John F. Kennedy Jr. was piloting a Piper Saratoga II HP when he, his wife Carolyn Bessette-Kennedy, and her sister Lauren Bessette tragically crashed into the Atlantic Ocean off the coast of Martha's Vineyard. The flight originated from New Jersey, and the group was en route to the Kennedy family compound in Hyannis Port, Massachusetts. Around 8:30 p.m., the plane, which was flying in darkness and with poor visibility, went missing from radar less than a half-hour after takeoff, prompting an extensive search operation by the U.S. Coast Guard and local agencies. The National Transportation Safety Board later determined that the probable cause of the accident was pilot disorientation due to the lack of visual reference from the horizon, compounded by cloud cover and darkness.

The search lasted for several days, during which time hope slowly faded for the families and friends of the victims. On July 21, the wreckage was located at a depth of approximately 100 feet, and recovery efforts soon began. Tragically, the bodies of the three individuals were discovered within the wreckage, confirming the worst fears of loved ones. The aftermath of the incident led to national mourning, reflecting the public's fascination with the Kennedy family legacy, and further elevated the scrutiny surrounding the lives of America's political elite.

Kennedy Jr. was known not only as the son of President John F. Kennedy but also as a published author and a figure in American media. His untimely death raised questions about pilot regulation and safety. Notably, Kennedy's death ignited various discussions about the aviation industry and the responsibilities that come with private flying, particularly involving high-profile individuals. The loss of Carolyn Bessette-Kennedy, a notable figure in the fashion world, contributed to the collective grief felt across the nation and among their many fans.