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Home Breaking News

All we know about Donald Trump and Jeffrey Epstein’s ‘friendship’

by DigestWire member
September 9, 2025
in Breaking News, US News, World
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All we know about Donald Trump and Jeffrey Epstein’s ‘friendship’
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Donald Trump has been fending off pressure from Democrats and his own Make America Great Again (MAGA) movement to release files related to the crimes of Jeffrey Epstein.

The paedophile financier was found dead in his Manhattan prison cell in August 2019, shortly after he was arrested on sex trafficking charges.

The president pledged to release files on Epstein during his campaign, as his MAGA movement accused the Biden administration of suppressing the extent of Epstein’s paedophilia and predatory behaviour. Epstein’s so-called “client list” is thought to contain names of the rich and famous who conspired with him in his child sex trafficking operation.

But Mr Trump made a controversial U-turn and instead started lashing out at supporters who are continuing to call for the files to be released.

The saga has thrust Mr Trump and Epstein’s former relations back into the spotlight over the past few months.

But what do we know about their history?

What has Trump said about their relationship?

What you need to know about Trump and the Epstein files

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Mr Trump and Epstein moved in the same circles in Florida and New York for many years, and were pictured together on several occasions in the 1990s and early 2000s, including at the real estate mogul’s club in Palm Beach.

There is now-infamous NBC News archive footage of the pair socialising in November 1992 at Mr Trump’s Mar-a-Lago estate, with the now-president appearing to point out women on the dance floor.

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In a 2002 interview with New York magazine, Mr Trump was quoted saying: “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.”

Allegations that Epstein had been sexually abusing girls became public in 2006 and he was arrested that year before accepting a plea deal. He was then arrested for a second time in 2019 and charged with sex-trafficking conspiracy.

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Trump was asked about his relationship with Epstein after he was found dead in his cell, and he played down the extent of their relationship.

He said he “knew him like everybody in Palm Beach knew him”, but added: “I had a falling out with him. I haven’t spoken to him in 15 years. I was not a fan of his, that I can tell you.”

Asked why the pair fell out, Mr Trump said: “The reason doesn’t make any difference, frankly,” and added that he had “no idea” about Epstein’s crimes.

Trump flew on Epstein’s plane numerous times

Epstein owned an island in the Caribbean, a location where he is known to have taken underage girls to abuse them.

He had a private plane which his acquaintances flew in, and some of the flight logs have been released to the public.

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Amid speculation in January last year, Mr Trump said on social media: “I was never on Epstein’s Plane, or at his ‘stupid’ Island.”

But the flight logs indicated he flew on Epstein’s plane at least seven times. There is no suggestion that Mr Trump was flown to the island.

The logs indicate that on one of the trips between New York and Florida he was accompanied by his then-wife Marla Maples and their daughter, Tiffany, and another listed his son Eric as a passenger.

Court documents name Trump

Court documents relating to Ghislaine Maxwell, her relationship with Jeffrey Epstein and alleged victims of sexual abuse were unsealed in January last year.

The documents, which were part of a 2015 defamation case by Virginia Giuffre against Epstein’s accomplice Ghislaine Maxwell, named Mr Trump, along with the likes of Prince Andrew and Bill Clinton.

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A woman named Johanna Sjoberg gave testimony and said that while flying to Manhattan with Epstein, Maxwell, Ms Giuffre and Prince Andrew, the financier’s jet was diverted to Atlantic City, New Jersey – where Epstein suggested going to one of Mr Trump’s casinos.

“The pilots told me to go back and tell [Epstein] that we can’t land in New York and that we were going to have to land in Atlantic City,” she said.

“Jeffrey said, ‘Great, we’ll call up Trump and we’ll go to’ – I don’t recall the name of the casino, but – ‘we’ll go to the casino’.”

She said she spent several hours with Epstein at a Trump casino but did not say if she met him. Mr Trump was not accused of any wrongdoing.

Birthday letter from Trump to Epstein

The Wall Street Journal (WSJ) claimed in July it had seen a letter written by Mr Trump as part of a collection of letters addressed to Epstein that his former girlfriend Ghislaine Maxwell planned to give him as a birthday present in 2003.

The paper said Mr Trump’s letter featured several lines of typewritten text framed by what appeared to be a hand-drawn outline of a naked woman.

Read more:
What you need to know about Trump and the Epstein files
How Ghislaine Maxwell could challenge her imprisonment

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It said the letter concludes “Happy Birthday – and may every day be another wonderful secret”, and featured the signature “Donald”, allegedly drawn across the woman’s waist, meant to mimic the appearance of pubic hair.

Mr Trump denied he wrote it in an interview with the WSJ prior to publication.

In September, the entire birthday album was released by Democrats on the House Oversight Committee, including the letter purportedly signed by Mr Trump.

The album also bore the names of other prominent figures, such as former President Bill Clinton and the current UK ambassador to Washington, Lord Peter Mandelson.

The White House again denied Mr Trump wrote the letter.

Press secretary Karoline Leavitt said in a statement that the president will “continue to aggressively pursue litigation”, referring to a $10bn (£7.5bn) lawsuit Mr Trump filed against the WSJ after it initially reported on his link to the letter.

Falling out

Any friendship that existed between Mr Trump and Epstein in the 1990s is said to have turned sour in the early 2000s.

The New York Times reports that the pair fell out in 2004 over a foreclosed oceanfront Palm Beach mansion that Mr Trump outbid Epstein for.

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In 2006 Epstein was indicted as part of an FBI and Florida police investigation. Two years later he pleaded guilty in state court to two felony charges, including soliciting a minor, as part of a plea deal that avoided federal charges that would have meant far more serious prison time.

There is little public record of Mr Trump and Epstein crossing paths from 2004 onwards. In 2019 Mr Trump said that he and Epstein had had a “falling out” and hadn’t spoken for 15 years.

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