Caroline and John

Although Jackie traveled frequently when her children were young, she gave them undivided time and attention when she was home. Jackie was their biggest cheerleader and also their most pointed critic. She was more than their mother — she was their touchstone. By the time they left the safety net of their childhood to start their own lives, they were thoughtful, well-adjusted young adults.

Caroline Kennedy

In 1975, Caroline graduated from Concord Academy. Instead of enrolling at Radcliffe right away, she decided to study abroad for a year first. Jackie gave her blessing, knowing how important her own time in Europe had been to her personal development. Like her mother, Caroline initially wanted to spend a year in Paris, but after learning about an art history program at Sotheby's in London, Caroline went to England instead.

It was arranged that she would stay with Hugh Fraser and his daughters, who were near Caroline's age. Fraser, recently divorced from author Antonia Fraser, was a Member of Parliament. Unbeknownst to Jackie, Fraser was on an IRA hit list for his views on Irish independence. In October 1975, the IRA detonated a bomb outside Fraser's Westminster home, killing a neighbor. Had it gone off five minutes later, Fraser would have been getting into his car to drive Caroline to the subway station. Jackie immediately moved Caroline in with her aunt and uncle, the Radziwills.


“I'm going to bring up my son. I want him to grow up to be a good boy. I have no better dream for him. I want John to be a fine young man. He's so interested in planes; maybe he'll be an astronaut or just plain John Kennedy fixing planes on the ground.”

Caroline turned eighteen that November. Although her classes were challenging, she still found time for a social life. She was photographed at several clubs with Mark Shand, who had broken up with his girlfriend to be with Caroline. Shand's sister was Camilla Parker Bowles, who would later divorce her husband and marry Prince Charles, so Shand's social contacts were extensive and he introduced Caroline to the cream of British society.

John F. Kennedy Jr.

Born less than three weeks after his father's election as president, John literally grew up in the public eye, known affectionately as John-John — a nickname his family never used. He got it when a White House reporter misunderstood what he heard Jack calling his son. What the president said was “John! … John!” He called his name twice, trying to get the boy's attention. What the reporter thought Jack said was John-John. The anecdote ran in the paper and the nickname stuck.


George was a glossy monthly magazine in the style of Vanity Fair that blended politics, lifestyle, and celebrity. Founded by John F. Kennedy Jr. and Michael Berman, it was published by Hachette Filipacchi. Its debut issue, which came out in September 1995, featured Cindy Crawford dressed as George Washington on the cover.

During the time his sister was in London, John attended Collegiate School. At fifteen he was maturing into a handsome youth, blessed with Black Jack's dark good looks and the Kennedy energy and athleticism. But academically he struggled with mediocre grades. He transferred to Phillips Academy for his junior and senior years and, despite his less than stellar grade point average, was accepted into Harvard, his father's alma mater and the school his sister Caroline was then attending. But John declined, not wanting to accept what was obvious preferential treatment based on family connections. Instead, he attended Brown University and majored in history. He graduated in 1983 and went on to study law. He failed the New York bar twice before finally passing in 1989. He worked in the Manhattan district attorney's office until leaving in 1993. Two years later he founded the magazine George.


“One must not dwell on only the tragedies that life holds for us all, just as a person must not just think of only the happiness and greatness that they've experienced…. Life is made up of both good and bad — and they cannot be separated from each other. It is a mistake to try and do that.”

Although Jackie kept his life as private as possible, John always appeared at ease when confronted with the media. More intrusive was the security Jackie insisted on for her children. Friends say he was relieved when his Secret Service protection ended on his sixteenth birthday. From the moment he was of legal age, John was considered one of America's most eligible bachelors. Unlike his sister, who lived her life quietly behind the scenes, John was gregarious and social, frequently spotted coming out of New York's hottest nightclubs. He dated an assortment of A-list celebrities including Madonna, Sarah Jessica Parker, and Cindy Crawford and had a long relationship with actress Daryl Hannah.

Grand Jackie

With John content with playing the dating field, it fell to Caroline to fulfill Jackie's dream of becoming a grandmother. After graduating from Radcliffe, Caroline was hired as the manager and coordinating producer of the Metropolitan Museum of Art film and TV office. There, she met her future husband, Edwin Schlossberg. They were married in 1986 at Our Lady of Victory Roman Catholic Church on Cape Cod at Hyannis Port. Caroline was given away by her uncle, Ted Kennedy. Two years later, the couple's first child, Rose Kennedy Schlossberg, was born on June 25, 1988. Weighing in at seven pounds, twelve ounces, Rose was born at New York Hospital–Cornell Medical Center. A second daughter, Tatiana Celia Kennedy Schlossberg arrived May 5, 1990. Their third child, John Bouvier Kennedy Schlossberg was born on January 19, 1993.

Jackie doted on her grandchildren. When Rose began nursery school, Jackie was the only grandparent who accompanied the class on a field trip. Rose and her classmates walked down the block and across the street to explore Central Park. Jackie came dressed in jeans and tennis shoes and won over the other parents with her genuine interest in their children. Jackie once wrote Caroline a note calling her grandkids a wonderful gift that restored her faith in the family's future.

John Jr.'s Marriage

Jackie did not live to see it, but her son did eventually settle down. John Jr. wed Carolyn Bessette, a publicist for Calvin Klein, on September 21, 1996. Life as a Kennedy, and the public scrutiny that came with it, proved stressful for Bessette. The fashion police named her a trendsetter and compared her to a young Jackie. Gossip columns speculated on just when the newlyweds planned to start a family. She tried to keep a low profile but paparazzi followed her and John everywhere — and recorded every public spat. Carolyn's way of dealing with the media — not speaking and trying to blend into the background — made her come off as cold and aloof.

In 1999, the tabloids reported that the latest source of friction between John and Carolyn was his new passion for piloting. Insiders claimed she disapproved and refused to go up with him. But John disputed the stories, claiming she enjoyed flying with him in his Piper Saratoga as much as he enjoyed piloting it. Flying was a hobby friends say Jackie had strongly discouraged when she was alive, claiming she had a premonition he would be killed flying his own plane, just as Ari's son had been.

On July 16, 1999, John was flying his Piper to Martha's Vineyard to attend the wedding of his cousin Rory, the youngest of Robert Kennedy's eleven children. He was accompanied by Carolyn and her older sister Lauren, a venture capitalist. Although the weather report John looked at before takeoff indicated clear skies, the evening turned foggy and misty. Relatively inexperienced, Kennedy was not certified to fly by instrumentation. Experts believe he became disoriented in the haze. The plane crashed, killing John, Carolyn, and Lauren.

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