Sarah Ferguson was "desperate" for money after her divorce from the former Prince Andrew
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While Princess Diana reportedly received $22 million in her split from then-Prince Charles, Ferguson received an estimated $475,000
Ferguson's money troubles involved a cash-for-access scandal and financial entanglements with Jeffrey Epstein
Sarah FergusonandPrincess Dianafound themselves in very different financial situations after divorcing their royal husbands.
Diana reportedly received a $22 million settlement as well as an annual allowance after divorcing the futureKing Charlesin 1996. Meanwhile, Ferguson's settlement after ending her marriage to the formerPrince Andrewthe same year was estimated at around $475,000.
In a 2010interview with Oprah Winfrey, Ferguson hinted that she accepted less money in hopes of a more cordial future relationship with the royals. "I chose friendship with the family. I wanted friendship with the boss," she said, referring toQueen Elizabeth.
However, the sum made it difficult for Ferguson to maintain her lifestyle following the divorce.
"She was introduced to this lifestyle and kept living it," Robert Jobson, author ofThe Windsor Legacy,tells PEOPLE forthis week's cover story. "She was desperate for money."
Ferguson became a spokesperson for Weight Watchers, wrote a memoir and a series of children's books, created a dinnerware line with Wedgwood China and more. While her ventures varied, the strategy remained the same: proximity for profit.
Her financial needs led to a scandal in May 2010, when she was caught on camera accepting cash in exchange for access to Andrew and the royal family. However, the man offering the money turned out to be an undercover reporter for theNews of the World.
"I was so out of control with desperation where I'd reached a point of no return," Ferguson told Winfrey a month after the video went public. She said that she'd done the deal because a friend "needed $38,000 urgently," but she asked for more money for herself.
The former Duchess of York said at the time that she'd gone into debt "trying to keep Sarah going," and was facing a "huge uphill battle" trying to get herself financially solvent.
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Ferguson's money troubles were also apparent in her relationship withJeffrey Epsteinand a subject that the pair seemingly communicated about on numerous occasions, as seen in therecently released Epstein filesfrom the Department of Justice.
In one email exchange from a certain "Sarah"from May 2010, the same month she was caught in the cash-for-access sting, Ferguson appears to plead with Epstein for a job.
"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," Ferguson seemingly wrote, according to the email. "Please Jeffrey think about it."
In others, she appears to thank him forhis help with brand deals, asks him tofund her travelsand praises his "generosity and kindness."
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Ferguson has been keeping a low public profile followingAndrew's arrest on Feb. 19on suspicion of misconduct in public office. The Thames Valley Police is investigating claims that the disgraced dukeshared confidential informationwith Epstein while serving as a British trade envoy.
King Charlesstripped his brother of his royal titlesin October, and Andrew and Ferguson were made to give up the lease on their longtime Windsor home,Royal Lodge.
A source close to Ferguson tells PEOPLE that, despite overcoming past scandals to remain in the royal orbit, the Epstein connection may end up being the final straw for the former Duchess of York.
"Shealways thinks she can bounce back," the insider says. "But this isn't something that can blow over."
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