Princess Diana’s Closest Confidant Reveals What She Would Have Thought of Meghan Markle — And the Truth Is Far More Complicated Than Expected
Princess Diana’s Closest Confidant Finally Reveals What She Would Have Thought of Meghan Markle — And the Truth Is Far More Complicated Than Anyone Expected
Richard Kay still remembers the sound of her voice on the phone. It was the last conversation Princess Diana ever had. Hours later, the world learned she was gone. Nearly three decades have passed, yet Kay remains one of the few people who truly knew the private Diana — the woman behind the headlines, the wry humor, the restlessness, the fierce love for her sons. Now, the veteran royal correspondent has broken his silence on a question that has haunted royal watchers for years: what would Diana have made of Meghan Markle?
His answer is neither the glowing endorsement some expected nor the quiet disapproval others predicted. It is something more nuanced, more human, and ultimately more revealing about the woman Diana was in her final years.
According to Kay, Diana would have found Meghan “intriguing” and even “slightly liberating.” He believes she would have admired Meghan’s independence and the way she offered Prince Harry what Kay calls “an escape route” from the suffocating weight of royal duty. In that sense, the late princess would have recognized something of herself in her younger son’s wife. Diana spent the last years of her life searching for freedom, for a life less constrained by protocol and public expectation. Meghan, in Kay’s view, represented exactly that possibility for Harry.
Yet the warmth stops short of full approval. Kay is clear that Diana would have been “very disappointed” by the bitter and prolonged rift between her two sons. The idea that William and Harry could remain estranged would have cut her deeply. Diana’s greatest fear was always that her boys would lose each other. She had seen enough of fractured families and royal isolation to know how easily love could turn into distance. The public feud, the separate lives, the carefully worded statements that only seemed to widen the gap — all of it, Kay suggests, would have left her heartbroken.
There is another layer to the story that makes Kay’s assessment even more poignant. In the final weeks of her life, Diana spoke to him about the possibility of living in America. She loved the United States. She believed she would be freer there, treated with a more nuanced attitude toward celebrity. Hollywood stars, she observed, managed to live relatively unhindered lives. She imagined she could become “one among many.” New York and California both appealed to her. The only thing that stopped her was her sons. William was 15. Harry was 12. She could not abandon them. “She couldn’t just abandon them — they were young boys,” Kay recalled. Had they been older, he believes, she might well have made the move.
The parallel with Harry and Meghan’s own decision to settle in California is impossible to ignore. Diana dreamed of the very life her younger son eventually chose. She understood the pull of America, the promise of space and reinvention. In that light, her potential reaction to Meghan becomes even more complex. She might have celebrated the escape while mourning the cost — the broken relationship with William, the public airing of private pain, the sense that the family she fought so hard to protect had fractured after her death.
Kay’s recollections paint a portrait of Diana that feels far removed from the tragic icon of popular memory. The Diana he knew was amusing, sharp, and possessed of a wry sense of humor that rarely made it into public view. They would have dinner, go to the movies, and take long drives along the Norfolk coast where she had grown up. She was not the solemn figure of the final photographs. She was restless, funny, and still searching. That searching quality is what Kay believes would have drawn her to Meghan. Independence. Self-determination. The refusal to accept a life defined entirely by others. These were values Diana herself had come to prize.
At the same time, Diana remained fiercely protective of family bonds. She understood the unique pressures of royal life better than almost anyone. She had lived them. She had watched how isolation and public scrutiny could poison relationships. The idea that her sons might one day stand on opposite sides of an unbridgeable divide would have been almost unbearable. Kay’s words suggest that Diana’s love for Harry’s happiness would have been real — but so would her sorrow at the price he paid for it.
The timing of Kay’s comments adds another layer of resonance. Harry and Meghan have now lived in California for several years. Their children are growing up far from the institutions that defined their father’s childhood. William and Kate continue to carry the weight of the monarchy in Britain. The distance between the brothers remains unresolved. Against that backdrop, Kay’s reflection feels less like historical speculation and more like a quiet judgment from the past.
What makes Kay’s perspective particularly powerful is his unique position. He was not a distant observer. He was the last person Diana spoke to before the Paris car crash that ended her life. Their friendship had deepened in the final five or six years of her life, a period when she was increasingly open about her frustrations, her hopes, and her dreams of a different existence. When he speaks about what she might have thought, he does so with the authority of someone who heard her private thoughts at a time when few others did.
The public has long projected its own hopes and grievances onto the relationship between Diana’s memory and Meghan’s reality. Some have cast Meghan as Diana’s spiritual successor — another outsider who challenged the system and paid a price. Others have rejected the comparison entirely, arguing that the two women faced entirely different circumstances. Kay’s comments cut through much of that noise. He does not claim Diana would have seen Meghan as a carbon copy of herself. Instead, he suggests something more interesting: that she would have recognized a kindred restlessness, even as she mourned the consequences of that restlessness for her family.
There is a quiet tragedy in the idea that Diana might have understood Harry’s choices better than almost anyone else — and still been devastated by them. She wanted freedom for herself. She wanted happiness for her sons. She never had to confront the possibility that those two desires might one day collide. Kay’s words force us to sit with that uncomfortable truth.
In the end, the most revealing part of Kay’s assessment may be how carefully balanced it is. Diana would have been intrigued by Meghan. She would have admired her independence. She would have welcomed her, at least initially. She would have understood the appeal of America. And she would have been deeply disappointed by the rift between William and Harry. None of these reactions cancel the others out. They coexist, just as Diana’s own contradictions coexisted — the longing for freedom and the fierce attachment to her children, the public grace and the private restlessness, the desire to escape and the inability to fully leave.
Nearly thirty years after her death, Diana still has the power to complicate our understanding of the present. Through the voice of one of her closest friends, she does so once again. The woman who once dreamed of California never lived to see her son make that dream real. Whether she would have celebrated or wept at the sight remains a matter of speculation. But according to the man who knew her best in her final years, the answer is both — and that is what makes it so heartbreakingly human.