Robert 'Bob' James McCaskill (27 September 1895 – 23 June 1952) was an Australian rules footballer who played for Richmond in the Victorian Football League (VFL) during the 1920s and coached both North Melbourne and Hawthorn. Early life Born in Cobram in 1895, McCaskill spent his childhood growing up around Numurkah near Shepparton, Victoria. It was here that he learnt to play the cornet. 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. He was issued with the service number 36704. He travelled to Royal Park in Melbourne in September 1916 to enlist again with the Australian Army. He was passed fit on this occasion. He fought in Europe rising to the rank of Sergeant. He returned to Australia in June 1919. Playing career After the war McCaskill returned to Shepparton where he re-established his business. He began to play football again after a time spend as an umpire. Strong performances while playing for Shepparton in the GVFL he was under the attention of the Richmond Club. At the age of 27 he got a permit to play with Richmond in June 1923. 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. After leaving Richmond he accepted a position at the Bendigo YMCA as secretary. Richmond refused to clear him so he stood out of football for the year. McCaskill joined Sandhurst, but he wasn't allowed to play the first year of his coaching. He had a lot of success as coach in the Bendigo Football League club, leading them to premierships in 1927, 1929, 1930, 1931, 1932, 1933, 1934, 1939 & 1940. Coaching career 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. This meant he relocated to Melbourne and the club offered him their coaching position. For 1941 and some of 1942 he was the honorary coach of North Melbourne. Warrant Officer McCaskill was relocated interstate by the Army and the job went to Bill Findlay as his replacement. Bob returned to