Jeffrey Epstein hinted that Trump spent 2018 holiday with mistress: 'That's for Madeline'
U.S. President Donald Trump speaks with members of the media on board Air Force One en route to Palm Beach, Florida, U.S., January 31, 2026. REUTERS/Nathan Howard

Jeffrey Epstein, who once boasted to be President Donald Trump’s “closest friend for 10 years,” hinted in 2019 that the president had ditched his own family over the 2018 holiday to spend time with Madeline Westerhout, then his personal secretary, newly published text messages have revealed.

Trump, 79, was first accused of having an affair with Westerhout, 35, last year, though Westerhout has fiercely denied the accusations as being “absurd.” After the Justice Department published around 3.5 million Epstein files on Friday, however, a text exchange between Epstein and Steve Bannon – Trump’s former White House chief strategist – appears to suggest that Epstein was aware of the rumor well before it was first publicly reported.

“The two things [Trump] dreads at the moment is that an email from his ex. Saying he has small d---. And his transcript,” Epstein wrote to Bannon in a text message on Jan. 1, 2019.

“The staying away from family over holidays huge tell,” Bannon responded.

“Thats for Madeline,” Epstein wrote back, along with a smiley-face emoji.

“Whoah!!!” Bannon responded, apparently unaware of the rumors around Trump’s alleged affair with Westerhout.

Epstein told Bannon to “wake up dude,” to which Bannon – apparently quoting Trump – wrote back: “‘She has a way about her’ ….!!!!”

Allegations that Trump had an affair with Westerhout stemmed from a 2019 email from author and Trump biographer Michael Wolff, sent to Epstein, where he suggested that Trump was “b------” Westerhout over the 2018 holiday during the government shutdown, opting to remain at the White House instead of spending time with his family at his Mar-a-Lago resort in Palm Beach, Florida.

Trump has not publicly addressed rumors of his affair, and outside of Wolff’s email and Bannon and Epstein’s text exchange, no other evidence exists to confirm the rumor.