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Tracing Donald Trump and Jeffrey Epstein's long, complicated relationship
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Tracing Donald Trump and Jeffrey Epstein's long, complicated relationship

FP Explainers • November 13, 2025, 19:18:38 IST
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Democratic lawmakers on the House Oversight Committee have published three email exchanges between Jeffrey Epstein and his accomplice Ghislaine Maxwell as well as with long-time Trump chronicler Michael Wolff. But what did the emails show? What do we know about the long, complicated relationship between the two men?

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Tracing Donald Trump and Jeffrey Epstein's long, complicated relationship
Donald Trump said he first met Jeffrey Epstein during the 1980s.

New revelations have come to light about the relationship between US President Donald Trump and Jeffrey Epstein.

Epstein, the late disgraced financier, died in prison during Trump’s first term in 2019. Authorities termed his death a suicide. Now, Democrats in the House of Representatives have released new emails tying Trump to Epstein. Many, including Trump ally Elon Musk, have long speculated that the US president is on the so-called Epstein list. The White House has claimed that the emails are a “selective leak” and an attempt to “smear” Trump.

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Trump has long maintained that he and Epstein had a falling out decades ago. The development comes as House Republicans are preparing next week to vote on releasing the Epstein files. But what do the new revelations show? What do we know about the long, complicated relationship between Trump and Epstein?

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Let’s take a closer look.

What new revelations show

Democratic lawmakers on the House Oversight Committee have published email exchanges between Epstein and his partner in crime Ghislaine Maxwell, who is currently serving two decades in prison for sex trafficking young girls to wealthy and powerful individuals.

In April 2011, Epstein sent an email to Maxwell that read, “I want you to realise that that dog that hasn’t barked is Trump. Victim [name redacted] spent hours at my house with him, he has never once been mentioned, including by a police chief.” To which Maxwell wrote back, “I’ve been thinking about that.”

Though the Democrats had redacted the name of the victim in the emails, the unredacted version is available in the tranche released by the committee. The White House has since identified the individual as Virginia Giuffre, an Epstein accuser who died by suicide earlier this year.

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The White House has claimed that Giuffre repeatedly said President Trump was not involved in any wrongdoing whatsoever and “couldn’t have been friendlier” to her in their limited interactions.

They also published a number of emails between Epstein and author Michael Wolff, a long-time chronicler of Trump and author of Fire and Fury: Inside the Trump White House. Wolff, incidentally, is being sued by Melania Trump for a billion dollars for comments he allegedly made linking her to Epstein.

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The exchanges between Epstein and Wolff came as Trump was running for his first term as president. In 2015, Wolff alerted Epstein that CNN was planning to ask Trump about the nature of the relationship “either on air or in scrum afterwards”. To which Epstein replied, “If we were able to craft an answer for him, what do you think it should be?”

Prince Andrew is seen holding Virginia Giuffre by her waist, as Ghislaine Maxwell looks at the camera from behind them, at the London home of Maxwell on March 10, 2001. (Photo: AFP)

Wolff responded, “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 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. 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 wrote.

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The email exchange between the two men appears to be an attempt by Epstein to come up with a satisfactory answer about the nature of their relationship.
The third email released was written in January 2019, when Trump was president.

It discusses Epstein and Mar-a-Lago, Trump’s club and resort in Florida. Epstein wrote to Wolff that “Trump said he asked me to resign” and added that he was “never a member ever” of Mar-a-Lago. “Of course he knew about the girls as he asked Ghislaine to stop,” Epstein added.

This email raises questions as to how much Trump knew about the sex trafficking operation that Epstein and Maxwell were carrying out.

Long, complicated relationship

Trump, in interviews, has said that he first met Epstein during the 1980s.

“I’ve known Jeff for fifteen years. Terrific guy,” Trump told New York Magazine in 2002. “He’s a lot of fun to be with. It is even said that he likes beautiful women as much as I do, and many of them are on the younger side. No doubt about it — Jeffrey enjoys his social life.”

