After retiring as a player, Leonard worked as a truant officer, served as a physical education instructor and started a realty company. From 1962 to 1972, he was vice president of the Rocky Mount Leafs and then, from 1973 to 1975, of the Rocky Mount Phillies. The Leafs were a Class A Carolina League farm team for the Detroit Tigers from 1965 to 1972. In 1962 and 1963. the Leafs were a farm club of the Cincinnati Reds and in 1964, the Leafs were a farm club of the Washington Senators. The Phillies were a farm team for the Philadelphia Phillies.