Jimmy Leeward really never had much of a chance. His parents eloped in an Aeronca C-3. The couple settled down on a grass strip outside of Tarentum, Pa., and as soon as Jimmy could walk, he was at the airport, cleaning and eventually working on many airplanes. Of course, he, too, would become a pilot.
“Every summer, I lived at the airport. I worked during the day and slept at night in a hangar,” remembers Leeward. “In the evenings, I would just fly anything we had on the field. There wasn’t much of a checkout of anything; I just flew.”
Al Leeward, Jimmy’s father, did about anything he could to make a living in the flying business. He sold aircraft, flew charter and he even delivered the mail in a Stinson SR-9. On weekends, he flew air shows, performed parachute jumps and taught his wife, Ginny, to fly. Needless to say, it was an all-aviation family.
“When Dad would buy an airplane, we would head out to pick it up. We would just get in it and fly it back; it didn’t matter if it was a twin or a single. We had to get it home somehow; we owned it, so we flew it. Running a dealership, instructing, doing air shows kept us pretty busy.”
But one day, Al said to Jimmy, “You know, this is a hard, up-and-down business. If you really like flying, you should do something else and fly for fun; that way, you won’t spoil it.” It was sage, fatherly advice.
“Lots of people fly for a living, and they don’t like it anymore,” says Jimmy. “My dad’s advice made sense to me, and so I got into real estate. Eventually, I moved to Florida and built retirement homes for folks moving here from the Northeast. Then I branched out into residential and commercial development.”
He followed his father’s sage suggestion to the letter. While he completed successful real-estate projects, Jimmy continued to fly—just for fun. Lots of fun!
In 1986, Jimmy’s Cloud Dance
, a stock P-51 Mustang, won the unlimited silver race at the Reno Air Races. He also flew the first jet races there in a MiG-17. Jimmy and his two sons, Chad and Dirk, fly in air shows all over the country and are heavily involved with the EAA.
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