Leonard was born and raised in Chicago and attended public schools. He graduated from Senn High School where he played football and baseball. After graduation he received a scholarship to the University of Idaho where he was a member of the football team for two years.
After returning to the Midwest he entered Bradley University, Peoria, II, where he was a member of the football team. He received a BA in Liberal Arts and graduated in 1956. In 1961 he received a MA degree from Roosevelt University, Chicago. In addition he received certification in driver education from Northeastern Illinois University, Chicago, Illinois.
After graduation he was a teacher and coach at Starr Commonwealth, Albion. Michigan. After leaving Starr Commonwealth I spent ten years teaching and coaching in Waukegan City Schools.
In 19671 moved on to Tremper High School, Kenosha, WI. teaching P.E, health and driver ed. I coached JV basketball for nine years and was head sophomore football coach for 24 years and one year varsity coach. I had an outstanding win-loss record including undefeated seasons in 1978 and 1983. I was also Athletic Director for 14 years. I was a true advocate for the coaches and the kids of all sorts.