For many, details of Donald Trump’s peculiarly close relationship with his 35-year-old aide, Natalie Harp, have been hard to stomach. But for others, the love letters she’s penned to him, the images of her sprinting after him in a golf cart, and the access she has to his personal cellphone aren’t so surprising.
That’s according to Sarah Matthews, Trump’s deputy press secretary during his first term, who argued in an essay penned for The Bulwark on Thursday that the key to winning Trump’s favor is unwavering, shameless devotion.
“Long before Harp sprinted down the fairways of a Scottish golf course in an effort to catch up with Trump’s motorcade, I heard plenty of stories about the absurd lengths people went to for ‘the boss,’” Matthews, who resigned from the Trump administration on Jan. 6, 2021, wrote.
Matthews detailed instances in which staffers steamed Trump’s pants while he was wearing them, occasions when he instructed his sycophants to steal mirrors from events “if he thought they made him look especially flatteringly slim,” and one encounter where he asked aides to steal sculptures from the U.S. embassy in London.
“While their relationship is deeply bizarre, I think Harp simply understands just how Trump operates,” she wrote. “He wants emotional support blankets; he wants people who never push back; he wants to be put on a pedestal. Harp is just better at the game than anyone else . . . for now.”
Matthews, who testified against Trump to the Jan. 6 committee, noted that currying favor with her former boss also had its downfalls. “During my time in Trump 1.0, knife-fighting among White House staff constantly went on behind the scenes,” she wrote, noting that the leaks about Harp appear to be an echo of the infighting that plagued Trump’s first administration.
“The steady stream of leaks about Harp tells me some of her colleagues clearly have it out for her,” she added. A White House spokesperson did not respond to a request for comment.
Reports have swirled that several members of Trump’s inner circle—including his own family members—have sought to sow distance between the president and his devoted aide, to no avail. Perhaps the most stunning example was when Trump moved his campaign operation from Palm Beach to his golf club in Bedminster, New Jersey, in 2023, and Harp was refused a room.
Ultimately, the scrappy, former conservative news anchor found a solution: She set up a bed for herself in the maids’ quarters before managing to move even closer to Trump by camping out in the women’s locker room, according to author Michael Wolff.
But Matthews’ essay suggests that being one of Trump’s favorites can come with its own risks—particularly for young female staffers. She cited one press wrangler whom Trump requested so often that it became a subject of concern among other aides.
Former White House Press Secretary Stephanie Grisham echoed her account of Trump’s interest in one female staffer in her 2021 memoir, I’ll Take Your Questions Now: What I Saw at the Trump White House. Grisham alleged that when the unnamed staffer accompanied Trump on trips, “he often asked me to bring her to his office cabin in the aircraft, which he’d rarely done with anyone else.”
Once, Grisham recalled being told that the president requested the press wrangler so he could “look at her a–.”
“After that, I tried to keep her off trips,” Grisham wrote.
Harp’s rise into the spotlight has been fueled in part by the adoring letters she wrote to Trump that were leaked to the press. On Aug. 21, the Daily Beast published the letters, in which she says she is “unworthy” of Trump and that he is “all that matters” to her, in full.
