Washington — Newly uncovered photos, archival footage, and conflicting accounts are shedding fresh light on the decades-long and often murky relationship between former President Donald Trump and the late financier Jeffrey Epstein.

The two men, once prominent fixtures in Palm Beach and Manhattan’s social circles, were photographed at weddings, fashion shows and private parties throughout the 1980s and 1990s. Their friendship appeared to fracture in the mid-2000s, though the precise reasons — and timing — remain disputed. Today, amid renewed political controversy over the handling of Epstein-related files, Trump’s past ties to Epstein continue to fuel debate about his judgment and transparency.

Parties, Jets, and Shared Company

According to The New York Times, Trump and Epstein met around 1990 after Epstein purchased property near Trump’s Mar-a-Lago resort in Palm Beach. Both outer-borough New Yorkers who had climbed Manhattan’s social ladder, the pair cultivated reputations as flamboyant playboys.

Photos and video chronicle their friendship: NBC cameras captured the men at a 1992 Mar-a-Lago party with Buffalo Bills cheerleaders; a 1997 Victoria’s Secret event in New York placed them side by side; and CNN’s KFile recently unearthed footage from the 1999 Victoria’s Secret fashion show showing the two laughing together. Trump was also a guest at Epstein’s Manhattan dinners and flew multiple times on Epstein’s private jet, flight logs show.

“It is even said that he likes beautiful women as much as I do, and many of them are on the younger side.” — Donald Trump, quoted in New York Magazine, 2002

In 2002, Trump described Epstein to New York Magazine as a “terrific guy,” noting that they shared an interest in “beautiful women … many of them on the younger side.”

Epstein at Trump’s Wedding

One of the most striking revelations came this summer, when CNN reported that Epstein attended Trump’s December 1993 wedding to Marla Maples at the Plaza Hotel. Photos reviewed by the network show Epstein among guests, an appearance that had not been widely reported until now.

White House spokesman Steven Cheung dismissed the images as “out-of-context frame grabs” and emphasized that Trump later barred Epstein from Mar-a-Lago for “being a creep.”

Disputed Break

While both men were once publicly close, their split is clouded by competing narratives:

• Mar-a-Lago spa staff: In remarks from Scotland this July, Trump said Epstein had “stolen” young women who worked at his Palm Beach spa, including Virginia Giuffre, who later accused Epstein of sexual abuse. PBS NewsHour and PolitiFact noted that Giuffre’s family questioned Trump’s latest explanation.
• Teenage incident in 2007: The Miami Herald and Wall Street Journal reported that the break came in October 2007, when Trump banned Epstein from Mar-a-Lago after he allegedly behaved inappropriately toward a member’s teenage daughter. The New York Times added that Trump relayed a similar story to lawyer Brad Edwards in 2009.
• Real estate rivalry in 2004: A Washington Post investigation pointed to a contentious bidding war over the Palm Beach mansion Maison de l’Amitié. Trump won the property for $41.35 million, outbidding Epstein. A trustee overseeing the sale called it a clash of “two very large Palm Beach egos.”

Whatever the cause, records show Epstein’s membership at Mar-a-Lago was closed by late 2007, months before his first conviction.

Criminal Cases and Political Fallout

Epstein pleaded guilty in 2008 to state charges of soliciting prostitution from a minor and registered as a sex offender. He was arrested again in 2019 on federal sex-trafficking charges and died in jail that year, a death ruled a suicide. Maxwell, his longtime associate, is serving a 20-year sentence for sex trafficking.

Trump has never been accused of wrongdoing in the Epstein cases and has insisted he knew nothing about the abuse. When Epstein was arrested in 2019, Trump told reporters, “I wasn’t a fan of his.”

Still, his past comments and photographs have kept the association alive. This year, the Wall Street Journal reported that a 2003 birthday note allegedly sent by Trump to Epstein contained a sketch of a nude woman and a cryptic line about a “secret.” Trump has denied writing it and has filed a libel suit.

More recently, Trump’s own supporters have pressed him to release Epstein-related government files after some of his appointees suggested explosive revelations were forthcoming. Instead, the administration has since concluded no such “client list” exists. Under pressure, Trump has directed the Justice Department to seek the unsealing of grand jury transcripts from Epstein’s 2019 case and Maxwell’s 2020 prosecution.

A Relationship That Still Shadows

From Manhattan dinner tables to Palm Beach runways, Trump and Epstein’s friendship once played out in full view. Their eventual rupture, whether over women, reputation, or money, remains contested. What is certain is that the connection between the two men — long before Epstein’s crimes were public — continues to shadow Trump’s political career, ensuring the story remains part of the national conversation.

Sources

• CNN: Newly uncovered photos and footage of Trump and Epstein
• New York Magazine, “Jeffrey Epstein: International Moneyman of Mystery,” 2002.
• PolitiFact: What we know about the Trump-Epstein falling out
• PBS NewsHour: The facts and timeline of Trump and Epstein’s falling out
• New York Times: Inside Trump and Epstein’s Friendship
• Washington Post: Trump and Epstein’s falling out over Palm Beach mansion
• The Wall Street Journal: Jeffrey Epstein’s Friends Sent Him Bawdy Letters for a 50th Birthday Album. One Was From Donald Trump.