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

As multiple generations of Kennedys said goodbye to Tatiana Celia Kennedy Schlossberg at her funeral service on Monday, Jan. 5, memories of the family’s private grief and public losses were ever present.

“Whenever a Kennedy dies, and certainly when they die in a tragic way, it just brings to mind all the others,” says presidential historian Steven M. Gillon. “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 beautifully written 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.”

The storied political dynasty’s heartbreak is unimaginable: Not only have they lost a vibrant young woman who leaves behind her husband of nine years, George Moran, and their two small children, Edwin, 3, and Josephine, 18 months, but it’s also a reminder of the private agony of her mother, Caroline.

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

Friends have long said that if there was anyone who could understand Caroline, it was her brother, John, who died in 1999 when a plane he was piloting crashed, killing him at 38, as well as 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,” says Gillon.

Gillon puts it into perspective — beginning with the assassination of Caroline’s 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.”

Chronicling her grief, 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 loss “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.”

Still, Caroline, the beloved presidential daughter turned steady U.S. diplomat, remains a mystery in many ways.

“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.”

As multiple generations of Kennedys said goodbye to Tatiana Celia Kennedy Schlossberg at her funeral service on Monday, Jan. 5, memories of the family’s private grief and public losses were ever present.

“Whenever a Kennedy dies, and certainly when they die in a tragic way, it just brings to mind all the others,” says presidential historian Steven M. Gillon. “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 beautifully written 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.”

The storied political dynasty’s heartbreak is unimaginable: Not only have they lost a vibrant young woman who leaves behind her husband of nine years, George Moran, and their two small children, Edwin, 3, and Josephine, 18 months, but it’s also a reminder of the private agony of her mother, Caroline.

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

Friends have long said that if there was anyone who could understand Caroline, it was her brother, John, who died in 1999 when a plane he was piloting crashed, killing him at 38, as well as 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,” says Gillon.

Gillon puts it into perspective — beginning with the assassination of Caroline’s 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.”

Chronicling her grief, 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 loss “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.”

Still, Caroline, the beloved presidential daughter turned steady U.S. diplomat, remains a mystery in many ways.

“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.”