And then there’s the MAGA wing of the Republican Party who see those people as part of the problem.And they’re not classic conservatives who believe in lower taxes and judicial restraint and engagement overseas for national security and diplomatic reasons.They want the United States to withdraw within itself.They think the government is the problem, not the solution, and if they need to destroy parts of it, that’s fine.Even if it’s contrary to their own interests, contrary to the economy, or contrary to civil society, they want to do it anyway.And I think one of the things you’ll see play out in this term, in Trump’s second term, is, who wins that battle within the Republican Party, and will the Republican Party and some of its representatives in Congress be a brake on the White House?I think you’ll have to watch and see whether or not the Supreme Court is going to be a brake on the White House. …

I think the Democrats are going to have to revisit their character and strategy as a party and their relationship to American voters.But they still got—you know, almost half of the country voted for Harris.It’s not like suddenly half the country just disappeared.But Donald Trump won a strategically resounding election, and the Democrats are going to have to come to terms with that.

It’s almost like you’re saying he’s going to push the system as far as he can, and we’ll see how far he can go.

Yes, and I think Donald Trump has always pushed systems to their breaking point, and he has bent institutions.That has already happened in American life.I think the second term will be whether they actually snap in half and what’s left and what functions properly after that happens.

So the film is going to air the day after the inauguration, this biography.Just help me understand your thoughts on that moment when we see him raise his hand to be sworn into a second term, what it means for him and what it means for America.

Well, when he was sworn in the first time, he famously gave the “American carnage” speech, and that was somebody standing in front of the Capitol who had a view of the United States that was irretrievably dark.He saw it as a country that was being invaded by outsiders, that had been taken over by culturally inauthentic and dangerous people, that had lost its mission in the world and was bleeding and suffering from wounds across all parts of society.So the question is, what kind of a speech does he give on Inauguration Day this time?I would bet that that speech is not going to be a speech about unity, and I don’t think it’s going to be a speech about healing or bipartisanship.I think it will be a speech about someone who sees himself as a whirlwind and as a tornado that is going to touch down on different parts of American life and uproot things, and you’d better get ready for it.And it will smack of that because he likes people to be ill at ease.He likes people to be afraid, and he likes people to be afraid of him.He is not someone who traffics in hope and opportunity and unity.He traffics in images of fire and division and destruction.But I hope he chooses a different path.I’m just not optimistic that his speech on Inauguration Day will capture that.

And you know him as well as anyone, really.Let me just see if there’s anything else.

[Producer Vanessa Fica] Just going back in time a little bit.The raid at Mar-a-Lago, what happened there, and can you tell me a little bit about politically what happened after that raid with Republicans, how they reacted to it as well?

Well, you know, I think that the rate at Mar-a-Lago was– I should be looking– sorry about that.This is like a game show or something with a voice off the stage.

Sorry.

No, I'm just joking.The raid at Mar-a-Lago was this very real prosecutorial moment.The investigators were at the gates of the house, and they had reason to be there.Trump had multiple opportunities to return the documents that were at Mar-a-Lago to the National Archives, and he chose not to.And he not only chose not to return them, but he tried to hide them from prosecutors, from investigators, from law enforcement.You don’t hide things unless you feel like you’ve got something to hide.And the narrative that came out of that was, here’s the law again showing up at this guy’s home, which, by the way, Mar-a-Lago is a club.It’s not his home. …And these people show up at his club, and he’s an ex-president, and how dare they?But they were just doing their jobs, and they’re doing the jobs we expect law enforcement to do if they suspect wrongdoing has occurred.And in this case, it was a possible theft of classified documents having to do with Iran’s nuclear program that should not have been out in the wild, and that there’s a reason we retain these documents as a country, regardless of which power’s in the White House.And he ran roughshod over that.And it got spun as overreach and as another instance of law enforcement unfairly targeting him because he had views that weren’t popular with the people behind law enforcement. …

And the political resonance of the raid, of the prosecutions for him?

It got portrayed as prosecutorial overreach and someone prosecuting a president who had different political views than they did, and it had nothing to do with law enforcement or the rule of law.It just had to do with settling scores.And he survived, just like he survived the assassin’s bullet, and just like he survived the cases in New York, and just like he survived the election defeat in 2020.He kept coming back, and ultimately, he won.

… One other thing I wanted to ask you about was the mug shot.How did he transform that mug shot into something iconic? What did it mean?

Well, I think that it’s not only Donald Trump who transformed the mug shot; it’s the people around him.They all know that Donald Trump being defiant, even when he’s being booked at a courthouse and in a jail, is their hero, and he’s their protector.And so a mug shot that for most people might have been a badge of shame—and he’s glowering; he’s got his blond, carefully coifed, saucer-shaped hair planing down over his face, and it looks like, if you put a knife in his hand, he would gut you—becomes a decoration on Christmas stockings that are sold at the Republican National Convention in Milwaukee.And it becomes the front of T-shirts and all sorts of Trump bling gets emblazoned with Donald the Defiant, which is exactly where his supporters want him to be.

It’s amazing branding from a guy who spent his whole life branding things, branding himself.

Yes.

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