Newly released Justice Department emails reveal Sarah Ferguson turned to Jeffrey Epstein for help managing a £6m debt mountain while the convicted sex offender was still behind bars for soliciting prostitution from a minor.

The documents lay bare how far Ferguson was willing to go to dig herself out of trouble, from knocking on the doors of wealthy businessmen to contemplating selling her personal jewellery collection.

Ferguson found the experience “so so demoralising” and said she was “about to freak with exhaustion.”

“Death is easier than this,” she appears to have said.

Ferguson was invited to comment via her representatives.

Duchess left exposed by debt crisis

By 2009 Ferguson had divorced Andrew Mountbatten-Windsor but retained her Duchess of York title. The end of a lucrative Weight Watchers deal had left a significant hole in her finances, and with debts spiralling to £6m, she was running out of options.

The emails make clear how Ferguson’s financial vulnerability made her an easy target for those who could offer a lifeline – none more so than Epstein, who manoeuvred himself into the role of her financial guardian.

Epstein’s main point of contact regarding Ferguson was David Stern, a German national operating out of London whose business interests stretched across China and who had developed strong relationships within royal circles. Stern appears to address Epstein as “boss” throughout the emails.

Stern apparently warned Epstein that Ferguson had headed to the “middle east” where “chances are she is with people who take advantage of her once again.”

The tone of exchanges between the two men regarding Ferguson was contemptuous throughout. Epstein apparently wrote that come September “its time to be serious. be very tough. like a girlfriend that has cheated.”

“Treating her as cheating girlfriend is working,” came Stern’s apparent reply.

Billionaire’s extraordinary offer

Ferguson appears to have contacted Epstein directly on 13 July 2009 as he approached the end of his Palm Beach County jail term, reports the BBC.

“Jeffrey, you are true friend,” the email reads, before seeking his guidance on a remarkable proposal from Phones4You founder John Caudwell, who had offered to clear her entire 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 he did “discuss a potential business transaction to help clear her debt”, but said he was completely unaware Ferguson was simultaneously consulting Epstein and had no dealings with him whatsoever. Nothing was ever signed.

Epstein takes control

Back on the outside, Epstein immediately set about taking charge, telling Stern to get Ferguson to identify every creditor she had. “She is a woman with no sense of this whatsoevr [sic],” he wrote.

Stern’s frustration was evident the following month: “fergie data collection remains slow and unbelievable what it takes to get basic info.”

Ferguson herself sent Stern a lengthy email, signed “Sarah”, setting out her various income streams across books and television and demanding to know who was managing them.

“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 passed it to Epstein with a curt note: “Don’t waste time reading the below, just scroll through it for a flavour of the mess.”

The toll on Ferguson was clear. She apparently confided to Stern that September: “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.”

Strict financial controls proposed

Stern proposed installing a chief executive to take charge of Ferguson’s business dealings. Ferguson would receive a $200,000 yearly salary under the arrangement, but Epstein would hold ultimate authority over any purchase exceeding $1,000. A minimum 30% ownership stake would be required to make the whole thing “remotely worthwhile.”

Stern also told Epstein that Ferguson had asked him to meet someone she described as a Russian billionaire going by the name Vladimir – she had no recollection of his last name, states the report.

“She thinks he will finance everything in case you will not” – a line that hints Epstein himself may have been contemplating putting money into Ferguson’s rescue package.

Vladimir Zemtsov was subsequently identified as the mystery Russian. Stern apparently vouched for him as “substantial, pragmatic, and for russian standards discreet”, adding that he was prepared to step in financially if a “hired professional firm believes that the revenue side is more than the debt”. Nothing came of it.

Bankruptcy looms

All three appear to have moved beyond discussion into active preparation for insolvency proceedings. Stern sent Epstein a message headed “F liabilities” – the single initial being their habitual way of referring to Ferguson – with an attached liability statement of the kind typically drawn up when someone is on the verge of declaring bankruptcy.

Stern reported back to Epstein in October 2009 after spending time with Ferguson. “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 refused to let the chaos derail her efforts to make money, continuing to pursue commercial tie-ups with American retailer Target and cruise line Cunard.

While discussions with Target showed some promise, Epstein threw cold water on the prospects, noting: “i see little revenue for quite a while.”

Ferguson apparently told Stern that Cunard had committed to paying her a million dollars a year in exchange for four trips aboard their ships. When Stern checked, the cruise line’s president gave an entirely different account of their meeting with the Duchess, saying there were “no specific opportunities” despite having “enjoyed meeting” her.

Andrew steps in

Word reached Stern in January that Andrew may have been putting his hand in his pocket. He wrote: “Just received this mail from Eric the lawyer: I met w PA [Prince Andrew]. He’s putting up 1mm.”

April brought fresh trouble when Ferguson found herself in court over a claim brought by Davenport Lyons, a case that generated significant media coverage.

“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.

Stern could not have known how quickly events would prove him right. Ferguson was soon caught in a News of the World sting operation, captured on film apparently offering to sell access to Andrew for £500,000.

Crisis eventually resolved

Ferguson never filed for bankruptcy.

It remains unclear whether Ferguson’s creditors were ever paid in full. One former member of her personal staff received around half the amount owed to him in 2011, with the money apparently coming from Andrew via an indirect route.

An email from PwC revealed that creditors had been quietly approached with an “informal” offer of just 25p in the pound.

A deal struck in September 2010 for a six-part series called Finding Sarah, broadcast on Oprah Winfrey’s television network, ultimately gave her finances a much-needed boost.

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