Prince Andrew's Worst Moments That Left Royal Fans Cringing

Few royal stories have unraveled as disastrously in public as Prince Andrew's has. Once lauded as a favorite son of the monarch — complete with naval honors and signature royal charisma — the Duke of York has developed such a problematic public image over the years that the possibility of any redemption seems difficult for him. The fall his reputation has taken since he assumed his position within the British monarchy decades ago has been a culmination of not just very prolonged serious scandals, but also momentary cringe-worthy incidents that have painted him as somewhat of a royal caricature. 

Summing up the central theme of Andrew's public legacy in one line, veteran journalist Peter Allen told the BBC: "He's been afforded every type of privilege, all his life, while displaying very poor judgment and getting into highly compromising situations." From tone-deaf television appearances to friendships with controversial figures, Andrew has consistently been involved in scandals that have fueled low-grade tabloid fodder to even very grave political catastrophes. And where other royals manage to use a controversial moment to rehabilitate their public personas, the Duke of York has repeatedly stumbled from one disaster to another. 

The biggest, most irreparable blow to his image was hands down his association with convicted financier Jeffrey Epstein, which dismantled his royal status and compelled him to nearly disappear from public life. Scroll on to revisit the details of that scandal alongside more of Prince Andrew's worst moments, all of which left royal fans cringing. 

The shenanigans that shaped Prince Andrew's transformation as a scandal-making prince go back all the way to the 1980s, when he dated an actress called Koo Stark. As many royal romances do, this pairing sparked significant interest among the press. The good-looking young couple was photographed together at social events and holiday getaways — usual fodder for gossip-hungry tabloids — and by some accounts, was in love. However, this high-profile relationship was allegedly a source of some tension within the palace walls. 

A couple of films from Stark's past oeuvre, like "Emily" and "Cruel Passion," comprised sexual overtones and had prompted the press to tag her as a "soft porn actress." Tabloids threw the term around loosely while referring to her in articles about her relationship with Andrew — a tricky situation that apparently made the conservative British monarchy squirm. "What starts as sexual innuendo turns into a cruel joke, then quickly descends into a vicious verbal attack that leaves deep emotional scars," Stark said in a piece for the Daily Mail decades after her relationship with Andrew ended. 

Though his relationship with Stark didn't seemingly end on the happiest note, it opened the gateway to his long-standing reputation as the womanizing "Randy Andy" and then later, "The Playboy Prince." As for Stark, she took the tabloids to the cleaners and in 2022, won damages from the Daily Mail for calling her a porn star. 

Prince Andrew's appearance on a long-forgotten television game show in the '80s may not have the usual make of the kind of scandals he finds himself in, but it still earns a spot on his most cringe-worthy royal moments. In 1987, the Duke of York joined other esteemed members of his family — including Queen Elizabeth II, Princess Anne, Prince Edward, and Sarah Ferguson — for a game-show style charity event titled "It's a Royal Knockout" that the BBC aired. It was a lighthearted competition that pitted the British royals and each of their color-coded teams against each other in a series of slapstick physical challenges. 

The format of the game was in stark contrast to the stiff upper lip ethos of the British aristocracy and, according to the Mirror, didn't fully have Queen Elizabeth convinced. Unfortunately, she still signed off on it. While much of the post-broadcast humiliation was reserved for Edward and Ferguson, the most enthusiastic royal participants, Andrew could hardly absolve himself of the embarrassment, even though he was one of the more composed members of the royal troupe. The event was widely panned as a royal PR disaster that Buckingham Palace would have liked to forget. But because the internet records most scandals for posterity, videos of the game resurfaced on social media decades later, bringing a fresh batch of mortification for Andrew and the others.

More pics of #PrinceAndrew not partying and exercising discretion with pictures pic.twitter.com/7nVsCsuQV0

— Nomia Iqbal (@NomiaIqbal) November 16, 2019

Following his divorce from Sarah Ferguson in 1996, Prince Andrew's reputation as an outgoing womanizer accelerated with great force. A major contribution to his public image as "The Playboy Prince" came from a series of scandalous photographs of him letting his hair down in the luxurious French town of St.-Tropez in the 2000s. Some of the wildest moments from these parties caught on camera dated back to 2007, when Andrew cozied up to popular socialites like Chris Von Aspen and Pascale Bourbeau (via The U.S. Sun). 

His photos with Von Aspen, which showed up in tabloids and later on the internet, were particularly intimate and showed the socialite simulating sexual gestures to the prince, who was many years her senior. "He followed her everywhere she went, even to the bathroom, and at one point he gave her a head massage," a mutual friend was quoted as saying by The Standard. 

