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Diana Would've Been "Very Disappointed” in Harry for This Reason, Sources Say

She had vowed she "would never allow herself to be painted as the victim again," an insider said.

Diana, Princess of Wales with Prince Harry on holiday in Majorca, Spain on August 10, 1987.
Georges De Keerle/Getty Images

There is no question that the death of Princess Diana was the single most traumatizing event of Prince Harry's life. On the cusp of becoming a teenager when his mother was tragically killed in a car crash in Paris (he turned 13 less than a month later), the young prince was consumed by grief. In 2017, Harry told Bryony Gordon on her podcast Mad World it would take 20 years before he was ready to fully confront his feelings about his mother’s death.


It was after Harry's own experience with therapy back then that led him to join forces his brother, Prince William, and sister-in-law, Kate Middleton, to launch their mental health campaign, Heads Together, whose mission is to remove the stigma around talking about mental health. Harry is no longer involved in the initiative, which is now run by The Royal Foundation of the Duke and Duchess of Cambridge.

Ever since, he has shown tremendous unresolved anger towards the Royal Family that began to resurface when he married Meghan Markle and became a husband and father. In his new five-part series for AppleTV+, The Me You Can't See, which the prince co-produced with Oprah Winfrey, each installment features Harry talking about the traumatic memories from his childhood, his and Meghan’s claim that his family was unwilling to help Meghan when she struggled with suicidal thoughts during her first pregnancy, and his unresolved feelings of anxiety from those events that he still struggles with today. The prince's revelations on the series come on the heels of a series of interviews where he said much of the same, openly criticizing the Royal Family and his father, Prince Charles, in particular, who he said passed down a "cycle of genetic pain and suffering" to him. On the AppleTV+ series, Harry even bared his soul participating in on-air therapy sessions.

The prince told Winfrey on the series, "I have no doubt my mum would be incredibly proud of me. I'm living the life that she wanted to live for herself, living the life that she wanted us to be able to live."

But, according to some insiders, there’s one thing Harry’s done that would have disappointed Diana. In fact, they say she would be "greatly concerned" about some of her son's choices since leaving the Royal Family. Read on to find out what they are.

Diana would have wanted Harry to be seen more as an advocate rather than a "victim."

Diana and Prince HarryAllstar Picture Library Ltd / Alamy Stock Photo

During the final year of her life, after her divorce from Charles had been finalized, Diana was intent on redefining herself as a modern humanitarian who would harness her worldwide popularity to shine a light on the issues she cared most about. The princess traveled to Bosnia and Angola to highlight the blight landmines in those countries. While with a team of Red Cross workers, Diana visited hospitals where young children lay dying, toured areas torn apart by war, and even walked through an active landmine field. With hundreds of cameras pointed at her, Diana wordlessly conveyed a very important message that the world needed to pay attention to this issue.

As a humanitarian, Diana wanted to bring attention to a story, but not become one in the process. A source told Best Life, "Diana would have encouraged Harry to champion the humanitarian causes he cared about. She would be proud to see him take on the issue of mental health, but she would have wanted him to be seen as more of an advocate and less of a victim." The insider continued, "She would have been very disappointed to see so much of Harry's campaign for mental health revolve around him and his issues with the Royal Family, revealing so much of his personal story. She would think he'd been taken advantage of by the media and would be concerned he'd exposed too much of himself. After that disastrous interview with Martin Bashir, the one thing the princess vowed was that she would never allow herself to be painted as the victim again."

RELATED: The One Person Who Tried to Stop Diana From Doing the BBC Interview.

Diana would not have approved of Harry being openly critical of William and Charles.

Prince Harry, Prince William, and Prince Charles sit in the front row during the global premiere of Netflix's 'Our Planet' at the Natural History Museum in Kensington, London, hosted by Sir David in 2019John Sibley / PA Images / Alamy Stock Photo

During his two-hour interview with Meghan and Oprah Winfrey in March, the prince claimed his father had cut him off financially and stopped taking his calls during the Megxit negotiations. He went on to say both his father and brother were "trapped" inside the institution of the monarchy.

Appearing on talkRADIO in April, royal biographer Andrew Morton said Diana would not have approved of Harry openly criticizing family members closest to him. He explained (via Express), "He wasn't just attacking an institution. He was also attacking his brother and his father." The author, who secretly collaborated with the princess on the bombshell tell-all Diana Her True Story, also revealed, "I don't think she would have approved of Harry calling his brother 'trapped' in his situation because he's not supposed to throw his brother under the bus." Diana had often told Morton Harry "is supposed to be there" for William "as a back up in the nicest possible way."

Harry's commercialization of the crown would have "caused some concern" for Diana.

By the time Diana had divorced Charles, she was one of the most famous and beloved women in the world. When I was writing my book, Diana The Secrets of Her Style, a close friend of the princess told me, "There were offers every day coming in from fashion companies and brands begging to go into business with the princess. She laughed them off as silly ideas."

Diana was very proud of her British heritage and was an ardent monarchist. "Diana wanted William to be king, the kind of king that would lead the British people with intelligence, empathy, and compassion. He knew it was his destiny," said one insider. "She would never want it threatened or cheapened in any way."

According to the source, Harry's multi-million dollar deals with Netflix, Spotify, and Apple TV+ would have "caused some concern" over the appearance that he was cashing in on the crown. "Diana was a great philanthropist as she showed with her dresses auction. She used the relics of her royal life to raise money for AIDs and cancer charities. She never used them for personal gain. She would have been troubled by the idea that the only way Harry was making money was by talking about his experiences as a royal or trading—intentionally or not—on his title.”

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Diana's definition of freedom would vary a great deal from Harry's.

Prince Harry talks to his mother, Diana, Princess of Wales who wears a suit designed by Tomasz Starzewski to VJ Day commemorations Tim Graham Photo Library via Getty Images

In the last year of her life, Diana did speak of moving to America with several friends, including royals reporter Richard Kay. At the inquest into her death, The Daily Mail correspondent said she had told him: “My destiny is to go abroad.”

Unlike Harry's surprise announcement that he and Meghan were stepping down from royal life to find "financial independence" and seek privacy in North America, Diana had a plan. She had been looking at properties in California and New York. On a lunch at the Four Seasons during the summer of 1997, Diana told Tina Brown that she was planning to produce a series of documentaries highlighting various causes. Kay revealed that the princess also wanted to open a network of worldwide hospices.

“Diana did long to be free and seriously considered living in America,” said one insider. But, the source added, she ��wasn't going to leave Britain without knowing how it would work and she wasn't going to just leave everyone behind. Diana knew she had to find a new way to live, but unlike her son, she would not feel the need to destroy everything and everyone in her former life as a royal in order to do so."

The source said she's be worried that Harry hadn't fully healed from the hurts and trauma of the past. "Harry can't stop making terrible accusations against the Royal Family. He's left, but he hasn't moved on," said the insider. "Diana knew finding happiness in her own life and leaving the past behind was the best revenge. She would not drag the hurts and grievances of the past behind her."

RELATED: 3 Things Princess Diana and Meghan Markle Did to Change the Royals Forever.

Diane Clehane is a New York-based journalist and author of Imagining Diana and Diana: The Secrets of Her Style.