Sarah Ferguson asked Epstein for bankruptcy advice while he was in jail, emails suggest

Sarah Ferguson asked Jeffrey Epstein for advice in dealing with her £6m debt pile, while he was still in jail for soliciting prostitution from a minor.

Emails recently released by the Department of Justice appear to show the desperate measures Ferguson considered to rescue her finances, from bailouts funded by two billionaires to selling her jewellery.

Ferguson found the experience "so so demoralising" and said she was "about to freak with exhaustion", the emails suggest. "Death is easier than this," she appears to have said.

Ferguson did not reply to a request for comment.

Ferguson was still Duchess of York in 2009, but divorced from Andrew Mountbatten-Windsor. A lucrative deal to promote Weight Watchers had just come to an end.

The emails highlight what a desperate financial position she was in at the time, and how it left her vulnerable to manipulation by anyone with the means to help her deal with her finances - most notably, Epstein himself.

Epstein apparently discussed Ferguson's situation in a long correspondence with David Stern, a London-based German businessman with extensive China connections. Stern had close links with the Royal Family, but appears to call Epstein "boss" in the emails.

He apparently warned Epstein that Ferguson was in the "middle east" where "chances are she is with people who take advantage of her once again".

Stern and Epstein discuss their approach to Ferguson in remarkably disrespectful tones. In one, Epstein apparently writes that September "its time to be serious. be very tough. like a girlfriend that has cheated."

"Treating her as cheating girlfriend is working," Stern seems to reply shortly afterwards.

Epstein was near the end of his sentence at Palm Beach County jail when Ferguson appears to write to him on 13 July 2009.

"Jeffrey, you are true friend," the email says, and asks for his advice on a remarkable offer from John Caudwell, the British billionaire founder of the mobile phone shop Phones4You, to clear her mounting debt burden.

"He has decided he would like to give me 10 million pounds, but for that he wants 50% of my net profits for life."

Epstein apparently replies: "Have him put the deal in writing."

A spokesperson for Caudwell confirmed that he did "discuss a potential business transaction to help clear her debt", but had no idea she was talking to Epstein, and had no contact with him. The deal was never signed.

The week after Epstein was released, the emails show he apparently told Stern that Ferguson needed to get together details of who she owed money to. "She is a woman with no sense of this whatsoevr [sic]," he writes.

The following month, Stern appears to write: "fergie data collection remains slow and unbelievable what it takes to get basic info."

A long email to Stern, signed "Sarah", lists all the projects she was working on, from books to TV, and demands to know who was keeping track of them and collecting the money she was owed.

"It is imperative I employ a CEO or Manager who sorts all of my life out. The warts and all, all the little tiny boring jobs like cleaning up my royalty statements from all my book deals. I have written 26 books. There must be revenue there," the email apparently says.

"I know we do not need to go Bankrupt as the revenues are with [sic] and can be generated. But I am one person, and I cannot be my accountant, brand police manager, personal assistant, TV manager, etc etc it is simply not possible," she continues.

Stern apparently forwards it to Epstein with the words, "Don't waste time reading the below, just scroll through it for a flavour of the mess".

Ferguson seemed to be struggling with the process too. In September, she apparently confides to Stern: "Just spoke to Jeffrey. I told him we are working on everything. Wow it is so so demoralising. I am about to freak with exhaustion."

One proposal apparently put forward by Stern would see a chief executive hired to run Ferguson's business affairs. She would be paid a $200,000 salary, and any spending over $1,000 would need to be signed off by Epstein. He says they would need to own at least 30% of the business to be "remotely worthwhile".

In September, Stern apparently writes to Epstein that Ferguson asked him to meet someone she said was a Russian billionaire, Vladimir. She couldn't remember his surname.

"She thinks he will finance everything in case you will not" - possibly suggesting that Epstein was considering a financial contribution to Ferguson's financial rescue.

This turns out to be Vladimir Zemtsov, who Stern apparently describes as "substantial, pragmatic, and for russian standards discreet", and willing to bail Ferguson out if a "hired professional firm believes that the revenue side is more than the debt". There is no sign the conversation went further than this.

Together Epstein, Stern and Ferguson appear to be making detailed preparations for a personal bankruptcy. Stern apparently sends Epstein an email headed "F liabilities". Ferguson was often referred to by a single initial in their correspondence.

Stern says he had attached a liability statement - a document often drawn up in a bankruptcy process, where a person compiles a list of all the money they owe.

In October 2009, Stern appears to have reported on a meeting with "F". "Met [redacted] yesterday with her girls. As you predicted, she made statements such as: 'I surrender, I am ready to die, death is easier than this' My mission continues."

Ferguson continued to chase brand endorsements and other moneymaking deals, including tie-ups with the US retail giant Target and the cruise line Cunard.

The Target discussions seem positive, but Epstein notes: "i see little revenue for quite a while."

Stern apparently complains that Ferguson told him Cunard would pay her a million dollars a year to take four trips on their ships, but notes that the president of Cunard said "something totally different" – he "enjoyed meeting" the Duchess but there were "no specific opportunities".

The following year, the money worries still seemed to be continuing. An email apparently from Stern said: "F asked me where she can sell her jewellery. I told her I have never done this and its not my field of expertise..."

In January, Stern suggests that Andrew might be making a contribution: "Just received this mail from Eric the lawyer: I met w PA [Prince Andrew]. He's putting up 1mm."

In April, Stern notes that she was being taken to court by the law firm Davenport Lyons - a case which was widely reported in the time.

"F. is being sued, PA [Prince Andrew] agreed to pay. Strange things going on. I feel it may blow up soon," Stern apparently told Epstein in May 2010.

It was a strangely prophetic remark. A few weeks later Ferguson was entrapped by the News of the World newspaper, videoed apparently offering to sell access to Andrew for £500,000.

In the end Ferguson did not declare bankruptcy.

It is not clear if all her debts were paid in full - one of the people she owed money to, a former personal assistant, received around half his claim in 2011, paid indirectly by Andrew, the emails suggest.

An email from the accountancy firm PwC said that creditors were "informally" offered 25p in the pound.

And in September 2010, Ferguson agreed a deal for a six-part series, 'Finding Sarah' with Oprah Winfrey's TV network, which helped to ease her financial burden.

Vladimir Zemtsov and David Stern did not respond to a request for comment. Andrew has consistently denied any wrongdoing.