He took risks, but he wasn't stupid.

"John F. Kennedy Jr. used a co-pilot on a flight to the Buttonville airport last week because he didn't feel safe flying with a broken foot. Kennedy was in town for a meeting about a possible magazine investment according to Keith Stein, vice-president of corporate affairs for auto parts giant Magna International Inc.

He says Kennedy told him he had brought along a flight instructor - to make sure he could operate the plane safely.

Kennedy had broken his foot in a recent a paragliding accident.

Stein said he met Kennedy to discuss a possible investment in the four-year-old American political magazine George.

Kennedy was flying the same plane that has since gone missing off Martha's Vineyard."

https://www.cbc.ca/news/canada/jfk-jr-s-last-previous-flight-was-to-toronto-with-a-co-pilot-1.184063