Having sex with an assistant?
Trump is said to have bragged about having extramarital affairs in the White House
November 15, 2025 – 21:57Reading time: 3 minutes
Recently published emails from convicted sex offender Jeffrey Epstein have the US President in hot water. Is Trump having an affair with his assistant?
Recently published emails from convicted sex offender Jeffrey Epstein contain interesting claims from renowned US journalist Michael Wolff, who has written several best-selling books about President Donald Trump. In his March 2019 message to Epstein, Wolff wrote that Trump had bragged to friends about his affair with his then-28-year-old assistant, Madeleine Westerhout.
In his email to Epstein, Wolff reported that Westerhout told friends how he found Trump wearing underwear in his private suite at the White House when he went to bring him papers to review. When asked why Trump chose to spend a weekend at the White House in January 2019 rather than, as usual, at his Mar-a-Lago estate in Florida, he explained to friends: Because he “hit” Madeleine, Wolff quoted the then-president as saying.
Wolff himself apparently was unable to adequately prove Trump’s statement. In the email he asked Epstein to assess whether the information was credible. However, there was no response from Epstein in the collection of more than 20,000 emails. Westerhout himself rejected the claims in the British Mirror as “absurd and out of touch with reality.” But the possibility of an affair may not be completely unreasonable – at least not from Trump’s perspective.
Before working as an aide 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, he publicly led Trump’s cabinet candidates into office – and in doing so achieved a certain level of notoriety. In late 2016, Westerhout also helped Trump at his Mar-a-Lago estate. Even now, Trump is said to have glanced at Westerhout, who was born in 1990, several times and said: “He has a way of doing it,” Michael Wolff wrote to Jeffrey Epstein. Wolff himself never published the episode.
Wolff is considered an expert close to the establishment 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. Earlier 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 it,” Wolff said.
