Three Conversations With Donald Trump
“Can you believe these are my customers?” Donald Trump once asked while surveying the crowd in the Taj Mahal casino’s poker room. “Look at those losers,” he said to his consultant Tom O’Neil, of people spending money on the floor of the Trump Plaza casino. Visiting the Iowa State Fair as a presidential candidate in 2015, he was astounded that locals fell in line to support him because of a few free rides in his branded helicopter. In the White House, he was sometimes stunned at his own backers’ fervor, telling aides, “They’re fucking crazy.” Yet they loved him and wanted to own a piece of him, and that was what mattered most.
Almost immediately after his defeat in 2020, Trump began fundraising off his claims of fraud, turning to his ardent fans for support. Plenty of people donated small amounts of money to continue a fight he swore was valid and building toward action. It was difficult to discern, though, whether Trump actually believed what he was saying about the election.
I learned in the spring that Trump was repeating a claim from one of his most vocal allies, the self-made pillow-company CEO Mike Lindell, that Trump would be reinstated as president by August 2021. Trump liked the idea, telling aides he did not want to have to sit through another three and a half years of a Biden presidency. He quietly encouraged some conservative writers to publicize the idea in their own voices, telling the National Review editor Rich Lowry as well that he anticipated being reinstated by August 2021. Trump encouraged Lowry to write about it, saying it could help the magazine. When Jenna Ellis, his former adviser, protested on Twitter the notion that Trump could be reinstated to office, Trump told Ellis that her reputation would be damaged. She took that as pressure to reverse her statement. Trump conceded to her that the scenario was “almost impossible,” but that he wanted to keep the idea alive.
Other moneymaking opportunities arrived, ostensibly tied to the reverent memory of the Trump presidency. The most audacious plan was for a social-media company of Trump’s own. In the days immediately following the riot at the Capitol on January 6, 2021, Trump was suspended from Twitter, Facebook, Instagram, and YouTube; he spent most of the next year insisting that he did not care about being banned while also suing the companies to get his accounts restored. In October, he announced that he would launch his own social network as part of a merger with a so-called blank-check company, whose stock price shot up when the merger was announced. The funding mechanism, which sparked an SEC investigation prior to the platform’s launch, was completely opaque.
None of this came as any surprise to me. For much of the past decade, reporting on Trump has been my full-time job as a correspondent for The New York Times. To fully reckon with Donald Trump, his presidency, and his political future, people need to know where he comes from. The New York from which Trump emerged was its own morass of corruption and dysfunction, stretching from seats of executive power to portions of the media to the real-estate industry in which his family found its wealth. The world of New York developers was filled with shady figures and rife with backbiting and financial knife fighting; engaging with them was often the cost of doing business. But Trump nevertheless stood out to the journalists covering him as particularly brazen.
I have found myself on the receiving end of the two types of behavior Donald Trump exhibits toward reporters: his relentless desire to hold the media’s gaze, and his poison-pen notes and angry statements in response to coverage. His impulse to try to sell his preferred version of himself was undeterred by the stain that January 6 left on his legacy and on the democratic foundations of the country—if anything, it grew stronger. He had an almost reflexive desire to meet with nearly every author writing a book about him. Trump’s aides offered me an interview, and I asked for two additional ones.
Trump typically welcomed visiting authors for interviews in an indoor area at Mar-a-Lago that gets converted to a dining room at night, where a model of the redesigned Air Force One sits proudly on a low table. But after the headiness of being at the center of the world’s gaze, his time after the White House made him seem shrunken. He often played golf and then went to his newly built office at the club for meetings with whoever traveled down to seek his approval. He would watch television before going to dinner, where club members would sometimes applaud him, and then it would start all over again the next day, so removed from the daily rhythms of the broader world that he was oblivious to holidays on the calendar and staff had to remind him.
