The paparazzi hiding in bushes and four-wheel drives outside the grand New York townhouse never expected the Queen's rumoured favourite child to walk out with a convicted sex offender.
But there he was, dressed in a black parka, dad sneakers and faded Levis: Prince Andrew, deep in conversation with disgraced financier Jeffrey Epstein.
As they took a turn around Central Park, the only hard, indisputable proof the pair knew each other was captured.
"I'm sure we were used," former News of the World reporter Annette Witheridge told Vanity Fair last year.
"In a sense, it suited Epstein to be pictured with Prince Andrew. He would have been told that we were outside."
If the photograph never existed, the Duke of York could have minimised his relationship with Epstein, or perhaps denied altogether that they'd ever met.
On that chilly day in December 2010, under the sparse wintry trees in the park, the Prince didn't know this moment would be a harbinger of things to come.
He was, after all, the Queen's favourite — the blue-eyed boy who would never inherit her throne, but would always capture her heart.
But 11 years after the shutter clicked, Jeffrey Epstein is dead, Prince Andrew is fighting for his future in a courtroom, and the woman who introduced them is contemplating a life behind bars.
'The golden boy'
Sibling dynamics are always complex, but throw a crown into the mix and those relationships become incredibly tricky.
Prince Charles may be the first born and heir apparent, but royal watchers say it was his younger brother Andrew who shone bright.
"Andrew has always been the Queen's favourite son and he has never done anything wrong in her eyes," Princess Diana's butler Paul Burrell said in the documentary, The Royal Family at War.
Andrew was born eight years into the Queen's reign, when she was more settled into the role and had more time to spend with her children.
Gregarious where Charles was shy, athletic where his brother was artistic, Andrew was also a Royal Navy helicopter pilot in the Falklands War.
"He came back a hero and was very much the golden boy of the royal family," Katie Nicholl said.
More than 500 million people around the globe tuned in when he married Sarah Ferguson in 1986, Prince Andrew resplendent in his ceremonial lieutenant's uniform.
But as he grew older, Andrew earned a reputation for having a short temper and a spending habit.
He was called "Air Miles Andy" over his penchant for luxe travel — $180,000 on a private jet to the US in 2008, $40,000 in hotel bills from a trip to Switzerland in 2009 — paid for by the taxpayer because he was the UK trade envoy.
He was even censured by the National Audit Office for taking a $6,800 helicopter ride just 80 kilometres for lunch with foreign diplomats.
In 2016, unwilling to drive 1.6 kilometres around, he rammed his Range Rover through closed gates at Windsor Great Park.
But still he remained in the Queen's favour, according to palace aides.
"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.
"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."
'Under-financed' royal found friends with deep pockets
As the ninth in line to the throne, Prince Andrew is entitled to an annual tax-free salary of nearly $450,000.
This money is taken directly from the Queen's private estate, the Duchy of Lancaster.
He earns another $36,000 from a naval pension.
An unnamed friend told Vanity Fair that this income leaves the prince "hunting for money".
"Outside of the direct line of the ascendancy to the throne — Prince Charles and Prince William — peripheral family members are severely under-financed and have limited options on how commercial they can be to make money," the unnamed source claimed.
His wife Sarah Ferguson, who he divorced but remained close to, was also beset by money issues.
In 2010, an undercover journalist posing as a businessman caught the former duchess of York appearing to offer a sit-down with her former husband — for $930,000.
"I very deeply regret the situation and the embarrassment caused," she said after the video was sensationally splashed across the tabloids.
"I can confirm that the Duke of York was not aware or involved in any of the discussions that occurred."
Ferguson was reportedly millions of dollars in debt, and desperate for help in paying it off.
In 2011, it emerged that one man had offered to help with a cheque for $28,000.
His name was Jeffrey Epstein.
A powerful connection that would come back to haunt the prince
While mystery surrounds Prince Andrew's first fateful meeting with Epstein, he has always been clear that they were introduced by a mutual friend.
"On balance, could I have avoided ever meeting him? Probably not," Prince Andrew would later ponder, in an interview with BBC's Newsnight.
"Because of my friendship with Ghislaine, it was … inevitable that we would have come across each other."
The Duke of York and Ghislaine Maxwell, a glamorous young socialite and daughter of wealthy media mogul Robert Maxwell, had been hobnobbing at the same parties since the 1980s.
They reportedly met while she was studying at Oxford University and climbing the social ladder, building a network of powerful friends and associates.
It was during his reclaimed bachelor years in the mid-1990s, fresh off his divorce from Sarah Ferguson, that the prince was drawn ever closer into that influential circle.
In 1999, Maxwell would introduce Prince Andrew to Jeffrey Epstein — though the nature of their relationship has been subsequently disputed during Maxwell's sex trafficking trial, Prince Andrew understood she was Epstein's "girlfriend".