While the women in these photos from St.-Tropez kept changing, what remained vividly constant was Andrew's penchant for reckless indulgence, which contrasted with the dignified public persona expected of a senior royal. These St.-Tropez outings became emblematic of Andrew's lavish lifestyle and added fuel to the glamorous "party prince" narrative that surrounded him at the time. Years later, they would also become important visual cues challenging Andrew's bizarre claims during the Jeffrey Epstein scandal of never having partied all that much. 

Prince Andrew claims 2010 Jeffrey Epstein visit in NYC was to end friendship https://t.co/54NrvJJ6DW pic.twitter.com/tsPNaY67P7

— New York Post (@nypost) October 6, 2019

In December 2010, just two years after Jeffrey Epstein was convicted of soliciting a minor for prostitution, Prince Andrew was photographed casually strolling with him through Central Park in New York. The viral photos were damning, to put it mildly, and appeared to confirm an ongoing connection between the British royal and the disgraced financier, despite mounting allegations and public outrage against the latter. Prince Andrew and Epstein's friendship went back all the way to the 1990s, when they were introduced by their mutual friend Ghislaine Maxwell. Over the next few years, the scandal-prone prince became a regular presence in Epstein's star-studded social orbit and, as a result, came under intense scrutiny when Epstein's criminal activities became more widely known. 

In that context, the Central Park photos didn't just look bad; they sucked Andrew deeper into the Epstein case. Andrew later went on the defensive, insisting that he had only met Epstein in New York to cut ties with him. But his justification was hard to digest in the face of reports claiming that he spent several days at Epstein's Manhattan townhouse during that same visit. What's more, court documents also later revealed that Andrew and Epstein had continued to remain in contact even after the incriminating 2010 blow-up, according to the BBC. 

🚨NEW:
Newly released emails show Ghislaine Maxwell's attempts to intimidate and smear the late Virginia Giuffre, who was the most vocal of their survivors until her death this year by suicide.

Photo of the late Virginia Giuffre 🖤✊🏼 with Prince Andrew and her convicted sex... pic.twitter.com/oXGcfF6W8a

— Amber Speaks Up (@AmberWoods100) September 11, 2025

Prince Andrew was already standing on precarious ground in the Jeffrey Epstein case in 2011, when an explosive photo made its way to front-page news around the world and pulled him deeper into the scandalous quicksand. The now-infamous picture — which was in many ways the beginning of the end for the royal prince — showed him posing with his arm around a young woman while Ghislaine Maxwell lurked in the background. This woman, one Virginia Giuffre, came forward to claim that Andrew sexually abused her when she was just 17, after Epstein and Maxwell recruited her. 

Daily Mail was reportedly the first to go public with the photograph, which dates back to March 2001 and is said to have been taken on the day of the alleged crime (via The Telegraph). For Andrew, the photograph was dynamite, giving a face and name to the serious allegations surrounding him. For Giuffre, on the other hand, the picture served as a crucial piece of evidence that countered Andrew's claims of never having met her. Years later, when Giuffre filed a lawsuit against the British royal in 2021, the photograph became the centerpiece of the case once more. Though Andrew eventually settled out of court without admitting liability, the photo lived on as visual proof of his place in the larger Epstein scandal.

Hoping to clear the air around his ties to Jeffrey Epstein, Prince Andrew agreed to an ill-fated interview with journalist Emily Maitlis in 2019. Little could he have known that the sit-down at Buckingham Palace would turn out to be one of the biggest royal blunders in recent history. Right from the outset, the almost one-hour-long BBC Newsnight broadcast shaped up to be a complete trainwreck. 

The royal prince offered clumsy explanations of his friendship with Epstein, speaking casually about finding a "convenient" place to stay at the financier's mansion in 2010 and even describing their association as "very useful." When the subject turned to Virginia Giuffre, Andrew only dug himself deeper. He made some infamously bizarre claims about having been at a Pizza Express in Woking on the night in question and attempted to refute her allegations by insisting that he suffered from a medical condition that prevented him from sweating. 

The fallout was immediate. The interview was described as a PR disaster in headlines around the world, doing little to salvage Andrew's already worsening reputation. From royal watchers to social media users, criticism for Andrew's catastrophic presentation was near-universal, and in essence, proved to be the final nail in his coffin. Within days of the BBC Newsnight interview, Buckingham Palace announced that the Duke of York would step back from his public duties. 

