In the mid-1990s, two of the world’s most recognizable women—Princess Diana and Carolyn Bessette-Kennedy—found themselves navigating a relentless spotlight, each facing the kind of media scrutiny that most people can only imagine. Their parallel struggles with the paparazzi and the press, along with the lessons they hoped might help the next generation, have come into sharper focus thanks to recent documentaries and biographical accounts.
According to PEOPLE Magazine and a new CNN docu-series titled American Prince, Princess Diana and John F. Kennedy Jr. first met in 1995. The meeting was more than a casual encounter; John, then at the helm of his magazine George, tried to persuade Diana to appear on its cover. He wanted, as his assistant RoseMarie Terenzio later wrote in her book Fairy Tale Interrupted, to do a "respectful piece" on the late Princess of Wales. Diana, however, politely declined, sending John a note that read, "Thank you so much, but not right now."
That meeting left a lasting impression on Diana. Shortly afterward, she lunched with Vanity Fair's Tina Brown and Vogue editor Anna Wintour. Over their meal, Diana confided her deepest hopes for her sons, Prince William and Prince Harry, especially when it came to handling the media. As Tina Brown recounted in an essay for The New Yorker, Diana said, "All my hopes are on William now. I don’t want to push him. I try to din into him all the time about the media—the dangers, and how he must understand and handle it. I think it’s too late for the rest of the family. But William—I think he has it. I think he understands." She added, "I’m hoping he’ll grow up to be as smart about it as John Kennedy, Jr. I want William to be able to handle things as well as John does."
This hope—rooted in Diana’s own fraught relationship with the press—was not unfounded. Both she and Carolyn Bessette-Kennedy, wife of John F. Kennedy Jr., were, as the American Prince documentary reveals, forced to grapple daily with the pressures and ugliness of fame. Gary Ginsberg, a close friend and colleague of John F. Kennedy Jr., offered his perspective in the documentary, as reported by Us Weekly: "Princess Diana was living that struggle [with the paparazzi] so publicly, her fights with the paparazzi during that period [were notorious]." Ginsberg continued, "I’m sure Carolyn was watching it and feeling like she was the American version of it. It probably just increased her sense of isolation and frustration."
Royal biographer Tina Brown, who also appeared in the documentary, suggested that Diana and Carolyn lived "very, very similar lives." The actual reality of living with the media firestorm, Brown explained, "was something that came with so much pressure and so much ugliness." She drew a direct parallel between the two women, noting, "[John] was like the number one pin-up of the world and, I guess, only Princess Diana comes close in terms of the star power that he carried around." Brown also recalled Diana’s private hope that her son William would become as adept at handling the press as John F. Kennedy Jr. had been.
For both Diana and Carolyn, the constant attention was more than an inconvenience—it was an ongoing battle. As two of the most famous women of the 1990s, they were forced to navigate a world where every move was scrutinized, every misstep magnified. Brown observed, "Diana understood that there was no shucking off of the responsibility. They were the most famous people in the world, so there was very much a parallel."
These insights are echoed by those who knew Diana personally. In 2017, Prince William spoke candidly about his relationship with the media in the documentary Diana, 7 Days. As reported by Newsweek, he reflected, "I can understand, sometimes having been in those situations, when you feel incredibly desperate, and it’s very unfair and, you know, things are being said that aren’t true. The easiest thing is to say, or to go to the media yourself, or you know, open that door. But once you’ve opened it, you can never close it again."
That sense of desperation was all too real for Diana. Her life, and ultimately her death, were shaped by the relentless pursuit of photographers and the hunger for tabloid stories. The tragic events of August 1997—when Diana’s driver attempted to outrun paparazzi in the Pont de l’Alma tunnel in Paris—are well documented. According to Town & Country, the car crash that followed claimed Diana’s life at just 36 years old. The world mourned, but the circumstances of her death served as a grim reminder of the dangers that can come with constant media attention.
Carolyn Bessette-Kennedy, too, struggled with the isolating effects of fame. As Gary Ginsberg pointed out, seeing Diana’s public battles with the paparazzi likely heightened Carolyn’s own sense of vulnerability. The documentary suggests that the parallels between their experiences were not merely coincidental, but symptomatic of a broader culture that places celebrity women under a microscope, often with little regard for their well-being.
What’s perhaps most striking in these accounts is the way both Diana and those around her looked to John F. Kennedy Jr. as a model for navigating the press. John, himself no stranger to the spotlight as the son of a U.S. president, managed to maintain a certain grace and savvy in dealing with the media. Diana’s admiration for his approach was clear—she wanted her son William to emulate John’s ability to handle the pressures of fame, hoping he would "grow up to be as smart about it as John Kennedy, Jr."
The new focus on these intertwined stories, brought to light through documentaries and biographical essays, offers a poignant look at the costs of celebrity. It also raises questions about how public figures—and especially their children—can learn to live with, and perhaps even thrive under, the scrutiny that comes with their roles.
As the world continues to reflect on the legacies of Princess Diana and Carolyn Bessette-Kennedy, their stories serve as both a cautionary tale and a source of inspiration. Diana’s hopes for her son, and her recognition of the challenges she faced, remain as relevant today as they were decades ago. The struggle to balance public duty with personal privacy is ongoing, and the lessons learned by one generation may yet help the next.
In the end, the lives of Diana and Carolyn remind us that fame, for all its allure, often comes with a heavy price. Their perseverance in the face of overwhelming pressure continues to resonate, offering both warning and wisdom for those who follow in their footsteps.
