Wildon Bennett began his athletic career by earning four letters in football at Gurley Madison County High School in the late 30s. Wildon played on the 1938 Madison County championship football team and also played in the first Tennessee Valley North-South All-Star football game in Decatur. Wildon also starred for the American Legion Baseball team under Coach Cecil Fain in 1938. His high school coach, W.O. Wooley named Wildon as one of the six greatest athletes during his time at Gurley. Wildon graduated high school with six scholarship offers to play college football, including offers from Vanderbilt, Auburn , and Alabama. Wildon signed a scholarship to play football at the University of Alabama under the legendary Frank Thomas. Wildon had a very successful freshman year at the Capstone, but was forced to leave school and serve his country during World War II. In the Army, Wildon achieved the rank of Staff Sergeant and was awarded the ATO Medal, the Good Conduct Medal, and the World War II Victory Medal.