The Prince and The Princess

Jeff Cunningham
6 min readAug 31, 2022


In Newport, RI, with Prince Charles

“The road to achievement is littered with shards of broken glass.”

On a sunny September day in 1997, a middle-aged man wearing scuffed boat shoes and stylish flip sunglasses walked up the gangplank, a mop of brownish hair bleached to straw blond where it was thinning. He was dressed in the manner of a handsome New Englander but the son of a queen of Great Britain and so decidedly old England. When his mother Elizabeth was crowned in 1952, he began the world’s most extended apprenticeship. Thirty-five years later, the future king had been through some rough patches, and the most recent had ended in tragedy not only for his immediate family but also for the Royal Family. His mother called 1992 “annus horribilis” as she watched her three children’s marriages collapse, and 1997 was destined to be Charles’s annus horribilis.

The problem was he did nothing wrong.

What had the gods rollicking and rolling on Mount Olympus that September day was that Prince Charles was my guest for a fundraiser. These events are arranged at least a year in advance. No one could have known that Diana Princess of Wales would die a month earlier when her Mercedes limousine spun out of control. The driver attempted to evade seven photographers, slamming into a tunnel wall at 65 mph ( twice the speed limit). Diana was not wearing a seatbelt. As a direct result of that oversight and prompting the driver to step on it, the impact threw her body forward with such force that it tore a vein in her lung and caused cardiac arrest. She died in the hospital several hours later. As soon as Charles heard about the accident, he flew over from Balmoral, the Royal family home in Scotland so that he could be by Diana’s side. It was too late to see her alive and save his reputation.

The death shocked the world. Charles and the royals saw the news in the most agonizing personal terms. She had been the “people’s princess,” and it didn’t help that the media cast Charles as the villain. It was the low point of his life and career. Now, fast forward to Newport, RI, and he was to join me for a cruise around the harbor. I was wondering how is this going to work?

Charles Philip Arthur George Windsor was born November 14, 1948. He was named after Charles Ist, a British King unceremoniously beheaded by Oliver Cromwell. It was a bad omen. If Charles had not already learned the meaning of an old media adage, “fame is like a fountain, it goes up, up, and out, ” he would shortly. Royalty may have its privileges but extracts a heavy price. He was proof that having an extraordinary life can be extraordinarily challenging.

It seemed to have begun right after he married. In 1981, the publicity-shy royal gave an interview that sent his world into a tailspin. He committed the most egregious sin— he told the truth. When a journalist said to Charles and Diana, “You both look very much in love,” Diana replied, “Oh, yes. Absolutely.”

Charles responded philosophically with a nod of his tousled head. “Whatever ‘in love’ means.” Oops. He was lost speaking about personal emotions on television. As the four words stumbled out of his mouth, imagine the displeasure of the media that he dared keep intimate thoughts to himself. The new world order focused a powerful lens. It examined each word like a petri dish. Charles was the perfect perp if you could get a life sentence for stupidity. Although the interview preceded social media, tabloids were a proxy for mob behavior. As sensationalism took center stage, facts became supporting actors, and they would never get a lead role again.

In hindsight, it spelled the beginning of the end, certainly insofar as public affection was concerned. He could never get the media world quite right, and society would judge him mercilessly for the sin of being a lousy storyteller. The “in love” soundbite was the subject of more long-distance analysis than Kim Jong Un. Amateur psychologists fell all over themselves, connecting it to the ups and downs of the marriage, “he couldn’t even say he loves her.” The meme would replay on Youtube and be shared by millions.

Still, with even greater irony, the interview ended happily. As an Englishman, the interviewer understood royals don’t speak in gushy OMGs or LOLs. He took Charles’s comment in stride and said, “you look like two very, very happy people.” This time, there was no hesitation, and Charles said, “yes.”

“Diana added, “As you can see.”

But no one saw. General Stan McChrystal once noted in the war against ISIS, “you can’t defeat a network without a network.” For all its power and glory, the British monarchy was defeated by a network of nobodies.

The second moment in Charle’s patchy relationship with the media was an interview on June 29, 1994, on ITV, marking the 25th anniversary of his investiture. Charles touched upon his life, philanthropy, the Royal Family, and Britain’s future. But this time, it took two words for assassins to start shooting.

Reporter Jonathan Dimbleby asked if Charles had been “faithful and honorable” during his marriage. Charles replied: “Yes,” but an instinct which is downright unhelpful because it does not allow him to utter an untrue statement tacked on the word, “Until.”

A less naive person would know that nothing before “until” matters in an interview. He then said, “Until… it became irretrievably broken, us both having tried.” A better response would have been: ‘Whatever faithful means.”

There is a sense now that truth is just another variable. When we are offended or hurt, we cry. But if you confess truthfully, that’s nearly criminal. Charles’s sterling reputation for good works didn’t matter. That he and Diana were separated didn’t matter. That the marriage was loveless didn’t matter. Diana had dalliances (unadmitted until later). Again, it didn’t matter. Charles was the future king, and kings don’t admit to cheating. It’s just not done. Presidents do not admit to lying. It whetted the appetite of a beast called scandal.

As we sailed around Newport, Diana’s death hung over us like a wayward kite that did not know which way to go. As you have guessed, the fellow who didn’t know what “in love” meant had other things he wanted to talk about. Charles inquired about the boat’s maker (how would I know?) and whether the tennis courts were grass (they were). He suggested we visit the Mary Rose, Henry VIII’s ship that sunk offshore and Charles’s favorite. Leave it to Charles to be obsessed with Henry VIII. I could practically hear the gods chortling that they both had wife problems.

Poetic justice.

He parted in the best English tradition. An endless goodbye: “bye, excellent to meet you. Bye. Do take care. Bye now.” Then, Charles saluted me like a future king and strode into the sunset, reminding me of Fitzgerald’s line, “We beat on, boats against the current.” Not everyone’s idea of a hero perhaps, but most undoubtedly heroic. In all, a memorable time with a bloke whose lineage went back further than my ancestors ate with knives and forks.

The day brought home a lesson. Those who aim for an extraordinary life soon discover the road to achievement is littered with shards of broken glass. So if you could be sipping single malts at Balmoral and wearing kilts, would you bother carrying the Sisyphean boulder on your shoulders for forty years? Why bother? The answer is that somewhere in the recesses of his soul there is a yearning to hold the torch high even if being the Queen’s son gets you squat.

Whatever squat means.



Jeff Cunningham

Writing about extraordinary lives. Came for the people; stayed for the stories.