Sarah Ferguson appeared to plead with Jeffrey Epstein to hire her as a house assistant because she "desperately" needed money.
The former Duchess of York allegedly emailed the late convicted paedophile in May 2010, asking about the role, just three months before it emerged she was doing "everything she can" to avoid bankruptcy.
Emails inside the more than three million documents released by the US Department of Justice appeared to show Ms Ferguson writing: "But why I don't understand, don't you just get me to be your House Assistant.
"I am the most capable and desperately need the money. Please Jeffrey think about it."
The former Duchess of York appeared to plead with Jeffrey Epstein to hire her
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Ms Ferguson allegedly continued: "Also had David Stern down for tea yesterday with Andrew he has an update for you."
The email, sent on May 16, 2010, appeared to be followed up by Mr Stern half an hour later, allegedly telling Epstein: "I guess she wants to get involved somehow to get $$."
Mr Stern allegedly acted as a middleman between the former duchess and Epstein, emails appeared to show.
The revelation comes after separate documents relating to Mr Stern and Ms Ferguson appeared to show the pair trying to secure a deal with the former duchess and the luxury cruise liner Cunard in 2009.
Sarah Ferguson appeared to say she is 'the most capable and desperately need the money'
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Bosses at Cunard appeared to dodge Mr Stern's alleged attempts in September 2009, around the time Ms Ferguson's debts were being reported.
The then-president of the luxury cruise line, Peter Shanks, eventually followed up with emails saying that the firm would not pay for these endorsements.
He appeared to say that while Cunard did invite "Insight Speakers" on its luxury voyagers, it did not "provide any form of fee".
Mr Stern allegedly emailed Epstein on October 26, writing: "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."
David Stern appeared to email Epstein about Sarah Ferguson getting 'involved somehow'
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Mr Stern appeared to attach the lengthy response from Mr Shanks, adding: "The Cunard President says something totally different below."
Mr Shanks wrote in his email: "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.
"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."
Sarah Ferguson appeared to have been photographed in the initial release of the Epstein files
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A spokesman for Cunard said: "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."
Around the time, the former duchess admitted to receiving £15,000 from Epstein to pay off her debts.
Separate emails suggest Ms Ferguson sought help from Epstein to set up a business centred on supporting mothers, which appeared to say the former duchess would receive a salary of $250,000 under the plan.
Ms Ferguson has stated in the past her regret with being associated with Epstein, saying: "I would never have anything to do with Jeffrey Epstein ever again. I abhor paedophilia and any sexual abuse of children. It was a gigantic error of judgment."
Being named or pictured in the Epstein files does not show any sign of wrongdoing or misconduct.
GB News has approached Ms Ferguson and Mr Stern for comment on the emails.
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