For years, the 2002 New York Magazine quote lingered like an inconvenient echo. “I’ve known Jeff for fifteen years,” Donald Trump told a reporter. “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.” At the time, the remark read as casual locker-room talk from two wealthy men who moved in overlapping social orbits. Today, it lands differently.
Newly unsealed court documents, released as part of ongoing civil litigation tied to Jeffrey Epstein’s estate, include detailed flight logs from Epstein’s private Boeing 727—infamously dubbed the “Lolita Express” by tabloids and investigators alike. The records, cross-referenced with manifests and pilot testimonies, show Donald Trump’s name appearing on at least eight flights between 1993 and 1997. Destinations included Palm Beach, New York, and on two occasions, the Caribbean island now central to the trafficking allegations.
The logs do not indicate the purpose of the trips or name any other passengers on those specific flights. Several entries list Trump traveling alone or with unnamed companions, while others note family members, including his then-wife Marla Maples and infant daughter Tiffany on one early journey. Trump’s representatives have consistently maintained that any association with Epstein was social and limited, ending well before the financier’s 2008 conviction. A 2019 statement from the former president described Epstein as a “fixture in Palm Beach” whom he had not spoken to in fifteen years.
Still, the frequency documented in the unsealed files—eight confirmed flights—far exceeds what Trump or his team have previously acknowledged. Earlier public statements referenced only a single known trip and emphasized that Trump banned Epstein from Mar-a-Lago after an unspecified incident involving a member’s daughter. The newly revealed manifests complicate that timeline and raise fresh questions about the depth of the relationship during the 1990s, when both men were prominent figures in New York and Florida real-estate and social circles.
The release has reignited partisan battles. Supporters argue the flights predate any known criminal activity and prove nothing beyond ordinary wealthy networking. Critics point to the 2002 quote, the island’s reputation, and the sheer number of documented trips as evidence of a closer, longer-lasting connection than previously admitted.
Whatever the full context, the unsealed files have done what years of speculation could not: replace rumor with primary records. Eight flights on the Lolita Express are now part of the public record. The old
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