Boris Epshteyn, Donald Trump’s forty-year-old Russian-born legal adviser, came on to the Microsoft Teams call with his video off. Then his screen came to life in a sudden reveal.
Bearish, balding, and overweight, Boris, confounding all Trump’s other lawyers, was Trump’s most recent candidate to replace Roy Cohn, the lawyer whom Trump had elevated into the diabolical magician who could get him out of any jam, were he only still alive.
Here, in his home office, in his onscreen box, was a bare-chested Boris, showing off his massive torso and dense pelt to quite a collective gross-out.
Susie Wiles, the sixty-five-year-old Florida political op and the closest thing Trump had to a campaign manager, recoiled. “Oh, God, Boris—put on a shirt!” Everybody else on the call guffawed, groaning and shielding their eyes.
It was spring of 2023, and Trump’s political and legal staff had had its heart in its mouth for several weeks, anticipating an inconceivable blow to the campaign, the first criminal indictment of an American president in history. Worse news: They needed to rely on Boris, the architect of the entire Trump defense and the effective legal team manager, to keep them informed enough to deal with the mess.
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Boris had been in the Trump orbit since 2016. And often—and not least of all for his social impairments—pushed out of it. But he’d always clawed his way back. Mock him—and he was aware that everyone did—but today Boris was taking a victory lap.
With no firm information, Trump had jumped the gun and announced his own coming indictment in the hush-money case brought by Manhattan district attorney Alvin Bragg. Trump was pre-empting Bragg if he did indict, and highlighting Bragg’s weakness if he didn’t. Win, win. And that was the news that a delighted Boris now brought: The grand jury had announced that it was taking a month off, and that, according to Boris, was as good an indication as any that it was a dead-duck case.
Boris hadn’t practiced law in more than a decade. He wasn’t in fact one of Trump’s lawyers in New York. But Boris had personally chosen the lawyers on each case and then had wedged himself between them and Trump and between the lawyers and the campaign staff.
Nothing would happen, Boris was assuring his boss. “Delays are bad for them”—that is, for the New York City prosecutors. “It means they’re trying to come up with a new theory of the case. They don’t have a case, in other words.”
Boris was born in Moscow in 1982 and was part of the great migration of Russian Jews to the United States in the 1990s. After law school and his brief stint in a New York law firm, he shifted into the emerging field of conservative media, a career opportunity which included, none too successfully, helping to prep Sarah Palin in 2008 for campaign interviews. In 2016, he became involved with the Trump campaign as a television defender, a surrogate when it was still difficult to find people to front for Trump, when, basically, any willing body would do.
As the Russian mess unfolded, he lasted in a White House job for a matter of weeks before being bounced for “security concerns.” His perennial outsider status perfectly positioned him in the days after the 2020 election. He was among the first Trump representatives (albeit self-appointed) to fly into Arizona to help contest the state’s vote count and then to try to overturn it. As the ensuing election dispute hurtled forward, Boris aligned himself with Rudy Giuliani, traveling with the former New York City mayor on his mission to secure new electors in various states and to seek legislative overthrow of the official votes..
After January 6, Giuliani, demanding payment for his fruitless efforts, was cast out of the Trump circle, even deprived of Trump’s new cell phone number when he left the White House. But Boris continued.
His bona fides with Trump were his foot soldier loyalty in the election fight. As almost everyone else in Trumpworld tried to distract Trump from his election obsession, Boris, ever on the phone, diligently fed it.
Given the rage with which Trump continued to damn the “witch hunt” against him, he remained, in fact, fairly sunny about his situation. This was in part because he was, by nature, impervious to the outside world. He lived in a highly controlled universe populated only by lackeys, flunkies, and sycophants. And, too, the vulnerabilities that undermined ordinary mortals—the doubts, shame, and fear—were absent in him. Conflict made him feel alive.
