It was 2019 and Queen Elizabeth II's rumoured favourite was in trouble.
Then known as Prince Andrew, the monarch's second-born son had just stepped back from public life after a cataclysmic interview with the BBC failed to address concerns about his association with convicted sex offender Jeffrey Epstein.
The former prince has always claimed that his friendship with Epstein may have been ill-advised and was certainly deeply regretted, but never involved any criminal activity.
And yet, the interview, in which he made bizarre claims about his inability to sweat and failed to show any sympathy for Epstein's victims, was deemed so damaging to the monarchy that he had no choice but to give up his status as a senior working royal.
It was a spectacular fall from grace for a man known to be the Queen's "golden boy".
Two days later though, conveniently placed photographers captured the Queen in a long coat and hood riding her horse around the grounds of Windsor Castle with Andrew by her side.
"There had been a cloud hanging over his reputation, and the Queen was a realist. She essentially fired her own son," Gyles Brandreth wrote in his biography, Elizabeth: An Intimate Portrait.
"However, she showed us how much she loved him by taking him riding with her through Windsor Great Park in the rain and ensuring that there were photographers on hand to capture the shot."
The photo became emblematic of the Queen's handling of the man now known as Andrew Mountbatten-Windsor.
As her son, he was the undisputed favourite. But as a member of "The Firm", he became an increasing threat to the institution she led.
"She just had this blind spot with her son," royal biographer Andrew Lownie said.
"It was ridiculous. He would be quoted as doing something with Epstein, and she would give him another honour or ask him to sit beside her at church."
Now, just over three years since Elizabeth died, her son King Charles III is grappling with the monarchy's greatest crisis since the abdication of Edward VIII.
Mountbatten-Windsor is facing an investigation into allegations of misconduct in public office.
It's the first time in 377 years that a royal has been arrested.
A picture of the King's brother looking shell-shocked and terrified in the back of a car will likely be a defining image of the House of Windsor. And one British newspaper has asked of both Charles and his late mother: "What did they know?"
It will be up to Charles to shepherd his family's institution through its darkest hour. If he fails, a 1,000-year-old institution could die with him.
But could his own mother have done more to snuff out this crisis before he inherited it?
Andrew's 'indulged' youth
King Charles once described his mother as a "remote and glamorous figure who came to kiss you goodnight, smelling of lavender and dressed for dinner".
The young queen, who acceded to the throne at the age of 25, was said to be busy learning her new constitutional duties while preparing Charles to one day succeed her.
But by the time Andrew was born in 1960, Elizabeth had reigned for eight years and was growing more confident in her role.
"With no small irony, insiders say he owes his self-assurance to the mothering of the Queen, who indulged her second son as she never did her older children and continues to shield him," Catherine Mayer wrote about Andrew in her 2015 biography Charles, The Heart of a King.
Extroverted and sporty, where his older brother was studious and shy, Andrew grew up to be a Royal Navy helicopter pilot in the Falklands War.
At the conflict's end, the Queen greeted her 22-year-old son with a red rose, which he promptly placed between his teeth.
"He came back a hero and was very much the golden boy of the royal family," royal commentator Katie Nicholl said.
The young prince gave the monarchy a much-needed injection of youthful glamour.
"Having arrived as a royal celebrity in his own right, Andrew's image evolved, and it wasn't long before he was presented as a 'playboy prince' fond of parties and female company," historian Ed Owens said.
But with the adulation of a grateful kingdom and the unyielding favour of the monarch, some commentators say Andrew became overly indulged.
"It meant that all the way through his life, he was protected," biographer Andrew Lownie told Peter FitzSimons last year.
"He was told he was wonderful. Anyone who didn't say that didn't progress in their career.
"So he was over-promoted in the navy, and everyone just indulged him. And he just realised — he could do exactly what he wanted, from when he was five years old to now."
Andrew's plum role defined by scandal
The problem with being the spare is that your sole purpose in life is to exist in the event of an emergency.
While then-Prince Charles had a lengthy but purposeful wait to fulfil his destiny, his brother Andrew found himself at something of a loose end.
The births of Princes William and Harry pushed him further down the line of succession. He retired from the Royal Navy in 2001. And his status as the dashing playboy began to slip away with his youth.
Soon after he left the navy, Andrew was given the plum position of UK special representative for international trade and investment, which allowed him to travel the world and rub shoulders with senior government and business contacts.