When I arrived for the first interview, in March 2021, I was ushered away from the usual room to a smaller area where Trump sometimes dined with guests. I learned as we wrapped up that the club was empty because it had been closed off after a COVID-19 scare, but Trump decided to have us sit there regardless, without checking to see if I was vaccinated. “COVID,” Trump said as he described the club’s closure, “turns out, not good.”
Trump greeted me cordially before taking a seat across the table from me; he was in sales mode, not combat mode. His history in New York was the focus of our interview. He thought back to the first major political figure he had observed up close, the Democratic Party boss Meade Esposito, who dominated Brooklyn politics when Trump joined his father’s real-estate business. “Meade ruled with an iron fist,” Trump said. “And he was a very strong leader, to put it mildly. And when I came to Washington, I said, ‘Oh, well, this is now the big league. So as tough as they were, this must be even tougher.’ But I said, ‘How could anybody be tougher than Meade?’ Meade had a cane at the end. He used to start swinging the cane at people. I mean, he was wild.”
Trump had seemed to try to emulate Esposito’s style in his post-presidency, receiving visitors who came to kiss his ring, and picking favorites in primaries to try to determine the outcomes of those races. Trump’s view of strength never changes, regardless of the context, flattening all situations so they appear the same. He used identical language—“with an iron fist”—when describing how Esposito presided over his boroughwide fiefdom and when he praised China’s President Xi Jinping after his own term ended.
I asked him if he had expected the presidency to function the same way. Rather, Trump said, that is how he thought congressional leaders would act on his behalf: “Well, I figured that the Mitch McConnells would be like him, in the sense of strength.” There were plenty of factual problems with the criticism. In fact, McConnell had kept Republican senators in line over and over to advance Trump’s policy and personnel concerns and generally protect his political standing as the leader of the Republican Party. Nevertheless, Trump said to me in another session, using his favorite new nickname for McConnell, “The Old Crow’s a piece of shit.”
Trump also complained to me about senators successfully practicing this type of power politics against him, as Lindsey Graham and Ted Cruz had when they persuaded Trump not to back a challenge to a colleague, Nebraska’s Ben Sasse; Trump gave a surprise endorsement to Sasse, who then, after winning reelection, voted to convict Trump during his second impeachment. “Like a schmuck, I went along with it,” Trump said.
Trump was clear that he did not believe he would have faced any of the same legal problems that had dogged him if Manhattan’s longtime district attorney, Robert Morgenthau, had still been in office. “No. He was a friend of mine. He was a great gentleman. He was a great man. He was highly respected. No. And I run a clean organization. This is a continuation of the witch hunt.” He added, “Bob Morgenthau would not have stood for this.” The investigation by Morgenthau’s successor, he insisted, was part of “an attack on the Republic.” He was perhaps even more dire when describing the threat he had faced from the special counsel investigation into his campaign’s ties to Russia. It forced him, he said, to perform “two jobs when I was president, running the country and survival.”
At one point, Trump made a candid admission that was as jarring as it was ultimately unsurprising. “The question I get asked more than any other question: ‘If you had it to do again, would you have done it?’” Trump said of running for president. “The answer is, yeah, I think so. Because here’s the way I look at it. I have so many rich friends and nobody knows who they are.” He then went on to talk about how much easier his life would have been had he not run. Yet there it was: Reflecting on the meaning of having been president of the United States, his first impulse was not to mention public service, or what he felt he’d accomplished, only that it appeared to be a vehicle for fame, and that many experiences were only worth having if someone else envied them. (When I asked him in a later interview about what he’d liked about the job, he replied, “Getting things done,” and listed a few accomplishments.)
We met for a follow-up interview five weeks later, again at Mar-a-Lago, again in the late afternoon. He was not in a good mood. By way of greeting, he told me, “I’m watching the Arizona situation very carefully.” A private company called the Cyber Ninjas was conducting a so-called audit of Maricopa County ballots and tabulation equipment that had been handed over by the Republican-led state senate. He had talked about his claims of widespread fraud in our first interview, but not about trying to undo the results. He seemed to be going backward. I learned later that he’d tried getting the Republican National Committee to fund the “audit” in Arizona, to no avail (the “audit” ultimately affirmed the results of the state’s election).
