Inside Princess Diana's Falling Out With Princess Margaret

If there was any point that revealed the true relationship between Princess Diana and Princess Margaret, it very well might have been at Di's lowest point. After all, the '90s were a chaotic decade for the royals, but especially for Diana and Charles. During that decade, the couple dealt with secret lovers, not-so-secret affairs, and increasingly dramatic headlines. Even after their scandalous divorce was finalized, the royal exes were under constant scrutiny — Diana especially. That's when secret recordings were leaked to the media that revealed one of Diana's deepest, "darkest" secrets.

Known as the "Squidgygate Tapes," these recorded telephone calls between Princess Diana and an admirer who called her "Squidgy" became a media circus. Practically overnight, an innocent nickname became yet another embarrassment for Diana to endure. The transcripts provided both a risqué look into Di's love life and a scathing critique of the royal family she married into. The leak should never have happened in the first place — talk about an invasion of privacy! — but it did, and it wasn't just one person who leaked the private conversation, but two.

Funnily enough, the first person to leak the conversation wasn't a personal-space-invading journalist, a mean-spirited gossip, or even a loose-lipped member of Diana's staff. It was thanks to a radio scanner that retired bank manager Cyril Reenan accidentally recorded most of the "Squidgy" conversation. Even though it was said Reenan had no idea what to do with the recording, he eventually sold it to the tabloid newspaper, The Sun, in order to make a little extra cash. And then there was the other eavesdropper.

Not only did Reenan manage to record the conversation, but so did a mid-twenties typist. She was your average citizen who just happened to have the juiciest scoop of the year fall into her lap! And Jane Norgrove was in a similar predicament about how to handle the material. Unsurprisingly, she eventually mailed her copy to other tabloid agencies. Strangely, The Sun chose to not publish the material... but The Enquirer in the U.S. jumped on it.

While the scandal exploded, there was someone who could have foreseen the inevitable end of Diana's marriage. Princess Diana found an ally in Princess Margaret, who allegedly felt compassion for her niece-in-law. "I’ve always adored Margo. I love her to bits, and she has been wonderful to me from day one," Diana said. Additionally, the older royal easily recognized what Diana had to deal with in the media. Decades earlier, Princess Margaret had been thrust into the same spotlight, and she found the light to be just as harsh.

Princess Margaret was a tabloid favorite due to her undeniable beauty, but also because she was involved in a rather chaotic divorce. For nearly twenty years she was married to the popular photographer Antony Armstrong-Jones. Both he and Princess Margaret had strong personalities, and although their highs together were high, their lows were devastatingly low. It was the low points that ultimately led to a divorce. Although Princess Diana was not divorced from Charles during the peak of "Squidgygate," Princess Margaret made a bold statement on the matter.

Having endured decades of unhappiness in a complicated and often unpleasant marriage, Princess Margaret could easily see that Diana and Charles' relationship was more than strained. In fact, it was Margaret who eventually suggested the idea of an early divorce for Charles and Diana. During that time, the two were only separated. But Charles, despite his not-so-secret affair with another woman, allegedly disagreed on the matter. Nonetheless, Princess Margaret made her nephew understand that she was going to maintain her relationship with Diana.

After all, Princess Margaret was more than a supporter to Diana. According to the book Elizabeth & Margaret by Andrew Morton, Princess Margaret made a habit of joining Diana during many social events. They were even paired together at leisure outings, such as while shopping or on vacation. It sounds trite, but at a time when tabloids ripped Diana and Charles apart and questioned the monarchy's purpose, Margaret's show of support was huge. But even though they grew close, Diana and Margaret's allyship wasn't to last. It took just one daring interview for their carefully-constructed relationship to crumble.

The sit-down between Diana and interviewer Martin Bashir for BBC's Panorama was a royal nightmare. On television, Diana addressed many taboo issues. She opened up about her postpartum depression, her belief that Charles wouldn't make a good king, and her dislike of fame. Even if Diana was telling the truth about her years of mental health struggles and loneliness in the royal family, the damage was done. It was one scandal too many, and Princess Margaret had to make another difficult decision.

