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American Focus > Blog > Celebrities > The One Reason Andrew Windsor Kept Going Back to Epstein Revealed
Celebrities

The One Reason Andrew Windsor Kept Going Back to Epstein Revealed

Last updated: February 6, 2026 3:15 pm
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The One Reason Andrew Windsor Kept Going Back to Epstein Revealed
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Andrew Windsor’s ties to Jeffrey Epstein have once again come under scrutiny with the release of new Justice Department files, shedding light on the Duke of York’s desperate financial situation that led him back into the orbit of the disgraced pedophile. According to RadarOnline.com, the documents reveal how Andrew found himself entangled with Epstein once more during the financial collapse of his ex-wife, Sarah Ferguson, around 2010.

The files detail how Andrew sought Epstein’s help to cover unpaid bills linked to Ferguson as creditors closed in and the risk of public embarrassment loomed large. At the center of the crisis was Johnny O’Sullivan, Ferguson’s personal assistant of 18 years, who was owed a substantial sum in wages and education fees after the former duchess went bankrupt in the United States.

In a bid to settle the debts, Andrew and advisers from Buckingham Palace concluded that Epstein could be the solution. The simplest way out of the crisis was for Epstein to pay off O’Sullivan, as revealed in the three million documents on Epstein released by the U.S. justice department. This led to the infamous photograph of Andrew and Epstein walking through Central Park in December 2010, a moment that would later haunt the royal with allegations of poor judgment and questionable associations.

Epstein agreed to intervene, albeit with disdain for O’Sullivan, whom he described as a “little s—” for pursuing the money. In an email to Andrew dated February 28, 2011, Epstein confirmed a deal had been struck, expressing his lack of trust in O’Sullivan. The focus was on cash flow and damage control for Andrew, with Epstein serving as a means to an end rather than a friend.

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The documents also exposed the dire financial situation Ferguson found herself in, owing nearly $7 million to creditors by late 2010. Creditors were offered a fraction of what they were owed, and O’Sullivan received a meager settlement offer far below his outstanding amount. Epstein was made aware of the situation and the potential threat of O’Sullivan going public with damaging information if left unpaid.

O’Sullivan continued to press for full payment, particularly his Columbia University MBA debt, highlighting the lack of progress despite concerted efforts. The attempt to quietly resolve a financial issue through Epstein only deepened the scandal surrounding Andrew, eventually leading to his downfall.

The newly released files make it clear that money, not friendship, was the driving force behind Andrew’s repeated returns to Epstein. The financial arrangement with Epstein not only failed to resolve the crisis but also exacerbated the scandal that would later have severe consequences for the royal.

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