After the BBC Newsnight interview chipped away at the last shreds of his reputation as a royal figure, criticism for Prince Andrew spilled over from social media into the streets of Britain. In London's Shoreditch area, known for its edgy and politically charged street art, a striking roadside mural appeared in 2020 with the word "shame" emblazoned across the Duke of York's forehead. It was a powerful public response to Andrew's contentious associations with Jeffrey Epstein and the serious allegations surrounding him, showing that the people of Britain were no longer willing to stand by indifferently before the misuse of power. 

The artwork became a symbol of Andrew's fall from grace, turning a dashing royal once known for his high-profile engagements and reputable life as a naval officer, into a background face on a street corner. To add to this visual humiliation of the prince, in 2024, the National Portrait Gallery in London considered acquiring an exclusive photo of Andrew taken on the day of his infamous 2019 interview as a marker of the sensational turning point in his legacy. While some royal commentators disputed the decision to display Andrew's embarrassment to the millions of visitors who stop by the National Portrait Gallery, some, like royal biographer Andrew Lownie, agreed that "the interview and the photograph is a piece of history" (via Daily Mail). 

Queen Elizabeth II's funeral in September 2022 painted a haunting image of Prince Andrew's downfall, from the late monarch's favorite son to a royal whose reputation hung in the balance. He cut a striking figure beside siblings King Charles III, Princess Anne, and Prince Edward as the only one in the bunch without his military uniform and decorations, of which he had been stripped after his 2019 BBC Newsnight interview. His appearance in a plain dark suit marked a major embarrassment for the formerly glorified naval officer and drew massive attention on social media, even though he was not the only royal present there without his uniform.  

His nephew Prince Harry, too, was in civilian clothes, owing to the palace's decision to allow only working royals with military ranks to wear their uniforms to the funeral. But placed beside Harry's self-imposed exit from the royal family, Andrew's scandal-tinted appearance carried a far heavier weight and signaled a mortifying downgrade from his high royal position. The humiliation did not stop there. During a procession in Edinburgh, videos of which circulated widely on social media, he was heckled by someone in the crowd who shouted: "Andrew, you're a sick old man." Many also took issue with a controversial exception that the palace made for Andrew, allowing him to wear his military uniform to the final ceremonial vigil for his mother.

My column on Prince Andrew and the alleged Chinese spy https://t.co/olckrGsr2D

— Marina Hyde (@MarinaHyde) December 17, 2024

Prince Andrew's already tarnished public image took another massive hit in 2024, when he found himself neck-deep in a controversy that surrounded him with serious claims of alleged espionage. His involvement in the matter came about through his links to a Chinese businessman called Yang Tengbo, or H6, who was accused of being a spy and was first intercepted by British authorities in 2021 over suspicious dealings. His closeness to Andrew became a focal point of the investigation, with emerging details exposing the shocking degree to which Tengbo had managed to entrench himself in the uppermost echelons of British society, thanks in no small part to his royal friend. 

Tengbo had been a frequent guest at royal residences, including Buckingham Palace, and was deeply involved in Andrew's Pitch@Palace initiative. Documents also showed that he had been authorized to act on behalf of the Duke of York in international financial dealings, with one internal letter describing him as sitting "at the very top of a tree that many, many people would like to be on" (via The Guardian). It was reported that their associations deepened after Andrew's trainwreck interview with BBC Newsnight. In 2023, Tengbo was barred from reentering the U.K., citing national security risks. He appealed the decision denying claims of espionage, but in 2024, authorities upheld the ban and brought the case back into public imagination, once again highlighting Andrew's contentious role in all of it.

Prince Andrew was out riding in Windsor. His Horse spooked while riding and almost threw him! The poor horse!
News Licensing / MEGA pic.twitter.com/SfsaAQB8Hg

— Theresa Longo Fans (@BarkJack_) November 20, 2024

Prince Andrew had a decidedly un-royal moment in late 2024 when photos of him struggling to maintain his balance on horseback went viral on the internet. In the photographs, captured during his early morning ride around Windsor Castle, the Duke of York looked visibly shaken as his horse appeared to buck beneath him, nearly throwing him off its back. It was an unsightly slip for the controversial prince, whose equestrian talents are especially well-known. But to be fair, this goof-up was hardly his doing and, according to the Daily Mail, happened on account of the majestic stallion, who was momentarily spooked. 

In fact, the incident was actually an exhibit of Andrew's mastery over the royal sport. While social media got a good laugh out of the viral photos of the flustered prince, his then-3-year-old granddaughter Sienna — whom he was teaching to ride that morning — likely received a master class in real-world horsemanship, as Andrew brought the animal under control within seconds. The incident also offered a rare, humanizing glimpse of Andrew in his regular role as a hands-on grandfather, showing the public a side of him that's barely visible amid the usual storm of controversies that always surrounds him.