A week before Donald Trump prevailed in the 2016 election, an email landed in Jeffrey Epstein’s inbox encouraging him to change the fate of the world.
“There’s an opportunity to come forward this week and talk about Trump in such a way that could garner you great sympathy and help finish him,” the sender, journalist Michael Wolff, wrote to Epstein. “Interested?”
It’s unclear what Wolff specifically expected Epstein to say to damage Trump’s candidacy, though Trump’s adversaries have long highlighted the relationship between the president and Epstein amid revelations about Epstein’s purportedly prolific sex trafficking of minors. Trump has long denied any wrongdoing or knowledge of Epstein’s misdeeds.
The emails also show Wolff, despite his work as a journalist, taking on a role as an unofficial Epstein image consultant of sorts, offering him messaging and PR strategies as Epstein’s legal and criminal exposure began to mount.
It’s unclear if the late convicted sex offender ever replied to Wolff’s Oct. 29, 2016 email, but he stayed silent in the final days of Trump’s campaign and watched as his longtime acquaintance — with whom he’d had a falling-out a decade earlier — prevailed over Democrat Hillary Clinton. The exchange with Wolff — one of several in which Wolff pushed Epstein to help tear down Trump — was among hundreds released Wednesday by the Republican-led House Oversight Committee.
“I think you should let him hang himself,” Wolff wrote of Trump to Epstein in a Dec. 16, 2015, email.
A lawyer for Wolff didn’t immediately respond to a request for comment. Wolff made no public statements Wednesday.
The White House downplayed the newly released emails, saying they “prove nothing” and are a Democratic-driven distraction from the recent shutdown. Trump leaned on Republicans — who released the tranche of emails Wednesday — to stop talking about the files, which he described as a “hoax.”
But House Democrats are predictingthat dozens of their Republican counterparts will join an effort to force a vote for the release of even more Epstein documents against the wishes of GOP congressional leadership and the White House.
Wolff gained notoriety during Trump’s first term for explosive books about the president that the White House at the time claimed were inaccurate and unethical — even though he had gained access to figures close to Trump, including the president himself, during the course of his reporting. White House officials pointed to those assessments again Wednesday when asked about Wolff’s email exchanges with Epstein.
In October, Wolff sued first lady Melania Trump, claiming she threatened to sue him for $1 billion over Epstein-related comments Wolff made about her. A spokesperson for Melania Trump said at the time that she “is proud to continue standing up to those who spread malicious and defamatory falsehoods.”
The broader tranche of emails reveal Epstein’s vast web of connections to power centers around the world: He bantered with former Treasury Secretary Larry Summers and invited billionaire Peter Thiel to visit him in the Caribbean. He connected far-flung associates such as Wolff with Trump ally Tom Barrack and attorney Ken Starr. And he gabbed about current events with Soon-Yi Previn, Woody Allen’s wife.
Summers and Barrack didn’t immediately respond to requests for comment. A person close to Thiel who was granted anonymity to discuss private conversations said Thiel didn’t visit Epstein’s island in the Caribbean. Previn couldn’t be reached for comment.
A review of hundreds of emails Epstein exchanged — with lawyers, foreign dignitaries, prominent business executives and political power players — underscores his dim view of Trump, whom he repeatedly disparaged as shallow, unintelligent, needy and, in one exchange, “borderline insane.”
“You might want to tell your dem friends that treating trump like a mafia don ignore[s] the fact that he has great dangerous power,” Epstein wrote in a Dec. 20, 2018, email to Reid Weingarten, a prominent white-collar attorney who represented Epstein during his federal prosecution. “Tightening the noose too slowly risks a very bad situation. Gambino was never the commander in chief … not so with this maniac.” Weingarten declined to comment.
However, Epstein often stopped short of endorsing the most heated invective of Trump that his associates lobbed in their correspondence.
Many of Epstein’s cozy friendships with influential figures have been exposed in recent years, sometimes with disastrous consequences for them. But the tranche of emails released Wednesday shed new light on the late financier’s relationship with Wolff. In them, Wolff appears to operate as a sort of image consultant, advising Epstein on how to respond to damaging storylines, how to weave Trump into his PR pushback and how to use his relationship with Trump to his benefit amid his legal travails.
The two exchanged scores of messages, gossiping about politics and at one point even bonding over the realization that the son of the doctor performing Epstein’s upcoming colonoscopy attended an elite Manhattan private school with Wolff’s son.
In early December 2018, days after the Miami Herald published a series of stories exposing Epstein’s sex-trafficking ring, his exploitation of vulnerable women and girls and the sweetheart plea deal he secured to serve little jail time, Wolff strategized with Epstein about how to “game everything out.”
“I don’t think it’s a question now of directly debunking this,” Wolff wrote. “That’s going against virtue itself. What I’d like to do is game out everything, creating a structure for thinking this through. Definitely not a piecemeal response. Figure out where we want to be and where we can reasonably get and work backwards.”
“im thinking what would trump do,” Epstein replied. “Claims are ludicrous and self-serving, media is working with the other side’s lawyers, this is all about Donald Trump,” Wolff wrote.
Epstein agreed: “…all about Donald Trump, the real villain.”
If Wolff helped Epstein execute on those plans, however, their strategy failed. The newspaper series led to the federal prosecution of Epstein for sex-trafficking crimes, and in 2019 while awaiting trial on the charges, he killed himself in a Manhattan jail.
The documents released Wednesday show that Epstein, while not directly communicating with Trump or his inner circle, obsessively tracked Trump as a candidate and then as president. Friends and confidants emailed him news clips about Trump’s political scandals and economic moves, and Google alerts swept up what they missed. Epstein even closely tracked the location of Air Force One, primarily to ensure the associated airspace restrictions didn’t affect his own travel plans to and from Florida.
Epstein’s friends appeared well-versed with his Trump ties. Jonathan Farkas, a fixture of the New York society pages, told him the day before the 2016 election, “I think you are going to have a winderful [sic] life from now on.” Farkas’s wife, Somers, declined to provide an immediate comment.
In an email dated shortly after Thanksgiving of 2016, Epstein told Dangene and Jennie Enterprise, founders of the private, members-only CORE club, “im in palm with the trump crowd.”
“Cool!,” they replied, “Lets go to the inauguration together!!!” A club representative didn’t immediately respond to a request for comment.
Around the same time, Epstein asked an acquaintance to delay an acquaintance’s planned visit, writing: “trump related issues occupying my time.”
Once Trump took office, Epstein appeared bullish about the possibilities. In January 2017, he emailed an acquaintance: “all good with trump lots of opportunity.”
Gregory Svirnovskiy, Cheyanne Daniels and Aaron Pellish contributed to this report.
