Lynn Chewning was born in Columbia, South Carolina on February 28, 1926 and moved to Richmond, VA in 1931. He attended Westhampton High School and Saint Christopher’s Prep School. The Richmond native was selected in football to the 1942 All-City team at Saint Christopher’s Prep School as an end. In 1943-44, Chewning served as team captain for All Southern High School and as a running back. He enrolled in the United States Naval Academy and spent the year 1946 at that institute where he was an outstanding running back and played in the Army-Navy game in Philadelphia before 102,000 fans. Chewning transferred from the Naval Academy and spent 1947-48 at Hampden-Sydney, where he excelled in both football and track. He served as co-captain of the Tigers football team and led them to their first winning campaign in 26 years with a 6-2-1 record. He was All-State in both football and track, and in 1948, served as captain of both sports.
Chewning was a first team Little All-American Fullback with the Tigers in 1948, being named to the Little All-Southern and Virginia All-State football teams. The second time he touched the ball at Hampden-Sydney he raced 49 yards against Wofford College in 1948, leading the state in scoring with 78 points and was named honorable mention on the United Press International All-American team. Chewning was runner-up as the Most Valuable Player among small colleges in the Southern Conference area, and was selected to play in the Inaugural North-South football game in Miami, Florida on Christmas night. Considered an outstanding track star, he was the 1948 Mason Dixon champion in the 100 yard dash.
Chewning played professionally in football for the New York Bulldogs in 1949, the Richmond Rebels in 1950, and after going into the service, played for the Army in 1951 and 1952.