The Tragedy Of Caroline Kennedy Gets Sadder & Sadder

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The checkered history of America's most famous — and in some cases most infamous — political dynasties, the Kennedys, is back in the spotlight again thanks to "Love Story," the latest venture from prolific showrunner Ryan Murphy focusing on the whirlwind marriage and fatal denouement of John F. Kennedy, Jr., and Carolyn Bessette. And as the former's older sister — played by "Mr. Robot" star Grace Gummer — Caroline Kennedy also features heavily in the must-watch eight-part drama.

Of course, unlike most of the senior family members depicted in the gossipy miniseries, Caroline is still very much alive, having just celebrated her 68th birthday. But sadly, her life — even as recently as December 2025 — is still being plagued by sadness, hardships, and unimaginable despair. From the deaths of multiple loved ones and daddy issues to career setbacks and cousin betrayals, here's a look at 13 times her story took a turn for the tragic.

Caroline Kennedy was only five years old when she experienced the first of the many tragedies that plagued her life. In 1963, the youngster was out horse riding in Massachusetts with her younger brother, John F. Kennedy Jr., and her heavily pregnant mother, Jackie Kennedy, when the latter started suffering severe labor pains. Rushed to the hospital, she subsequently gave birth to son Patrick Bouvier Kennedy via cesarean section five weeks prematurely.

Medics had noticed that Patrick was having difficulty breathing within minutes of his birth, and after being diagnosed with hyaline membrane disease, he was transferred to Boston Children's Medical Center and placed in a hyperbaric chamber. But despite best efforts to save his life, the baby succumbed to the condition after just 39 hours.

Patrick was buried at Brookline's Holyhood Cemetery following an intimate funeral mass conducted by the Archbishop of Boston. Caroline and John Jr., however, were considered too young to attend. The tragedy inspired John to lead the charge for more funding for premature care.

On November 22, 1963, just five days before she turned five, a young Caroline Kennedy experienced the most unimaginable tragedy. This was the historic date that the 35th POTUS, John F. Kennedy, was fatally shot by Lee Harvey Oswald during a motorcade through Dallas' Dealey Plaza.

In her memoir, the Kennedy family nanny Maud Shaw claimed she was the individual who had to inform his daughter about the horrific development. "I took her in my arms," she wrote in "White House Nannie" (via People). "'I can't help crying, Caroline, because I have some very sad news.' Then I told her. It was a dreadful time for us both. Eventually she fell asleep while I sat on the bed, still patting her."

Caroline has often talked about the short but impactful length of time she spent with her dad, and how his untimely death deeply affected her. "I have thought about him and missed him every day of my life," she said in a video for the John F. Kennedy Library Foundation commemorating what would have been JFK's 100th birthday. "Growing up without him was made easier by all the people who kept him in their hearts, who told me that he inspired them to work and fight and believe in a better world, to give something back to this country that has given so much to so many."

In June 1968, another member of America's most famous political dynasty was gunned down in cold blood. Robert Kennedy, the younger brother of the 35th, was assassinated on the same day he'd won the California primary by Palestinian Sirhan Sirhan, reportedly for backing Israel in the wake of the Six-Day War.

It was another devastating blow for a young Caroline Kennedy who'd looked upon Robert as a surrogate father figure. According to Jackie Kennedy's assistant Kathy McKeon, she and her younger brother John F. Kennedy Jr. enjoyed spending a significant amount of time with their uncle, who'd often treat them to piggyback rides.

"He was very, very good to them," McKeon told People. "It was a very sad day, it was a sad day for everybody." The assistant also recalled how she was tasked by Jackie with helping the two siblings deal with the shocking news. "I found John and Caroline crying in John's room. 'Your Uncle Bobby is up in heaven,' I tried to console them. 'Let's choose a dress for you to wear,' I suggested gently to Caroline. She knew without asking that I meant for the funeral." 

Robert F. Kennedy's assassination impacted Caroline Kennedy's life far beyond grief. Her mom, Jackie Kennedy, became so concerned that her two children were now the ultimate targets, she announced plans to leave America. Within a few months, she'd wed Aristotle Onassis, a Greek shipping magnate, and moved to his own private island of Skorpios with her daughter and son, John F. Kennedy Jr., in tow.

Unfortunately, Caroline didn't appear to enjoy her Mediterranean experience. When asked by her cousin David how she felt about Onassis during a brief return to the States to attend their grandad Joseph P. Kennedy Sr.'s funeral, she reportedly replied (via Daily Mail), "I don't like him."

And further evidence Caroline wasn't a fan came when she tried to block any mention of Onassis' name at her mother's funeral service in 1994. In an interview five years later, Jackie's stepbrother Yusha Auchincloss claimed (via J. Randy Taraborrelli's "The Kennedy Heirs") that while younger brother John believed their stepfather — who'd died in 1975 — merited at least a mention, his sister was adamant the focus should be elsewhere: "In terms of Jackie's place in American history, she reasoned, she should only be remembered as a former First Lady who'd been married to an assassinated President."

