A British royal historian says Prince Harry, now 41 and living in California, bears an uncomfortable resemblance to the last royal who walked away from duty, and that neither man found happiness on the other side of the exit.
Hugo Vickers, author of "Behind Closed Doors: The Tragic, Untold Story of the Duchess of Windsor," told Fox News Digital he uncovered striking parallels between Harry's post-royal life and that of Edward VIII, who abdicated the British throne in 1936 to marry American divorcée Wallis Simpson. The comparison is not flattering to either man.
Vickers put it bluntly:
"The one thing in common is that the two husbands both look pretty miserable."
The observation lands at a moment when Harry's public profile is increasingly defined not by what he left behind but by what he has failed to build in its place. He and Meghan Markle, 44, stepped back as senior royals in 2020, citing what they called unbearable press intrusions and a lack of palace support. They moved to California, aired grievances in an Oprah Winfrey interview, a Netflix documentary, and Harry's memoir "Spare." They launched commercial ventures. And yet, five years on, the question that hangs over the whole project is whether any of it has made the Duke of Sussex happier than the life he abandoned.
Vickers does not think so.
Vickers told Fox News Digital he noticed the resemblance while researching Edward VIII's later years. The former king spent decades in exile, mostly in Paris, where he and Wallis created what Vickers described as "a miniature court in exile", complete with coronets, portraits of Queen Mary, and footmen in livery.
"If you look at photographs of the Duke of Windsor in old age... I've never seen such sad eyes on a man because of what happened. In both cases, they decided not to do the duty which they had been born to undertake."
He contrasted that image with Queen Elizabeth II, who served until her death. Vickers said he sometimes shows her photograph during school talks, "sparkling eyes at the age of 90, having done her duty and feeling the calm, level gaze, conscious of duty fulfilled." Then he offered the comparison that gives the story its edge:
"Whereas the Duke of Windsor looked pathetic, and he looked very sad. And Prince Harry also looks very, very sad most of the time and rather angry."
That word, "angry", tracks with the public record. Harry's memoir was a catalog of resentments against his family, the press, and the institution he grew up in. Royal experts told Fox News Digital the last time Harry and his brother Prince William spoke was during Queen Elizabeth II's funeral in 2022. The estrangement from a family that biographers say suffered real damage from the couple's public accusations appears total.
Vickers drew a careful distinction between Wallis Simpson and Meghan Markle. Both were American. Both were divorced before marrying into the royal family. Both, in his telling, married men who doted on them. But their approaches to life outside the palace could not be more different.
Wallis, Vickers said, "wrote a book of memoirs. She gave one or two interviews, but she was very discreet, to be quite honest. She was very much in the background." Meghan, by contrast, launched a lifestyle brand called As Ever on April 2, 2025, and has used her title to build a commercial portfolio.
"She is using her title and her name to market things.... She's been selling products and the like.... I just personally don't think Prince Harry looks happy. My theory is that he is terrified of losing her, which is a very understandable syndrome to get into."
British broadcaster Helena Chard echoed that assessment. She told Fox News Digital that both Edward and Harry "wanted out of the institution" and that their wives were their "get out of jail" cards. She pointed to the Netflix documentary's "freedom flight" footage, Harry and Meghan gleefully filming themselves as they left royal duties behind.
But Chard suggested the mood has shifted.
"Harry and Meghan built their exit. However, it doesn't guarantee safety or peace. Prince Harry continuously worries about Meghan, his family, their safety and media backlash. He seems to be reverting to what he knows and enjoys, his previous royal life."
That reversion was on display in recent weeks. Harry made an unannounced visit to Ukraine on April 24, delivering a speech at the 18th Kyiv Security Forum in Kyiv and participating in a panel with Ukrainian veterans. He and Meghan also spent four days in Australia, posing for selfies at the Sydney Opera House, greeting crowds at the Cruising Yacht Club of Australia, and visiting Melbourne, where Harry attended a Q&A session at Mission Whitten Oval. When asked during his Ukraine trip about being "not a working royal," Harry responded firmly: "I will always be part of the royal family.... I am here working, doing the things I was born to do."
The statement carried a note of defiance, and perhaps longing. It is hard to claim you are doing the things you were born to do when the institution you were born into no longer counts you among its working members.
Vickers offered a theory about what separates royals who thrive from those who don't. It has nothing to do with talent or ambition. It comes down to whether you support the monarch or compete with the monarch.
