Carolyn Jeanne Bessette was born in White Plains, Westchester County, New York, the youngest child of William J. Bessette and Ann Messina Freeman, an administrator in the New York City public school system. She grew up in Greenwich, Connecticut, and attended St. Mary’s High School, where she was voted an “All-Around Beautiful Person”. She graduated from Boston University in 1988. While at Boston University she met and dated John Cullen, an NHL player.
She had two older sisters, twins Lauren and Lisa Bessette.
After college, she worked as a saleswoman at the Calvin Klein store in Boston before being transferred to the corporate office/headquarters in New York, where she worked as a publicist and met John F. Kennedy, Jr. while at work. The couple became a popular paparazzi target, with gossip columns detailing where they ate and shopped and even covering the arguments they had. Photographers waited outside the couple’s Tribeca apartment to snap photographs. She was reportedly uncomfortable with the media frenzy and the repeated comparisons to her mother-in-law, Jacqueline Kennedy Onassis.
Carolyn’s wedding dress was designed by Narciso Rodriguez.
On July 16, 1999, Carolyn died, along with her husband and older sister Lauren, when the Piper Saratoga II HP Kennedy was piloting crashed into the Atlantic Ocean off Martha’s Vineyard. The National Transportation Safety Board (NTSB) determined that the probable cause of the crash was: “[John Kennedy Jr.’s] failure to maintain control of the airplane during a descent over water at night, which was a result of spatial disorientation.” Their ashes were scattered from the Navy ship USS Briscoe off the coast of Martha’s Vineyard.