Career
Caldwell played through the centre and was a premiership player with Victorian Football Association (VFA) club Williamstown before joining South Melbourne in 1909. In his debut season, South Melbourne reached the Grand Final but Caldwell missed playing due to a nine-week suspension for striking in the Preliminary Final. Almost a decade later, in 1918, he captained the club to victory in the 1918.
By then, Caldwell was playing as a rover and had become a regular Victorian interstate representative.
In 1921, Caldwell captain-coached Williamstown to a premiership. Caldwell coached VFL club Carlton in 1925.
In 1929, Caldwell was appointed South Melbourne coach but died season, on 21 August. He is the brother of the Street Kilda football player Arthur Caldwell.