"The most successful members of the royal family are those who support the monarch without competing with him or her.... People like Sophie, Duchess of Edinburgh. She is a classic example. Catherine, Princess of Wales, likewise, does not compete with her husband, does not compete with the queen, does not compete with the king. Camilla actually also does not compete with the king. She supports him."
That framing puts Harry and Meghan squarely in the competitor column, a position the monarchy's centuries-old structure was not designed to accommodate. King Charles III continues to represent the Crown on the international stage, while his younger son carves out a freelance version of royal life from Montecito.
Kinsey Schofield, host of YouTube's "Kinsey Schofield Unfiltered," told Fox News Digital that Meghan entered the royal family with instincts shaped by Hollywood, not by constitutional tradition.
"The monarchy isn't just a family. It's a centuries-old constitutional machine with high expectations, limited personal autonomy and a hierarchy that doesn't bend easily to modern celebrity culture. Meghan approached it with a more Hollywood-adjacent framework, where personal brand, narrative control and visibility are assets. Inside the monarchy, those same instincts can be liabilities."
Schofield also noted the structural parallels between Meghan and Wallis, both American, both divorced, both "perceived as disruptive", while cautioning against oversimplifying the comparison. Wallis triggered a constitutional crisis in a rigid, pre-war monarchy. Meghan's departure produced what Schofield called "more of a reputational and cultural crisis" within an institution that had already survived divorce and tabloid scandals.
The sadness Vickers described is not merely a matter of facial expressions in photographs. Harry's post-royal identity has been built in large part on charitable work, and that foundation is showing cracks.
The New York Post reported that Harry feels "deeply depressed and embarrassed" over a probe into Sentebale, the charity he co-founded in 2006 with Prince Seeiso of Lesotho in honor of Princess Diana. The Charity Commission opened an investigation after chairwoman Dr. Sophie Chandauka accused Harry of "harassment and bullying," following his resignation as patron amid a governance breakdown. A source told NewsNation's Paula Froelich: "He loves his charities, this is what he wants to spend his life doing and now, one of them is gone... and in the most horrible way."
Harry and Seeiso issued a joint statement: "With heavy hearts, we have resigned from our roles as Patrons of the organization until further notice, in support of and solidarity with the board of trustees who have had to do the same."
For a man who told reporters in Ukraine that he is doing "the things I was born to do," losing a charity tied to his mother's legacy is not a minor setback. It is a blow to the very identity he has tried to construct outside the palace walls.
The late Prince Philip apparently saw something coming. Majesty magazine editor-in-chief Ingrid Seward previously claimed, as reported by The Telegraph, that Philip gave Meghan the nickname "DoW", short for Duchess of Windsor. Whether intended as a warning or a barb, the label now reads like a prophecy.
Meanwhile, Harry's ongoing legal battles with the British press continue to churn, keeping his name in headlines for reasons that have nothing to do with service or duty. A source recently told People magazine that the couple is "not reliant on Harry's father or taxpayer-funded money." Financial independence is an achievement. But independence from purpose is another matter entirely.
Schofield summed up the uncertainty around Harry's future path:
"For Harry, his long-term positioning still feels less defined. He has leaned heavily into advocacy and legacy projects, but there's an ongoing tension between his royal identity and his post-royal reality. That ambiguity can be difficult to sustain over time."
Chard noted that both Wallis and Meghan "earned independently before marrying into the family, and both landed husbands who completely doted on them." She went further: "I'd go as far as saying both husbands feared losing their wives and would do absolutely anything not to lose them."
Vickers made a similar observation about Harry's apparent anxiety, calling it "a very understandable syndrome to get into." Whether or not that fear is justified, it shapes the decisions of a man who once had a clearly defined role and now must invent one from scratch, while managing a brand, raising two young children (Prince Archie, 6, and Princess Lilibet, 4), and navigating a family rift that shows no sign of healing.
The comparison to Edward VIII is not perfect. Edward gave up the throne itself. Harry gave up a supporting role. Edward spent his exile in a Paris mansion filled with royal trappings. Harry spends his in a California estate filled with Netflix cameras and lifestyle-brand launches. But the emotional arc Vickers describes, duty abandoned, happiness not found, sadness settling in, tracks across nearly a century.
The monarchy, whatever its faults, continues to generate its own controversies. It is not a perfect institution. But it offers something Harry's freelance royal career cannot: a structure that gives meaning to sacrifice. Queen Elizabeth served for seven decades and, by Vickers' account, had sparkling eyes at 90. Edward died in exile looking hollow. Harry, at 41, still has time to choose which photograph he wants to resemble in old age.
Duty is not glamorous. But it tends to age better than freedom without purpose.
