Michael Wolff writes in this 2025 book:
* [In 2021] Mar – a – Lago, as one Trump intimate put it, was less Camelot than Jonestown.
* the man on the tightrope without a net. Who can take their eyes off him? As Trump’s third presidential campaign came to life — or, unaccountably, did not die — and as the stakes for him became crystal clear, his proposition as a candidate playing both hero and martyr became utterly straightforward: Elect me or destroy me.
* Wiles and LaCivita were the professional leadership team tasked with handling the mercurial former president. The press had noticed this — the two had cordial and professional relationships throughout the political media, even as Trump made it his favorite enemy — and had begun to see this as the reason for Trump’s buoyancy and better and better numbers.
* All Trump’s relationships with family, wives, staff, friends, are…unusual, everybody serving him in roles that he has more or less concocted from his own imagination. Of all these relationships, the strangest and unhappiest is probably with his lawyers, a revolving door of hundreds over the years. At the heart of this relationship is a profound contradiction: He wants his lawyers to be savvy, canny, astute, and aggressive, pulling him from every pickle he gets himself into, but at the same time, he wants them to be abject suck – ups to his every whim and desire — and to reassure him at every turn that he will prevail. In this, he elevated Roy Cohn into a myth of defense lawyer – fixer omnipotence to whom no one might ever measure up (and who, too, he ultimately found fault with and spurned). Also, in seeing lawyers as essentially dramatis personae rather than technicians, he often chose for his ideal models characters of the type that populated 1960s win – every – trial television shows.
Almost every major Washington and New York firm had refused or deflected an inquiry to represent him during Trump’s White House years. Being a lawyer who was actually willing (professional reputation and accomplishments not particularly relevant) to represent him was a way into Trumpworld, and being a lawyer who could be utterly abject was a way into the inner circle.* The worst thing that might befall a candidate for office, a criminal indictment, had now happened. In any understanding of the nature of U.S. politics, this was a disqualifying event. But immediately, the campaign put out an online fundraising appeal, which almost instantly began to reflect a wholly different reality: the fastest minute – to – minute fundraising hours of the campaign so far.
The campaign, grasping to explain this reality, not least of all to itself, started at that moment to talk about the “split screen.” On one side, what you saw could not be worse: an inescapable legal quagmire, threatening and perhaps mortal — yes, likely to be mortal. But here on the other side, an entirely positive political outlook: overwhelming support in his party, ever – rising polling numbers, lackluster opposition. In the first twenty – four hours after the indictment, they’d raised four million dollars, with a remarkable 25 percent representing new donors.
• • •
Behind his desk, Trump’s mood is buoyant. He yells, “Bring me the poison.” His basket of Starbursts, Hershey’s Miniatures, Laffy Taffy, and Tootsie Rolls instantly appears. “Okay, get the poison out of here,” he says, taking two handfuls.
“This is big. This is very big,” he now analyzes — he’s simultaneously on the phone and talking to people in and out of his office. “They’re only doing this because they’re afraid of us. This puts us in front of every camera in the world.”
His lawyers are suggesting an incremental and procedural response, which Trump waves away. As he has told his staff, repeatedly, he now instructs his lawyers: “Our legal strategy is our media strategy; our media strategy is our legal strategy.” This is the premise uttered so often that no one can remember the first time they heard this foundational belief.* Trump’s people, many of them, anyway, don’t think of him all that differently from how the rest of the world does: He’s mercurial, capricious, lazy, ill – informed, inattentive…The difference is, having been around him, having seen him survive what other mortal politicians never could, they’ve come to believe he knows something, sees something, gets to the heart of something — some new reality — that the rest of us don’t.
* Jason Miller is one of the few staffers who’s been with Trump for all three campaigns, and, taking one for the team (or, in versions of this story, thrown under the bus), he’s sent in to talk to Melania. In December 2016, slated to be the communications director in the new administration, Miller got another Trump staffer pregnant, simultaneously with his wife’s pregnancy. He lost his prospective White House job in the ensuing mini – scandal, but he remained a Trump favorite, coming back to help manage the 2020 campaign. His conversation with the former First Lady prior to the first court appearance will become an oft – shared cautionary tale of managing the Trumps’ relationship. “Nice try,” she says, after Miller makes his stand – by – your – man pitch.
