The Rampant Donald Trump & Madeleine Westerhout Affair Rumors, Explained

You may remember Madeleine Westerhout as the Trump aide who was fired for speaking publicly about the president's family, but there's been a renewed interest in the nature of her relationship with the former "Apprentice" host — including a wild rumor that the two were embroiled in an affair. Speculation that Donald Trump enjoyed a tryst with one of his White House staffers first began doing the rounds in 2019. This came shortly after Michael Wolff's "Siege: Trump Under Fire" included a claim that he was "banging" an underling. For years, the identity of that employee remained shielded. 

But, in late 2025, a batch release of the Epstein files included an email between Wolff and the disgraced financier related to an excerpt of what the author was working on for his book, which specifically named Westerhout as the aide in question. A few months later, another batch was released, which included a text conversation between Trump's then-White House Chief Strategist Steve Bannon and Epstein. They seemingly discussed the affair and the businessman even claimed that Trump's decision not to spend the 2018 holiday period with his family was, "For Madeline [Sic]," (via Newsweek). 

It's worth noting that both Westerhout and the White House denied there was any truth to the claims. In November 2025, the former Trump staffer gave a statement to The Mirror in which she decried Wolff's email as: "Absurd and defamatory accusations from a discredited writer who has been known to peddle falsehoods." In February 2026, after the text exchange was made public, the White House's deputy press secretary told Newsweek, "This is a salacious and false rumor that has proven to be fiction." At the time of writing, Westerhout has not commented again.

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. 

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.