Born Youngstown, Ohio, moved to Bowling Green as an infant. He lived in many states during his childhood but enrolled in Western Kentucky State College in 1957. Entered the Air Force in 1959 as an aviation cadet and was commissioned a second lieutenant in 1960. He served as a navigator and then entered pilot training in 1964, where he graduated first in his class.

As a fighter pilot, his career took him to assignments in Germany, Thailand, Korea, Kansas, Florida, Washington, D.C., Nevada, Georgia, Hawaii and Texas. He flew 295 combat missions during the Vietnam War and shot down a North Vietnamese Mig-21.

Gen Cherry was commander and leader of the Air Force's aerial demonstration team, the Thunderbirds; this is truly one of the most cherished and most competitive leadership positions in the entire Air Force. Gen Cherry also commanded two different fighter Wings, was Inspector General of the Pacific Air Forces and served as commander of the Air Force Recruiting Service. He is a Command Pilot with more than 4,000 flying hours in the T-38, F-105, F-4 and F-16.

His military decorations include the Distinguished Service Medal, the Silver Star with one Oak Leaf Cluster, Legion of Merit with two Oak Leaf Clusters, Distinguished Flying Cross with nine Oak Leaf Clusters, and the Air Medal with thirty-four Oak Leaf Clusters. Gen Cherry is a former Secretary of Justice for our Commonwealth. In that capacity he was responsible for managing the day-to-day activities of the 6,000 employees within the departments of Corrections, Kentucky State police, Juvenile Justice and Criminal Justice Training. He is now president of the Intermodal Transportation Authority (ITA) in Bowling Green, Kentucky.