Royal author Robert Jobson says the Queen approved giving Andrew the job over the objections of Charles because she "indulged him".
"She was surrounded by people whose job it was to protect her, including a prime minister who appointed him as a trade envoy," he told PEOPLE magazine.
'[Charles] thought he wasn't qualified for it and, with him just out of the navy, he should learn the job first. But he was ignored."
Andrew proved to be a controversial trade envoy during his decade in the job.
He earned the nickname "Air Miles Andy" from the tabloids for his frequent taxpayer-funded travel. He was criticised for lunching at Buckingham Palace with a member of Tunisia's dictatorial regime. He holidayed with a convicted Libyan gun smuggler. And ambassadors described his conduct as "cocky … verging on rude".
It was during his time as trade envoy that rumours began to spread about Andrew's friendship with Epstein and his accomplice, Ghislaine Maxwell.
"Epstein played Andrew," Lownie wrote in his biography.
"The prince was a useful idiot who gave him respectability, access to political leaders and business opportunities. He found him easy to exploit."
While Andrew has long denied any knowledge of or participation in the sex-trafficking ring run by Epstein and Maxwell, it now appears that his communications with Epstein as trade envoy led to his arrest this week.
Police are yet to go into detail about why they're investigating the former prince for misconduct in public office, but in a glut of files released by the US Department of Justice, several emails appear to show that Andrew forwarded on sensitive materials to Epstein in 2010.
Being named in the Epstein files is not an indication of misconduct, but trade envoys are required to maintain confidentiality over sensitive, commercial or political information related to their work.
After a decade in the job, UK politicians were openly calling for the Queen's son to be removed from the post, with one going so far as to describe him as a "national embarrassment" for his questionable business dealings and his friendship with a known sex offender.
"I am sure there are some countries in the world where having a visiting royal makes a difference, it makes it possible to have some meetings which wouldn't otherwise be possible," Chris Bryant, a Labour MP and former foreign minister said.
"My worry is that, sometimes when he goes on these trips, I am not sure whether he is helping us out or he is just helping himself."
In 2011, Andrew resigned as trade envoy.
While he was out of a job, Andrew retained his status as the Queen's rumoured favourite — until a looming scandal forced her hand.
Epstein connection catches up with him
After stepping down from his post, Andrew became a full-time working royal and was a frequent visitor to the Queen.
"Whenever she hears that Andrew is in Buckingham Palace, she'll send him a handwritten note, and he always goes to see her," a former palace aide told Daily Mail reporters Geoffrey Levy and Richard Kay in 2011.
"If he's in jeans, he'll change into a suit. And he always greets 'Mummy' in the same way — bowing from the neck, kissing her hand, and then kissing her on both cheeks. It's a little ritual that she adores. Believe me, he can do no wrong."
But the controversies and damaging headlines continued.
He was slammed in 2016 for ramming his Range Rover through some closed gates in Windsor Great Park when they didn't open in time.
Then a young woman called Virginia Giuffre made a bombshell allegation. She claimed that Epstein trafficked her to the then-prince when she was only 17 years old.
Andrew denies ever having met Giuffre, even though a widely-circulated photograph shows him with his arm around her waist in Maxwell's apartment while the sex trafficker watches on.
"Nobody can prove whether or not that photograph has been doctored, but I don't recollect that photograph ever being taken," he told the BBC.
But in 2019, when Epstein died by suicide in a New York prison cell, Andrew's past could no longer be ignored.
He invited the BBC's Newsnight program to interview him in the grand rooms of Buckingham Palace.
What followed was one of the most excruciating interviews in television history.
When asked what led him to stay at Epstein's New York mansion after the disgraced financier was released from prison following his conviction for soliciting underage girls for sex, Andrew said "it was a convenient place to stay," and that he thought ending their friendship in person was "the honourable and right thing to do".
The public was outraged, and the Queen found herself scrambling to appease her own subjects.
Andrew announced that he would voluntarily step back as a senior working royal to avoid any further "major disruption to my family's work".
Yet, the royal family still claimed him as one of their own.
"He remains a member of the royal family, and as a Royal Colonel and a war veteran, he will still take part in Trooping the Colour and Remembrance Sunday," a palace aide told Vanity Fair at the time.