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Trump has claimed that he knew Epstein socially in Florida circles. Trump, of course, owns Mar-a-Lago, and Epstein had a mansion in the same area. Epstein was reportedly seen several times at Mar-a-Lago over the years.

“Well, I knew him like everybody in Palm Beach knew him. I mean, people in Palm Beach knew him. He was a fixture in Palm Beach,” Trump said in 2019 soon after Epstein’s fall from grace.

The two men are said to have remained close over the years. Footage from 1992 from NBC shows Trump and Epstein at Mar-a-Lago talking as they watch women dance. Maxwell is also present on the scene. Trump, his first wife Marla Maples, and daughter Tiffany flew several times on Epstein’s private jet during the 1990s.

People holds signs calling for the release of files regarding late sex offender Jeffrey Epstein. File image/AFP

In 2003, Trump is said to have contributed to a book put together for Epstein’s 50th birthday. Trump, in his personalised message to Epstein, wrote: “Happy Birthday—and may every day be another wonderful secret” and “enigmas never age”. Trump has insisted that he did not write the letter and has sued Rupert Murdoch’s Wall Street Journal and the two reporters who brought the story to light.

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The two men are believed to have fallen out in 2004 over a business deal.

The Washington Post reported that it involved the property by the ocean in Palm Beach called Maison de L’Amitié. Things ended after Trump outbid Epstein for the property, with one source calling the tiff “two very large Palm Beach egos going at it.”

Trump, after becoming president, sought to distance himself from Epstein. He claimed that the two men fell out in the mid-2000s after Epstein tried to recruit people who worked for Trump. “He took some of the people who worked for me,” Trump said. “Once he did that, that was the end of him.”

Trump White House reels from Epstein backlash

The Trump administration has been receiving flak over Epstein ever since Attorney General Pam Bondi earlier this year announced that they would not release the files relating to the late financier. Even some Republicans and conservative influencers have been upset with the administration over its reluctance to release the Epstein files.
Trump, in July, seemed to turn on his own supporters, claiming “weaklings” who had “bought into” the “Jeffrey Epstein hoax”.

“I don’t want their support anymore!” Trump announced, in a statement that turned heads.

Attorney General Pam Bondi and President Trump at a roundtable at the White House on June 5. AFP
Attorney General Pam Bondi and President Trump at a roundtable at the White House on June 5. AFP

The Wall Street Journal earlier this year reported that the US Justice Department had told Trump that his name was in the Epstein files. Democrats have claimed that the Trump administration is engaging in an active cover-up over the Epstein files. This came after the Justice Department sent attorney Todd Blanche to meet with Maxwell in prison. Maxwell has since been transferred to a lower-security facility in Florida.

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There are rumours that she is being given preferential treatment and may even be pardoned by Trump. There were reports that Trump and top members of his administration held a meeting in the Situation Room in the White House over the release of the Epstein files. Trump is said to have personally called two Republican members of the House – Lauren Boebert and Marjorie Taylor Greene – in an attempt to get their names removed from the discharge petition.

White House slams Democrats

White House spokesperson Karoline Leavitt claimed the Democrats had “selectively leaked emails to the liberal media to create a fake narrative to smear President Trump”.

Leavitt pointed out that the name of the redacted victim was Giuffre, whom she said “repeatedly said President Trump was not involved in any wrongdoing whatsoever”.
“Trump kicked Jeffrey Epstein out of his club decades ago for being a creep to his female employees, including Giuffre,” Leavitt added. “These stories are nothing more than bad-faith efforts to distract from President Trump’s historic accomplishments, and any American with common sense sees right through this hoax and clear distraction from the government opening back up again.”

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“These emails,” Leavitt added, “prove absolutely nothing other than the fact that President Trump did nothing wrong.”

With inputs from agencies

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