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In his adult life, Andrew Mountbatten Windsor's reputation is in tatters - the disgraced ex-duke has been stripped of his Royal titles and ordered by King Charles to vacate Windsor's Royal Lodge.
During his time as a working royal he was often regarded as imperious, bad-tempered and rude towards his aides, with his collateral downfall prompted by his relationship with convicted sex offender Jeffrey Epstein and 'car crash' Newsnight interview.
But Andrew's unfavorable traits can be traced back to his childhood, with Tom Jackson, a former playmate of the ex-Prince, describing him as a 'tiresome little s**t', while the late Princess Diana also spoke unaffectionately about the youngster.
Writing in his book Entitled: The Rise And Fall Of The House Of York, royal biographer Andrew Lownie revealed how Andrew's boisterous nature and desire to cause trouble was far from appealing for the late Diana.
Later sharing her inner thoughts on the ex-Prince in his youth, Diana wrote: 'He was very, very noisy and loud... It occurred to me that there was something troubling him.'
Adding that his personality type 'wasn't for me', Diana also noted that Andrew, 65, was 'very happy to sit in front of the television all day watching cartoons and videos' and described him as 'not a doer'.
At the age of eight, Andrew was sent to Heatherdown Preparatory School in Ascot, Berkshire, where he gained a reputation as a bit of a bully - or 'a natural boss', according to his father, Prince Philip.
It was during this period that the Royal Family's 1969 documentary aired on British television, showcasing that while Andrew was a 'lively, cheerful boy', he possessed a 'touch of the daredevil' and was already beginning to 'display the contrary behaviour that would bedevil his life', according to Lownie.
He added: 'One moment he would be diligent and polite, the next aggressive and rude. Like his father, he had a short temper, a rather Germanic sense of humour and did not bear fools gladly.'
But despite Andrew's faults, he was widely believed to be the late Queen Elizabeth II's favourite son, giving the young boy a licence to get away with behaviour that his other siblings may not.
He was also adored by Philip, who took particular notice of his outgoing and sociable nature. 'Whereas Charles was sensitive and thoughtful, Andrew was macho, confident and extroverted, the sort of son Philip had always wanted,' Lownie wrote.
Yet his spirited personality was held in a less high regard by his schoolmates.
During his time at Heatherdown, one of his contemporaries, Frank Egerton, recalled how fellow pupils were 'always aware he was a member of the Royal Family'.
He was said to be insistent that his peers call him 'Prince', with Mr Jackson, who would frequently play alongside Andrew, then aged six, recalling to Lownie how Andrew 'once informed me when playing that he was a "Prince".'
Yet Mr Jackson refused to back down to the young royal, recalling: 'I immediately informed him that I was actually a "King", which seemed to shut him up.'
Meanwhile, another fellow pupil remembered Andrew as being 'someone who threw his weight around', describing him as a 'cocky' child who 'had a high opinion of himself'.
Egerton also shared how Andrew's rather reckless and imprudent nature was ever-prevalent in his early years, adding: 'He was impetuous and would often say something without thinking which would get him in trouble.'
Indeed, Andrew's proposed inability to adequately consider his words before they are spoken certainly seemed to follow him into adulthood - with his notorious Newsnight interview with BBC's Emily Maitlis serving as a perfect indication of such trait.
The 2019 interview, which Andrew hoped would clear his name, backfired when he said he did 'not regret' his friendship with Epstein, who was by then a convicted sex offender and accused of trafficking Virginia Giuffre while she was a teenager.
A firm failure of Andrew's ability to read the room - it served as a catalyst for Andrew's momentous fall from grace, with the Queen removing Andrew's title of His Royal Highness, military roles and royal patronages in January 2022.
In the years that followed Andrew's scandalous interview, he became gradually exiled from the Firm and his family members - as fellow royal's became fearful of the implications of associating themselves with the disgraced ex-duke.
Yet, Andrew's inability to retain a close circle was also seen in his formative years, with Mr Egerton recalling how as a youngster, he didn't have 'any close friends'.
And the then-Prince also seemed incapable of acknowledging when he had grave errors - with Egerton recalling a particular instance in which a box of 'exotic stamps' were discovered in Andrew's desk.
When the naughty schoolboy Prince was caught, he was said to have 'simply shrugged it off' rather than apologise for the mistake.
Meanwhile, royal biographer Tom Quinn wrote in his book, Yes Ma'am: The Secret Life Of Royal Servents, that Andrew's frustration at being the so-called 'spare' had led to him becoming 'a bit of a bully in private'.
Mr Quinn wrote how one servant recalled: 'A bit like his aunt Margaret, Andrew always behaved as if he was frustrated about not being the first-born and therefore destined to become king.
'If he liked a member of his staff, he could be very loyal and supportive, but he couldn’t resist being imperious and bossy and bad-tempered if anything went wrong or wasn’t done exactly to his liking.'
