Roberts is one of many great Crusader athletes to have his collegiate career impacted by WWII. He was an outstanding end for the football team in 1940 and 1941 and then served in the military from 1942 to 1946. He returned to Holy Cross and continued to play great football, earning All New England and All American honors, and playing in the East-West Game in California. In his career at Holy Cross he played the entire 60 minutes in 20 out of the 29 games that he started. After graduation he coached high school football and baseball for 25 years, and served as the President of the Massachusetts State Football Coaches Association.