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A ‘racy’ birthday letter, ‘terrific guy’ to not a ‘fan’: Mapping Trump’s relationship with Epstein over the years
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  • A ‘racy’ birthday letter, ‘terrific guy’ to not a ‘fan’: Mapping Trump’s relationship with Epstein over the years

A ‘racy’ birthday letter, ‘terrific guy’ to not a ‘fan’: Mapping Trump’s relationship with Epstein over the years

FP Explainers • July 18, 2025, 10:43:32 IST
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Amid growing pressure on US President Donald Trump to release ‘Epstein files’, a Wall Street Journal report has claimed that the Republican leader sent a bawdy letter to the disgraced financier for his 50th birthday in 2003. Trump once called Jeffrey Epstein a ‘terrific guy’. But in 2019, he said he was not a ‘fan’ of the convicted sex offender. Did they have a fallout?

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A ‘racy’ birthday letter, ‘terrific guy’ to not a ‘fan’: Mapping Trump’s relationship with Epstein over the years
Donald Trump’s relationship with convicted sex offender Jeffrey Epstein is under scrutiny. AP

A purported bombshell letter to convicted sex offender Jeffrey Epstein bearing United States President Donald Trump’s signature has come to light. The letter, which had an outline of a naked woman, was part of an album of letters gifted to Epstein for his 50th birthday in 2003, according to a Wall Street Journal (WSJ) report.

Trump, whose relationship with Epstein has grabbed public attention, has called the letter “fake” and threatened to sue the American newspaper. The letter has once again put the spotlight on the US president’s connection with the multimillionaire financier who died in prison in 2019.

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We map Trump and Epstein’s relationship throughout the years.

Trump’s ‘bawdy’ letter to Epstein

The letter, which, as per the Journal, Donald Trump sent at the request of Jeffrey Epstein’s right-hand woman, Ghislaine Maxwell, had a drawing depicting a woman’s breasts and a “Donald” signature in the place of pubic hair.

The 2003 letter “contains several lines of typewritten text framed by the outline of a naked woman, which appears to be hand-drawn with a heavy marker,” according to the WSJ.

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It concluded with the line: “Happy Birthday — and may every day be another wonderful secret.”

According to the WSJ, it was not clear “how the letter with Trump’s signature was prepared.”

“Inside the outline of the naked woman was a typewritten note styled as an imaginary conversation between Trump and Epstein, written in the third person,” the paper said.

Maxwell, a close associate of Epstein, was convicted of child sex trafficking in relation to the financier. She collected the letters from Trump and dozens of others for Epstein’s 50th birthday, the Journal reported.

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Later, the album became a part of the documents examined by the US Department of Justice during their investigation into Epstein several years ago, the newspaper reported.

In an interview with the Journal on Tuesday, Trump denied writing the letter or drawing the image and threatened to sue the newspaper if it published the story.

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“This is not me. This is a fake thing. It’s a fake Wall Street Journal story,” he said. “I never wrote a picture in my life. I don’t draw pictures of women,” he said. “It’s not my language. It’s not my words.”

Reacting to the WSJ story, US Vice President JD Vance wrote in a post on X, “Forgive my language but this story is complete and utter bulls—.”

“The WSJ should be ashamed for publishing it. Where is this letter? Would you be shocked to learn they never showed it to us before publishing it? Does anyone honestly believe this sounds like Donald Trump?”

After the WSJ story was published, Trump wrote on his Truth Social on Thursday (July 17) that he had ordered Attorney General Pam Bondi “to produce any and all pertinent Grand Jury testimony, subject to Court approval.”

Trump’s relationship with Epstein

It is not known when Trump first met Epstein; however, as per the US president’s utterances, they were friends for over a decade, starting in the 1980s.

Trump told New York Magazine in 2002, “I’ve known Jeff for 15 years. Terrific guy. 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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The duo was spotted together at parties over several years.

In 1992, Trump threw a party with the National Football League (NFL) cheerleaders at his Mar-a-Lago estate in Florida. Footage from NBC archives shows the future US president socialising with Epstein. They were seen watching and pointing at girls dancing, as per a Time report.

The same year, Trump allegedly held a “calendar girl” party just for him and Epstein that included “28 girls”. It was organised by Florida businessman George Houraney on Trump’s request, The New York Times (NYT) reported in 2019.

trump epstein
A protest group called ‘Hot Mess’ hold up signs of Jeffrey Epstein and US President Donald Trump in front of the Federal courthouse on July 8, 2019, in New York City. File Photo/AFP

Trump and Epstein were also present together at a Victoria’s Secret “Angels” party in New York in 1997.

In the 1990s, Trump flew on Epstein’s private jets. His name appeared seven times in flight logs from Epstein’s personal plane, which had been previously made public.

Trump and Epstein are believed to have had a falling out in 2004 over a business deal related to an oceanfront Palm Beach mansion, according to the Washington Post. Trump ultimately outbid Epstein for the property.

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As per NYT, there is not much public record of the two men interacting after their rivalry over real estate.

Trump began distancing himself from “terrific guy” Epstein after the financier was first convicted in 2008 in relation to sex trafficking.

In 2017, Trump Organization attorney Alan Garten told POLITICO that there was no relationship between the two men. “As I have previously explained, he had no relationship with Mr. Epstein and had no knowledge whatsoever of his conduct. This has all been reported countless times in the press.”

Epstein was arrested again in 2019 on sex trafficking charges. He was accused of trafficking girls, including 14-year-olds, and engaging in sex acts with them.

After he was charged, Trump said in 2019, “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. I had a falling out with him a long time ago. I don’t think I’ve spoken to him for 15 years. I wasn’t a fan.”

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In August 2019, Epstein was found dead in his jail cell while awaiting trial, with local and federal authorities saying he hanged himself.

Trump faces heat over ‘Epstein files’

Over the years, Trump has hinted that rich and powerful people, including Bill Clinton, were involved with Epstein and went to his infamous island .

During the 2024 presidential campaign, the Republican leader even indicated that the Epstein files would be released. The term is used to refer to evidence collected by the Justice Department related to the Epstein investigation, which is thought to include a “client list” that the convicted sex offender used to allegedly blackmail powerful people.

In a memo last week, the Justice Department confirmed Epstein died by suicide and said its review of the files “revealed no incriminating ‘client list’”.

“There was also no credible evidence found that Epstein blackmailed prominent individuals as part of his actions. We did not uncover evidence that could predicate an investigation against uncharged third parties,” it said in the unsigned memo.

Trump has since tried to shut down curiosity over Epstein. He has lashed out at his MAGA base for falling for a “hoax” by fixating on the case.

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“Their new SCAM is what we will forever call the Jeffrey Epstein Hoax, and my PAST supporters have bought into this ‘bullshit,’ hook, line, and sinker,” Trump posted on Truth Social on Wednesday (July 16).

“Let these weaklings continue forward and do the Democrats work, don’t even think about talking of our incredible and unprecedented success, because I don’t want their support anymore!” he added.

Amid growing pressure on him to release the Epstein files, Trump later said Attorney General Bondi could release “whatever she thinks is credible”, before claiming that the entire thing was a “Democratic hoax.” He also lamented “stupid and foolish Republicans” for continuing to press the matter.

With inputs from agencies

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