Leonard was the first varsity coach of Crater High football and basketball teams. He was instrumental in the selection of the school colors and the athletic nickname “Comets”. Addtionally, he played an instrumental role in the develpment of the football field and stadium.

While coaching at Crater, his teams were league champions 4 times in football and 4 times in basketball. His 1953 football team defeated Medford Senior High before they belonged to the Southern Oregon Conference. That was the only time Crater defeated Medford Senior High School in football.

In 1964, Leonard became Vice Principal at Crater, and in 1968 he moved to Eagle Point to become Principal and later Assistant Superintendent.