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John F. Kennedy Jr. (JFK Jr.) and Carolyn Bessette Kennedy were on the cusp of many changes when their lives were tragically cut short. They died in a plane crash on July 16, 1999, along with Bessette Kennedy’s sister, Lauren Bessette. Ahead, we break down the changes that remain what could have been for the couple. 

JFK Jr. and Carolyn Bessette Kennedy were ‘in the middle of a shift’ when they died

When they died at the age of 38 and 33 respectively, JFK Jr. and Bessette Kennedy had a lot going on in their lives as to be expected of their high-profile status. 

JFK Jr. needed to figure out how to move forward with his magazine, George, which brought together politics and pop culture. The publication had been a runaway hit in September of 1995 when it launched featuring supermodel Cindy Crawford as George Washington on the cover. 

But after George failed to meet the goal of being profitable within three years, ad sales rapidly decreased, leaving JFK Jr. to decide what the future of his magazine looked like. 

John F. Kennedy, Jr. and his wife Carolyn Bessette Kennedy.
John F. Kennedy, Jr. and his wife Carolyn Bessette Kennedy arrive at the annual John F. Kennedy Library Foundation dinner and Profiles in Courage awards in honor of the former president’s 82nd birthday, May 23, 1999, at the Kennedy Library in Boston, MA. | Justin Ide/Newsmakers

“This was a time,” Matt Berman, creative director of George and a close friend of the couple’s, told Town & Country. “George had to be figured out; his cousin’s dying. Maybe Carolyn has to decide how she wants to live her life. Does she want to work? Does she want to have kids? Does she want to lead charities?”

“Here you are in the middle of a shift like that, and that’s when the accident happened,” he added. 

Bessette Kennedy met JFK Jr. when she worked in New York City for Calvin Klein and had always worked, according to Colleen Curtin her roommate in college told Town & Country in 2016. 

“She always worked,” Curtis said. “Always.”

Bessette Kennedy worked throughout her college years at Boston University but by the time she and JFK Jr. were married, she no longer worked at Calvin Klein, likely because of the press who followed her every move.

Carolyn Bessette And Sister Lauren Bessette
Carolyn Bessette Kennedy and her sister, Lauren Bessette. | Mario Magnani/Getty Images

As Berman said, like her husband, Bessette Kennedy stood at a crossroads having to decide what the future looked like for her. 

While giving a eulogy at a memorial mass at St. Thomas More Church in New York City on July 23, 1999, Bessette Kennedy’s close friend, Hamilton South, said she wanted to someday have an office in Tribeca where she could make documentary films about people dealing with adversity.

Sadly, we will never know if Bessette Kennedy would have pursued her dream of being a documentary filmmaker.

Carole Radziwill: ‘The summer of 1999 was difficult for all of us’

While JFK Jr. and Bessette Kennedy had major decisions to make about their own lives, the life of someone close to them neared its end. 

Anthony Radziwill, JFK Jr.’s cousin and best friend, had sarcoma, which devastated both JFK Jr. and Bessette Kennedy. 

John F. Kennedy Jr. and Anthony Radziwill during RFK Pro-Celebrity Tennis Tournament Party at Rainbow Room in New York City, New York, United States. (Photo by Ron Galella/Ron Galella Collection via Getty Images)

Radziwill’s wife, Carole Radziwill, recalled the difficult time that year. 

“The summer of 1999 was very difficult for all of us,” she said. “We knew that it was likely Anthony would not survive to see Labor Day, and we were all on edge, not knowing what to do or say. We were all doing our best to keep smiles on our faces.”

Radziwill died three weeks after JFK Jr. and Bessette Kennedy’s plane crash at the age of 40. 

Carolyn Bessette Kennedy and JFK Jr. had marriage struggles but they wanted to make their relationship work and even went to counseling together. 

JFK Jr.’s decision to fly: ‘He shouldn’t have done it’

On the day of their deaths, uncertainty hung in the air. Bessette Kennedy didn’t know if she even wanted to accompany her husband to a wedding in Hyannis Port, Massachusetts. 

John F. Kennedy Jr. and bride Carolyn Bessette Kennedy stand in front of their apartment in Tribeca, 1996.
John F. Kennedy Jr. and bride Carolyn Bessette Kennedy stand in front of their apartment in Tribeca. | Jon Naso/NY Daily News Archive via Getty Images

JFK Jr. confirmed the weather would be good for takeoff at his office but by the time he arrived at New Jersey’s Essex County Airport, the weather took a turn for the worse as a dense fog rolled in. They took off at 8:39 p.m. with JFK Jr. flying his plane accompanied by his wife and his sister-in-law, Lauren. 

Lauren who lived in Tribeca near her sister and brother-in-law hitched a ride with the couple because she headed for Martha’s Vineyard. The plan was to drop Lauren off on the island then continue to Massachusetts. 

At 9:40 p.m. JFK Jr. became disoriented because of the lack of visibility which led to their plane crashing seven miles from Martha’s Vineyard.

“He wasn’t fully instrument trained; he shouldn’t have done it,” Sasha Chermayeff, who knew JFK Jr. from high school said. “It was a pilot negligent mistake in which he died and two people died with him. I have nothing but sadness about that.”

Once their bodies were recovered five days later they were laid to rest at sea.