It’s Justin Caporale who takes over the physical management of the indictment. Caporale, a Florida political op whom Wiles recruited into the campaign, is the logistics guy — by which is meant not just making the trains run on time, but staging the entire look and feel of Trump’s movement, presence, and message. Caporale’s central mandate is to make the former president continue to look like he is still president — and running for re – election. He isn’t a private citizen being hauled into court. He’s President Trump.* Alina Habba furiously resents the suggestion by various of the other Trump lawyers that she got her job as a Trump defender by hanging out in a bikini by the pool at Trump’s Bedminster club, which she and her husband, a parking garage owner, joined in 2019, threatening to sue anyone, if she knew who they were, who says as much. But she does hang out by the pool and, proudly so, in a bikini. The 2010 graduate of Widener University Commonwealth Law School practicing with a small firm in New Jersey did actually get her job representing “the President” because of her membership at Bedminster, and getting recommended, she takes pains to explain, by other Bedminster members and thereby offering her services to the Trump family. Trump, in 2021, had her file several more or less frivolous lawsuits on his behalf, including against his niece Mary Trump, who had written a negative book about him; that suit, like others, would be dismissed. As his legal troubles mounted, he kept suggesting bringing Alina in. Although she had little experience germane to the issues he was facing, he seemed satisfied, pleased to be able to show her picture on his phone — along with that of Lindsey Halligan, another comely lawyer he had hired in Palm Beach — whenever the subject of his legal talent came up, which it did often. “I may not have the best legal team,” he took to saying with pride, “but I have the hottest.”
* Along with Boris in the top tier of the Trump bubble — ever reinforcing the bubble — was thirty – year – old Natalie Harp.
She was a Fox News – type blonde, although not on Fox. She had been a “host” on OAN, the distant – third conservative news channel behind Fox and well behind even the lagging Newsmax. Trump had seen her on television at the same time that she was lobbying almost anyone in his circle whose email she could get. Natalie Harp, the 2012 Point Loma Nazarene University graduate and 2015 Liberty University MBA, had a story: She had recovered from bone cancer because of Trump’s “Right to Try” law, which, she said, allowed her to get the experimental medication she needed. While there were holes in this tale, she nevertheless earned herself a speaking role at the 2020 Republican convention: President Donald Trump had saved her life. In 2022, she came into the nascent campaign as a fetch – it girl, hovering around Trump in anticipation of whatever needs or desires could be instantly satisfied. This settled into a more specific function: She would accompany Trump during his three to four hours a day on the golf course and, riding in her own golf cart, keep him abreast of events by printing out emails and news stories on the wireless mini printer in her charge.
In doing this, she became a significant gatekeeper. Trump was frequently seen with a cache of papers. He would often demand time in his schedule to go over “my papers.” (In the past, he had militantly eschewed papers.) His workload — “my papers” — was almost entirely what Natalie had printed out. The curation was largely her own. Hers was solely a good – news printer — and she, a worshipful acolyte.
This was one of Trump’s set pieces: always to be surrounded by attractive women who worked for him. It was an inverted feminist credential: In another outdated culture pin, he referred to them as “Charlie’s Angels.” His relationship with them was avuncular and flirtatious. Alina Habba and Lindsey Halligan and Natalie Harp were part of the great entourage that accompanied him to the spring NCAA wrestling championship. Trump’s subject of discourse at the NCAA event was which wrestlers the “ladies” found most attractive. Everyone seemed happy to play along, critiquing the various bodies, rating them as their type or not. But Natalie couldn’t be moved. Trump kept pressing her, trying to make her obvious point even more obvious to everyone listening in with disbelief and embarrassment: “Oh, none of them, none of them, sir. I didn’t find any of them attractive or anything worth looking at” — which was to say, I only have eyes for you.
“I mean, this is how it is. He just likes people who are, you know, entirely in the sycophant territory,” one entourage member explained.
Every effort by the staff to create distance between Natalie and the boss was met by redoubled efforts on her part to remain close, her doggedness amusing and impressing Trump. The weirdness of it all only belied the comfort Trump felt around her — not least because she was literally there all the time, at his beck and call, utterly attentive, hovering and interrupting when others sought his attention — and her growing importance.* Letters had started to surface from Natalie to Trump, passed around by his political and legal teams with bewilderment and concern…and incredulity, portraying a relationship of an imagined alarming intimacy or one of genuinely strange submissiveness. She slipped them into the stack of papers with which she was constantly supplying him.
…I want things always to be right between us. I also know I’ve been distracted all week (forgetting to eat through the days, and even forgetting to sleep, and only catching a couple of hours at a time). I haven’t been myself, dwelling on the Past, and the pain of losing my Dad, and I started letting the remarks of people who haven’t bothered me before, get to me — not because I care what others think, but because I see myself being lowered in your eyes and good opinion. That is the fear you see, because I never want to bring you anything but joy. I’m sorry I lost my focus. You are all that matters to me. I don’t want to ever let you down. Thank you for being my Guardian and Protector in this life…
With all my heart, Natalie
Now this is the Note I wanted to write (But the apology needed to come first.)…After going through all this self – analysis, my conclusion? I need to reunite my past self with my current into a better version who will make you proud. And please, when I fail, will you tell me? You have the absolute right to cuss me out, if need be, when I deserve it, because no one knows or cares about me more. Thank you for always being there for me — I’ll never forget when you made that promise to me after losing my Dad, and I know how happy he is right now that I did get to go to Scotland and Ireland, as he always wanted for me. To modify a classic, “I could not have parted with you, to anyone less worthy” — and, I will add, it is I who is unworthy. Always, Natalie.
