Previously unreleased emails reveal sustained, strategic, and often personal communications between journalist Michael Wolff and Jeffrey Epstein, with exchanges focused on political messaging, media influence, and repeated discussions about Donald Trump—including efforts to shape public narratives about his candidacy and presidency.
Among the newly released records from the Department of Justice—part of a 3.5 million-page document production under the Epstein Files Transparency Act signed by President Trump—are emails between author Wolff and Epstein that reveal a striking level of political discussion, media planning, and apparent coordination related to Trump’s rise in 2015 and beyond.
The released records include a February 2016 message from Wolff warning Epstein, “NYT called me about you and Trump. Also, Hillary campaign digging deeply. Again, you should consider preempting.” Epstein responded simply, “Lots of reporters.” To which Wolff replied, “Yeah, you’re the Trump bullet.”
In another exchange from October 2016, Wolff said, “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. Interested?”
Wolff workshopped talking points and responses with Epstein, in December 2015 musing: “If we were able to craft an answer for him, what do you think it should be?” The question came in response to a heads-up from Wolff the night before: “I hear CNN planning to ask Trump tonight about his relationship wit= you–either on air or in scrum afterwards.” The next afternoon, Wolff followed up with strategic advice:
I think you should let him hang himself. If he says he hasn’t been on the plane or to the house, then that gives you a valuable PR and political currency. You can hang him in a way that potentially generates a positive benefit for you, or, if it really looks like he could win, you could save him, generating a debt. Of course, it is possible that, when asked, he’ll say Jeffrey is a great guy and has gotten a raw deal and is a victim of political correctness, which is to be outlawed in a Trump regime.
In May 2016, Wolff reached out again ahead of a planned interview, asking, “Anything you think I should ask?” Epstein replied with a list of what he considered damaging topics for Trump, including “revenue of golf courses as income,” “total debt of all cost,” and “how much did his father leave.”
In a March 2016 email titled “Patterson,” Wolff advised Epstein that he needed an “immediate counter narrative” to the upcoming James Patterson book, proposing that Donald Trump offered “an ideal opportunity.” He wrote that “Becoming an anti-Trump voice gives you a certain political cover which you decidedly don’t have now,” and urged Epstein to go public. Wolff outlined a media strategy that could include a television interview, an op-ed, and social media efforts and suggested assembling a group of media allies to support the effort.
An April 2016 email shows Wolff responding to a forwarded message about a Reuters inquiry into a lawsuit alleging that both Epstein and Donald Trump raped a woman in 1994. After Epstein shared the press alert with Epstein, Wolff replied, “Well, I guess if there’s anybody who can wave thus away, it’s Donald,” and added, “Let me know if there’s anything I can do.”
In January 2018, Wolff wrote, “Trump is going to go down—why doesn’t he use this opportunity to strike out on his own?” He suggested subtly implying that he had tapes and speculated, “I wonder, btw, if he isn’t interested in talking to you about in fact bringing down Trump. Can’t wait to hear?”
One message sent by Epstein to Wolff on January 15, 2019 breaks down alleged financial strategies involving Trump’s brand. It claims that Trump rents out his name to building projects without direct ownership and receives royalties or profit shares. The message describes how wealthy buyers use “trophy properties” for positive media exposure and cites examples involving Hyatt Hotels, the GANZ art collection, and offshore financial structures in Cyprus and the British Virgin Islands. It concludes by alleging that Trump’s public financial disclosures are misleading because they reflect gross revenues or asset valuations, not net value or liabilities—calling them “meaningless.”
Additional emails include offhand characterizations. In a July 2017 thread, Epstein noted, “Donald now down on tillerson,” prompting an exchange about Sam Waksal, whom Wolff said he had met at dinner the night before, adding, “He had some good Trump stories.” In an October 2016 email, Wolff relayed a remark he attributed to Roger Ailes, claiming Ailes said he gave up trying to advise Trump, describing him as “the boy in pre-school who you just knew was going to throw a truck at another kid’s head.”
As late as 2019, Wolff continued to send Epstein story drafts for input. “This is what I’m now going with—what do you think?” he wrote in March of that year, including a highly speculative passage implying salacious behavior by Trump.
In a February 2017 email thread, Wolff told Epstein he was working on a Trump book “for a pile of money” and asked him to arrange introductions to Tom Barrack and Kathy Ruemmler. Epstein replied that “kathy agreed,” indicating her willingness to connect.
Even seemingly mundane messages reinforce the intimacy of their exchanges—coordinating meetings, discussing travel, and navigating weekend plans. In one February 2016 thread, Epstein invites Wolff to meet that same day following a scheduled meeting with Ehud Barak, writing, “ehud barak at 1, would you like to join at 2?” He later adds that he’ll be in Paris but suggests they “can do it then” upon his return on the 5th. In another message, Wolff mentions he has to attend a funeral for an old relative in New Jersey and asks, “What’s your weekend look like?”
A 2018 email from Wolff to Ken Starr, with Epstein copied, reflects further coordination. Wolff wrote of sending Starr his Trump book and seeking input for a sequel focusing “on the legal case against Trump and Trump’s response to it.” Starr replied warmly, crediting Epstein for the connection: “With thanks to Jeffrey, I’m delighted to come into your orbit.”
As Breitbart News has previously reported, Wolff has repeatedly framed his work on Trump as an effort to discredit and ultimately remove him from office. In early 2018 media appearances promoting Fire and Fury, Wolff stated that his book would “end this presidency,” argued that Trump was “intellectually incapable” of serving as president, and asserted that “100%” of the people closest to Trump believed there was “something fundamentally wrong” with him.
Wolff further suggested that the 25th Amendment was actively discussed inside the White House and acknowledged having extensive access to Trump advisers and officials, recording dozens of hours of conversations—many of which participants believed were off the record—and using those accounts to construct a narrative of dysfunction and instability.
He described Trump as both sexist and racist, stating, “Yes,” when asked directly if Trump was sexist and again, “Um yes I do,” when asked if he was racist. Wolff added that Trump treats women “in as transactional a way as he thinks about everything.”
Breitbart News has also covered Trump’s strong dispute of Wolff’s claims, noting that Trump issued cease-and-desist letters ahead of the book’s release and publicly denied granting Wolff access, writing, “I authorized Zero access to White House (actually turned him down many times) for author of phony book!” and calling it “Full of lies, misrepresentations and sources that don’t exist.”
