Colonel Cockshutt was born in Brantford, Ontario, in 1868. He entered his family's plow company and served as its President from 1911 to 1934. In 1896 he married Anna Rolls. He was Mayor of Brantford from 1899 to 1900. During World War I, Colonel Cockshutt organized and commanded the 215th Infantry Battalion. He served as Lieutenant Governor from 1921 to 1926, during which time he opened Government House to the public and allowed charitable organizations to use its rooms for meetings. A prominent businessman, he used his connections to encourage developement in Northern Ontario. Colonel Cockshutt died in 1944.