Analysis: 5 big questions about Trump's ties to Epstein

CNN

19-07-2025

A Wall Street Journal report late Thursday added new scrutiny to President Donald Trump's relationship with the late sex offender Jeffrey Epstein.
The Journal reported that Epstein associate Ghislaine Maxwell asked Trump and many others to submit letters for an album for Epstein's 50th birthday in 2003.
A letter bearing Trump's name included a lewd outline of a naked woman and an imagined conversation between Trump and Epstein, according to the Journal. In the conversation, the two men reflect on how they share some kind of secret knowledge about how there's 'more to life than having everything.'
'Happy Birthday — and may every day be another wonderful secret,' Trump concludes in this imagined conversation, according to the Journal.
The president has denied he wrote the letter, and on Friday, he filed a libel lawsuit against the publisher of the Wall Street Journal and the reporters who wrote the story.
'This is not me. This is a fake thing. It's a fake Wall Street Journal story,' Trump told the Journal in an interview earlier this week. 'I never wrote a picture in my life. I don't draw pictures of women.'
Trump added in a social media post after the story published: 'These are not my words, not the way I talk. Also, I don't draw pictures.'
It's been no secret that Trump and Epstein were friendly in the period before Epstein was charged with solicitation of prostitution in the mid 2000s. There are plenty of photos of them together.
But the new report – along with Trump's demands that his supporters stop pursuing questions about Epstein in the wake of his administration's botched handling of promised disclosures – has rekindled interest in the matter.
Trump has now relented a bit on disclosure, instructing the Justice Department to seek to unseal 'any and all pertinent Grand Jury testimony, subject to Court approval.' (The DOJ moved to do that on Friday, but it's possible that won't reveal much or happen anytime soon, given grand jury testimony is typically kept secret. And that testimony is only a small piece of the relevant information.)
So, what do we know so far about Trump and Epstein's relationship? Here are some key questions.
There are conflicting signals on this. And Trump's strained efforts to downplay their ties have raised plenty of questions.
After Epstein was arrested and charged with sex trafficking of minors in 2019, Trump distanced himself.
'Well, I knew him like everybody in Palm Beach knew him,' Trump told reporters during his first term. '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.'
Trump then repeated twice more that he had not been 'a fan' of Epstein's.
His account of not speaking to Epstein since the 2000s is backed up by reporting. The Washington Post has reported that the two men had a falling-out while competing over the same Palm Beach oceanfront property in 2004.
That would place the falling-out before Epstein began getting in serious legal trouble; in 2006, Epstein was charged with soliciting a prostitute, and that same year reports surfaced that he had been under investigation for allegedly having sex with minors.
But Trump's suggestion that his relationship with Epstein was more incidental and his claim that he 'was not a fan' of Epstein's has been called into question, including by Trump's own commentary.
Their relationship appeared to stretch back to the 1980s. Trump flew on Epstein's jets between Palm Beach and New York, according to flight logs. They socialized at each other's properties.
The New York Times reported that, in 1992, Mar-a-Lago played host to a 'calendar girl' competition in which about two dozen women were flown in. But the only guests present were Trump and Epstein, according to a Florida businessman who organized the event, George Houraney. (Trump's White House didn't comment to the Times for the 2019 story.)
Most infamously, Trump in 2002 told New York magazine that Epstein was a 'terrific guy.'
'He's a lot of fun to be with,' Trump said. '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.'
Former Trump aide Sam Nunberg told the Washington Post in 2019 that he had pressed Trump about his ties to Epstein in 2014 when Trump was considering a presidential run.
'Bottom line, Donald would hang out with Epstein because he was rich,' Nunberg said, assuring Trump had severed ties long ago.
Precisely how close Trump and Epstein were isn't totally clear. Was this just a situation of powerful men occasionally partying together and sharing Epstein's private plane because that's what rich guys do? These are social situations tough for most Americans to understand.
But even if Trump really was somehow 'not a fan,' he's made other dodgy claims.
In January 2024, he said on social media: 'I was never on Epstein's Plane …' In fact, flight logs had already shown Trump flew on it seven times in the 1990s.
Trump also claimed in 2019 that he didn't 'know Prince Andrew' of Britain, who has been the subject of Epstein-related allegations, despite a number of photos showing Trump with the Duke of York.
Trump often lies and misleads in his public statements. And he certainly has reason to downplay his ties to Epstein. But going too far in that direction undercuts your credibility and feeds suspicion about what you might be hiding.
Precisely what the Journal's story will mean going forward isn't clear – although it's already rallied MAGA influencers who were critical of the administration's handling of the Epstein files to Trump's side.
