In the hushed glow of late-night phone calls and the electric buzz of lavish 1990s parties at Mar-a-Lago and New York penthouses, Donald Trump and Jeffrey Epstein nurtured a fiercely competitive friendship—swapping stories of glamour, deals, and women in a rivalry that thrilled them both, forging ties deeper than the public ever knew.
Newly unsealed DOJ files from December 23 reveal flight logs showing Trump aboard Epstein’s private jet at least eight times between 1993 and 1996, including four with Ghislaine Maxwell and one with only Trump, Epstein, and a redacted 20-year-old woman—far more trips than Trump has acknowledged.
Photos capture them grinning together, while a 2020 prosecutor’s email highlights the intimacy Trump later distanced himself from, insisting the bond faded years ago with no wrongdoing.
No island visits or charges noted, yet the details evoke a closeness that ended in estrangement—what sparked the sudden chill?
In the hushed glow of late-night phone calls and the electric buzz of lavish 1990s parties at Mar-a-Lago and New York penthouses, Donald Trump and Jeffrey Epstein nurtured a fiercely competitive friendship. The two men swapped stories of glamour, real estate deals, and women in a rivalry that thrilled them both, forging ties deeper than the public ever fully understood at the time.
The U.S. Department of Justice’s third major release of nearly 30,000 pages of Epstein investigation files on December 23, 2025—part of ongoing disclosures under the Epstein Files Transparency Act signed by President Trump last month—offers new insights into that relationship. A January 2020 email from a federal prosecutor in New York notes that flight logs showed Trump aboard Epstein’s private jet at least eight times between 1993 and 1996, far more trips than Trump has publicly acknowledged.
At least four of those flights included Ghislaine Maxwell, Epstein’s convicted accomplice now serving a 20-year sentence for sex trafficking. One 1993 flight listed only Trump and Epstein as passengers; another had just the pair and a redacted 20-year-old woman. Other trips involved Trump’s then-wife Marla Maples and his young children Eric and Tiffany. All were domestic routes between Palm Beach, New Jersey, and Washington, D.C., with no records of visits to Epstein’s private island.
Newly disclosed photos capture Trump and Maxwell grinning together at social events, while documents include subpoenas to Mar-a-Lago for employment records linked to Epstein’s recruitment of staff there.
Trump has long insisted the bond faded years ago, describing Epstein as a “creep” after their falling out and denying any wrongdoing or knowledge of Epstein’s crimes. Federal authorities have never alleged misconduct on Trump’s part related to Epstein.
The DOJ cautioned that some materials contain “untrue and sensationalist claims” against Trump, including a purported jail letter from Epstein to abuser Larry Nassar with crude references—confirmed fake by the FBI due to inconsistencies in handwriting, postmark, and timing.
On December 24, the department announced the discovery of over one million additional potential documents, requiring further review for victim privacy.
While the files highlight the intimacy of their 1990s interactions—shared flights, parties, and elite circles—they add no evidence of criminal involvement by Trump. The details evoke a closeness that ended in estrangement, with Trump publicly banning Epstein from Mar-a-Lago around 2007 after a reported dispute over a real estate deal and Epstein’s behavior toward a member’s underage daughter. As more documents emerge, the records continue to illuminate one of the most scrutinized relationships among America’s powerful figures.
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