Yesterday marked the 23rd anniversary of the most famous interview the Prince of Wales has ever given, though I think it’s safe to say it’s not a milestone marked by either him or his staff. On June 29, 1994 a two-and-a-half hour documentary on Charles premiered, touching on his philanthropy, his role within the Royal Family, and his views on religion, policy and Britain’s future. It is best known, however, for being the interview in which he admitted to cheating on his then-wife, Diana, Princess of Wales.

While I have certainly discussed the Wales marriage in the past, this wouldn’t normally be a topic I would cover on its own. However, in light of Prince Harry’s recent Newsweek profile (as well as its backlash) and a slight change of course in how the younger set of royals are handling public interviews, I think it’s worth considering the ramifications of this event.

God knows, it has haunted Charles ever since.

At the time that it aired, Charles and Diana had been separated for well over a year. The dust had somewhat settled from the shock of the Andrew Morton tell-all with which Diana had participated. Less engagements and time spent together also meant at least the couple wasn’t being evaluated and judged based on how they interacted with one another at work, however much the media glare hadn’t lessened.

Charles was well-positioned to address his unpopularity – or rather, his role as the “bad guy” in his marriage. He was fresh off of a successful tour in Australia where he had spoken directly on the question of the country remaining in the Commonwealth and remained cool under pressure following an assassination attempt.

The idea behind the documentary was to tell Charles’s side of the story – not just in opposition to Diana, but also as a man who was still waiting in the wings for the “top job” and was inconsistently given due credit for his entrepreneurial attitude towards his role and philanthropic success. And all of that is laudable – one can certainly understand the inclination to fight fire with fire and address the elephant in the room.

But the confession to having cheated on Diana drowned out everything else. Indeed, the gossip hit the tabloids 48 hours before the series premiered, both ensuring higher ratings and that anyone who didn’t watch it would only hear the juiciest royal scandal.

You can watch the relevant clip here:

The exact wording was that the interviewer, Jonathan Dimbleby, asked Charles if he had been “faithful and honorable” during his marriage.

Charles: “Yes, absolutely.”

Dimbleby: “And you were?”

Charles: “Yes. Until it became irretrievably broken down, us both having tried.”

The Duchess of Cornwall (then Camilla Parker-Bowles) was referred to as a “great friend” who had been “important and helpful.”

Later on, his then deputy private secretary, Stephen Lamport, said:

“I don’t know why he answered. He did, and that was the upshot. He would have answered as he felt was right and honest.”

And I think that fundamentally answers the question of why Charles did it. There may have been some naiveté as to how people would react, but I don’t think that was the driving force. As strange as it sounds given the nature of the confession, I think it was basic honesty. Charles isn’t a liar and it’s not in his nature to not consider and answer questions thoughtfully and, yes, honestly.

It’s a trait I think he’s passed along to Harry, actually, however his son possesses the charisma and charm of his mother – that, and he is also by far plainer-spoken than his father. The Duke of Cambridge, on the other hand, seems to have inherited both his mother’s savviness and her ability to equivocate (neither of those are bad qualities.)

The moment is perhaps a case study for why Charles has felt like the victim of extreme bad luck against his ex-wife. Diana would later also admit to infidelity, but the reaction was far paler in comparison. After all, Charles’s affair resulted in yet another love story, whatever you might think of it – Diana’s “great friends” may have gained notoriety, but have largely faded into the background.

Even more, his comment was mostly taken out of context. The point that the marriage had “irretrievably broken down” was lost in the mayhem, Diana was painted the victim and Charles the unfeeling husband who had poorly used his wife.

And yet…the great failing of Charles and his operation during these years was that they didn’t anticipate the highly obvious pitfalls. They were wildly mismatched against Diana, whose expertise can best be summed up her reaction – showing up to an event that evening wear a low cut black dress that immediately became known as “that dress.”

The headlines wrote themselves – you gave up all this for that? And by some accounts, when the dress was suggested to Diana for the evening she giggled and admitted wearing it would be “naughty.” She knew exactly what she was doing.

Charles, on the other hand, was horrified by the reaction to the interview, including that of the rest of the Royal Family, including his parents. A few months later, when asked why he had admitted to infidelity – and effectively wiped out nearly two years of PR rehabilitation – he angrily pointed at his private secretary and said he had made him do it.

Suffice to say, it wasn’t a good look.

To say it deepened a mistrust of reporters would be an understatement, but the lesson to be learned from this was not to avoid them at all costs, but rather to understand the nature of the beast. William and Harry grew into adulthood with a different media – they have both been burned by media attention, tabloid stories and intense speculation, but the intensity of a 24/7 news cycle is no longer new. They are better prepared for the reality of royal adulthood than Charles ever was and better able to protect themselves, their significant others and their children.

One could argue that William has veered too far in the other direction – and many do – but historically when and how he and Harry choose to make themselves public displays a certain know-how. The exposure in the lead up to the 2007 Diana concert, Harry’s video with the Queen before the Invictus Games, William’s Attitude cover and the timing and cadence of remarks over the years. They might not like it much, but they do know what they’re doing.

And Charles, for better or worse, illustrated why that was a skill set worth having.