Roanoke College

A member of the Monogram Club, Caldwell directed the fortunes of the football squad for four years in the quarterback position.  His teammates and coach describe him as the most outstanding field general in the state. 

In 1923, he led the team to the State Collegiate Football Championship and was captain of this team.  For his efforts on the gridiron, he was recognized on the All-State squad.

During World War II, he was awarded the Legion of Merit.