One person who could understand grief like she did was Caroline’s brother, John F. Kennedy Jr., who “suffered the same losses” she did before his own death in a 1999 plane crash.

Caroline suffered the same losses that John suffered, except that she also suffered the loss of her brother," presidential historian Steven M. Gillon tells PEOPLE

Page Six has broken down the Kennedy family tragedies and heartbreaks throughout the years, from assassinations and plane crashes to overdoses and accidents.

JFK, the son of Joseph Patrick Kennedy and Rose Fitzgerald Kennedy, was born in Brookline, Massachusetts, on May 29, 1917. He was the second of nine children the couple shared.

Carolyn Bessette-Kennedy relied on a tight, timeless color palette—like black, navy, gray, beige, and white. Sticking to neutrals makes mixing and matching effortless, and ensures your wardrobe feels cohesive rather than trend-driven.

Ryan Murphy is being dubbed “insensitive” for failing to push back his new Kennedy drama in the wake of Tatiana Schlossberg’s death, a source told Page Six.

Caroline Kennedy has been left fearing over her daughter Tatiana's life after she was diagnosed with terminal cancer.

JFK bought a home behind his father's Big House in 1956. It became known as the President's House. Robert F. Kennedy and his wife, Ethel, bought another adjacent home—and those three properties made up the compound, which now spans 6 acres of waterfront property.