JFK Jr. ‘Was the Only One’ Who Understood Caroline Kennedy’s Losses — and Her Daughter’s Death ‘May Be the Hardest’

As multiple generations of Kennedys gathered to say goodbye to Tatiana Celia Kennedy Schlossberg at her funeral service on Monday, Jan. 5, the family’s long history of private grief and public loss felt impossible to ignore.

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

In November, Tatiana — the 35-year-old daughter of Caroline Kennedy, 68, and Ed Schlossberg, 80 — first shared her diagnosis of a rare cancer in a moving New Yorker essay. Five weeks later, she was gone.

“Our beautiful Tatiana passed away this morning,” read the family statement posted by the JFK Library on Dec. 30. “She will always be in our hearts.”

Her death has left the storied political dynasty grieving a woman remembered as vibrant and deeply loved. Tatiana is survived by her husband of nine years, George Moran, and their two young children, Edwin, 3, and Josephine, 18 months. For many, the loss also underscores the quiet sorrow carried by her mother, Caroline.

“It’s this contrast between this incredibly private person and this very public tragedy that is striking,” Gillon says. He has studied the Kennedys and authored a biography of John F. Kennedy Jr., titled America’s Reluctant Prince.

Friends have long noted that if anyone could truly understand Caroline, it was her brother, John — who died in 1999 when a plane he was piloting crashed. He was 38. Also killed were his wife, Carolyn Bessette, 33, and her sister, Lauren, 34.

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

Gillon places the family’s grief within a timeline that stretches back to Caroline’s childhood, beginning with the assassination of her father, President John F. Kennedy, 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 says. “Robert Kennedy became a substitute father for her and for John, and then he’s assassinated in 1968.”

Reflecting on the years that followed, Gillon continues: “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,” adding that Tatiana’s death “may be the hardest of them all.”

“In many ways, she reminds me of her mom,” Gillon adds, “although her mom was more public than Caroline was.”

Even so, Caroline — the former presidential daughter who later became a steady U.S. diplomat — remains an intensely private figure.

“We can document the different tragedies in her life, but what we don’t know is how she dealt with those things,” Gillon says. “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.”