Epstein died in prison in 2019. On Wednesday, a huge cache of his emails was released by the House Oversight Committee. Alongside Speaker Mike Johnson finally saying he would hold a vote on releasing Epstein materials held by the U.S. government, the release produced sensational details and headlines.
A day later, in what was billed as Wolff’s only interview about his presence in the Epstein emails — though he is himself a co-host of a Daily Beast podcast, Inside Trump's Head — the writer was quizzed by Court of History co-hosts Sidney Blumenthal, a former adviser to Bill and Hillary Clinton, and Sean Wilentz, a Princeton history professor.
Wolff has often discussed his relationship with Epstein, including extensive interviews about Trump that Wolff conducted as he wrote books on the property magnate turned two-term Republican president.
Blumenthal cited an email “from December 2015 and Trump has announced he's running for president in 2016 and you explained to Jeffrey Epstein that CNN is likely to ask Trump about his relationship with him”, which was long close, until the two men fell out.
“And Epstein asks you what you thought Trump would answer, and you reply, and I'm going to quote you, ‘I think you should let him hang himself. If he says he hasn't been on the plane or to the house, you can hang him in a way that potentially generates a positive benefit for you, or if it looks like he could win you could save him, generating a debt.”
Asked why he wrote that email, Wolff said that in late 2015, he, “among many people, was increasingly alarmed about” Trump’s candidacy “and understood that the one person who had the potential to damage this candidacy was Jeffrey Epstein.
“I'm not the only person who understood that … when I was with [Trump ally and adviser] Steve Bannon, when he met Jeffrey Epstein in 2017 the first thing that Bannon said to Epstein was, ‘You were the only person I was afraid of during the campaign.’”
Wolff added that in advising Epstein, he had been “trying to encourage Epstein to use what information he had to get Trump, and in this instance, that would have been an interesting way to approach this: let Trump publicly tell a lie, then expose the lie.
“Now, Epstein … he would go back and forth, and I think he would suddenly entertain this possibility that he could do this. But at the same time, Epstein was, without a doubt, very much afraid of Donald Trump. So in the end … I think that he was starting to get to this point that he might publicly talk about this relationship. But then he was arrested and died.”
First convicted and sentenced in 2008 — on Florida state charges of solicitation of prostitution and of solicitation of prostitution with a minor under the age of 18 — Epstein was freed in 2009 but arrested again in July 2019, when Trump was two years into his first White House term.
Charged with sex trafficking of minors and conspiracy to commit sex trafficking of minors, Epstein was found dead in his prison cell in New York in August.
Five years later, in 2024, Trump campaigned for president on a promise to release Epstein materials held by the federal government, and thereby expose his links to powerful men. Once in office, Trump reneged, to the fury of many of his own supporters.
Deferential and favorable Department of Justice treatment of Ghislaine Maxwell, Epstein’s former partner who was jailed on sex trafficking charges in 2022, has also fueled suspicions about Trump’s Epstein links and the content of the so-called Epstein files.
The emails released this week also contained a bombshell reference to Trump having spent “hours” at Epstein’s house with an Epstein victim whose name was redacted but who the White House said was Virginia Giuffre.
Giuffre killed herself earlier this year. Last month, the publication of a posthumous memoir re-surfaced scandalous claims about Prince Andrew and other men. Giuffre did not accuse Trump of wrongdoing. Though widely accused of sexual misconduct, and found liable for sexual abuse in a New York civil case in 2023, Trump vehemently denies all allegations of improper conduct, linked to Epstein or not.
In the released emails, Epstein hinted that Trump knew a lot about his exploitation of young girls but stayed quiet, making Trump the “dog that hasn't barked.”
Another email, written by Epstein to himself on Feb. 1, 2019, said, “Trump knew of it, and came to my house many times during that period. He never got a massage.”
In another email, Epstein wrote, “of course he [Trump] knew about the girls as he asked Ghislaine to stop.”
Wolff told the Court of History that was a reference to a court case.
“At that point, Ghislaine is pursuing a lawsuit, stupidly … with Virginia Giuffre. And … that had not worked out well for Ghislaine, because … as I recall, Virginia Giuffre counter-sued, and there's lots of depositions and Ghislaine will have to testify, and that will mean that she will have to testify about all of this, including quite possibly about Trump. So that's what that's about.”
Wolff himself recently sued Melania Trump, the first lady, after she tried to silence him in relation to her own Epstein links. He told Blumenthal and Wilentz that crowdsourcing to pay for the suit was going well.
“As for [Trump] knowing about the girls,” Wolff said, “that's a direct reference to what Trump knew about what was going on at Jeffrey Epstein's house. And it goes back to a couple of things.
“I've talked here before about the photographs that I've seen of Trump around Epstein's pool with a set of the girls who were often at Epstein's house.”
Wolff has repeatedly said Epstein showed him photos of Trump with young girls and a stain on the crotch of his trousers, photos Wolff believes likely to have been taken by the FBI when Epstein was finally arrested.
He continued: “But then it was also Epstein's view that it was Trump who first alerted the police to what was going on … at Epstein's house. So this was always a thing, and this was a thing that I prodded Epstein on because I thought it was a smoking gun.
“Did [Trump] know what was going on at Epstein's house? If so, why did he keep quiet about it? And if he knew, what was the nature of how he knew, etc, etc.
“And you know, throughout my discussions with Epstein about Trump, it was always, ‘You have the goods here. You have the power to cause Trump an enormous amount of trouble, and possibly to bring him down.
“Actually, jumping six years later, that may, in fact, be what is happening now.”