Caroline Kennedy suffered a major scare in 1984 when Chicagoan Herbert Randall Gefvert phoned her workplace, New York's Metropolitan Museum of Art, and claimed he'd planted a bomb there. The man, who offered his name and address while making the call, was later arrested for the threat, which thankfully proved to be a false alarm. But this wasn't the first time the ex-First Daughter had been subjected to such an ordeal.

Indeed, Kennedy experienced a particularly close call during her year-long study at London auction house Sotheby's in 1975. The incident happened one morning as she was getting ready for work while living with politician Sir Hugh Fraser and his other half, Antonia Fraser. Shortly before the Conservative MP was due to give her a lift, a bomb placed by the IRA under his car exploded. But while Kennedy and the Frasers were left unscathed, a passerby, oncologist neighbor Professor Gordon Hamilton Fairley, was killed.

Sir Hugh, who was the IRA's main target, had actually been walking toward the vehicle when he heard the home telephone ring and subsequently returned to answer it. The caller, fellow politician Jonathan Aitken, later told the Daily Mail how shaken the incident left Kennedy, who was physically blown onto her bed by the bomb: "I spoke to her recently and she was still immensely grateful that I had saved her life. I wish her all the best."

Caroline Kennedy was made an orphan at the relatively young age of 36 when her mother, Jackie Kennedy, died from non-Hodgkin lymphoma. The former First Lady had been diagnosed in 1993 after receiving medical attention for a horse fall, and within a year, she'd succumbed to the condition at just 64 years old.

Caroline, who was particularly close to her mom, was understandably left distraught by the loss, which came 31 years after her father was assassinated. And the diplomat has often publicly spoken about their relationship since her untimely death.

"My mother was a woman of tremendous courage and commitment and she worked hard to do her very best, every day of her life, whether that was in raising her children or being First Lady or working as a book editor," Caroline said in a Mother's Day video posted by the Washington Post. "And I feel so fortunate to have had such great role models, and I hope that I have been able to pass some of the lessons they taught me on to my children," she added, referring to her offspring, Rose, Tatiana, and Jack Schlossberg.

Following the scandal of the "Chappaquiddick incident" in which Ted Kennedy fled the scene of a car accident, which resulted in the death of his aide Mary Jo Kopechne, the curse which inflicted America's most famous political dynasty appeared to lie dormant for a good 15 years. But it appeared to reawaken in 1984 with another untimely passing.

On this occasion, it was Robert F. Kennedy's son, David Anthony Kennedy, who was the victim. The 28-year-old suffered a fatal overdose, having spent years battling addictions to heroin and the demon drink. Cousin Caroline Kennedy had tried to contact the victim without any luck just 24 hours before the tragedy while he was staying at Palm Beach's Brazilian Court Hotel. But in court papers made available to the public, she denied any knowledge of the drug use that led to his death.

Just 13 years later, Caroline also lost another cousin at a relatively young age. Michael L. Kennedy, David's brother, was skiing on New Year's Eve in Colorado when he crashed into a tree without wearing any protective gear. He was subsequently rushed to the hospital but died soon after, aged just 39.

Caroline Kennedy suffered another tragedy within her immediate family in 1999 when her younger brother lost his life in a plane crash. John F. Kennedy Jr. had actually been piloting the aircraft, which got into difficulties while flying over the coast of Martha's Vineyard. And he was on board with his wife, Carolyn Bessette — rumor has it their marriage was in trouble at the time — and sister-in-law Lauren Bessette, both of whom perished in the accident, too.

Caroline and John had been particularly close during their turbulent childhoods, a period in which both their father and uncle were assassinated, their mother remarried Greek shipping magnate Aristotle Onassis, and they were forced to deal with growing up in the glare of the public eye.

While giving a speech at the Harvard's Institute of Politics' John F. Kennedy Jr. Forum four years later, Caroline paid a glowing tribute to her late sibling: "More than anyone that I've ever known, John had a way of looking at the world that was all his own, and he was not afraid to go his own way," she told the audience, referencing how he'd rejected the family's traditional alma mater for Brown University. "John would also get a giant kick out of this event, and I know the joke would be at my expense somehow. 'You went to Harvard and now they're naming half the building after me.'"

Caroline Kennedy may have forged an incredibly tight bond with her younger brother while they were growing up in the national spotlight. But according to Steven M. Gillon's 2019 book "America's Reluctant Prince," the siblings had been at loggerheads shortly before John F. Kennedy Jr. died in a plane crash off the coast of Martha's Vineyard, aged just 38.

