Massey entered the Royal Military College, Sandhurst in 1915, and was commissioned as a second lieutenant into the Nottinghamshire and Derbyshire Regiment in April 1916.
On 4 February 1917, Massey was wounded and his observer killed when their aircraft was shot down by German ace Werner Voss.
[1] Transferring to the newly created Royal Air Force in 1918, Massey continued his military career through the interwar period.
6 Squadron in operations during the Arab Revolt in Palestine, for which he was awarded the Distinguished Service Order, and was a station commander during the early years of the Second World War.
[4] Massey was the basis for the character "Group Captain Ramsey" in the film The Great Escape (1963), played by actor James Donald.