Prince Andrew has argued it would be "a stretch" to describe Epstein as being among his close friends during that time, but their contact was no secret.
The high-flying financier and his socialite companion were spotted with the prince at the Royal Ascot horse races and Donald Trump's Mar-a-Lago club in 2000, and even joined a "shooting weekend" at the Queen's Sandringham Estate around the time of Maxwell's birthday.
In 2006, just days before his arrest on charges of soliciting a minor for prostitution, Epstein and Maxwell were invited to an 18th birthday party for Andrew's eldest daughter Princess Beatrice at Windsor Castle.
Prince Andrew says he had no further contact with Epstein until 2010, when he decided he needed to explicitly distance himself from the now-convicted sex offender. So he flew to New York to break up the friendship.
It was on this trip that the infamous Central Park photograph was taken.
In the months following, the friendship with Epstein and his assistance with Sarah Ferguson's money problem — on top of questionable connections with a notorious member of the Tunisian regime and a Libyan gun smuggler — proved too much to withstand.
Prince Andrew stood down from his role as trade envoy in 2011.
Though he has since rejected suggestions that he was in New York as a "guest of honour" to celebrate Epstein's release, or used as a pawn to rehabilitate his image, Prince Andrew conceded it was a strange choice to stay at Epstein's home for four days.
"With the benefit of all the hindsight that one could have, it was definitely the wrong thing to do. But at the time, I felt it was the honourable and right thing to do," he told Newsnight in 2019.
"I admit fully that my judgement was probably coloured by my tendency to be too honourable. But that's the way it is."
The damage had been done. Prince Andrew was now inextricably linked with a convicted sex offender, and a cloud of allegations was about to rain down on Epstein's inner circle, including the prince himself.
The sticky friendship had always loomed, but #MeToo brought things to a head
Before #MeToo took off as a viral hashtag and shook the worlds of entertainment and politics to the core, whispers had begun to implicate men of power and privilege across the globe.
Allegations of sexual misconduct against Prince Andrew first emerged in late 2014, when he was named in a court filing against Epstein lodged by Virginia Giuffre.
The palace vigorously denied the allegation that the prince had sex with Ms Giuffre against her will at Epstein's residences, and the case was eventually thrown out.
But the stench of the accusation would linger.
By the end of 2017, a dizzying number of Epstein's associates had been accused of abusing their power for sexual gain, including film mogul Harvey Weinstein, then-president Donald Trump, former president Bill Clinton and actor Kevin Spacey.
What had begun as a grassroots movement to bring about justice for victims of sexual assault had grown into a global movement seemingly overnight.
In 2019, Epstein was arrested again, this time on sex trafficking charges. Police alleged he intentionally sought out minors to abuse at his lavish homes and paid some of his victims to recruit other girls.
But just months before his first trial date, Epstein was found dead in his jail cell.
While his alleged victims missed their day to face him in court, the investigation did not stall, with several further lawsuits filed after his suicide.
Last month, advocates hailed Maxwell's conviction over her part in the sex trafficking ring as a symbolic win for abuse survivors.
All the while, the stain of Prince Andrew's connection with Epstein and Maxwell has proved difficult to shift.
His infamous interview with Newsnight in 2019 — in which he said he could not have had sex with Ms Giuffre because he'd been taking his daughter out for pizza on the night in question and also was unable to sweat so did not fit the description she gave — did little to help his cause.
In August 2021, Virginia Giuffre launched a civil lawsuit against the Duke of York claiming he sexually abused her on multiple occasions, enabled by his powerful friend Epstein.
Where is Andrew now? Stripped of his titles, sidelined by everyone but his mum
As the Prince's legal team prepared their response, he stepped back from public duties and headed to the Queen's Balmoral Estate to ride out the storm.
Though he retained his place at the table for Christmas dinner, the Queen didn't mention her second-born son in the annual Christmas Day speech.
With his legal costs spiralling and other debts coming back to bite, Prince Andrew is expected to sell the Swiss chalet that he bought in 2015 for an estimated 13 million pounds ($24 million).
This week, after a US judge rejected his bid to have Guiffre's lawsuit thrown out, the Prince officially stepped back from his military affiliations and royal patronages and gave up the His Royal Highness title.
Royal watchers and legal experts are split on whether the case will continue to trial later this year, or if Prince Andrew will reach a settlement with his accuser.
Some have speculated that as the Queen looks ahead to her Platinum Jubilee in February, the pressure will be on for Prince Andrew's legal team to secure a swift settlement, rather than dragging out the scandal.
The Telegraph has reported in that scenario, the Queen may be asked to help cover the cost of a settlement.
In any case, Prince Andrew faces a lonely wait.