He was also a fast running wingman and in 1914 his team, Shepparton, lost the Goulburn Valley Football League grand final.
In December 1915 with the fighting in Europe during World War I McCaskill enlisted in Shepparton only to be discharged in May 1916 for synovitis of the knee.
McCaskill was a centreman while at Richmond and played finals football in 1924 with his side eventually finishing second in that year's unique round robin format.
The outbreak of the Second World War, he again enlisted in 1940 and led the Southern Command Band at Royal Park and later became an Army Amenities Officer.
Warrant Officer McCaskill was relocated interstate by the Army and the job went to Bill Findlay as his replacement.
McCaskill as coach also wanted to make changes to the playing group, starting with Kevin Curran to be captain.
Outgoing captain-coach Alec Albiston was angry as he was told by a member of the board that he would remain as captain.