Inexperience

Kennedy was not, by his own admission, a superb pilot. He was like most other pilots with a few months of experience—eager to learn, but immature in his skills and judgment.

Kennedy’s sense of his own limitations might have caused him to look, with a growing anxiety, at the setting sun, whose disk was probably touching the horizon at about the time he was paying for his merchandise at the Sunoco convenience store. The sky was already becoming hazy, and Kennedy had many minutes of preflight preparation, weather checking, plane inspection, taxiing, and preflight engine check left to complete before takeoff. He must have realized at the gas station, and maybe as early as leaving his office, that he would have to fly in the dark over Long Island Sound to reach Martha’s Vineyard, the most challenging leg of the trip.

Pressure.

Kennedy no doubt felt tremendous pressure to get to his destination. The Kennedy family was gathering in Hyannisport for a Saturday wedding, and John Jr. must have felt pressure to arrive in time.

In flying vernacular, the pressure to get to the destination regardless of the risk is called “get-there-itis,” and it’s often a fatal disease. If Kennedy was feeling rushed, it would explain some of his decisions before and during the flight. A pilot in his position needed to rethink the notion of flying at all that night. In fact, other pilots with more experience than Kennedy had examined the persistent coastal haze that day and called off their flights.

Challenging Weather Conditions

The weather conditions were perhaps the most difficult factor to deal with. Had conditions been better, Kennedy’s visual flying skills would have been up to the task of making the flight. Had the weather been worse, FAA rules would have taken the decision out of his hands. As fate would have it, conditions that night fell into the gray area that forced Kennedy to make a difficult decision himself—and make the wrong one.