And his family were also slightly displeased with Andrew's behaviour - while Prince Philip was proud that 'at least one of his sons was a chip off the old block' he was 'also conscious of the dangers' that Andrew could bring for the family.
Philip had also often warned that Andrew shouldn't always get his own way. And yet, according to the royal author, he often did.
'Wherever they went, the skylarking continued', wrote Nigel Cawthorne, who added that Andrew did not always endear himself to the target of his pranks.
Even the late Queen, described as the 'master of the understatement' by Ingrid Seward, conceded he was 'not always a little ray of sunshine'.
It seems that while the late Queen and even Prince Philip may have found Andrew's boisterous antics rather amusing as a child, they had less time for his challenging behaviour during his adulthood.
Indeed, royal biographer Ingrid Seward revealed in her bestselling book My Mother And I that Philip 'berated' Andrew for being 'pointless' because he never fulfilled his early potential.
It is likely that Philip's scathing comments about his son were in reference to Andrew's actions outside of the military.
During the 1980s 'randy Andy' - as the press called him - gained a reputation for being the 'playboy Prince' during his bachelor years, with Andrew linked romantically to a string of models and actresses.
While he did eventually settle down and marry Sarah Ferguson in 1986, their marriage was short-lived and ended in a high-profile separation in 1992 and subsequent divorce four years later.
Since he left active service in the Navy in 2001, Andrew's ventures have routinely come under intense scrutiny.
While for many years he was celebrated as the Royal Family's 'scallywag', royal biographer Robert Lacey wrote the former Prince's 'dubious choice of business contacts came to shadow his reputation'.
And certainly his relationship with convicted sex offender Epstein was to serve as the final straw in his sensational demise.
In October, the Mail on Sunday revealed how Andrew had secretly told the disgraced paedophile 'we are in this together', just months after he had said he had cut ties with him in December 2010.
The email ended with the line: 'We'll play some more soon!!!!!'
It served as definitive proof that the disgraced ex-Prince, now a commoner, had lied in his Newsnight interview when he claimed that he had 'never had any contact' with Epstein after the pair were famously pictured walking together in New York's Central Park in December 2010.
Then, just days after Andrew was forced to give up his Dukedom, the MoS revealed how Andrew tried to get the Met Police to dig up dirt on Ms Giuffre by handing over her confidential social security number - something the force are said to be probing.
Speaking to Victoria Derbyshire on the BBC Sunday With Laura Kussenberg show last month, Maitlis said that King Charles's decision to relinquish Andrew's royal titles was 'inevitable'.
She said: 'It feels like it's been a long time coming this. I mean, the interview was done nearly six years ago, and in the weeks and months after it, he renounced, relinquished a lot of his royal duties, a lot of his public duties, a lot of his charities, his patronages.
'And yet there has been this sort of drip, drip effect, and we've all had to follow. And in a way, I think this was an inevitable place that the palace was going to end up at, I mean, pretty soon after we realised the ramifications from what he said.'
The former Duke of York is now facing further pressure to appear in front of US politicians after Epstein was revealed to have confirmed that the infamous image of him with Ms Giuffre, then aged 17 and known as Virginia Roberts, was real.
But 2011 messages in a bombshell cache of emails showed Epstein urged a journalist to investigate Ms Giuffre while admitting: 'Yes she was on my plane, and yes she had her picture taken with Andrew, as many of my employees have.'
Epstein took the photo on a disposable camera before the group, along with socialite Ghislaine Maxwell, headed out for dinner and then to a nightclub, Ms Giuffre said.
His account will come as a devastating blow to embattled Andrew, who for years has sought to cast doubt over the authenticity of an image showing him holding Ms Giuffre, who took her own life in April this year.
In a statement announcing Charles's decision to strip Andrew of his titles, Buckingham Palace declared that the King's moves were 'deemed necessary notwithstanding the fact that he continues to deny the allegations against him.
'Their Majesties wish to make clear that their thoughts and utmost sympathies have been, and will remain with, the victims and survivors of any and all forms of abuse.'
Andrew continues to vehemently deny any allegations against him.
Yet the significance of his departure from the Royal fold is certainly not to be understated.
It is almost unprecedented for a British prince or princess to be stripped of their title - having last occurred in 1919, when Prince Ernest Augustus, a UK royal and also a Prince of Hanover, had his British title removed for siding with Germany during World War I.
The exile also serves as the most dramatic royal departure since 1936, when King Edward VIII abdicated the throne so that he could marry twice-divorced American socialite Wallis Simpson.
Yet given Andrew's early childhood traits, royal onlookers may be rather unsurprised that he has become enthralled in such an unprecedented royal scandal - indicative of his life-long deviant and unrepentant nature.