In the course of a public appearance to a cathedral in Staffordshire on Monday, King Charles was confronted by a individual who questioned him about Prince Andrew's relationship with convicted sex offender Epstein.
The individual asked how long the monarch had been known about his brother's association with Epstein, and also raised doubts about whether he had asked the authorities to "cover up" for Prince Andrew.
Despite the heckling, there were crowds of well-wishers and cheers for the King, who was in Staffordshire for an engagement.
The Duke of York's associations with Jeffrey Epstein have been under close examination in recent weeks. The prince, who gave up his titles earlier this month, has strongly denied any wrongdoing.
"How long have you known about Prince Andrew and Jeffrey Epstein? Did you request the authorities to cover up for Andrew?"
The monarch remained silent but carried on greeting supporters, some of whom shouted "Long live the King". One fan can be overheard requesting him for a embrace.
Another woman outside the venue was also observed telling the heckler to "leave" and to "be quiet".
The scandal over the Duke of York's connections to Epstein has been brought back into focus by misconduct claims repeated in Virginia Giuffre's recently released book.
In the memoir, the accuser says she had sexual encounters with the royal on three separate occasions, including one instance with Epstein and "eight other young girls"
Andrew, who agreed to a out-of-court agreement with Ms Giuffre in 2022, has repeatedly denied any misconduct. In a previous interview, he told BBC Newsnight he did not recall meeting Ms Giuffre "at all", and that they "did not have any sort of sexual contact."
But recently, fresh questions have been raised about how he is able to fund his way of life despite not being a working royal.
The disclosure that he has only ever paid a token annual rent on his Windsor mansion has intensified the examination over his living arrangements - even though he made large payments initially, including for improvements.
The political party said he should be called in before members of parliament to give evidence about his rental agreement of his lodge.
But last week, the authorities declined to give parliamentarians time to discuss the royal's titles or his home, despite increasing calls for scrutiny.
The royal household has not issued a statement on whether the Duke of York might move out of his home - or where he might go.
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