But the other thing was that bad news did not easily get through to him. There were no realistic appraisals of the situation he was in. Boris kept all the other lawyers, already a constantly changing cast, at bay. It was Boris’s legal appraisal that got through to the boss—and that was always rosy. Lawyers who disagreed with Boris soon found themselves out of favor with the client.
Preparing to leave for a long weekend, Boris was on the phone with Trump offering a buoyant view: “I think they’re delaying this a month so that they can drop it. Mr. President, I promise you this whole thing just goes away.” Trump, who might otherwise have mocked Boris for his constant good cheer, now widely reported Boris’s assurance as grail.
That same day, April 4 at 5:30 p.m., the Manhattan district attorney announced the first-ever criminal indictment of a president of the United States. It was yet unclear what the charges were, whether they were related to Trump’s business issues, that long-simmering investigation, or to other matters, of which there could be many.
Boris, having left town, was unavailable. The political team had, in fact, on its own, sketched out a contingency response, but now there were no lawyers available to approve a statement. Trump was looking for whom to blame.
“Why do I have such shitty lawyers? How is this happening? How did the lawyers get this so wrong?” (Boris had gotten this wrong, but Boris was not among the lawyers Trump was blaming.)
But it was amazing how quickly Trump’s mood could shift. By that evening, the calls were coming in at a rate he couldn’t respond to. More than 50 percent, maybe 60 percent, of the House GOP conference, plus senators, governors, state AGs—many of whom had turned against him after January 6—all were supporting him, everybody tweeting, rushing out statements of support.
The worst thing that might befall a candidate for office, a criminal indictment, had now happened. In any understanding of the nature of US politics, this was a disqualifying event. But immediately, the campaign put out an online fundraising appeal, which began to reflect a wholly different reality. In the first 24 hours after the indictment, they’d raised $4 million, 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.
“Our legal strategy is our media strategy; our media strategy is our legal strategy.”
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 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. 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.
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.
. . . 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!
Her fixation was an open secret—and discomfiting for all. But it existed side by side with her better-than-anyone proximity to Trump. Her golf cart had become the literal mechanism for shadowing him. 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.
The summer move to Bedminster became an 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 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.
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.”
Almost every week a new rumor, usually sparked by a media inquiry, and promoted by other lawyers, swept through the team about Boris himself being indicted. In close confines, Boris was often on the phone heatedly talking in Russian. It was a shared joke (even Trump shared it): “Hey, Boris, are you setting up your exfil order for the Russian sub to get you back to the homeland?”
Among the Trump hands, quite a list of current and former aides, who had been called for Jack Smith interviews and who had analyzed among one another the nature of the inquiry by the questions they had been asked, all noted one thing: There were lots of questions about the lawyers involved in the election denial and the lead-up to January 6 (Giuliani, Jenna Ellis, Kenneth Chesebro, and John Eastman), but no questions about Boris, arguably the one guy in the middle of all the lawyers, the key connector. Why weren’t the Smith prosecutors asking about Boris? Trump aides and lawyers were asking. Could it be he’d already told them everything?
On August 1, 2023, a grand jury in DC indicted Trump in the January 6 case. Along with Trump, special counsel Jack Smith’s indictment cited six unindicted (as of yet), unnamed co-conspirators. This appeared to transparently include Rudy Giuliani, John Eastman, Sidney Powell, Jeffrey Clark, and Kenneth Chesebro. The identity of “co-conspirator number six,” “a political consultant who had helped implement a plan to submit fraudulent slates of presidential electors to obstruct the certification proceeding,” remained unclear and might have pointed to any of the political hands who were around Trump in the two months after the election.
But the inside money was certain that number six had to be Boris.
The next day, Boris was on the plane with Trump—proximity was Boris’s go-to move whenever he was in hot water. And somehow that news was immediately out there—Boris accompanying the president. The president would not be traveling with number six, would he? But he was traveling with Boris. Therefore, don’t be stupid. Boris could not possibly be number six (according to Boris).
That evening, Boris reached out to a friend for some PR help. “So, just, hypothetically, if it were to be me. It’s not, but hypothetically, if it were to be me, how would it be handled from the press side?”
