President Donald Trump's one-time friendship with disgraced sex trafficker Jeffrey Epstein has plagued his second term in the White House.

While members of Trump's current administration have for years called on federal officials to release their files on Epstein, they changed their tune in recent months, saying that no "client list" exists.

On Nov. 12, new layers in the Trump-Epstein saga were peeled back when Democrats released emails that appear to have been written by Epstein and allege Trump "spent hours" with one of Epstein's victims.

White House Press Secretary Karoline Leavitt said the emails, which were released by Democrats, are part of "a fake narrative to smear President Trump."

While Trump was acquainted with Epstein in the 1990s, he has long denied knowing about any alleged sex trafficking. Epstein died by suicide in prison in 2019 while awaiting trial.

Here's a timeline of key moments in the president's connection to Epstein.

1990s and 2000s: Background of Trump and Epstein's connection

Epstein and Trump reportedly met in 1990 when Epstein bought a mansion two miles from Trump's Mar-a-Lago club and estate.

Over the next decade or so, the two would party and socialize together between Florida and New York, where they also at one point lived within miles of each other.

Trump famously called Epstein a "terrific guy" for a 2002 article in New York magazine.

"He’s a lot of fun to be with," Trump told the magazine. "It is even said that he likes beautiful women as much as I do, and many of them are on the younger side."

At some point, the two businessmen had a falling out and ended their friendship. When and why it happened has been the point of much speculation.

Trump told reporters earlier this year that he stopped talking to Epstein after the sex offender poached staff members who worked at his Mar-a-Lago resort.

"The fact is that the president kicked (Epstein) out of his club for being a creep," said White House Communications Director Steven Cheung earlier this year.

In 2004, Trump outbid Epstein for an oceanfront mansion in Palm Beach called Maison de l’Amitie − the House of Friendship.

2024: Trump says he would release files on Epstein

During Trump's 2024 campaign, the then-candidate as well as members of his family and future Cabinet picks, called for the release of files on Epstein.

"Yeah, yeah, I would (declassify the Epstein files)," Trump said on "Fox & Friends Weekend" on June 3, 2024.

His son, Donald Trump Jr., also said while campaigning on June 17, 2024, "How is it that my father can be convicted of 34 crimes, but no one on Epstein's list has even been brought to light?"

February 2025: Trump administration says it is investigating Epstein files

Several members of Trump's administration, including Attorney General Pam Bondi, said in February that it would be imminently releasing documents on Epstein.

"It's sitting on my desk right now to review. That's been a directive by President Trump. I'm reviewing that," Bondi told Fox News host John Roberts on Feb. 21.

On Feb. 27, the Justice Department released documents that it said had previously been leaked, but were never formally released by the government. The department said it was the "First Phase" of declassifying Epstein files.

July 2025: Trump's DOJ says Epstein did not have a client list

On July 7, the Justice Department announced that a "systematic review" of files on Epstein "revealed no incriminating 'client list'" and confirmed that he died by suicide.

After some questioned the findings, Trump expressed surprise at the continued interest in the Epstein case.

"I don’t understand why the Jeffrey Epstein case would be of interest to anybody," he told reporters in July. "It’s pretty boring stuff."

July 2025: WSJ releases alleged Trump birthday card to Epstein

The Wall Street Journal on July 17 published a report detailing a lewd letter bearing Trump's name that was sent to Epstein for a 2003 birthday album.

The letter contained text inside a hand-drawn outline of a nude woman, with Trump's signature displayed as "a squiggly 'Donald' below her waist, mimicking pubic hair," the Journal wrote.

The letter ends with "Happy Birthday — and may every day be another wonderful secret," the Journal reported.

Trump denied writing the card in a series of social media posts, calling it "FAKE" and saying, "These are not my words, not the way I talk. Also, I don’t draw pictures."

The president has sued the newspaper over the article.

November 2025: Epstein emails allegedly mentioning Trump released by Dems

House Democrats on Nov. 12 released emails apparently written by Epstein that said Trump "spent hours at my house" with one Epstein's victims.

Epstein mentioned the president in emails with someone whose email was Gmax, a potential reference to associate and convicted sex trafficker Ghislaine Maxwell, and Michael Wolff, a journalist and biographer.

"I want you to realize that that dog that hasn’t barked is trump," Epstein wrote in one email to Ghislaine Maxwell on April 2, 2011.

Another Epstein email to Wolff on Jan. 31, 2019, said "of course he knew about the girls as he asked ghislaine to stop."

Leavitt, who called the emails a smear, told reporters the emails "prove absolutely nothing other than the fact that President Trump did nothing wrong."

Michael Wolff was a freelance USA TODAY contributor from 2012 to early 2017. USA TODAY had no knowledge of any relationship between him and Jeffrey Epstein, nor any actions beyond his submissions for publication. We are committed to integrity and transparency, as we uphold our editorial standards and maintain the trust of our readers.

Melina Khan is a national trending reporter for USA TODAY. She can be reached at melina.khan@usatoday.com.

Contributing: Laura Trujillo, Aysha Bagchi, Erin Mansfield and Bart Jansen, USA TODAY

This article originally appeared on USA TODAY: See timeline of recent events in Donald Trump-Jeffrey Epstein saga

Reporting by Melina Khan, USA TODAY / USA TODAY

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