Gillon, reportedly a close pal of John F., alleged (via People) that Caroline saw her sibling and his inner circle as "potheads." And in return, he saw her friendship group as "entitled snobs." It was a claim apparently backed up by the playboy's wife, Carolyn Bessette, who also lost her life in the air tragedy alongside her sister, Lauren Bessette. Indeed, she reportedly felt her sister-in-law and her other half, Edwin Schlossberg, treated John F. as the "family f***-up."

"John believed that he and Caroline were the only two Kennedys, the only descendants of their mother and father, and the only two who could make decisions related to the family," Gillon added about another cause for their ever-growing estrangement. In a cruel twist of fate, however, the pair seemed open to patching up their differences in the last ever discussion they had: "They agreed they needed to do a better job of staying in touch. John loved Caroline. I think they probably both thought they had time to work it out."

Caroline Kennedy looked destined to take over the U.S. Senate seat previously occupied by Hillary Clinton in 2009 when she suddenly pulled out of the race. The former First Daughter had first surprised everyone when she announced she was running, having previously never expressed an interest in holding public office. But she soon emerged as the hot favorite, making her withdrawal all the more puzzling.

And no one was more shocked than Caroline's cousin Robert F. Kennedy, Jr., who told the press (The Guardian), "There was strong support within the family, from Teddy, from all the Kennedys. She would have made a great senator." New York University's politics professor Steven Brams was also left perplexed, remarking, "This came as a surprise to me." Everything suggested she was about to be appointed."

Caroline, who is rumored to have a net worth of $250 million, revealed in a statement that "personal reasons" had forced her to wave goodbye to her political ambitions, but didn't go into detail as to what they were. Inevitably, rumors began to surface, with some experts claiming she'd been unsettled by the seizure her lawyer uncle Edward Kennedy suffered at a recent inauguration luncheon and others believing she may have simply been saving face if New York's governor David Paterson had decided to appoint another name instead.

Caroline Kennedy suffered another career setback in 2009 when she was rejected by none other than the Vatican. And her stance on abortion was reportedly a key factor.

Indeed, Kennedy was put forward as one of three names by Barack Obama's administration to serve as the U.S. Ambassador to the Holy See. But following a disgruntled response from America's more conservative Catholics, the home of the Pope decided the former First Daughter wasn't a suitable candidate.

In a Q&A answered by Kennedy and her staff for The New York Times in December 2008, the diplomat had made her feelings on the pro-choice movement crystal clear. When asked whether she supported late-term abortion restrictions, the response was "Caroline supports Roe v. Wade, which prohibits third-trimester abortions except when the life or health of the mother is at risk." And when questioned whether parents should be notified before a minor gets an abortion, the answer was, "Caroline believes that young women facing unwanted pregnancies should have the advice of caring adults, but this should not be required by law." Here's a look at what other former first kids are doing today.

Caroline Kennedy sure didn't hold back when discussing her continually scandalous cousin Robert F. Kennedy Jr.'s attempts to become the United States' Health and Human Services Secretary in 2025. Indeed, in a video message posted on social media, the diplomat essentially implored senators to look elsewhere.

"I have known Bobby my whole life; we grew up together," Caroline said (via BBC News). "It's no surprise that he keeps birds of prey as pets because he himself is a predator." The ex-First Daughter went on to argue that Robert's fervent anti-vaccine views should automatically prevent him from a role that oversees both the FDA and Centers for Disease Control and Prevention, claimed he'd been responsible for enabling and encouraging several family members' substance abuse issues, and even alleged he enjoyed blending live mice and chickens together to provide food for his beloved hawks.

If that wasn't enough, Caroline also said both her dad and uncle Robert would be "disgusted" at what her cousin had become and expressed her own sense of betrayal over how he'd weaponized their dads' assassinations: "It's incomprehensible to me that someone who is willing to exploit their own painful family tragedies for publicity would be put in charge of America's life and death situations."

Caroline Kennedy suffered yet another unimaginable tragedy in 2025 when her middle child, Tatiana Schlossberg, died from leukemia. The environmental journalist, whose younger brother Jack has grown up to be JFK Jr.'s twin and sister Rose is basically Jackie Kennedy's twin, learned she had a particularly aggressive form of the condition in 2024 shortly after welcoming her second child, Josephine, into the world. And in an emotionally raw piece for The New Yorker, she wrote about the battle she'd endured.

"My first thought was that my kids, whose faces live permanently on the inside of my eyelids, wouldn't remember me," she wrote, referring to both Josephine and her firstborn, Edwin. And she also expressed regret at adding to her Caroline's list of hardships: "For my whole life, I have tried to be good, to be a good student and a good sister and a good daughter, and to protect my mother and never make her upset or angry. Now I have added a new tragedy to her life, to our family's life, and there's nothing I can do to stop it."

Caroline has yet to publicly comment on the devastating loss. But a friend of the family told People she has no doubts she'll continue to be a rock: "Caroline has to do the same thing her mother did with her and John, in raising those kids: To make sure they remember their mom — and she has the playbook."