Andrew Windsor’s secret reason for repeatedly reconnecting with Jeffrey Epstein has finally come into focus — and newly released Justice Department files point to one thing: cash. Lots of it, and fast.
According to the documents, the former Duke of York circled back to Epstein in 2010 as his ex-wife Sarah Ferguson’s finances imploded, dragging him into a crisis that would eventually help destroy his royal reputation.
Inside Andrew and Fergie’s Money Meltdown
Ferguson was drowning in nearly $7 million of debt while creditors closed in. At the center of the storm was longtime personal assistant Johnny O’Sullivan, who was owed more than $126,000 in unpaid wages and education fees.
Emails in the Epstein Files show Andrew’s team scrambling for a solution — and concluding that the simplest option was to ask Epstein to quietly pay off O’Sullivan before the story went public.
That trip Andrew took to New York in December 2010, the one that produced the now-infamous Central Park stroll? It wasn’t a social call. It was a bailout mission.
Epstein Steps In — With Conditions
Epstein agreed to help, but his emails reveal how he really felt about taking on the problem. In one message to Andrew, he blasted O’Sullivan as a “little s—” and warned that if the payment ever leaked, it would look like a payoff.
Still, he promised that O’Sullivan had accepted a reduced deal: “He said he would take 60k in wages, pay tax, and be done.”
A former palace aide summed up Andrew’s motives bluntly: this was about cash flow and keeping a potential scandal buried.
Ferguson’s Debt Spiral Gets Worse
Behind the scenes, Ferguson’s situation was even more dire. Creditors were being offered just 25 pence on the pound, and O’Sullivan was told he’d have to settle for a fraction of what he was owed.
One internal message warned that if the assistant didn’t get paid soon, he was likely to go public with stories from nearly two decades inside the duchess’s inner circle.
The emails show Epstein was looped in on the brewing trouble weeks before Andrew’s New York visit — and that he knew exactly how fragile the situation was.
The Assistant Who Refused to Stay Quiet
Despite months of promises, O’Sullivan repeatedly pressed Andrew’s office and Epstein’s aides about the missing payments, especially his Columbia University MBA debt.
On February 7, 2011, he wrote: “Both the Duke and Duchess have asked what’s happening but I don’t have any information to share with them.”
Ten days later, he escalated again: “I still remain unpaid… This is completely unacceptable to me.”
The tension behind the scenes only grew — and years later, the irony couldn’t be clearer.
Andrew tried to quietly solve a financial mess by leaning on Epstein. Instead, it became one more thread in the scandal that ended his public life.
A legal insider put it simply: “The attempt to avoid embarrassment created a far bigger one.
Royal Schitt! Nothing new here!