Like any young couple in love, they looked as if they had life all figured out. Home for John Kennedy and his wife, Carolyn, was a cozy loft in New York City’s trendy Tribeca, where they entertained friends and frolicked with Friday, their dog. They hoped to add to their happiness by having a child—perhaps a son called Flynn, if the father had his wish. Above all, they had each other, and that was enough to make the future seem bright. “The next five years should have been the great years for them,” says good friend Paul Wilmot.
“They were a dream couple in every way.”
Kennedy, in particular, had begun to find his own way in the world. After his mother, Jacqueline Kennedy Onassis, died of cancer in 1994, the son, it seemed, had finally become the man. “John really matured after his mother’s death,” says friend and former Brown University classmate Richard Wiese. “He said it was a clarifying moment because he took note of all the things that were important to her, like family.”
It wasn’t all that long after his mother passed away that Kennedy proposed to the tall and graceful Carolyn Bessette, a modern American beauty. “There was a striking similarity between Carolyn and John’s mother,” says historian Barbara Kellerman, author of several books about the Presidency. “Good-looking, slender, fashionable—even the lyrical French last name. John’s choice of wife was very much in keeping with who his mother was and what her tastes were.”
Yet Bessette had developed her own unique style long before she met her future husband. Her mother, Ann, a public school teacher and administrator, and her father, William, divorced when Carolyn was very young. Ann soon married orthopedic surgeon Richard Freeman and raised Carolyn and her older twin sisters in ritzy Greenwich, Conn., where at St. Mary’s high school, Carolyn cut a memorable figure. “She had such a great body,” former classmate Claudia Slocum told PEOPLE in 1997. “She was the only one who could pull off wearing the ill-fitting school uniform pants.”
Bessette majored in education at Boston University, but not long after she graduated in 1988, she went to work for designer Calvin Klein in New York City. As a publicist, she became a fixture at fashion shows and “the incarnation of modern style,” as Oscar de la Renta told Women’s Wear Daily. “She was very sophisticated, and everyone in the business loved her,” says Wilmot, her former boss at Calvin Klein. “And she had the most spontaneous, cracker-jack sense of humor. We’d go to these dinners, and she would be the life of the party.”
At one fateful bash in 1993, Bessette was introduced to the dashing Kennedy. “It was love at first sight,” says Wilmot, while Kennedy’s friend Richard Wiese says, “John was intrigued by Carolyn because she was challenging. He was used to a lot of women who would melt in front of him.”
For her part, Bessette was encountering a man at a crossroads. For years, Kennedy had done little to dispel the public perception of him as a goof-off, more interested in a good game of Frisbee than in a meaningful career. The great hope of many, of course, was that he would take up the family business and run for office. While Kennedy never ruled out the possibility, he doggedly refused to blindly retrace his father’s career path. “I really grew up in a political environment, going to fund-raisers, you know, seeing that stuff,” he explained to Oprah Winfrey in 1996. “And it was important to really do something different.”
Politics would nevertheless prove to be the engine of Kennedy’s defining professional accomplishment. In September 1995, he and pal Michael J. Berman launched the irreverent political magazine George with some $20 million in backing from the French publishing empire Hachette-Filipacchi. Far from being a front man, Kennedy edited copy, devised stories and “had his hands on everything,” says former George copy editor Don Armstrong. “We’d all be there with John on deadline eating pizza at 1 a.m.”
His unlikely turn as a journalist sometimes got Kennedy into hot water with his press-shy family. In a 1997 essay, Kennedy rankled his cousins Joseph—the Massachusetts congressman derided for annulling his 12-year marriage—and Michael—accused in 1997 of sleeping with an underage babysitter (and killed in a ski accident months later)—by referring to them as “poster boys for bad behavior,” a charge accompanied by a shot of Kennedy posing seminude. Still, George, now in its fourth year, defied early predictions that it would suffer a quick demise. Reports that it loses some $4 million annually and may soon be resold hardly diminish the triumph it represented for its editor-in-chief. “One of the great themes of John’s life was his search for a way to express his individuality, separate from his famous parents,” says author Ed Klein. “In George, he found a path in which he could be his own person.”
It was a path Kennedy chose not to travel alone. In September 1996, after two years of dating, Kennedy and Bessette slipped off to Georgia’s secluded Cumberland Island and got married in a small (40 guests), secret, paparazzi-free affair. It would be one of the last times their movements escaped the media glare. Though both dearly wanted children, “they were holding back because neither of them could bear the idea of all the media attention,” their friend Christa D’Souza told London’s Daily Telegraph. And yet, for the most part, the couple “refused to change their lives because they were Mr. and Mrs. JFK Jr.,” says Wilmot. “She’d jog in the park and he’d play Frisbee and they’d both walk the dog.”
It almost seemed too good to last—and, sadly, it didn’t. But in their short, sweet time together, Kennedy found the inner peace and confidence to be the regular guy he wanted to be. “John had this theory,” says Don Armstrong. “If famous people didn’t act weird, they wouldn’t be treated weird. He tested the theory, and it worked.” With Carolyn at his side, the man so many expected to be a Kennedy found happiness being just John.