P.S. My hands looked worse in Scotland and Ireland because the Cold turns the old “scars” purple. Still on the road to recovery!Since the start of his presidency, Trump had nearly always had a young woman to buffer and boost him and act as his aide – de – camp, body girl, gatekeeper, and, often, interpreter (“what he means…”). This included Hope Hicks, his most senior body girl; Madeleine Westerhout, who would be fired for gossiping about the Trump family; and Margo Martin, his current assistant. All looked the part: thin, tall, with long straight hair, short skirts (in winter, high boots). The fact that these women without political backgrounds, relevant educations, or even long histories with Trump — and each with a clear devotion to or infatuation with him — came to assume outsize influence at the highest levels of government was written off as just one more Trump characteristic. But Natalie Harp now pushed this to a further extreme.
Her fixation was an open secret. This was schoolgirlish and eye – rolling — and discomfiting for all. But it existed side by side with her better – than – anyone proximity to Trump, the deference and authority he accorded her, and her remarkable persistence in overcoming every effort to short – circuit her access.
Her golf cart had become the literal mechanism for shadowing him. In his three or four hours on the golf course every morning, Natalie — close behind in her designated cart with her printer, and holding his phone — was his connection to the world. At every hole, she supplied him with what she thought he might need or want to know. Equally, he told her whom to call for him, and what to post, with her composing many of his outbursts. Political teams often need to deftly and tactically deal with a candidate’s bad habits. Natalie’s golf cart became conveniently unavailable. Undaunted, and with a thirty – pound printer on her back, she yet pursued, running madly after Trump’s golf cart on his spring golfing trip to Scotland.
The summer move to Bedminster became another opportunity to deal with what was now deemed officially “the Natalie situation.” In Bedminster, she needed housing — so none was allotted. Out of sight, for Trump, was out of mind. And even Natalie would not presume to speak to Trump about her accommodation. (Who got what room at what Trump property was hard – fought politics, largely unbeknownst to Trump.) And yet, in Bedminster, suddenly there she was. She had reached out to the grounds staff at the country club and gotten herself a maid’s room. And when that proved too far from the main house to respond quickly enough to Trump’s calls, she relocated herself to the much closer women’s locker room, where, with undiminished proximity to Trump, she would spend the summer.
The earlier joking about Natalie being the true chief of staff took on a darker meaning. The more peculiar she seemed to be, the more obvious her obsession with Trump and her lovestruck adulation, the more integral she became. She was taking over the social media accounts; she was communicating, sometimes on a daily basis, with Trump’s coteries in Congress — a daily texting relationship with as many as two hundred members of the House and Senate, most more and more confused: Why were they hearing from this person, and why were they hearing so often? The body girl was, in effect, a chief spokesperson.
Trump’s girls had always existed in relative harmony with his principal body man, Dan Scavino.* Natalie was now foremost among those unexploded bombs that a candidate’s staff needs to keep aware of: More and more of Trump’s moods and outbursts seemed directly connected to the clippings and reports she brought him; and more and more reliably, she was there to interpose herself in meetings with the political team, using her printer to re – direct or override their concerns. The aggressiveness of her attention, and her fury when she was denied bestowing that attention on Trump, was also of increasing concern to the security team. The Secret Service, with her letters in their possession, was now noting the strangeness of her behavior.
Nonsense, declared Trump. “She just loves her president.”* Steve Bannon, whose life’s work had become getting the attention or even the fleeting favor of the man who fired him six years before — a rarely successful effort…
* As the team returned to New Jersey, Alina Habba, going through the Twitter (X) commentary, noted her place in the sun: “The only thing anyone is talking about is my tits. It’s all about my tits. Oh my God. I guess I should have worn something else. My mom is going to kill me.”
* A Trump staffer would not presume, other than by specific invitation, to have privileges to the buffet. But when Natalie was in Palm Beach — that is, when Trump and his entourage were in Palm Beach — she and her mother, under the attentive eye of club members, reliably showed up for their Sunday meal, and put it on the Trump tab.
Curiously, there was little supposition that Natalie might be the “bit on the side.” That issue, for a man who had spent most of his adult years in open, proud, undaunted, and, in repeated accusations, predatory pursuit of women, had been largely expunged as a possibility. Since the first year in the White House, when Trump’s sex life was a persistent mystery or puzzle, it had drifted off or flatlined. No one said it. No one would ever say it — of all things, you did not tread into personal territory with Donald Trump. But he was, if you had to draw the obvious conclusion, post – sex. “He replaced it with politics. There’s a liberal dilemma: Would they rather he preyed on women or on the country?” remarked an amused Steve Bannon in the waning years of the Trump presidency.
Natalie being the bit on the side would have been a reasonable explanation. Beyond that, she fell into the context of the Sun King’s court: Insofar as she amused him, or her efficiency with respect to his desires was useful to him, or the way her irritation of everyone else reaffirmed his dominance, she was welcome at the buffet. Her mother, too.
