Carolyn Bessette-Kennedy's Family Is Still Grieving Almost 25 Years After Her Fatal Flight

It has been 25 years since John F. Kennedy Jr., his wife, Carolyn Bessette-Kennedy, and her sister, Lauren Bessette, died in the plane crash that shook America and contributed to the Kennedy family’s troubles. On July 16, 1999, JFK Jr. was piloting a flight to Martha’s Vineyard for a wedding that resulted in all three of their premature deaths. The Bessette sisters were survived by their parents and Lauren’s twin, Lisa.

Today, people are wondering if Bessette’s parents, William and Anne Marie Bessette (née Messina), are still alive and how they’re handling their grief. In addition, Lisa Bessette has continued to maintain privacy, but some reporting has figured out where she is today.

Growing up, the Bessette sisters were raised mostly by their mother, Anne, and their stepfather, Richard Freeman. Anne and William Bessette, the girls’ father, married in 1963 and divorced in 1974, when Carolyn was just 8 years old and her twin sisters were 10 years old. Anne then remarried Richard, an orthopedic surgeon, and the family moved to Greenwich, Conn., where Carolyn attended high school.

After the crash in 1999, Anne blamed JFK Jr.’s recklessness and settled with the Kennedys. “Anne is still mad at John — she blames him for her daughters' deaths,” a friend told the Irish Sunday Mirror at the time. “I also think Anne regrets that her daughters weren't buried in a cemetery. She doesn't have a place to visit them and grieve. Their ashes were spread at sea off the coast of Martha's Vineyard.”

"Anne Freeman has been through hell in the five years since the plane crash off Martha's Vineyard,” said another family friend. “With the exception of attending the burial at sea for Carolyn and the memorial service in Greenwich, Conn., for Lauren, Anne has remained indoors." Anne’s mother passed away the same year while Lisa moved to Europe to manage her own grief.

She privately filed a wrongful death lawsuit and was awarded $15 million from the Kennedy estate after federal investigators concluded that pilot error and inexperience were the cause of the crash. Anne and Richard built a new home in Old Greenwich on a more secluded road according to the Hartford Courant in 2000.

While managing her grief, friends say Anne continued to go out and meet with close friends, but was living a “broken life.” She set up a fund in Carolyn’s memory at the Greenwich-based Kids in Crisis shelter and set up a scholarship fund in Lauren’s name at Hobart and William Smith College.

While the New York Post reported that Anne was still married to Richard in 2019, other sources claim she passed away on April 24, 2007, at 67 years old. Richard, however, seems to still be alive, now 93 years old. He seems to have moved back to White Plains, N.Y., where he continued his orthopedic practice after Anne’s death. “We never cooperate with the media, no interviews, no questions, and that is still our position,” he told the Post in 2019.

Carolyn’s father, William, was similarly living in grief until his death. "William Bessette has been living in awful grief,” a family friend told the Irish Sunday Mirror. “He won't talk about his daughters' deaths. He is very bitter about what happened. 'It seems like the only piece of happiness he's had in the past year has been a new lady he has been dating — a flight attendant."

While his relationship with his daughters was allegedly “distant,” Williams also remained mum whenever the press reached out. “He no longer answers the phone or the door at his White Plains, N.Y., apartment,” the Hartford Courant wrote. William passed away on Nov. 21, 2014, “peacefully in his sleep” at 85 years old in Hampden County, Mass.

After losing her sisters and later her parents, we can imagine that Lisa hasn't lived the easiest life. Sources say that she occasionally works part-time at the University of Michigan Art Museum as a “contract editor.” In 2010, Lisa, who has a Ph.D, was appointed as a Lecturer in History of Art at the University of Michigan.

“I can imagine that this anniversary with everything happening is a really difficult time for her,” an unnamed acquaintance told The Post around the 20th anniversary of her sisters’ deaths. “She was devastated. She had a really hard time when they passed away and was strong for her mother and her family and has since decided that she doesn’t want to be in any way public.”

Lisa allegedly never married but has been in a long-term relationship with a University of Michigan art history department professor, Howard Lay. Lisa’s colleagues and friends have continued to respect her privacy throughout the years, while she has kept her past tragedy behind closed doors. “I house-sit for them in the summer and she’s never breathed a word about it to me,” a woman named Martha who answered the door to their home told The Post.

Other neighbors added similar sentiments. “They don’t socialize,” she said. “They’re a little quiet,” and don’t have children. Others had kind words. “They do a lot of nice gardening, especially Lisa,” said one neighbor, while another added, “She’s a good neighbor. They keep up that place. They don’t have loud parties.” It seems like peace, quiet, and privacy are the best ways to respect Carolyn and Lauren’s memory on the 25th anniversary of their death.