Andrew Morton detailed the fallout of the interview in Elizabeth & Margaret. Allegedly, despite ignoring how she was negatively viewed after her own divorce, Princess Margaret was enraged with the People's Princess. She not only saw the Panorama interview as a destructive move against her family, but as a threat to the stability of the monarchy overall. As one of the most popular royals, Diana's influence couldn't be ignored. So, "Margo" didn't just stop talking to Diana — she decided to cut ties for good.

Princess Margaret committed to a very British way of handling the separation between herself and Diana. The Queen's sister wrote a letter that author Andrew Morton described as "wounding" and "excoriating." We'll never know the exact contents of the letter, but we do know one particularly gutting line from Princess Margaret: She accused Diana of being "incapable of making even the smallest sacrifice" in order to support the monarchy — this "small sacrifice" being a life trapped inside a loveless marriage. The letter devastated Princess Diana, but that wasn't the end of Margaret's revenge.

Not content to just insult the Princess, Margaret wanted Diana to be completely eviscerated from her life. At a particularly petty moment, Princess Margaret ordered every magazine with Diana on the cover to be instantly removed from royal grounds. She forbade her own children from communicating with Diana — and Margaret's children were already into their 30s at that point. Clearly, the People's Princess had become an enemy to the royal family, and even to her former ally. The animosity continued beyond Diana's tragic death.

Not even the fatal car crash in Paris several years later relieved Princess Margaret's scorn for Diana. It's admittedly impossible to tell how someone really feels based on their facial expressions and body language alone, but Margaret's demeanor during Diana's funeral may still have been telling. During the sad occasion, Margaret hardly seemed interested as the carriage passed by. As it turns out, however, a more recent news development turned Margaret and Diana's falling out into something even more tragic.

If anyone wondered why Princess Diana had gone forward with the confessional interview for Panorama, they might have come to simple conclusions. The most obvious was that Diana had wanted to reveal the exhausting and escalating issues within the royal family. This reason alone is perfectly believable! We all saw time and again how the tabloids loved to drag Diana's personal life onto their front pages, which must have been extremely frustrating for the Princess. But there was another, far bigger reason behind Diana's decision that most people didn't know about.

Leading up to the Panorama interview in 1995, Princess Diana knew her husband had been cheating on her. But up until that point, the "mystery woman" in his life wasn't actually a huge mystery; she was long thought to be his "ex", Camilla Parker-Bowles. But to Diana's dismay, rumors spread that Charles had been romantically involved with someone in her own personal circle: her children's nanny. She even believed the mistress had become pregnant by her husband! Determined to find out the truth, Diana tasked an aide with a clandestine investigation into the matter.

If this all sounds like the plot of a soap opera, that's because it turned out to be completely untrue. But Diana was so paranoid after years in the spotlight that she allegedly had trouble believing that the rumor wasn't valid. As we know now, the Princess had probably been lied to. You see, Erin Hill of People magazine eventually uncovered a revelation about the Panorama segment. It turns out that the interviewer, Martin Bashir, manipulated Diana into the bombshell 1995 appearance, using the Princess's concerns about her husband and the nanny against her.

Bashir cleverly knew that the best way to gain Diana's trust was to initially make contact with someone in Diana's inner circle. So Bashir went to Charles Spencer, Diana's brother, and showed him supposed payments that had been made for an abortion for the royal nanny. Charles Spencer told Diana about Bashir and the "payments." Bashir made it look as if someone inside Diana's inner circle had betrayed her; obviously, this made Diana feel even more suspicious — and made her trust Bashir, the person who had alerted her to the leaks.

After Spencer learned of the "receipts," he told People in November 2020 how he'd been tricked by Bashir. "This, in turn, led to the meeting where I introduced Diana to Bashir, on September 19, 1995. This then led to the interview." In the following months, an investigation looked into the matter. The hope was that Spencer could, at last, provide some justice for the dearly departed Diana, who had risked everything to do the infamous interview with Bashir. Spencer had to prove that his sister had been tricked into doing the interview.

