Trump biographer claims he has ‘cringeworthy’ relationship with young staffer

President Donald Trump speaks in the Oval Office at the White House, February 2, 2026. REUTERS/Evelyn Hockstein

President Donald Trump appears to have a new "trusted confidante" in the form of a younger staffer, his one-time biographer claimed, with their dynamic being described as "cringeworthy."

Michael Wolff is a longtime journalist and author, best known for his extensive coverage of Trump's life and political career, including several books about his first term sourced from White House insiders. In the latest edition of his Daily Beast podcast, "Inside Trump's Head," Wolff touched on Trump seeming to be "totally alone" and "without any kind of… basic warmth" during his second term, and further noted that the president is being "tended to" by a new staffer, after losing the staffer who did the same job during his first term.

“I mean, in the first administration, he had Hope Hicks, who really tended to him. And now he has this woman, Natalie Harp,” Wolff said. “But he functions essentially… like an old-time monarch, you know. Who has… married someone for political reasons… as was done. And there was really no pretense of a… domestic life, and then he’s tended to by factotums.”

Hicks worked as an aide for Trump during his first term and beyond, dating back to his time working for the Trump Organization. She fell out of his favor, however, when she testified for the prosecution in his criminal hush money trial, providing details about his affairs with adult performer Stormy Daniels and Playboy model Karen McDougal. Now, Harp, a former right-wing news anchor, has seemingly taken up the same role in his second administration, reportedly helping him with his overnight posting screeds on Truth Social.

Wolff further claimed that Harp appears to be "hopelessly in love with" the president, citing a selection of "cringeworthy" letters she has allegedly written to him, while ultimately noting that their exact relationship remains a mystery. One of the letters, reported on by the New York Times, included Harp writing to Trump, "You are all that matters to me."

“Natalie Harp, you know, has become—as Hope Hicks was—this kind of curious person in his life. We don’t really understand that relationship,” Wolff explained. “She appears to be hopelessly in love with him, and we’ve seen a series of… cringeworthy letters that she has written him.”

He added: “But, you know… I think that… he’s generally regarded among his staff as… post-sexual,” Wolff said. “There is, at least, nobody who is… rushing to say, nor whispering, that he has a relationship—a sexual relationship—with anyone.”

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