Recently uncovered emails highlight the ongoing and often personal conversations between journalist Michael Wolff and Jeffrey Epstein, emphasizing their discussions around political messaging, media influence, and particularly their views on Donald Trump. These emails illustrate efforts to shape the narrative surrounding Trump’s candidacy and presidency.
These records are part of a larger release by the Justice Department, which totals 3.5 million pages under the Epstein File Transparency Act, enacted by President Trump. The correspondence reveals a remarkable degree of political strategy, media planning, and collaboration between Wolff and Epstein regarding Trump’s emergence since 2015.
One email from February 2016 features Wolff informing Epstein of inquiries from The New York Times about him and Trump. He warns Epstein that the Hillary campaign is investigating further, suggesting he should be proactive. Epstein replies, remarking, “There are a lot of reporters,” to which Wolff retorts, “Yes, you’re Trump’s bullet.”
In a later exchange from October 2016, Wolff indicated he had a chance to present Trump in a way that could sway public sympathy against him. “Would you be interested?” he asked Epstein.
Earlier, in December 2015, Wolff had previously facilitated a workshop to help strategize responses to Epstein, surmising, “If we could give him an answer, what do you think it should be?” This came after he’d warned Epstein about possible questions from CNN regarding his connections to Trump. Wolff continued to offer strategic advice the next day.
Wolff speculated about how Epstein might handle inquiries, suggesting that if Trump claimed he hadn’t been on a plane or gone home, it would give Epstein valuable political leverage. He noted that Epstein could frame himself as a victim of political correctness under the Trump administration.
By May 2016, Wolff reached out again ahead of an anticipated interview, asking Epstein if there were any particular questions he should pose. Epstein, in turn, provided a list of topics that could potentially harm Trump, like his golf course income and his total debt.
In another email from March 2016, designated “Patterson,” Wolff urged Epstein to respond immediately to a forthcoming book by James Patterson and suggested Trump as the perfect opportunity for this engagement, encouraging Epstein to position himself publicly against Trump.
In correspondence from April 2016, Wolff acknowledged Epstein sharing a press notice about a Reuters investigation into allegations involving Trump and Epstein. Wolff commented, “If anyone could wave and get away with it like that, it’s Donald,” offering his assistance.
Fast-forwarding to January 2018, Wolff expressed to Epstein that Trump would eventually be out of office and questioned why Trump didn’t attempt to counter him directly. He hinted at having information that could be detrimental to Trump and was curious if Trump wanted to engage with Epstein about defeating him.
On January 15, 2019, Epstein detailed in a message some financial strategies linked to the Trump brand, analyzing how Trump manages to associate his name with major projects and profit mechanisms. The communication pointed out that Trump’s financial statements are misleading, reflecting only gross revenues without considering debts.
Other emails captured candid exchanges. In July 2017, Epstein noted Trump’s criticism of Tillerson, leading to Wolff sharing anecdotes about Trump from conversations he’d had with others. In an October 2016 message, he described Trump as a “preschool boy” whose antics were becoming more problematic.
Even routine messages revealed the closeness of their interactions, whether coordinating trips or weekend plans. In February 2016, Epstein invited Wolff, post a meeting with former Israeli Prime Minister Ehud Barak, prompting casual discussions about their schedules.
A 2018 email to Ken Starr from Wolff, also copied to Epstein, showed further collaboration as he sought feedback for a sequel to his Trump book focusing on ongoing lawsuits against Trump.
Wolff has transparently presented his efforts to discredit Trump, expressing in media appearances and in his writings his assertion that his book could ultimately end Trump’s presidency, claiming Trump lacks the mental competence required for the office.
He has also claimed that the 25th Amendment discussions were actively occurring within the White House, citing extensive interactions with Trump’s team to shape narratives surrounding Trump’s perceived dysfunction.
In earlier discussions, Wolff directly labeled Trump a sexist and a racist, affirming his views candidly. Trump’s rebuttals have included strong denials of Wolff’s claims, emphasizing that he restricted access to Wolff and described his account as filled with inaccuracies.