British Supreme Court Judge John Dyson led the charge in 2020. At that time, Bashir claimed that he wasn't the source of the rumors that convinced Diana to do the interview. The person behind the damaging rumors was, he insisted, Diana herself! It was she who suspected her husband of having an affair with William and Harry's nanny, Bashir claimed. Even so, Bashir's false bank statements couldn't be denied. Judge Dyson decided that the false bank statements did indeed convince Princess Diana to keep the interview on her schedule, despite wanting to back out of it. The ripple effects were devastating.

Both Margaret and Diana knew how it felt to be manipulated by the press. Could this common ground have saved their relationship? Princess Diana died in 1997, and Princess Margaret followed suit in 2002; neither was alive to learn of the recent news developments, although perhaps their relationship wouldn't have healed either way. The deceitful push to go on Panorama disrupted more than a royal establishment. It ended the bond between two women who should have supported each other. And thanks to recently released documents, we're still learning just how brave Diana really was.

In 2019, Lawrences Auctioneers listed two personal letters from Princess Diana. The first, dated December 5, 1990, was listed for £3,000, or about $4,000. Only about three pages, the letter was addressed to one Ivy Woodward — an unfamiliar name, even in royal circles. Despite the letter's low page count and unknown recipient, however, the letter is hugely important to Diana fans. It not only provides a rare glimpse into Diana's personal life, but into a relationship very few people even knew she had.

Ivy Woodward and Princess Diana became friends completely by chance — and under stressful circumstances. They were both wrapped up in their own nightmarish moments when they first crossed paths. Their first meeting was not at some lavish royal event, as you may expect, but rather at a local hospital. It was September 1990, and neither woman knew the challenges that awaited them... and how badly they'd each need a friend over the coming months.

Princess Diana was at the hospital for her husband, Charles, who was recovering from a broken arm he'd suffered while playing polo. Of all the reasons Charles could've been at the hospital, a broken arm is on the milder end of the spectrum. Unfortunately, Ivy's reason for being at the hospital was much more serious. She was there visiting her son, Dean, who was in a coma from a motorbike accident. The compassionate princess couldn't help but connect with Ivy.

Ivy was distraught over her son's accident, and the pain and worry of potentially losing him was a heavy burden. She needed a friend to lift her up, but never expected it to be a total stranger — or someone she initially thought was a total stranger. Obviously, Diana was one of the most famous and recognizable people in the world; it wasn't long before Ivy realized who she was talking to at the hospital. Despite their different backgrounds, both women had something important in common: loved ones in the hospital. So, they started talking.

The two became close as Charles' arm healed and time passed for Ivy's son. Princess Diana even visited Dean and pulled strings in helping him awake from his coma. (Side note: imagine waking up from a coma and seeing who else but Princess Diana standing over you? Dean must have been shocked.) Diana and Ivy didn't lose touch, either. Even after both ladies were free from hospital visits, they stayed connected via letters and phone calls. Ivy eventually opened up to Diana about another struggle in her life.

Ivy's son Dean had a wife named Jane, and it was clear that she couldn't handle the difficult situation caused by her husband's accident. Jane allegedly became distant from her mother-in-law when Dean returned home, which created a terrible family drama. Ivy was torn. Should she back down from the fight with her daughter-in-law, or demand to see her son? No stranger to family drama, Princess Diana reached out with some kind words — and wise advice.

In her letter, the Princess shared how happy she was to hear of Dean's recovery. After all, she'd watched Dean struggle to recover from his coma herself! She made sure to remind Ivy of her importance in Dean's life. Ivy's love for him, Diana said, made all the difference. "He wouldn't be here now if it wasn't for his mother," she wrote. Addressing the wife's behavior, Diana was careful not to overstep. She understood better than anyone the often-complex role of daughter-in-law!

Princess Diana expressed that "time will iron things out" for the struggling family. Wise words from someone who definitely knows a thing or two about complicated family dynamics! The Princess made sure that everyone in the situation was treated with patience and respect, including her fellow daughter-in-law. Diana's kind words offered some sense of hope and peace for Jane, a woman she hardly knew. Finally, Diana signed off with a personal message.

