Newly surfaced files reveal the Duchess of York’s unexpected financial entanglements with Jeffrey Epstein, hinting at a complex web of desperation and ambition.

Ferguson approached the cruise operator hoping to land a deal (Image: Getty)

Jeffrey Epstein’s newly available files reveal the Duchess of York was chasing a lucrative Cunard agreement in 2009 while leaning on the sex offender for emergency cash.

Ferguson approached the cruise operator hoping to land a deal she believed would net her a quarter of a million dollars per voyage, with four annual sailings potentially worth $1million.

The push for a commercial partnership coincided with her plea to Epstein for £20,000 to settle outstanding rent bills.

Intermediary worked to broker cruise arrangement

Royal circles insider David Stern acted as middleman between Ferguson and the disgraced financier, making multiple approaches to Cunard on the Duchess’s behalf.

The shipping company’s leadership appeared to stall when Stern made contact in September 2009, a period when newspapers were running regular stories about Ferguson’s finances.

Cunard’s then-chief Peter Shanks took until late October to respond, writing that while he had “enjoyed meeting” Ms Ferguson, the firm didn’t operate on a paid endorsement model.

Shanks clarified that Cunard’s practice involved bringing “Insight Speakers” aboard its voyages, but compensation was limited to accommodation and transport rather than cash payments.

Confusion emerged over payment expectations

An October 26 email from Stern to Epstein outlined the conflicting accounts: “F. stated Cunard Line wants her to travel on their cruises, using this as endorsement and paying her US$ 250k per trip, 4 trips/year = 1m.”

But added: “The Cunard President says something totally different as below.”

Shanks’s full reply, which Stern forwarded, made clear no concrete proposals existed for Ferguson, reports the Daily Mail.

“I think the challenge is that our modus operandi is that we provide the stateroom and any travel arrangements, however we do not provide any form of fee for our Insight Speakers,” he said in the email.

The now retired Mr Shanks added: “As I mentioned when meeting with the Duchess if we were able to find a third party…..then that would be a great opportunity as they could provide the necessary funding.

“The trick of course in the current marketplace is finding such a third-party benefactor.”

Cunard runs luxury ships on world tours stopping at ports across the Mediterranean and Caribbean.

A spokesperson at Cunard told the Mail: “Our former President and Managing Director accurately reflected Cunard’s position in 2009 and no commercial opportunities for Sarah Ferguson were ever made then or since.”

Deal talks followed desperate rent appeal

Ferguson’s pursuit of the cruise partnership came shortly after she’d contacted Epstein with an urgent message stating she “urgently needed 20,000 pounds for rent today”.

Correspondence shows the Duchess routinely turned to the convicted paedophile for monetary guidance and loans, contradicting her public persona as an accomplished businesswoman and charitable figure.

She’s publicly acknowledged accepting £15,000 from Epstein to clear debts, though the released files point to substantially larger borrowing.

January 2010 correspondence shows Ferguson requested up to $100,000 for “small bills” while Epstein served house arrest for his child sex abuse conviction.

Separate correspondence reveals the late billionaire—who died in jail in 2019 while awaiting trial on sex trafficking charges—told acquaintances he’d been Ferguson’s financial backer for a decade and a half.

Several major charitable organisations cut their connections with Ferguson last year after September-released emails demonstrated her ongoing association with the late sex criminal.

April 2011 correspondence captured Ferguson describing Epstein as a “steadfast, generous and supreme friend” and “humbly apologised” for publicly disowning him under pressure.

A representative explained at the time that Ferguson acted following a “chilling” telephone threat from Epstein about legal action.

Representative of Sarah Ferguson have been invited to comment via email.