It suddenly surfaced that the linchpin of Trump’s legal defense had himself been arrested not long before. And there was video.
In early August, The Arizona Republic released police body cam footage it had been tipped off about. In 2021, Boris, on a night out alone crawling bars in Scottsdale, Arizona, in an establishment called the Bottled Blonde, and well past drunkenness, had pestered two young women to the point of the police being called—at which point the body cam picked it up. To the police, the girls, captured on video, described in vivid detail Boris’s insistent, unrelenting, and handsy drunken approach, rebuffed and repeated. Meanwhile, on video, Boris is reeling, dazed, sloppy, pitiful, and then handcuffed and forced helplessly to sit in the gutter—the Scottsdale nightlife happily and tawdrily playing on about him.
Insiders judged the leak about Boris’s arrest and drunken humiliation as having such a clear and obvious purpose that it was surely the work of other Trumpworld insiders: Killing Boris was necessary to save Trump (from himself).
In any other campaign, Boris would have been finished. But not so much in Trump’s. Here was a heightened lack of a double standard. If Trump’s own bad behavior did not, in his mind—or apparently in the mind of his voters—reflect badly on him, then the bad behavior of his staff ought not reflect badly on him, either. And if they were personally humiliated—well, that was their problem, not his. “They’re only coming after you because you work for me,” Trump reassured Boris.
By September 2023, the Trump campaign was a reliable fifty points ahead of its nearest primary opponent; it had survived four criminal indictments—indeed, had prospered from them. And yet, almost the entire top echelon of Trump advisers and functionaries found themselves having to consider their standing and future in the campaign.
It was Natalie or, as Trump idly entertained the team (or himself), “Maybe it should be Nathalie. Nathalie. That’s how the English say it. ‘Nathalie, would you please come here?’ Don’t you think there’s a ring to that, Nathalie? Do you like it?” (For a period, he repeated this constantly in his phone calls—his particular piece of cleverness.)
“Do you like it, Mr. President?”
This was more of the yucky theater, open flirtation, at once simpering and mocking, but which, Natalie proudly repeated, had brought everyone to the point of screaming, Enough! But it was also just the can’t-miss-it fact that something here was terribly wrong.
Trump’s son Eric, hearing often from a weirdly authoritative and demanding Natalie giving her opinion on legal developments, took a turn at trying to tackle the situation in a set of annoyed queries to the legal team: Who is she? Who’s letting her do this? Who gave her the authority? Why is she briefing on legal matters? This was meant to put the problem onto staff to solve. But it ignored, of course—because you had to ignore this aspect—the fact that she was a figure wholly of Trump’s own making.
She would bring him good news she uncovered from some far-flung, right-of-right sources, and he would direct her to get it out to everyone, putting her in direct touch with national political reporters and Trump family members as well as with Republican members of Congress. What is this, they were demanding of Wiles and LaCivita and other staffers: Who was this Natalie person, who was she speaking for, and what was this crazy spamming?
Even the Secret Service had now weighed in: Natalie was, as a security consideration, they advised, a potential danger to herself as well as to the president. But no one was going to tell Trump that.
And it was hardly just the personal weirdness. Once, earlier in the summer, on the plane, becoming a cautionary tale whenever Natalie’s name came up, an abrupt takeoff had sent the pages Natalie constantly fed Trump from the printer—carefully assembled with Trump’s signature gold paper clips, faithfully carried by him in a beige Lulu lemon bag—flying off his table, and everyone had to suddenly scurry to collect them, seeing, dumbfounded, the contents. What everyone saw was a random collection of out-of-date articles and printouts from obscure websites and fan artwork downloaded from strange Trump-adoring places on the internet—all of which he was hoarding like these were national secrets.
She had, too, become the keeper of the “Truth” phone. That is, she was wholly in charge of the Trump posts—that is, they were her posts. Sometimes as many as a hundred a day. Old articles, things not remotely relevant or germane, replies to comments from random people, re-postings of out-of-date polls. Here was a public window into the true oddness and chaos of the Trump campaign—and mind. Fortunately, no one in the press, or anywhere else, was looking too closely at Truth.
