According to reports, the former Duchess of York, now 66, responded to a question from Epstein with a deeply unsettling remark involving Princess Eugenie.
In an email from March 2010 reviewed by PEOPLE Magazine, Epstein is said to have asked Ferguson about potentially traveling to New York.
Her alleged reply read: “Not sure yet. Just waiting for Eugenie to come back from a sh*gging weekend!!”
At the time, Eugenie was 19 years old and spending time with her then-boyfriend, Jack Brooksbank, as she approached her 20th birthday, according to The Mirror.
The exchange reportedly occurred after Epstein had already been convicted and jailed for a sex offense involving a minor.
In June 2008, Epstein pleaded guilty to charges of solicitation of prostitution and solicitation of prostitution with a minor under the age of 18.
He was sentenced to 18 months in a minimum-security prison and was released in 2009.
Further Emails Reveal Warm Language
As reported by the BBC, another email exchange from 2009 allegedly shows Ferguson writing warmly to Epstein following a lunch meeting.
“In just one week, after your lunch, it seems the energy has lifted,” she wrote.