The New York Times reveals a previously unpublished photo of the Cuban dictator with the American businessman.
14ymedio, Madrid, 7 August 2025 — Fidel Castro and sex offender Jeffrey Epstein pose for the camera in the middle of a smiling group, who are all embracing, on Cuban soil. A recent report by The New York Times has revealed images and documents seized from the American financier’s New York mansion.
The image is part of a collection of letters, artifacts, and portraits that show Epstein’s ties to dozens of global power figures—from Bill Clinton to Pope John Paul II—and rekindles debate about the true extent of his network of influence.
The context of this image with Castro goes back to 2003, when former Colombian President Andrés Pastrana claimed he traveled to Havana on Epstein’s private plane, known as the Lolita Express, with the explicit purpose of meeting with the revolutionary leader. According to his testimony, Epstein hosted the trip and was allegedly invited by the Cuban leader himself. Among the flight companions was French model Jean-Luc Brunel, later implicated as a recruiter in the magnate’s sex trafficking ring.
Journalistic investigations, such as those by the Miami Herald, have suggested that Epstein’s trip to Cuba may have had ulterior motives.
Journalistic investigations, such as those by the Miami Herald, have suggested that Epstein’s trip to Cuba may have had ulterior motives. Among the hypotheses raised is that Epstein was exploring the possibility of requesting asylum on the island, anticipating his growing judicial exposure in the United States. However, there is no evidence that Castro offered him such protection. What does exist is the photograph, which adds a layer of mystery to an already murky episode with no clear answers.
So far, the Cuban regime has remained silent regarding the appearance of the image published by The New York Times. Meanwhile, pro-government media outlets such as Cubadebate have devoted extensive space to the relationship between Epstein and Donald Trump, including nearly a dozen recent articles.
There’s no doubt about the authenticity of the photos showing Trump and Castro with the tycoon—of course, never at the same time. However, there are many other fake images and videos generated by artificial intelligence showing Trump in compromising situations.
At least one manipulated video and seven images have accumulated more than 7.2 million views, according to the organization NewsGuard. The scenes show Trump and Epstein dancing with young people or sitting on couches surrounded by girls who appear to be minors. However, specialized tools such as Hive and IdentifAI have determined that the content is digitally fabricated to appear authentic.
The apocryphal materials have been interpreted by conservative sectors as maneuvers to divert attention from the real documentation, and at the same time protect certain elites from public scrutiny.
The viral spread of these montages has highlighted the dangers of automated disinformation and its ability to rewrite narratives in real time. Amid renewed public interest in the Epstein case—fueled by recent FBI and Justice Department reports that have debunked several conspiracy theories—the apocryphal materials have been interpreted by conservative sectors as maneuvers to divert attention from the real documentation while simultaneously shielding certain elites from public scrutiny.
The image of Castro with Epstein is not a part of this fabricated content ecosystem; it was recovered by the FBI in one of the official searches of the magnate’s mansion and its authenticity has not been denied by any source. On the contrary, the former Colombian president’s testimony confirms its existence.
Was it an informal meeting? Did it have diplomatic, personal, or strategic purposes? Was Epstein seeking some sort of political protection on the island? As long as the official documents remain sealed and Havana maintains its silence, the mystery continues. Only one thing is certain: Epstein’s reach extended further than many imagined, even into the corridors of power in Cuba.
____________
COLLABORATE WITH OUR WORK: The 14ymedio team is committed to practicing serious journalism that reflects Cuba’s reality in all its depth. Thank you for joining us on this long journey. We invite you to continue supporting us by becoming a member of 14ymedio now. Together we can continue transforming journalism in Cuba.