‘I enjoyed that’: The moment that revealed Prince Andrew’s big flaw

It was your standard moment on a royal tour. But this act by a 24-year-old Prince Andrew reveals a flaw that would eventually bring him down.

At Ascot. The Royal Chelsea Flower Show. While paling about with Justin Trudeau at an official function.

If you should ever feel inclined to do a Google image search for Prince Andrew laughing, you will find page after page of the Duke of York roaring with full-throttle, full-bodied merriment.

For years, decades even, this has largely been the image of the Queen’s third child - the fun-loving, guffawing HRH.

How much can change and how fast.

It has only just been a week since Andrew’s disastrous BBC interview in which he was grilled about his friendship with convicted sex offender Jeffrey Epstein.

After a number of backers and business partners pulled out of his signature pitch@palace initiative and a deluge of negative front page headlines, on Wednesday, he made the historic decision to resign from official royal duties.

It is a stunning and swift fall from grace for the 59-year-old Falklands War veteran who is widely held to be Her Majesty’s favourite child.

(In a letter after Andrew’s birth, the Queen wrote: “The baby is adorable. All in all, he’s going to be terribly spoiled by all of us, I’m sure.”)

Prince Andrew shares a laugh with Rear Admiral David Ledson in 2007. Picture: AFP

Laughing with brother Prince Charles.

As the fallout from the scandal continues, how much damage this has done to the royal family’s brand remains to be seen but perhaps we shouldn’t be surprised that Andrew has ended up as pariah, ignominiously forced out of the spotlight.

While Princess Anne is a redoubtable, hard-worker, clocking up a record number of official events and Prince Charles diligently waiting for the top job, Andrew has long struggled to truly get the knack for being an HRH.

One particular incident encapsulates Andrew’s buffoonish approach to royal life.

It was 1984 and Andrew was on an official tour of California. His schedule included a meeting with Nancy Reagan in Beverly Hills, a tour of the MGM studio lot and a visit to the set of 2010, the sequel to 2001: A Space Odyssey.

It also included a trip to Watts, a suburb in southern Los Angeles that was home to the infamous riots in 1965.

Throughout this particular tour, about 50 members of the press followed in his wake covering the official trip.

Andrew, in turn, largely ignored them according to a New York Times story from the time. That was, until he got to Watts.

Britain's Prince Andrew leaves his home in Windsor on Thursday. Picture: Steve Parsons/PA via AP

While inspecting an empty house with the LA County Supervisor, some members of the press leaned inside a window to get a view of the Prince, at which point the then 24-year-old royal sprayed reporters with a paint gun.

Afterwards he wiped his hands on a newspaper and said, “I enjoyed that.” (“A Playful Prince Paints The Press” the Times headline read.)

The truly immature moment left some reporters splattered with white paint spots while one British photographer worried that his equipment had been ruined.

And therein, you have Andrew: Behaving childishly and recklessly and with little thought for the consequences – and zero consideration for what image it projected of the royal family.

The image we are left with is one of an immature, selfish man who enjoyed having a laugh at others’ expense.

The more you think about the brief moment, the more you see the abject lack of basic respect for men and women who were there simply going about their job. (And that Andrew truly doesn’t understand the symbiotic relationship between the media and the monarchy.)

This moment reflects the Duke of York’s lack of understanding that members of the royal family are at least supposed to attempt to behave with some modicum of dignity and decorum and to at least try and occupy the moral high ground.

(Sure, they might not always be better than us but they are at least meant to try.)

As the second son, Andrew’s role in the royal family has largely been nebulous, by dint of birth he was “the spare” to Charles’ heir.

Prince Andrew during the trainwreck interview.

The reaction to the interview has not been good.

With no specific job or official function to fulfil in the creaky institution of the monarchy, he has been left to muddle through.

After nearly four decades “on the job” as a working royal, we are left with the impression that to him, being a member of the royal family means having the license to behave however the devil he wants.

Contrast that with his mother, or even his siblings, who are governed by a keen sense of duty and responsibility and who understand that their incredible privilege comes at a certain cost.

Likewise, their royal work ethics are unimpeachable.

“Above all, the Queen represents the institution of the monarchy,” biographer Sally Bedell Smith has told Vanity Fair.

“She has adhered to its principles for nearly seven decades. Andrew paid lip service to those values of service and duty in his disastrous interview – even as he was violating them through his activities and his apparent dissembling.”

Now that Andrew is no longer running pitch@palace (rechristened Pitch after his Palace office was shuttered) and is “mothballing” the hundreds of charities he has worked with, he is going to have a lot more time on his hands.

Perhaps now is the moment to actually start thinking about what service, duty and principles mean. That and penning a few apology notes to the some paint-splattered press.

Daniela Elser is a royal expert and writer with 15 years experience working with a number of Australia’s leading titles