In 2022, he reached an undisclosed out-of-court settlement with Giuffre to resolve her US civil sex abuse lawsuit against him. The settlement deal, rumoured to be about £12 million, did not include an admission of guilt.
Depending on whose version of events you believe, the Queen either paid the settlement, or, along with her husband and heir, lent him the amount needed with the understanding it would one day be paid back.
The Queen's final year was defined by a contradictory strategy when it came to her favourite son.
After the settlement, she removed his charitable patronages and banned him from using the title of His Royal Highness.
But she also hand-picked him to escort her into church for a memorial service for her late husband, Prince Philip, in full view of the world's press.
"It didn't happen by chance," former BBC royal correspondent Peter Hunt said.
"It's one thing to accept that he should attend his father's memorial service; it's quite another thing to then give him quite a prominent role."
The Queen's death in September 2022 saw Andrew lose not only his mother and his boss, but his greatest advocate.
"Mummy, your love for a son, your compassion, your care, your confidence, I will treasure forever," he said in his tribute.
As Charles finally acceded to the throne, royal watchers expected that the new king would take a hard-line approach to Andrew.
But like his mother, Charles found himself unable to act decisively — until his brother's legal woes threatened to bring down all of them.
Andrew's downfall: very slowly, and then all at once
It's no secret that Andrew and Charles are not especially close.
There is a significant age gap between them; they are very different men, and have suffered the inevitable tensions that always seem to divide male heirs and spares in the House of Windsor.
But as king, Charles adopted a similar strategy to his mother — occasionally slapping Andrew's wrist, while largely keeping him in the royal fold.
Charles removed his taxpayer-funded armed police detail in 2022, but paid for private security guards to protect him.
Rumours spread that Charles was determined to force his brother from Royal Lodge, a grand 30-room mansion in Windsor that Andrew leased for peppercorn rent on a 75-year lease.
But Andrew still appeared shoulder-to-shoulder with his relatives in public, he was allowed to adopt his late mother's corgis, and he was permitted to wear the ornate Garter Robes to his brother's coronation.
Sources close to Prince William allege that in 2023, his father ordered him to drive his uncle to church at Balmoral while photographers snapped away — a powerful visual symbol that was "more than [Andrew] could have wished for".
Perhaps this uneasy arrangement would have persisted for years to come.
But in 2025, Virginia Giuffre died by suicide. She was just 41.
Before her death, she had written a memoir and her family decided to honour her plans to publish it.
The book made for devastating reading. In it, Giuffre claimed to have been a vulnerable teenage girl who found herself ensnared in Epstein and Maxwell's web, before she was trafficked to the then-prince.
Days later, British newspapers published an email that Andrew allegedly sent to Epstein in 2011, in which he said: "I'm just as concerned for you! Don't worry about me!"
The next day, Andrew announced that he would voluntarily relinquish his honours and avoid family events, though he would retain the title of "prince".
The palace seemed to think this symbolic manoeuvre would be enough to satisfy an increasingly outraged public, but two weeks later, Charles was forced to move further and strip him of his remaining titles.
After a protracted negotiation to evict him from Royal Lodge and an incident in which Andrew merrily waved at passers-by in Windsor, Charles responded by exiling him to Norfolk.
But it was not until Friday, when Andrew was arrested, that the King cut all ties with his brother.
In his statement following the arrest, King Charles referred to him as "Andrew Mountbatten-Windsor" and pointedly separated him from the herd by declaring that "my family and I will continue in our duty and service to you all".
While his brother was being questioned by police, the King kept his schedule and went to London Fashion Week.
Can the monarchy survive?
Supporters of the monarchy have long claimed that the institution's survival depends on not letting "daylight upon the magic".
But that veil of mystery was never meant to obscure allegations of misconduct and assault, nor was it meant to come at the expense of abuse victims.
This scandal arrives at a precarious moment for the monarchy.
In 1983, 86 per cent of the British population said it was "very important" or "quite important" to continue having a monarchy, according to polling by the National Centre for Social Research.
In 2025, that sentiment dropped to just 51 per cent, with the steepest decline occurring in the years after Queen Elizabeth died.
But as her successor tries to keep this ancient institution going, some royal watchers say it was her handling of Andrew's scandals that led to this moment.
"There's a school of thought that she perhaps should have done more sooner," ITV's royal editor Chris Ship said.
"She left a ticking timebomb for her son to deal with and this has overshadowed part of the current king's reign."
