In his debut season (1909), South Melbourne reached the Grand Final but Caldwell missed playing due to a nine-week suspension for striking Carlton's George Bruce in the Preliminary Final.

Cleared from South Melbourne on 12 May 1920,[12] he played three matches for Footscray in the VFA — on 15 May,[13] 22 May,[14] and 29 May[15] — before resigning as a player and moving on to coach "Footscray Diggers", in the Victorian Junior Football Association;[16] and, at least, by 31 July 1920, he was serving as captain-coach of Camperdown in the Corangamite Football Association.

[22] On the resignation of Carlton's captain-coach Paddy O'Brien — who (later) went to play with Footscray in its first VFL season — Ray Brew acted as coach for four matches.

Caldwell (then in Perth) was appointed coached of Carlton for the remainder of the 1925 VFL season.

[30] Admitted to the Melbourne Hospital with "internal trouble", Jim Caldwell died of peritonitis some three weeks later, on 20 August 1929.