Sex with the assistant?
Trump is said to have bragged about an affair in the White House
November 15, 2025 – 9:57 p.mReading time: 3 minutes
Recently published emails from sex offender Jeffrey Epstein are putting the US President in distress. Did Trump have an affair with his assistant?
The recently published emails from the estate of sex offender Jeffrey Epstein contain a piquant claim from star US journalist Michael Wolff, who has written several bestsellers about President Donald Trump. In a March 2019 message to Epstein, Wolff wrote that Trump had bragged to friends about having an affair with his then 28-year-old assistant Madeleine Westerhout.
In the email to Epstein, Wolff reports that Westerhout told friends how she found Trump in his underwear in his private rooms in the White House when she went to bring him papers to review. When it came to the question of why Trump preferred to spend a weekend in the White House in January 2019 instead of, as usual, at his Mar-a-Lago estate in Florida, he explained to friends: Because he was “banging” Madeleine, Wolff quoted the then president as saying.
Wolff himself was apparently unable to adequately substantiate Trump’s alleged statement. In the email he asks Epstein to assess whether the information is credible. However, there is no response from Epstein in the collection of more than 20,000 emails. Westerhout himself dismissed the claims in the British Mirror as “absurd and divorced from reality.” But the possibility of an affair is probably not entirely unreasonable – at least not from Trump’s point of view.
Before working as an assistant in the White House, Westerhout served Trump as a receptionist and elevator operator at Trump Tower in New York. After his election victory in 2015, she publicly led candidates for Trump’s cabinet to his office – and thus achieved a certain level of notoriety herself. At the end of 2016, Westerhout also assisted Trump at his Mar-a-Lago estate. Even at this time, Trump is said to have looked at Westerhout, who was born in 1990, several times and said: “She has a way about her,” wrote Michael Wolff to Jeffrey Epstein. Wolff himself never published the episode.
Wolff is considered an intimate expert on the powerful in Washington. His 2018 book “Fire and Fury: Inside Donald Trump’s White House” highlighted the chaotic conditions in the US government during Trump’s first term in office. At the beginning of this year, Wolff spoke in an interview with t-online about his latest work “All or Nothing: Donald Trump’s Return to Power.” In it, Wolff also commented on Trump’s marriage to Melania, which was a “useful arrangement” for both partners. “And in Trump’s environment, everyone knows about it,” said Wolff.