He was at his most animated when I asked about why he had trusted Sidney Powell, given the concerns his other advisers had had about her. Since then, Powell had faced libel suits from voting-machine manufacturers she had accused of corruption; her defense had been, essentially, that no one should have taken what she had to say seriously. “I was very disappointed in her statement,” Trump said. “That is so demeaning for her to say about herself.” Then he essentially read stage directions on how to use public claims in lawsuits. “All she had to say,” he said, “was ‘Upon information and belief, I think such and such.’ Now all she says there, was take a thousand stories that were written over the last 10 years long before all of this, that are bad stories,” he said, “and that is information and belief, she read them. And that’s the end of that case. That’s true for everybody: ‘It’s upon information and belief and let’s go to court to find out if it’s true.’”
I pressed him on what, at that point, was one of the persistent mysteries of January 6, which would become central to the congressional select committee’s investigation: what he had been doing in the hours when the Capitol was under assault from his supporters. He insisted that he was not watching television, despite volumes of witness testimony and other evidence to the contrary. “I didn’t usually have the television on. I’d have it on if there was something. I then later turned it on and I saw what was happening,” he said. He lied throughout that bit of our interview: “I had heard that afterward and actually on the late side. I was having meetings. I was also with Mark Meadows and others. I was not watching television.”
Our third meeting was at the end of the summer, which he had largely spent at the quarters that he kept on the grounds of his New Jersey golf course.
When I arrived at the Trump National Golf Club Bedminster, I waited in a small room off the front entrance. I spotted Lindsey Graham outside, in golf pants; it was the second time I had encountered him in Trump’s vicinity that year. Trump eventually entered the room, having lost a noticeable amount of weight since I had seen him last. Graham followed a minute later and gestured toward Trump. “The greatest comeback in American history!” Graham declared. Trump looked at me. “You know why Lindsey kisses my ass?” he asked. “So I’ll endorse his friends.” Graham laughed uproariously.
I was curious when Trump said he had kept in touch with other world leaders since leaving office. I asked whether that included Russia’s Vladimir Putin and China’s Xi Jinping, and he said no. But when I mentioned North Korea’s Kim Jong-un, he responded, “Well, I don’t want to say exactly, but …” before trailing off. I learned after the interview that he had been telling people at Mar-a-Lago that he was still in contact with North Korea’s supreme leader, whose picture with Trump hung on the wall of his new office at his club.
He demurred when I asked if he had taken any documents of note upon departing the White House—“nothing of great urgency, no,” he said, before mentioning the letters that Kim Jong-un had sent him, which he had showed off to so many Oval Office visitors that advisers were concerned he was being careless with sensitive material. “You were able to take those with you?” I asked. He kept talking, seeming to have registered my surprise, and said, “No, I think that’s in the archives, but … Most of it is in the archives, but the Kim Jong-un letters … We have incredible things.”
In fact, Trump did not return the letters—which were included in boxes he had brought to Mar-a-Lago—to the National Archives until months later. The Washington Post reported on it in early 2022; the Justice Department began investigating how the classified material made its way in and out of the White House residence. (In one of our earlier interviews, I had asked him separately about some of the texts between the FBI agent and the FBI official working on the Robert Mueller investigation whose affair prompted the agent’s removal from the case; we had learned the night before Biden’s inauguration that Trump was planning to make the texts public. He ultimately didn’t, but he told me that Meadows had the material in his possession and offered to connect me with him.)
