JFK Jr. Shared a Unique Understanding of Caroline Kennedy’s Grief and Its Impact on Her Family

Caroline Kennedy and John F. Kennedy Jr. attend a gala at N.Y.C.’s Grand Central Terminal on Oct. 5, 1998.
Credit :

Sonia Moskowitz/Getty

Highlights

• Caroline Kennedy attended the funeral for her daughter Tatiana Schlossberg in New York City on Jan. 5.
• According to a Kennedy biographer, only her brother, JFK Jr., truly understood her losses before he died in a plane crash in 1999.
• “It’s this contrast between this incredibly private person and this very public tragedy that is striking,” said Kennedy biographer Steven M. Gillon.

As multiple generations of the Kennedy family gathered to remember Tatiana Celia Kennedy Schlossberg during her funeral service on January 5, reflections on both personal grief and public loss permeated the atmosphere.

Presidential historian Steven M. Gillon remarked, “Whenever a Kennedy dies, and certainly when they die in a tragic way, it just brings to mind all the others. You can’t look at it in isolation. It just reminds you of this horrible burden that this family has had to bear.”

John F. Kennedy and daughter Caroline Kennedy on Nov. 8, 1960.

Paul Schutzer/The LIFE Picture Collection/Shutterstock

In November, Tatiana, the 35-year-old daughter of Caroline Kennedy and Ed Schlossberg, disclosed her battle with a rare form of cancer in a heartfelt essay published in the *New Yorker*. Tragically, just five weeks later, her family announced her passing with a statement from the JFK Library, saying, “Our beautiful Tatiana passed away this morning. She will always be in our hearts.”

George Moran and Tatiana Schlossberg on Martha’s Vineyard with their children and dog in September 2025.

Elizabeth Cecil

The loss deeply affects the Kennedy family, who not only mourn the passing of a young woman with a vibrant life but also reflect on Caroline’s enduring personal struggles. Tatiana is remembered as a loving daughter, wife to George Moran, and mother to their two small children, Edwin and Josephine.

Gillon added, “It’s this contrast between this incredibly private person and this very public tragedy that is striking.” Friends of Caroline Kennedy believed that her brother, John F. Kennedy Jr., was one of the few people who could truly understand her losses. JFK Jr. died in a plane crash in 1999, taking him, his wife Carolyn Bessette, and her sister Lauren.

“Caroline suffered the same losses that John suffered, except that she also suffered the loss of her brother,” remarked Gillon.

John F. Kennedy Jr. and Caroline Kennedy at the Jackie Robinson Foundation Awards Dinner in N.Y.C.

Lawrence Schwartzwald/Sygma via Getty

Gillon notes the context of Caroline’s grief, starting with her father’s assassination in 1963. “She was old enough to know what happened, that he was gone. She was old enough to recognize her mom’s grief,” he remarked. Robert Kennedy served as a substitute father figure, only to be assassinated himself in 1968.

Caroline Kennedy holds her uncle Robert F. Kennedy’s hand as a JFK memorial is unveiled in England in May 1965.

Crawshaw Greenwell Reed Macdonald/Mirrorpix via Getty

Gillon detailed Caroline’s ongoing grief: “Her mom, Jacqueline Kennedy Onassis, dies at 64, a relatively young age. Then, in 1999, she loses her brother, and it’s just a series of horrible personal tragedies that leads up to the death now of her daughter,” noting that Tatiana’s death may be the most difficult loss for Caroline to bear. “In many ways, she reminds me of her mom,” Gillon added, “although her mom was more public than Caroline was.”

Despite her prominent background as the daughter of a president and her role as a U.S. diplomat, Caroline Kennedy remains a private figure. Gillon concluded, “We can document the different tragedies in her life, but what we don’t know is how she dealt with those things. She never talked about them, at least not publicly. We can only surmise based on the family tradition that she’s dealing with death the way Kennedys always deal with death, which is through resolve.”