‘I want to have kids, but whenever I raise the subject with Carolyn, she turns away and refuses to have sex with me.”

The speaker was John F. Kennedy Jr., and he was sitting on the edge of a king-size bed, a phone cradled in the crook of his shoulder, pouring his heart out to a friend. It was early in the evening of July 14, 1999—two days before John’s fatal plane crash—and the last rays of sunlight were flooding his room at the Stan-hope, a fashionable New York hotel located across Fifth Avenue from the Metropolitan Museum of Art.

“It’s not just about sex,” John told his friend, who recalled the conversation for me several days later, while it was still fresh in his memory. “It’s impossible to talk to Carolyn about anything. We’ve become like total strangers.”

For a moment the words caught in John’s throat, and his friend could sense his struggle to regain his composure. Then all of John’s pent-up bitterness and frustration exploded over the phone line.

“I’ve had it with her!” he said. “It’s got to stop. Otherwise we’re headed for divorce.”

A thousand days had passed since John exchanged wedding vows with Carolyn Bessette on a wild, unspoiled island off the coast of Georgia, and during that time the truth about their troubled marriage had been a well-guarded secret. Now John and Carolyn were living apart—he at the Stanhope, she in their loft in Tribeca—and John was on the verge of calling it quits.

For the life of him, John could not understand why his marriage had soured, especially since it had begun with so much sweetness and hope. An inveterate prankster, John eagerly endorsed Carolyn’s wish to keep their wedding plans secret. “This is one thing I’m in control of, not John,” Carolyn told a close friend. “No one’s going to know where or when we’re getting married.”

From the start Carolyn was in a quandary over who would make her wedding dress. Should she ask Calvin Klein, who until recently had employed her as a mid-level publicist? Should she choose her old roommate, the talented black fashion designer Gordon Henderson? Or should she turn to Narciso Rodriguez, a former Calvin Klein staffer who now worked for the Paris couturier Nino Cerruti? Carolyn knew that her choice would have major repercussions, for the designer was certain to get worldwide publicity.

Carolyn ultimately decided on the relatively unknown Rodriguez to design both her rehearsal-dinner dress and her wedding dress, as well as the matron-of-honor dress for Caroline Kennedy Schlossberg, John’s sister. Rodriguez worked for months on different designs, but it was not until 15 days before the wedding that Carolyn made her final pick.

Gordon Henderson, who was Carolyn’s closest friend, was devastated. He had dreamed of designing her dress and becoming a bigger fashion star. As a consolation, Carolyn asked him to make John’s suit and orchestrate the details of the wedding. Preparations were conducted with all the secrecy of a military operation. Only a few close friends and family members were invited. Everything seemed to go smoothly until, on the day of the wedding, Carolyn attempted to put on her dress and found that she could not manage to get the $40,000 pearl-colored silk-crêpe floor-length gown over her head. It was cut on the bias without a zipper, and like many such dresses it was difficult to put on. Try as hard as she might, she could not squeeze herself into it.

Under mounting pressure, Carolyn grew hysterical and began yelling at everyone around her. Henderson gently led her into a bathroom, put a scarf over her head, and managed to get her into the dress. Then, still in a state of high anxiety, she sat while her makeup and hair were re-done.