What we found in the Epstein trove: A $10K bet with Trump, #MeToo and more
Published in News & Features
MIAMI — The House Oversight Committee released over 20,000 files from Jeffrey Epstein’s estate Wednesday, many of which include emails with influential friends and reporters. Other documents come from lawsuits or work that was shared with him via email.
Though none include direct communication between President Donald Trump and Epstein, the exchanges between the financier and his friends, including Ghislaine Maxwell, suggest that Trump may have known more about Epstein than he has previously disclosed.
Trump is mentioned in emails over 1,000 times — more than anyone other than Epstein himself. Epstein also corresponded frequently with two reporters, former New York Times reporter Landon Thomas Jr. and author Michael Wolff, and sought to influence world politics.
Miami Herald reporters have been combing through the records. Here are some highlights:
Epstein implies he has dirt on Trump
He wrote in a 2011 email to his convicted accomplice Maxwell that Trump “spent hours” with a victim at his house — describing Trump as “the dog that hasn’t barked.” The White House and House Oversight Committee Republicans said that the victim, whose name was redacted in the emails, was Virginia Giuffre.
Giuffre, who died by suicide this past April, previously said that Trump never had sex with her nor did she see him partake in any sexual acts with other girls. She worked at his Mar-a-Lago resort, which is where Maxwell recruited her for Epstein, leading to years of sexual abuse.
In one missive on Dec. 8, 2015, Epstein offers a reporter photos of Trump with girls wearing bikinis in his kitchen. It is unclear if the photos exist. Later, in 2019, he told Wolff, the author, that Trump “knew about the girls.”
“of course he knew about the girls as he asked ghislaine to stop,” Epstein wrote in an email to Wolff on Jan. 31, 2019.
Soon after, on Feb. 1, 2019, Epstein wrote that Trump came to his house “many times” but “never had a massage.” The email was apparently sent as notes to himself on various talking points about the charges against him.
On other occasions, Epstein implied in his correspondence that he had some sort of leverage over Trump, and weighed using it.
On Dec. 3, 2018, an unidentified individual texted Epstein: “It will all blow over! They’re really just trying to take down Trump and doing whatever they can to do that...!”
“yes thx. its wild. because i am the one able to take him down,” Epstein responded.
Epstein claims he sent Trump a truckload of baby food
In an email exchange from 2016, Epstein wrote to Deepak Chopra, author and new-age guru, that he had lost a bet against Trump when Marla Maples, Trump’s second wife, got pregnant.
“I lost a 10k dollar bet with him, and sent him a truck of baby food in payment,” Epstein wrote.
The couple married in 1993 after the birth of their daughter, Tiffany Trump. Maples and Trump divorced in 1999. Epstein also repeated the story in an email to Thomas, the reporter.
Epstein mocks #MeToo movement
There are several emails and iChat messages in which Epstein mentions or mocks the #MeToo movement.
In an iChat exchange in early December 2018 with a user only identified as “E E,” Epstein writes “so many guys caught in the me too. reaching out to me. asking when does the madness stop. funny.”
Later in the conversation, while still discussing #MeToo, and the idea that “if it’s political” then it should have a “counter party,” Epstein writes “imagine pink dick hats” followed by “a million man march on wash. all wearing the hat.”
“Or a multi message lesbian deplorable march as, both groups can champion the idea of not doing dick!” he wrote in a third consecutive message.
The hat comment seems to play on the Women’s March on Washington the day after Trump’s first inauguration, where hundreds of thousands of women wore pink hats with kitten ears, called “pussy hats.”
Sexual innuendos
Scattered in his correspondence are sexual innuendos and discussion of the sex lives of the people around him.
In one exchange, Boris Nikolic, a biotech venture capitalist, told Epstein he was flirting with a “22 years old hot blond blue eyes mexican chick,” and it would “be a blast” if Epstein were there.
“It turns out she is with her husband. Did not have chance to check him out,” Nikolic wrote on Jan. 28, 2010. “But as we concluded, anything good is rented ;)”
Epstein later named Nikolic the successor executor of his will, but Nikolic told Bloomberg he was “shocked” to discover that and would not fulfill the role.
Epstein tracked Trump’s activities
The emails show that Epstein kept close tabs on Trump, constantly tracking his whereabouts over the years. Some of the comments raise questions about what, if any, contact Epstein had with Trump directly.
In 2017, Thomas reached out to Epstein offering to connect him with Japanese billionaire Masayoshi Son. Epstein suggested they meet up that weekend, “as donald arrives at 5pm tonight.”
“What is the latest from the inner circle?” Thomas said.
“they believe all on track,” Epstein responded.
When Manhattan modeling management executive Faith Kates wrote to Epstein, asking where he was having Thanksgiving dinner in 2017, he answered “eva” – apparently referring to Epstein’s ex-girlfriend Eva Andersson-Dubin. Kates asked “who else is down there?”
“david fizel. hanson. trump,” Epstein responds. Trump was in West Palm Beach for Thanksgiving and hosted a large public dinner at Mar-a-Lago. There is no indication that they met for Thanksgiving that year.
On March 24, 2018, Thomas urges Epstein to call Trump, after a Daily Beast article published with the title: “How Close Is Donald Trump to a Psychiatric Breakdown?”
“Maybe it’s time for you to jump in now. Given how he is throwing caution to wind in such epic fashion, why wouldn’t he take your call?” Thomas wrote.
Epstein seen as authority on Trump
Friends and acquaintances constantly asked Epstein for insight on Trump. What were his political chances? Who would be his Cabinet picks? Did the Russians have “stuff” on him?
The latter question about Russia — from former Secretary of Treasury and Harvard President Emeritus Larry Summers in July 2018 — went unanswered, but in most scenarios Epstein was happy to play along, building an image for himself as an authority on Trump.
Thomas, the reporter, asked Epstein on Nov. 10, 2016, if Steven Mnuchin would be Trump’s Secretary of Treasury. As a response, Epstein asks for his phone number.
Mnuchin was confirmed the following year.
Epstein played to his audience: when people wrote him with concerns about Trump, he disparaged him. He calls Trump “borderline insane,” a “con man,” and “stupid.”
In an email sent to Summers on Feb. 8, 2017, Epstein wrote: “i have met some very bad people,, none as bad as trump.”
“not one decent cell in his body,” he added. “so yes- dangerous.”
©2025 Miami Herald. Visit miamiherald.com. Distributed by Tribune Content Agency, LLC.







Comments