The night before Prince Harry boarded a plane to join his wife and child in Canadian exile, he chose to spend his last hours in the company of relative strangers at a fundraising dinner for his charity, Sentebale, which supports young people affected by H.I.V. in Lesotho and Botswana. It was a devastating conclusion to a story about a lost and troubled young man who has been one of the most famous people in the world since the age of 12, when he walked down the Mall behind his mother’s coffin.

“His words were so intense and personal,” says an attendee of the prince’s speech on that night. “It was like a bomb went off the second he started speaking. He explained the position he had been put in and how he had tried to do the best for his family.” The guest, who knows Harry socially, spoke with him briefly afterward. “I congratulated him on being so brave. He hugged me and said, ‘I’m leaving tomorrow and I’m so glad to be getting away.’ It was very sad, but very impressive at the same time.”

Having lived through the Diana years, I somehow find Harry’s defection much sadder. How did this happen? In the course of trying to find an answer, I spoke with royal insiders, members of the aristocracy, and friends of the couple—all of whom have extensive, personal knowledge of the prince. Almost all unanimously agreed that this is not a story about a bellicose and power-hungry Valkyrie, but one about an immature man who had been looking for an exit from his life long before Meghan Markle came along. What became clear is that, privately, the Windsors have always blamed themselves for Diana’s death, and accordingly, they have sought to atone for it by coddling the vulnerable young prince. He has grown up into a complicated adult—outwardly lovable, charming, and funny, but inwardly tortured and diminished by suffering.

Meaning or Nothingness?

A guest at a recent shooting weekend in Scotland, which included a group of royal-family intimates, recounts a post-dinner conversation: “They were saying how Harry has always been treated with kid gloves, particularly by his father [Prince Charles], and his grandfather [Prince Philip], who in particular blames himself for his mother’s death; that Harry has always been an upstanding man who briefly found real purpose in the army but has not been himself since he was abruptly airlifted out of Afghanistan following a serious security threat. That he has since tried to create new purpose by founding the hugely successful Invictus Games for injured former servicemen, but that alone hadn’t filled the hole. Even though the family had increasingly bent over backwards to accommodate his every whim, he became increasingly spoiled and petulant. They were not surprised that when succor presented itself in the form of Meghan Markle, an outsider, he grabbed it.”

Princes Harry and William playing a charity polo match in 2002. William found out only hours before the official announcement that his brother was engaged to be married.

Harry has hinted to friends over the years that marrying a British girl would not be the answer, because he did not want his future wife to be constrained by already entrenched conventions. So when he met Markle, he didn’t hesitate or overthink her suitability. His new American girlfriend came from a vastly different world; Meghan is an actress from a dysfunctional and broken family, whose life lessons were learned at the altar of another quasi-royal institution—Hollywood. It is well known that Harry immediately fell for the captivating, strong, and beautiful woman. He proposed hastily, even though they barely knew each other, their courtship consisting of the odd weekend and two holidays in Africa.

Oh, Brother

Prince William, Harry’s best friend and closest confidant, is well-meaning, but he took the matter more seriously—his view of the world is predicated on one day becoming King. When he was said to have warned Harry against romantic rashness, Harry reacted violently. And so Prince William found out two hours before the official announcement that his brother was engaged to be married. He had met Meghan only once before.

Meghan has been relentlessly portrayed as the villain, and it didn’t help matters that during the couple’s post-engagement televised interview she surprised many by doing most of the talking, rather than deferring to her royal husband-to-be, as is tradition. Then came the wedding, mired in an ugly family feud and where many celebrities were present, but only one member of the bride’s family—her mother, Doria Ragland. How odd that seemed. A female aristocrat told me how, when she was introduced to Oprah Winfrey on the wedding day, she asked her how she knew Markle. “Oh, I don’t know her at all” came the reply. Another noticed that at the post-wedding dinner, Hollywood types seemed to be prioritized over old friends.

A female aristocrat told me how, when she was introduced to Oprah Winfrey on the wedding day, she asked her how she knew Markle. “Oh, I don’t know her at all” came the reply.

Then there was the matter of Archie’s birth. Harry and Meghan refused to name not only the godparents, but also the attending obstetrician and the hospital. Failure to publicly thank those who have served members of the royal family was seen as ungracious. “But isn’t this what happens in countless families when a new wife from a different cadre comes on the scene?” an insider points out. “I know for a fact that Harry was complicit in all these decisions. He’s been shaking up the bottle for years. Meghan simply took the cork out.”