The idea that Trump would submit a letter for Epstein's birthday album isn't that surprising, given this was when the two of them were seemingly on better terms (2003) and that dozens of other letters were reportedly solicited. The idea that Trump would be lewd in that letter also tracks, given his past. (See: The 'Access Hollywood' tape.)
But Trump — and many of those vocal supporters — have said this doesn't sound like him or something he would create.
Far-right activist Laura Loomer — who'd called for the administration to appoint a special counsel to look into the handling of the Epstein files — quickly came to Trump's defense Thursday night. 'Everyone who actually KNOWS President Trump knows he doesn't type letters. He writes notes in big black Sharpie,' she posted on X.
But while Trump maintains he doesn't draw pictures, his drawings have surfaced before. A signed Trump sketch of the Manhattan skyline sold at auction in 2017 for more than $29,000. (The sketch was reportedly from 2005, two years after the letter in question.) Another 1990s Trump sketch of the Empire State Building auctioned off the same year.
And Trump in a 2008 book recalled donating an autographed doodle every year to a charity.
Of course, none of that proves he wrote this letter and drew the accompanying picture. But again, Trump is undercutting his own credibility. Why lie about doodling — especially since it's easily disprovable?
And it's possible we could learn more about this. There has been some talk about having Maxwell — who the Journal reported solicited the letter — testify before Congress.
Trump's efforts to quiet chatter about Epstein have only furthered suspicion in some corners that his name could be in the files his administration has failed to produce.
We already know that Trump's name was in Epstein's flight logs. An Epstein personal address book that leaked in 2009 contained 14 phone numbers for Trump, Melania Trump and Trump's staff, according to media reports. A 2005 search of Epstein's Palm Beach mansion produced two written messages about phone calls from Trump.
So, it's not inconceivable he's in the files his supporters have been clamoring for. Merely being named, of course, wouldn't mean Trump had done anything wrong. But it could create political headaches — as the fallout from the Journal story shows — and as demonstrated by Trump's very public reluctance to release more documents.
Former top Trump adviser Elon Musk alleged last month while lashing out at Trump that the president was indeed in the Epstein files, adding, 'That is the real reason they have not been made public.'
But he provided no evidence for his claims and later deleted the post.
Trump was asked Tuesday if Attorney General Pam Bondi had told him his name was in the files, and he didn't directly answer.
'She's given us just a very quick briefing in terms of the credibility of the different things that they've seen,' Trump said.
Trump's 2002 comment about Epstein's taste for women 'on the younger side' has also loomed over him, furthering theories that he might have known something about what Epstein had been up to.
That remains speculative and unproven. Trump also said nothing about underage girls; he cited young 'women.'
But questions about who knew what and when with Epstein's conduct have long lingered. Trump's Mar-a-Lago property was a backdrop to some of Epstein's misdeeds. And Epstein and Trump's social connections often revolved around women.
According to Nunberg's 2019 account to the Washington Post, Trump said he banned Epstein from Mar-a-Lago because of misconduct. Nunberg said Trump said he did so because Epstein had recruited a young woman who worked there to give him massages. This was years before the Epstein investigation became public knowledge, according to the Post.
'He's a real creep, I banned him,' Nunberg said Trump had told him.
Multiple reports, including a 2020 book by reporters for the Miami Herald and Wall Street Journal, have linked Epstein's ban from Mar-a-Lago to alleged overtures to the teenage daughter of a Mar-a-Lago member.
Late Epstein victim Virginia Giuffre said she was recruited into the sex-trafficking ring while working at Mar-a-Lago in 2000.
Houraney also told the Times in 2019 that he raised concerns to Trump about Epstein's conduct ahead of that 1992 'calendar girl' event.
'I said, 'Look, Donald, I know Jeff really well, I can't have him going after younger girls,'' Houraney said. 'He said, 'Look I'm putting my name on this. I wouldn't put my name on it and have a scandal.''
Trump appears to have been helpful to those probing Epstein's conduct, but we know little about what he said because he was never deposed. One attorney for Epstein's alleged victims has said Trump in 2009 was a very willing interview subject.
The attorney, Brad Edwards, said Trump 'gave no indication whatsoever that he was involved in anything untoward whatsoever.'
While Trump in 2019 quickly distanced himself from Epstein, his commentary the following year after Maxwell was charged was different — and somewhat bizarre.
'But I wish her well, whatever it is,' Trump told reporters in late July 2020.
Despite significant criticism of that — wishing an accused (and later-convicted) child sex trafficker well — Trump a couple weeks later doubled and tripled down when pressed by then-Axios reporter Jonathan Swan on how odd that sounded.
'Yeah, I wish her well,' Trump told Swan. 'I'd wish you well. I'd wish a lot of people well. Good luck. Let them prove somebody was guilty.'
Trump added, when pressed again: 'I do wish her well. I'm not looking for anything bad for her. I'm not looking bad for anybody.'
Even for a president who often says weird things, this ranks near the top.