In 2009, Sarah Ferguson, then the Duchess of York, reached out to Jeffrey Epstein, who was serving time for soliciting prostitution from a minor, seeking his advice on managing her significant debt of £6m.

Recently released emails by the Department of Justice reveal the extent of Ferguson's financial struggles, including her consideration of bailouts from billionaires and the sale of her jewelry to alleviate her debt.

The emails suggest that Ferguson found her financial situation "so demoralising" that she felt "about to freak with exhaustion", even stating that "death is easier than this" in one message.

Ferguson did not respond to a request for comment on the matter.

At the time, Ferguson was no longer married to Andrew Mountbatten-Windsor, but still held the title of Duchess of York, and had recently seen the end of a lucrative deal with Weight Watchers.

The emails highlight the desperate financial position Ferguson was in, making her vulnerable to manipulation by those who could assist her, including Epstein.

Epstein discussed Ferguson's financial situation with David Stern, a London-based businessman, in a series of emails, with Stern referring to Epstein as "boss".

Stern warned Epstein that Ferguson was in a vulnerable position, surrounded by people who might take advantage of her, while she was in the Middle East.

The tone of the emails between Epstein and Stern is remarkably dismissive, with Epstein suggesting that Ferguson be treated "like a girlfriend that has cheated" in order to manage her finances effectively.

Stern appears to agree with this approach, stating that treating her in this manner was "working".

On July 13, 2009, Ferguson reached out to Epstein, who was nearing the end of his sentence, seeking his advice on a proposal from British billionaire John Caudwell to clear her debt.

The proposal involved Caudwell offering Ferguson £10m in exchange for 50% of her net profits for life, which Epstein advised her to have put in writing.

A spokesperson for Caudwell confirmed that discussions had taken place, but stated that he was unaware of Ferguson's communication with Epstein and had no direct contact with him.

The deal ultimately did not come to fruition, and the emails show Epstein advising Ferguson to gather detailed information about her debts after his release from jail.

In the following month, Stern expressed frustration at the slow pace of collecting data on Ferguson's finances, describing it as "unbelievable" and "slow".

An email from "Sarah" lists her various projects, including books and TV appearances, and demands to know who was managing her finances and collecting the money she was owed.

The email emphasizes the need for a CEO or manager to oversee her finances and sort out the "warts and all" of her business dealings.

Stern forwarded the email to Epstein, describing it as a representation of the "mess" that Ferguson's finances were in.

Ferguson's frustration with her financial situation continued, and in September, she confided in Stern about her conversation with Epstein, stating that she was feeling "demoralised" and "about to freak with exhaustion".

One proposal put forward by Stern involved hiring a chief executive to manage Ferguson's business affairs, with a salary of $200,000 and the requirement that any spending over $1,000 would need to be approved by Epstein.

Epstein would need to own at least 30% of the business for the arrangement to be "remotely worthwhile", according to Stern.

In September, Stern informed Epstein that Ferguson had asked to meet a Russian billionaire, Vladimir, who she believed could finance her financial rescue.

The emails suggest that Epstein was considering a financial contribution to Ferguson's rescue, but it is unclear if this came to fruition.

Stern described Vladimir as "substantial, pragmatic, and for Russian standards discreet", and willing to bail Ferguson out if a professional firm believed her revenue exceeded her debt.

The conversation between Stern and Epstein appears to have been part of preparations for a potential personal bankruptcy, with Stern sending Epstein a document headed "F liabilities".

The document was a liability statement, often used in bankruptcy proceedings, which lists all the money a person owes.

In October 2009, Stern reported on a meeting with Ferguson, stating that she had made comments such as "I surrender, I am ready to die, death is easier than this".

Ferguson continued to pursue brand endorsements and other business deals, including discussions with the US retail giant Target and the cruise line Cunard.

However, Epstein noted that the Target discussions were unlikely to generate significant revenue in the short term.

Stern expressed skepticism about a potential deal with Cunard, stating that the company's president had expressed no interest in a formal agreement.

The following year, Ferguson's financial struggles continued, with Stern suggesting that she sell her jewelry to raise funds.

In January, Stern mentioned that Andrew might be making a contribution to help Ferguson, stating that he had received an email from a lawyer indicating that Andrew would provide £1m.

In April, Stern noted that Ferguson was being taken to court by the law firm Davenport Lyons, a case that was widely reported at the time.

Stern expressed concern that the situation might "blow up soon", and a few weeks later, Ferguson was embroiled in a scandal after being filmed apparently offering to sell access to Andrew for £500,000.

Ultimately, Ferguson did not declare bankruptcy, but it is unclear if all her debts were paid in full.

One of her creditors, a former personal assistant, received around half of their claim in 2011, paid indirectly by Andrew, according to the emails.

An email from the accountancy firm PwC stated that creditors were informally offered 25p in the pound, suggesting that Ferguson's debts were not fully paid.

The outcome of Ferguson's financial struggles is not entirely clear, but it appears that she was able to avoid bankruptcy.

However, the emails suggest that her financial situation was complex and challenging, and that she relied on the support of others, including Andrew and potential investors, to manage her debts.

The story highlights the difficulties faced by Ferguson in managing her finances and the challenges she encountered in her efforts to recover from her debt.

In September 2010, a six-part series titled 'Finding Sarah' was secured by Ferguson through a deal with Oprah Winfrey's television network, providing her with some financial relief.

Requests for comment from Vladimir Zemtsov and David Stern went unanswered, while Andrew has maintained his position of denying any involvement in wrongdoing.