Emails suggest Sarah Ferguson went after a $1million endorsement deal with a luxury cruise liner while privately begging Jeffrey Epstein to sort out her debts.
Emails, which emerged as part of the more than three million documents released by the US Department of Justice, allegedly show Ms Ferguson pursuing an agreement with Cunard Line in 2009.
The files appear to coincide with the former Duchess of York telling the convicted paedophile that she desperately needed £20,000 to pay her overdue rent.
Emails between David Stern, who allegedly acted as a middleman between the former duchess and Epstein, consistently press Cunard to secure a deal for Ms Ferguson.
Ms Ferguson appeared to go after a $1million endorsement deal with a luxury cruise liner
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Bosses at Cunard appeared to dodge Mr Stern's attempts in September 2009, around the time the Ms Ferguson's debts were being reported.
The then-president of the luxury cruise line, Peter Shanks, eventually followed up with emails saying that the firm would not pay for these endorsements.
He appeared to say that while Cunard did invite "Insight Speakers" on its luxury voyagers, it did not "provide any form of fee".
Mr Stern allegedly emailed Epstein on October 26, writing: "F. stated Cunard Line wants her to travel on their cruises, using this as endorsement and paying her US$ 250k per trip, 4 trips/year = 1m."
Mr Stern appeared to email Epstein regarding the cruise liner's response
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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."
Mr Shanks appeared to send a lengthy response to Mr Stern
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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.
The former duchess appeared to start a year-long effort to launch the company, with its mission to "help amplify the voices of mothers all over the world to tackle some of the tougher issues facing young people and families".
The former duchess has admitted to receiving £15,000 from Epstein to pay off her debts
| GETTYEpstein allegedly would be involved in Ms Ferguson's business, which stands "for integrity, consciousness, morals, etc".
The proposals for the business appeared to be sent after Epstein's 2008 conviction for child sex offences, allegedly stating he would hold a 51 per cent equity in Mother's Army, making him the majority stakeholder.
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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