The rumors filtering out of Kensington Palace made matters worse. “I’ve heard she doesn’t always treat everyone well,” one person told me. Some witnessed Meghan’s domineering and pushy manner with hair and makeup artists; she was said to have insisted that her Los Angeles–based publicity team be frequently present in meetings with the Palace staff. “I don’t think either side did enough to meet in the middle,” says an observer. “She was told, ‘This is not Hollywood. It is the royal family.’ But, again, I suspect Harry encouraged her to behave this way, too. Perhaps it is time things changed anyway.”

When the Sussexes informed Prince Charles that they intended to take an extended break in Canada over Christmas, he was said to have asked them to first come to Sandringham, and leave right after church. One insider recalls, “[Charles] said to them, ‘Come for one night and go on your break—you don’t have to stay for days. It could be Granny’s last Christmas, it could be Prince Philip’s.’ The reply was ‘Absolutely not.’” Again, the Los Angeles team was brought in to broker the details.

“[Harry’s] been shaking up the bottle for years. Meghan simply took the cork out.”

But there is also Meghan’s side of the story. From day one, she and Harry were treated as secondary royals, in an intensely hierarchical system that is mired in outdated convention. As with Diana before them, the senior royals failed to recognize how much good the Sussexes could have done internationally for the future profile of the monarchy.

And then there is the matter of the popular press, which Harry has always hated intensely. “Because of the circumstances of his mother’s death, he has always reviled the deeply dysfunctional relationship the royal family has with journalists,” one of his friends told me. “I’ve heard him say, ‘They slaughter us, they are deeply intrusive and hostile, and then we invite them into Buckingham Palace as if we were all old friends.’”

Culture Shock

Has Meghan been a victim of sexism and misogyny? Absolutely. But there are other factors at play. I’ve lost count of the number of American expat friends who over the years have said to me, “I really don’t understand you Brits. You’re very polite and friendly, but you’re impossible to get close to.” There is truth in that. We suffer from a collective case of suspicion of outsiders, and this subliminally played a role in why the country chose to leave the European Union. There are all sorts of caveats and nuances attached to that statement, but largely that is the world that Meghan Markle landed in. Even if she had transmogrified into a facsimile of Kate Middleton overnight, I’m still not convinced she would have stood a chance. “I’ve met her a few times, and she was fine,” says one aristocrat. “She’s amazing at making you think you’re the best person in the world, but then she moves on. But I’m not buying into this money-grabbing Kardashian type that Piers Morgan has been portraying.”

Some say there is a more personal angle, one which Markle in particular has struggled with—that she too comes from a broken home, one perhaps even more toxic than what has been reported. “There also might be more to her past, which has yet to come out,” a journalist who had dealings with the extended Markle family tells me. “I got the impression that her father is not well, that he has his own issues. He sounded quite seriously damaged mentally and physically, and I suspect there’s a reason why she decided to distance herself from him. Don’t forget he was paid to say the things he did. The telling of it in recent court documents [a reference to the Sussexes’ suing The Mail on Sunday, for the publication of extracts of Markle’s letter to her father] is heavily one-sided and only reflects their point of view.”

Princes William and Harry in 2018. Sources say there has been a genuine rapprochement between the brothers following the negotiation of the “leave agreement.”

But just one member of her family at the wedding? “It’s not that crazy,” one of the guests at the Scottish shooting weekend suggests. “I got the impression her mother doesn’t have an extended family. So Meghan is the circumstance of several broken families. She was effectively brought up as an only child. She was never close to her half-siblings; her mother is, and has always been, her rock. The rest are just chancing their arm. I’ve heard you’d get arrested for some of the things she [Samantha Markle] has said about Meghan.”

The pressure is now on the couple to take ownership of their future. Like the Obamas, Clintons, and Blairs, the Sussexes need to earn a very solid living, protect their reputations (and their child’s), and continue to do charitable work. The intense scrutiny will continue, although no one is certain that a life among celebrities in an unfamiliar culture will provide the peace Harry is looking for. A friend remembers a remark Harry once made during a trip to Africa. “He said, ‘I’d love to just stay here and be a park ranger.’ People thought at the time, ‘Yeah, right,’ but there was truth in that.”

No one is certain that a life among celebrities in an unfamiliar culture will provide the peace Harry is looking for.

There is one piece of good news. Despite daily rumors to the contrary, I hear that since the “leave agreement” was negotiated, there has been a genuine rapprochement between the brothers. “Their relationship is now in much better shape,” a source told me. “The media, as ever, overreacted.” Friends and family now dearly hope that their beloved Harry will finally find the lasting happiness and peace that has always eluded him. Whatever happens now, at least he has his brother.

Vassi Chamberlain is an Editor at Large for AIR MAIL based in London