“The boys," she wrote, referring to Princes William and Harry (who were 8 and 6 at this time, respectively), "are thrilled at the prospect of Christmas on the horizon and have searched high and low for any parcels that might be coming their way!” If we didn't know better, we'd think that these lines were written by any average mother about her young sons. Of course, the letter revealed so much more than what was written on the three pages.

Ivy Woodward was touched by the letter. How couldn't she be? The princess reached out to her as a gesture of kindness and friendship. It was yet another kind act on Diana's long resume. Despite the tabloids often dragging Diana's personal life through the mud, it was a secret to no one that Diana dedicated her life to helping others as much as she could. She was often seen speaking to and comforting the homeless, and visiting the roughest areas of London to make a difference. She'd transformed so many lives.

And Diana didn't only transform the lives of her close friends and family. It could be argued that she was even more dedicated to improving the lives of total strangers. One man by the name of Vincent Seabrook had his life turned around for the better thanks to the Princess. When he met Princess Diana, he was homeless and broken down. Unlike so many others in a position to help, Diana actually took the time to hear his story.

Seabrook had endured years of abuse as a child, and by the time he reached adulthood, he'd spent so much of his life evading this abuse that he didn't know how to be an adult. He was lost, emotionally and literally, as he had no where safe to go. Diana felt compelled to help and found a place for him to live, and all because she knew she could. "Without her help,"Vincent said, "I really believe I would be dead by now." His life has since changed in a big way.

With a secure place to take shelter, Vincent got a new lease on life. When the Princess tragically passed, Vincent made his way to Kensington Palace a new man. Working as a security guard with a place of his own, he carried with him a plaque of love and gratitude for the Princess, along with flowers. It was just another bouquet in a sea of flowers, but we like to think that Diana saw each and every one of them and knew the stories of the people who honored her with them.

The second letter available for auction revealed another side of Diana: her sense of humor. It's no secret that Diana faced struggle after struggle as a young royal, but even so, she always had a witty remark or sneaky grin for a few select individuals. Her humorous side was evident in a letter she once wrote to Sergeant Ronald Lewis, a bodyguard for herself and Charles. In the letter, she expressed her gratitude in a way only the People's Princess could.

After greeting Ronald in the letter, Diana wrote, "What with the extreme heat and often difficult conditions moving around was a nightmare for you and your luggage! Thank you from the boss's wife." With a big signature, she ended her letter. Not only are we giggling at the fact that she called herself and Charles "luggage", but it's hilarious how she also referred to herself as "the boss's wife" and not, you know, "Diana, Princess of Wales, Most Famous Woman In The Galaxy."

Experts supposed that the short but sweet letter would also earn a £3,000 payday. This is unsurprising, as it puts Diana's down-to-earth side on display. And those who really knew Princess Diana also knew that her kindness wasn't for good headlines; she loved making people smile. After battling with her own mental health issues, she knew what a kind word or a simple touch could do for the broken-down people of the world.

Before Princess Diana really dove into her humanitarian acts, she herself needed saving. It's been said, even by close friends, that the Princess of Wales suffered mentally from her marriage with Charles, and attempted several times to take her own life. This may not be easy to understand, since most people expect royalty to be happy beyond measure, given their vast wealth and resources. Because of the stigma surrounding mental illness, Diana had to find peace on her own. It was a dark path that only she could travel on.

Diana's closest friends and family tried to show her they cared however they could, but Diana's role as the Princess of Wales made her surprisingly isolated from her loved ones. Nowadays, her loved ones say that Diana's suicide attempts were more of a "cry for help," but those cries, for the most part, were ignored by the public for too long. Princess Diana could have fallen, but she eventually found love and strength in those who cared for her. She knew she had to share the same kind of love and strength with the world.

Diana inspired countless people around the world to stand up for themselves, for their own happiness, and for their loved ones. It wasn't just Ivy, Vincent, and Ronald who benefitted from her kindness, but all who were inspired by her positivity. Today, her sons continue her legacy of humanitarianism. They've spoken out about issues that were particularly important to Diana, including the plight of the homeless and the need for more resources to be provided to those dealing with HIV and AIDS. Perhaps most personally to Diana, her boys are also outspoken about the importance of mental health.