BREAKING: Trump Biographer Says Natalie Harp’s Letters Read Like “Someone in a Personal Relationship,” Not a Staffer
Michael Wolff spent years reporting on Trump’s inner circle. He says Natalie Harp’s letters were unlike anything else he’s seen come out of that world.
On his podcast Inside Trump’s Head, Wolff shared the full contents of two letters Harp wrote to Trump following a 2023 golf trip to Scotland, letters campaign staffers had already been quietly circulating among themselves out of concern. “I want things to always be right between us,” Harp wrote. “I haven’t been myself, dwelling on the past, and the pain of losing my dad.” In another passage, she asked Trump directly, “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.”
Wolff’s co-host Joanna Coles described footage from the same period showing Harp on Trump’s campaign plane, “tapping her feet,” looking, in Coles’s words, “as if she’s well and truly at home.” Wolff said the video itself was telling. “They were taken by people within the campaign who believed that her presence there was really strange,” he said. “That’s why they’re taking videos of, theoretically, one of their colleagues.”
Then came the line that cuts to the actual concern. “She’s not acting like a subordinate. She is acting like a lover, like someone in a personal relationship,” Wolff said. “That’s what is confusing here and what’s problematic, and certainly problematic from the point of view of his professional staff, which is why I am in possession of these letters. They recognized, ‘Oh my God, this is a real problem.'”
That’s not tabloid speculation. That’s Trump’s own campaign staff, years ago, deciding the dynamic was concerning enough to document and hand over. The letters didn’t leak by accident. People close to Trump kept them because they were worried.

