John F. Kennedy Jr. Reportedly Unsure Of Future With Wife Carolyn Bessette Before Deadly Flight 20 Years Ago

John Kennedy Jr. and his wife Carolyn Bessett arrive at the US Customs House in New York city May 19, 1999 for the Newman's Own/George Awards honoring generous American companies.
Diane Freed / Getty Images

A new book is shedding a different light on the marriage between John F. Kennedy Jr. and his wife Carolyn Bessette in the months prior to their death 20 years ago in a deadly plane crash. A new biography by Steven M. Gillon, titled America’s Reluctant Prince, claims to offer a fresh new look at how the couple, who appeared to have had it all, was, in fact, struggling to keep their marriage together.

“They were both very passionate,” said Gillon in the book, excerpted by People Magazine in its latest issue. “John believed once he got married, the press would leave him alone. He’d no longer be America’s most eligible bachelor. He’d be another married guy. And just the opposite happened.”

Gillon met the son of President John Kennedy when Kennedy Jr. was Gillon’s teaching assistant at Brown University. They maintained their friendship for many years after.

The press was enamored by the love affair between the blonde beauty, a former employee of the fashion brand Calvin Klein, and the man who was deemed People Magazine’s Sexiest Man Alive in 1988. The couple met in 1992 and began dating in 1994. Carolyn then became a permanent fixture for the lenses of the paparazzi, who watched her blooming love interest with JFK Jr. with great enthusiasm, hounding the couple as they walked their dog through the streets of New York City, attended social events, and tried to live as normal a life as possible.

Kennedy hoped that after the couple wed in a secret ceremony on Cumberland Island, Georgia, that interest in them would die down now that they were legally husband and wife, claimed Gillon. Unfortunately, public fascination in the couple spiked at a fever pitch, leaving Carolyn, said the author, having a difficult time adjusting to the spotlight.

“The paparazzi treated Carolyn horribly,” Gillon said in the book.

Reporters at the time claimed that Carolyn wouldn’t stop to pose for photos, something her husband did in order to allow photographers to get their coveted shot. Reportedly, she would also not smile and push past them in order to get to her intended destination.

Kennedy, who grew up in the glare of the media spotlight, understood how to politely allow photographers to do their job and they, in turn, would leave him alone. His mother, Jacqueline Kennedy Onassis, was determined to allow her children to live as normal a life as possible and raised them in New York City, where they would roam among other residents and behave just as any other New Yorker would. In fact, John Kennedy would often take the subway or ride his bike around Manhattan to get around and was rarely bothered by others.

That was until he met Carolyn. The constant pressures of the ever-present paparazzi reportedly strained their union, remarked Gillon in the book.

People Magazine revealed in their book excerpt that the pressure of being in the public eye led Carolyn to stay home more and go out less.


“She felt trapped. Many close friends suspected that she had been self-medicating with drugs. The media was hounding her and she couldn’t figure out how to have a career. She was uncomfortable going out,” Gillon wrote.

The couple dealt with the pressures of the outside world by allowing them to creep into their young marriage, which was rumored to be strained. The book revealed that Bessette was originally not going to join her husband for the wedding of his cousin Rory Kennedy in Martha’s Vineyard in July 1999, but at the last minute changed her mind and decided to attend.

The couple, who were rumored to be on a path to figuring out how to make their complicated relationship work, never made it to the wedding. Their plane, which Kennedy piloted and was carrying Bessette and her sister Lauren, crashed into the Atlantic Ocean on their way to Martha’s Vineyard that fateful evening. There were no survivors of the crash.