So tasteless it turns my stomach. Who in their right mind would find this ‘joke’ amusing?

PRINCE ANDREW has a talent. He is truly, exceptionally gifted in one specific area. It is not, unfortunately, a talent for anything especially useful. He is not particularly skilled at being a member of the Royal Family, given that such a role requires discretion, good judgment and an unimpeachable reputation in order to be carried out effectively.

Nor was he a success as a UK trade envoy. He stepped down from that made-up position in 2011 after a string of controversies and diplomatic incidents which saw one ambassador describe him as ‘cocky’ and ‘verging on rude’.

No, Prince Andrew’s natural flair and ability is for something else entirely. It is for making situations incalculably worse for himself. It is for taking terrible decisions and then myopically standing by them. It is for possessing a tin ear for how things appear to the ordinary people who have not been brought up in gilded palaces, attended to by whispering courtiers and ingratiating yes-men since the day they were born.

It is, in short, a gift for manufacturing shovels magically out of thin air with which to dig himself into an ever-deeper hole of ignominy. In this sport, Prince Andrew is truly an Olympic champion.

We saw his capacity for self-sabotage in full flow in the now-notorious Newsnight interview in November, during which Emily Maitlis quizzed him on his close association with the disgraced financier Jeffrey Epstein. It was an unwitting masterclass in misplaced defensiveness and unchecked self-aggrandisement.

In it, the Duke was so busy claiming to be ‘honourable’ and working up an improbable alibi involving malfunctioning sweat glands and Woking’s Pizza Express, that he couldn’t find a spare second in which to express a shred of compassion for Epstein’s victims.

Not once did he express concern for those young girls who had been trafficked and assaulted by his good friend, the convicted sex offender.

Instead, he repeatedly insisted he had done nothing wrong and would help the authorities if he could. But last week, the New York state attorney Geoffrey Berman accused the Prince of offering ‘zero co-operation’ with the US inquiry. If that is true, it seems an odd stance for a man who has nothing to hide.

NOW we have his messages to a friend and business associate. At first glance, they might seem relatively inoffensive – a couple of joshing missives exchanged with friends. A bit off-colour, maybe, but who among us doesn’t have a slightly creepy uncle who tells crude ‘jokes’ at Christmas and seems overly interested in the bridesmaids at family weddings?

Then you think about the timing. These were sent in March 2011, within days of this newspaper publishing a photograph of the Duke posing with his arm around Virginia Roberts’s waist and shortly after incriminating pictures emerged of him walking with Epstein around Central Park.

One of the emails consists of a cut-and-pasted fake news story about breast cancer that is so tasteless it turned my stomach.

It is a ‘joke’ which manages the double whammy of being utterly unfunny AND stupid.

There is no wit to it; it is a poorly constructed jibe which uses cancer patients as an excuse for a sexual punchline. I truly can’t think of anyone in their right mind who would find it amusing.

The other email refers directly to Roberts, one of Epstein’s victims who would later allege that she was instructed to have sex with Andrew on three occasions from the age of 17. The Prince categorically denies her claims. But at the time of this email, questions were beginning to be asked about the nature of his relationship to the young woman.

And what did the Duke of York have to say about it? Not much. He dismissed Roberts as ‘a very sick girl, apparently’.

With that short but telling phrase, the Prince manages to be both patronising (in his eyes, Virginia Roberts, who by this time was 28 years old and married, is a ‘girl’ not a woman) and to cast aspersions on her mental and physical wellbeing.

It reminds me of those men who seek absolution for their terrible past behaviour by referring to all their ex-girlfriends as ‘crazy’ or ‘hysterical’, as if instability is a peculiarly female trait; as if none of us can quite be trusted to keep our wits about us.

Also pay attention to that ‘apparently’ – a concession that this opinion is second-hand. Had this matter been mulled over with others, behind closed doors? Why would it need to be talked about if there were nothing to discuss?

EVEN if we were to give Andrew all the benefit of all of the doubt; even if we were to believe everything he says, wouldn’t most of us feel some sort of compassion towards a woman who had, in all likelihood, been one of the minors Epstein admitted to prostituting in 2008?

Instead of casually labelling her ‘very sick’ in an email to friends, wouldn’t we have taken a moment’s pause to wonder whether the sick one in this particular dynamic was Jeffrey Epstein? I think most of us would have done that, don’t you?

Not Andrew. He goes on to say that he will ‘shrug and move on’.

Of course he will. It is what, up until this point, he has been able to do all his life. He has never had to accept responsibility for his actions because he has been insulated by a bubble of privilege he refuses to see or acknowledge.

It’s why, when I interviewed him several years ago and asked him if he ever wondered what his life might have been like were he not a member of the Royal Family, he became visibly irate. He simply could not conceive of an alternate reality. He lacked the empathetic muscle to imagine himself into the life of an ordinary person and it angered him that he had been asked to try.

So I’m not surprised by the lack of compassion shown in these messages but I wish it were different.

I wish Prince Andrew could astonish us all with some vestige of self-reflection. I wish he could understand what others find offensive in the words he uses and in the way he behaves. I wish he could demonstrate a willingness to change, to co-operate with the authorities and to show he cares.

But I suspect that, in the end, he will always be blinkered to the plight of anyone other than himself – forever shrugging and moving on.

He’s always blinkered to the plight of anyone other than himself