How did the Queen’s favourite son end up in the back of a cop car?

Following Andrew Mountbatten-Windsor's arrest this week, we take a look at the downward trajectory of this once cherished and glamorous royal and ask, what went wrong?

Sixty-six years and two days ago, a big, bonnie, infinitely privileged baby bounced into a world that was poised and ready to welcome his arrival. His name was Andrew and he was a prince, destined to be a duke, second in line to king – a preordained big shot from birth.

But the young Prince Andrew’s status wasn’t just worldly, for within the palace he called home he would soon became his mother’s favourite. It might have been a family known for stiff upper lips and frosty handshakes, but little Prince Andrew was snuggled and cherished.

‘The baby is adorable, wrote his mother, the Queen of England, to her cousin. ‘All in all, he’s going to be terribly spoilt by all of us, I’m sure.’

The blessed prince grew up to be, as a young man at least, the most conventionally attractive person the royals had produced in some time. Dubbed “six feet of sex appeal” at just 16, he burst out of the finest schools (where he proved himself far from brightest jewel in the crown, but no matter) and into the adult world where women – suntanned '70s actresses, models and heiresses – clambered to be his girlfriend. There were many, but none could compete with Sarah Ferguson, an outgoing red-head and fellow ticking time bomb, with a polo-drenched background and insatiable inner void to match his own.

But, on the surface at least, things looked frightfully jolly. When the newly-weds kissed for the crowds, it must have been a healing moment for the British public, who’d gamely cheered Charles and Di’s “kiss that missed” on that same balcony five years before. A genuine couple, only semi-hampered by their future roles, Andrew and Fergie were the fun ones, the true love story. Roll the credits. This would have been such a tasteful place to end the tale.

But 40 years passed, each one more embarrassing than the last, with the ultimately divorced yet oddly attached couple attracting more ill-advised friends and shady financial deals than the queen had corgis.

And then it was Thursday, February 19, (the no longer Prince) Andrew’s 66th birthday and his deepest low yet, as he cowered in the back of a police car looking like a busted teenager in a bloated aging body. How did it all go so terribly wrong?

That question is essentially answered in Entitled, by English historian Andrew Lownie, which is part book/part encyclopaedia, so exhaustive is his detailing of Andrew and Fergie’s overspending and under performing in their public and private roles. It also examines their respective strengths and weaknesses, highlighting in Andrew's case an inner brew of arrogance bordering on boorishness and childlike naivety.

The book untangles the recent decades, including the insidious role of Jeffrey Epstein in the couple’s lives. But it also goes right back to the beginning in an attempt to answer the above question: how do people handed everything on a silver platter end up empty, broken, shamed and, in the case of Andrew, so allegedly damaging to others?

Some of Andrew's personality is undoubtedly due to excessive privilege. But if the British Royal Family has a use (and oh how it yearns for a use!) it’s as a mirror to the rest of us. An unnerving fun-house mirror maybe, but these wealthy, titled and entitled people have a knack for attracting problems that reflect our own, from eating disorders and messy breakups to money woes, family fallouts, stalkerish obsessions, and truly artless phone sex.

And they have flawed, favourite children who they strive to protect, even in the light of serious allegations.

In Entitled, Lownie makes clear Andrew's enduring reluctance to take accountability for his own actions (a trait plainly on display in his now infamous "I don't sweat" BBC interview). He also highlights Andrew's genuine inability to see things from others' perspectives. (Unlike the rest of the planet, Andrew thought that interview "went pretty well".)

He quotes UK journalist Elizabeth Day, who once asked Andrew what he thought his life would be like if he hadn't been born royal.

"'How on earth would I know?' Andrew responded, as if being asked something absurd."

Lownie writes: "Looking back, In the light of Virginia Giuffre’s claims, Day concluded that it was beyond Andrew to understand ‘what life might be like for someone else; for someone less privileged, less fortunate, more vulnerable … I can imagine him, this man with his teddy bear and his arrested development, being as self-centred as a child and not giving any thought as to the impact his behaviour might have on anyone else. I can imagine him, too, being baffled and semi-outraged that he is now being asked to account for his actions.’"

Dr Jo Prendergast is a Christchurch-based psychiatrist and the author of a book about parenting teenagers called When Life Sucks.

She says that, while few parents would claim in public to have a favourite child, it's not that unusual for them to admit to a favourite when talking to a mental health professional such as herself.

There can, she says, be both positive and negative outcomes of being a parent's favourite, depending on the family dynamics. "If you're the favourite child in a family where there are limits and consequences to your behaviour, then that feeling that you might be slightly more loved than your siblings is not necessarily a problem – as long as it’s not to the extent that it causes sibling rivalry and negativity.

"A very loved child in a family that has good parents and healthy structures will often end up being an adult with great self-esteem who's securely attached and can end up being one of the most high-functioning members of society," she says.

It's in a less functional family that favouritism is risky, she says. "That’s when the child will quite often develop a kind of entitlement and low empathy and grandiosity, in that they feel that they're more special than other people and that rules don't apply to them. You see that all the time, even in your own social world, you’ll see the little princes and princesses that are clearly the favoured child getting away with more than their sibling.

"Certainly that path towards narcissism can develop where a child feels that they're more special than others. You can end up then with an adult who is very grandiose and emotionally detached and doesn't have much empathy for anybody who they may have harmed."

How do parents raise children who can take accountability for their actions? "Personally, I'm a big believer in natural consequences," says Prendergast. "For example, if your young person is mucking around and disorganised and doesn't get to school on time, then the natural consequence is that they've got to go to the office and sign a late form, and they get the embarrassment of walking into the class late – things like that are more effective than parents saying, ‘right, you're not watching 15 minutes of TV tonight because you were late this morning’.

"Schools are often great for that – consequences happen quite naturally at schools. And I think one of the important things, especially in adolescence, is parents not interfering with that natural process by running down to the school and saying, ‘my daughter would never do that’.

"Having just graduated from parenting teenagers myself, I know how tempting it is to go in and try and rescue them and fix things and minimise distress. But I think it was the late Nigel Latta who had a wonderful staying saying about parenting: be the rock, not the ocean. So kind of be there, be present and available, but don't be all around them like the waves. Don’t be always trying to fix things and reduce consequences; that sort of anxious flapping around doesn't do your kids any favours."

Dr Jo Prendergast is performing a show called Dr Jo Prendergast is #coping at Dunedin Fringe and Nelson Fringe in March.