The origin of Jeffrey Epstein’s fortune has been for decades an unknown as disturbing as it is persistent. The American financier, later convicted of sex crimes and died in prison in 2019, managed to accumulate a wealth and a network of contacts difficult to explain from his official resume.
Now, an investigation by The New York Times sheds light on a little-known episode that places Spain (and his relationship with Ana Obregón) as a decisive turning point in his economic rise.
The U.S. newspaper does not claim that the actress was involved in illegal activities, but it does document how her sentimental link with Epstein was decisive for him to gain access to circles of high economic power in Spain. That access allowed him to carry out a key financial operation that transformed his status: he went from being a young financier with vague credentials to becoming, for the first time, a millionaire.
A romance that opened important doors in Spain
The relationship between Jeffrey Epstein and Ana Obregón began in the early 1980s, when she was already a well-known figure in Spain and belonged to a wealthy family with connections in business and financial circles. According to The New York Times, that relationship was much more than a personal story: it functioned as a social calling card of enormous value for Epstein.
Through Obregón, the U.S. financier made contact with several wealthy Spanish families who were in a critical situation. These families had lost large sums of money following the bankruptcy of Drysdale Securities, a U.S. brokerage firm that collapsed leaving funds blocked and hidden in opaque structures: Epstein offered himself, and was accepted, as an intermediary to recover this money.
The order that changed everything
Among those affected by Drysdale’s bankruptcy was Ana Obregón’s own family circle. According to the investigation, it was precisely this first order that allowed Epstein to demonstrate his practical usefulness to this social circle.
The actress did not act as financial advisor or manager, but her closeness and personal trust were key to legitimize Epstein in the eyes of these families. The financier presented himself as someone capable of moving in the intricacies of the international banking system, and that social endorsement was the springboard he needed.
The recovery of money and the birth of the millionaire
To carry out the operation, Epstein turned to Bob Gold, a former federal prosecutor and close associate. For more than a year, the two tracked the missing money through offshore banks and shell companies. Eventually, they located the funds in a bank branch in the Cayman Islands.
According to Gold’s testimony reported by The New York Times, the legal pressure exerted on the bank made it possible to recover the money for the Spanish families. The financial reward Epstein received for this work was enormous, and the newspaper emphasizes that this episode marked the exact moment when Epstein accumulated his first great fortune and went from being a minor financier to becoming a millionaire.
After the success of that operation, Epstein’s reputation changed radically: he came to be perceived as someone capable of “making money appear” that seemed to be lost. This story quickly spread among high economic circles, first in Spain and then internationally.
The relationship with Ana Obregón not only gave him access to his first client, but also provided him with a real-life success story with which to build his image. The New York Times notes that, from that moment on, Epstein began to move freely among large estates and to present himself as a solver of complex financial problems.
Ana Obregón’s public version
Ana Obregón has spoken in the past about Epstein on a personal level. In interviews given years later, she described him as a brilliant, extremely wealthy and attentive man, although she always insisted that there was no deep romantic relationship: “He was the perfect man I never fell in love with,” she said.
In these testimonies, the actress recalled how Epstein accompanied her in her life in New York, facilitating her travels and supporting her while she was studying acting. However, she never publicly linked their relationship with the origin of her fortune.
The New York Times investigation is the first to connect that romance with a concrete and decisive economic benefit for the financier.
A past that takes on new meaning
The report does not accuse Ana Obregón of any crime, but it does modify the role she played in a crucial stage of Epstein’s life. Her personal relationship acted as a catalyst: it opened doors for him, gave him credibility and allowed him to execute the operation that launched him to economic success.
That first great financial coup was the foundation on which Epstein built everything that followed: his entry into Wall Street, his closeness with great tycoons and the network of power that sustained him for decades. Spain and its link with one of its best-known public figures are thus integrated into the story of a rise that, in time, would reveal its darker side.
