Newly released correspondence from the US Department of Justice appears to shed fresh light on why Andrew Mountbatten-Windsor travelled to New York in December 2010 to meet Jeffrey Epstein, the disgraced financier who had already served time for sex offences.
The timing of the emails appear to suggest that Andrew, then still the Duke of York, flew to Manhattan specifically to request that Epstein settle an outstanding debt owed by his former wife Sarah Ferguson.
At the time, Ms Ferguson was facing bankruptcy in the United States, and the publication of these documents demonstrates just how desperate the family's financial situation had become.
The meeting between the two men would prove catastrophic for the then-prince's reputation, eventually resulting in him being stripped of his royal titles, abandoned by charitable organisations, and forced to leave his residence.
Newly released correspondence from the US Department of Justice appears to shed fresh light on why Andrew Mountbatten-Windsor travelled to New York in December 2010 to meet Jeffrey Epstein, the disgraced financier who had already served time for sex offences.
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The debt at the centre of this financial crisis was owed to Johnny O'Sullivan, who had served as Ms Ferguson's personal assistant for nearly two decades.
Mr O'Sullivan was due $126,721, a sum comprising unpaid wages and tuition fees for an MBA programme at Columbia University that Ms Ferguson had committed to funding.
Following Ms Ferguson's bankruptcy in the United States in 2010, her former employee found himself among the creditors seeking payment.
The scale of what was owed to Mr O'Sullivan, combined with his lengthy service to the then-Duchess of York, made him a particularly problematic creditor for the royal household.
His intimate knowledge of Ms Ferguson's affairs over 18 years of employment meant that any dispute risked becoming public in a damaging way.
Following Ms Ferguson's bankruptcy in the United States in 2010, her former employee found himself among the creditors seeking payment.
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It appears to be this outstanding obligation that prompted the then-Duke of York to seek assistance from Epstein in settling his ex-wife's affairs.
On 5 December 2010, while still serving as a UK trade envoy, Andrew was photographed alongside Epstein as the pair walked through Central Park in Manhattan.
This image of the two men engaged in conversation would cast an enduring shadow over Andrew Mountbatten-Windsor's public standing.
The newly published emails now suggest that this fateful Central Park encounter may have been connected to resolving Ms Ferguson's financial obligations.
Ms Ferguson's financial difficulties extended far beyond the debt to her former assistant.
The Epstein files reveal the approach taken to manage this mountain of debt.
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By late 2010, she owed as much as £5m to various creditors, including substantial legal fees in the United States.
Her spending habits had attracted criticism over the years, while a succession of business ventures had failed to generate sustainable income.
The Epstein files reveal the approach taken to manage this mountain of debt.
Creditors were presented with settlement offers amounting to just a quarter of what they were owed, described in the documents as "25p in the pound".
Mr O'Sullivan received an initial proposal of $31,680, presented as a final settlement despite being nearly $100,000 less than his entitlement.
This offer was sent to him on 7 January 2011 as a formal document marked "without prejudice and in full and final settlement".
The personal assistant rejected this drastically reduced figure, insisting on better terms.
Epstein agreed to intervene in the matter, though the negotiations proved protracted and contentious.
The financier was first informed of the problem on 23 November 2010, when an email forwarded to him noted that while most creditors had accepted reduced settlement terms, there remained "a fly in the ointment".
Despite his willingness to assist, Epstein expressed contempt for Mr O'Sullivan in his communications.
In an email to the then-Duke of York dated 28 February 2011, the financier confirmed that a deal had been reached, with Mr O'Sullivan accepting $60,000 rather than the full amount owed.
Epstein wrote: "He said he would take 60k in wages, pay tax and be done.. I don't trust him at all, and a payment from me at the moment if disclosed to the press would look like a payoff for the little s***."
The emails suggest the personal assistant had ultimately accepted less than half of his original entitlement.
Andrew Mountbatten-Windsor has consistently and strenuously denied wrongdoing in connection with Epstein and being named or pictured in the files does not imply wrongdoing.