Over the course of our conversations, he appeared reluctant to take shots at many of those people on whom I knew him to have been toughest behind closed doors. His campaign manager Brad Parscale spent money “unwisely,” he said, but he did not criticize him beyond that. I asked why he had given Jared Kushner expansive power. “I didn’t,” Trump said, although he had done exactly that. When I pressed, Trump said, “Look, my daughter has a great relationship with him and that’s very important.” (In the fall of 2016, ahead of the election, Trump once tried to call Kushner to complain about why the situation in Florida was bad for him. Kushner, who usually didn’t answer his phone on the Sabbath, was unresponsive. “Fucking Shabbat,” Trump groused, asking no one in particular if his Jewish son-in-law was really religious or just avoiding work. When I later asked him about this, he denied that he had said it.)
He was not so sanguine about Mike Pence, who had begun to defend his own actions on January 6 with increasing stridency, prompting Trump to escalate his condemnation of his former vice president’s judgment that day. “I said, ‘Mike, you have a chance to be Thomas Jefferson, or you can be Mike Pence,’” Trump recounted to me, repeating an inaccurate comparison to the election of 1800. “He chose to be Mike Pence.”
I brought up another potential future primary rival, by mentioning that he had been compared to New Jersey’s feisty Governor Chris Christie before the two men faced off in the 2016 primary. Trump replied, “I was compared to him? Why? I didn’t know I had that big of a weight problem.” A small smirk followed. Then: “He’s an opportunist.” I heard that Trump was describing Florida Governor Ron DeSantis in similar terms, calling him “fat,” “phony,” and “whiny,” while claiming credit for making his candidacy in 2018.
Even as he talked about launching another campaign for the presidency, Trump was more comfortable looking backward than forward. When I told Trump I wanted to talk about 2024, he asked, quizzically, “2024?”
By the time we spoke at Mar-a-Lago, I had covered Trump as a political figure for many years, and little was surprising. And still the choreography of in-person interviews could reveal moments of unintended candor. He started to explain why he doesn’t like when audiotapes of his interviews are released. Being on camera was “much different,” he said. “Whereas,” he said, in a “written interview, I’ll repeat it 20 times, because I want to drum it into your beautiful brain. Do you understand that?” He repeated himself again. “One of the things I’ll do, if I’m doing, like with you, for the written word, is I got to drum it into your head. So I’ll repeat something six times.”
His interest in repetition was not news to me, but his self-awareness of it was notable. At another point, he was going on a stem-winder about New York’s then-outgoing Mayor Bill de Blasio canceling a contract with the Trump Organization to manage a public golf course in the Bronx after January 6. De Blasio’s choice to replace Trump was deeply controversial, and a judge later ruled in Trump’s favor.
“It’s like communism,” Trump said, asking what the word was for when someone takes your property. (It came to him 20 minutes later. “Confiscate is the word,” he declared in the middle of another thought.) I tried redirecting him, but he cut me off. “Let me just finish it,” he said. “Just let me do this, and then I’m going to tell you.” He seemed to hear himself, and smiled. Then he turned to the two aides he had sitting in on our interview, gestured toward me with his hand, and said, “I love being with her, she’s like my psychiatrist.”
It was a meaningless line, almost certainly intended to flatter, the kind of thing he has said about the power of release he got from his Twitter feed or other interviews he has given over the years. The reality is that he treats everyone like they are his psychiatrists—reporters, government aides, and members of Congress, friends and pseudo-friends and rally attendees and White House staff and customers. All present a chance for him to vent or test reactions or gauge how his statements are playing or discover how he is feeling. He works things out in real time in front of all of us. Along the way, he reoriented an entire country to react to his moods and emotions.
I spent the four years of his presidency getting asked by people to decipher why he was doing what he was doing, but the truth is, ultimately, almost no one really knows him. Some know him better than others, but he is often simply, purely opaque, permitting people to read meaning and depth into every action, no matter how empty they might be.
This article is adapted from Haberman’s forthcoming book Confidence Man: The Making of Donald Trump and the Breaking of America.