The late Princess of Wales and the former Duchess of York ended up in very different circumstances after leaving their royal partners

Sarah Ferguson; Princess Diana.Credit : Ron Galella/Ron Galella Collection via Getty; Jayne Fincher/Princess Diana Archive/Getty

Sarah Ferguson and Princess Diana found 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 future King Charles in 1996. Meanwhile, Ferguson’s settlement after ending her marriage to the former Prince Andrew the same year was estimated at around $475,000.

In a 2010 interview 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 to Queen 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 of The Windsor Legacy, tells PEOPLE for this week’s cover story. “She was desperate for money.”

Sarah Fergusona nd Princess Diana in June 1987.Tim Graham Photo Library via Getty

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 the News 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.

Sarah Ferguson in November 2004.ShowBizIreland/Getty

Ferguson’s money troubles were also apparent in her relationship with Jeffrey Epstein and a subject that the pair seemingly communicated about on numerous occasions, as seen in the recently released Epstein files from 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 for his help with brand deals, asks him to fund her travels and praises his “generosity and kindness.”

Sarah Ferguson; Jeffrey Epstein. Mike Marsland/WireImage; Rick Friedman/Corbis via Getty

Ferguson has been keeping a low public profile following Andrew’s arrest on Feb. 19 on suspicion of misconduct in public office. The Thames Valley Police is investigating claims that the disgraced duke shared confidential information with Epstein while serving as a British trade envoy.

King Charles stripped his brother of his royal titles in 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.

“She always thinks she can bounce back,” the insider says. “But this isn’t something that can blow over.”