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 first Trump presidency.
Natalie was both rogue and yet official—with constant confusion over whether it was her voice or his; more and more, it was one voice. Earlier in the summer, it was Natalie who, taking offense on behalf of Trump that House Speaker Kevin McCarthy, in a fumbled interview, had suggested that Trump might not be the best general election candidate, funneled article after article on McCarthy’s slip to reporters in the right-wing echo chamber, who began the drumbeat that would end in the defenestration of McCarthy, otherwise a Trump ally.
She was, too, the reliable nutter conduit: Anyone who wanted to get to Trump could just text her. In late summer, at one of the Bedminster golf tournaments, Laura Loomer, dismissed as a hopeless liar and fabulist by even Marjorie Taylor Greene and a subject of constant effort by the Trump political team to keep her as far away as possible, was brought in by Natalie at the tournament to, in even Fox News’ characterization, “pal around with Trump.”
“Natalie’s so quick, she’s great, you guys just don’t like her because she’s so fast and so good” was a Trump rebut to questions raised about her. It was not that he was necessarily deluded about Natalie. Keeping people around him who were largely inexplicable to others, unsuitable and unseemly—wackos, even—was a way of reminding the people who believed themselves to be officially and appropriately in charge that he was, as demonstrated by how daft his preferences and impulses could be, the absolute boss, unregulated by anybody else’s expectations or measures.
If you forgot that, Natalie was there to remind you.
Yes, it was a troubling state of affairs, his remoteness from reality. This was as damning in its own way as Biden’s fragility. And yet . . . in the face of the thousand cuts that would have felled anyone else, he had maintained his extraordinary personal world of certainty and inner-sanctum ease—and was, he mostly felt, cruising to ultimate victory. He had come to regard the campaign itself as a technical operation. They got on with it as he lived in a world where everything went his way, where even bad news was quickly reinterpreted (“here’s why another indictment is in your favor”), which, with a little critical interpretation, may be the secret to actually getting things to go your way. “Yes-men” have a bad reputation when, really, these ultimate self-enhancers might be the necessary stuff of dreams.
In the days after the election, Trump named Matt Gaetz, Pete Hegseth, and Robert Kennedy Jr. as among his important cabinet picks.
In a phone call with a friend, he singled out, with amusement, that each of his headline nominees had gotten in trouble, lots of trouble, over women—“girl trouble”—and he was eager, with quite some cheerfulness, to see how his reprobate nominees handled this.
In among the most difficult to imagine developments, in some sense dwarfing most of the other difficult to imagine developments, Boris Epshteyn—along with Rudy Giuliani and Donald Trump, among the most culpable figures in the 2020 election overthrow attempt, and, indeed, under indictment in Arizona for it, and, to boot, widely suspected of being ready to sell out the new president elect, if that became necessary—was given effective carte blanche over the legal function and reach of the executive branch.
The bet Boris had made on wholly backing Trump’s preposterous all-or-nothing legal strategy—he would not bend, he would not give an inch, and by making all prosecutors and judges his enemy, would win on election day, solving all his legal problems—had paid off. Boris was on the verge of becoming the most trusted legal advisor to the President of the United States—and already his people were taking the top legal slots. This included ludicrous Matt Gaetz, delighting Trump (no less delightful to Trump for his quick exit); as the prospective acting attorney general, Emil Bove, from the Trump trial; the assistant attorney general, Todd Blanche, Boris’s own former attorney and the lead counsel in the New York trial; and John Sauer, Trump’s appeals attorney, the new solicitor general. These were all Boris’s picks.
Wars are fought over lesser power grabs.
Adapted from ALL OR NOTHING by Michael Wolff to be published February 25, 2025 by Crown, an imprint of The Crown Publishing Group, a division of Penguin Random House LLC. Copyright © 2025 by Michael Wolff.
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