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Madeleine Westerhout, known for her role as a Trump aide who was dismissed after discussing the Trump family publicly, has once again found herself in the spotlight. Speculation has resurfaced regarding an alleged affair with former President Donald Trump, a claim that emerged in 2019 following the release of Michael Wolff’s book, “Siege: Trump Under Fire.” Wolff’s book suggested Trump was involved with a staff member, but the identity of this individual remained a mystery for years.
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The intrigue deepened in late 2025 when a release of the Epstein files included an email between Wolff and financier Jeffrey Epstein that identified Westerhout as the alleged aide. Additional documents released months later contained text messages between Steve Bannon, the former White House Chief Strategist, and Epstein, discussing the rumored affair. Bannon reportedly mentioned that Trump’s absence during the 2018 holidays was “For Madeline [sic],” according to Newsweek.
Both Westerhout and the White House have consistently dismissed these allegations as false. In November 2025, Westerhout addressed the rumors in a statement to The Mirror, labeling Wolff’s claims as “absurd and defamatory” and criticizing him for spreading falsehoods. Following the public release of the text exchanges in February 2026, the White House’s deputy press secretary reiterated to Newsweek that the affair rumors were “salacious and false.” At present, Westerhout has not made any further comments.
Regardless of the affair rumors, Westerhout undeniably had a close rapport with Trump and his family, though tensions arose after she spoke candidly about his children during a journalist dinner. Despite the event being off-the-record, it was later reported that she claimed to have a closer relationship with Trump than his daughters and commented on Tiffany Trump’s weight. Surprisingly, Trump showed understanding towards Westerhout despite the controversy.
After her dismissal, Trump remarked to the media that he had personally spoken with Westerhout, acknowledging her distress and affirming she had performed admirably in her role, calling her “a very good person.” Trump even promoted her 2020 memoir, “Off the Record,” on X, the platform previously known as Twitter, praising her as “a very smart and already wise young woman.” Westerhout later testified in Trump’s hush money trial, offering positive testimony about her former employer.
Madeleine Westerhout was once super close with the Trumps
Even if Madeleine Westerhout and Donald Trump didn’t have an affair, there’s no question that the two had a close relationship. In fact, it seems like the former White House aide was pretty friendly with at the president’s entire family (though she notably had a big fallout with one of the Trump kids). The reason Westerhout is Donald Trump’s ex-assistant is because she spoke openly about his children during a dinner with journalists. Though it’s long been maintained that the event was off-the-record, it later came out that Westerhout had bragged about being closer with Donald than his two daughters were, alongside divulging that the president had complained that Tiffany Trump was overweight. Despite that, Donald’s stance on Westerhout in the wake of all the drama was surprisingly understanding.Â
Though she was ultimately fired, the divisive politician told members of the media that he’d spoken with her personally and, “She was very down,” (via People). Donald also confirmed that in spite of everything, he believed she’d done a great job, enthusing that Westerhout was, “A very good person.” The president subsequently promoted her 2020 book, “Off the Record,” on X, formerly known as Twitter, even going so far as praising the author as, “A very smart and already wise young woman.” Just a few years later, Westerhout also testified in Donald’s hush money trial, giving her former boss a similarly rave review.
“I just found him very enjoyable to work for,” the former White House staffer said on the stand, describing Donald as “a really good boss,” (via The Independent). Unfortunately, Westerhout’s relationship with Tiffany never really recovered. Affair or not, though, it’s pretty clear that she’s remained in very good standing with the president.