EXCLUSIVE: King Charles' 'Most Savage Order Yet' to Andrew Windsor Revealed — 'Wipe the Smile Off Your Face!'
King Charles continues to deal with the fallout of his younger brother's connection to Jeffrey Epstein.
Dec. 28 2025, Published 1:00 p.m. ET
The commoner formerly known as Prince Andrew has been told in unusually blunt terms that any remaining financial support from his brother King Charles depends on one thing – keeping a low profile and, above all, stopping public displays that deepen the family's embarrassment.
RadarOnline.com can reveal the warning follows the release of a photograph from newly published Epstein files showing Andrew Windsor, 65, grinning broadly while sprawled across the laps of five women inside Sandringham House.
A Brutal Ultimatum from the King
Andrew Windsor is seen grinning in the Sandringham saloon in a released photo, enraging his older brother.
The image, released by the U.S. Department of Justice as part of a tranche of material linked to the late financier Jeffrey Epstein, has reignited scrutiny of Windsor's past associations with pedophile s-- trafficker Epstein.
Taken in the saloon room at Sandringham – a space used by the Royal Family at Christmas and for the monarch's annual broadcast – the photograph shows the former duke in formalwear, smiling, with Epstein's now-jailed pimp Ghislaine Maxwell standing behind him.
Windsor stepped back from royal duties in 2019 and settled a U.S. civil case brought by one of Epstein's most high-profile trafficking victims, Virginia Giuffre, in 2022 without admitting wrongdoing, but the resurfaced image has already sharpened the massive tensions within the family.
According to palace aides, Charles, 77, was furious Windsor appeared grinning and carefree in a setting so closely associated with the monarchy in the photo from the Epstein files – leading to a brutal ultimatum being slapped on the disgraced ex-duke by his older brother.
'Wipe That Smile Off your Face'
Insiders claim King Charles warned Andrew Windsor to look contrite or risk lose royal financial support.
A palace source said: "The message from Charles now is stark after he saw the Epstein files photo of him smiling while surrounded by women – if Andrew expects his living arrangements and security costs to keep being covered by The Firm, he needs to show some contrition. Smiling for the camera, especially in that context, is not acceptable. Charles' ultimatum to Andrew has basically amounted to, 'Wipe that smile off your face.'
"Charles has told him he must look downcast, humble, and apologetic any time he steps outside of royal residences, and there is a chance he may be photographed."
"He does not want pictures out there of Andrew smiling as if he has nothing to be apologetic for or ashamed. It is perhaps Charles' most brutal ultimatum to Andrew yet," the insider added.
The Sandringham photo has reopened wounds Charles wanted buried, a source claimed.
The same source added the savage instruction was framed as a condition rather than advice.
"There is a palpable sense that Charles' patience has finally run out and that funding is not unconditional," another said. The setting of the photograph that has so enraged Charles has compounded the anger.
The saloon room at Sandringham, on the monarch's private Norfolk estate, is where Charles, Prince William, 43, and Catherine, Princess of Wales, also 43, traditionally gather with family members during the festive holidays.
A former royal aide said the symbolism matters "hugely."
They said, "This is a room loaded with history and family meaning. Seeing Andrew play up for the camera there has been deeply upsetting for the King."
Reputational Damage and the Firm's Future
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King Charles ordered Andrew Windsor to drop the smiles and show humility in public.
The image is believed to date from December 2000, when Windsor – who has now been stripped of his royal titles by Charles over his long-standing links to Epstein – hosted a birthday gathering for Maxwell, now 63, who is serving a 20-year prison sentence in the U.S. for sex trafficking offenses connected to Epstein.
Epstein, who died in a New York jail aged 66 in 2019 from an apparent suicide, had been a guest of the former Prince Andrew at Sandringham and other royal residences, including Balmoral.
Windsor has consistently denied any knowledge of Epstein's crimes and denies Giuffre's allegation she was trafficked to have sex with him when she was 17.
Those close to the King say the latest fallout has revived concerns about reputational damage at a moment when the monarchy is trying to project stability.
"Charles is acutely aware that every new image or document drags the institution back into a scandal it cannot control," another source claimed. "He believes Andrew does not grasp how his demeanor feeds public anger."
Since his latest Epstein disgrace, Windsor has been spotted riding his horse near Windsor. An insider said, "The King feels he has done all he reasonably can.
"What remains is a simple bargain – discretion and humility in public from Andrew – including not grinning in public as if he has nothing to worry about – in exchange for continued support."
