Born in Epsom, Ontario in 1858. Began working with Midland Railway in 1872. He moved to the Victoria Railway in 1877 and to the Credit Valley Railway in 1880, to the Ontario & Quebec Railway in 1883 and to the Canadian Pacific in 1884. Leonard was superintendent of various lines before 1901 when he became superintendent of western division. He was later superintendent of construction and general manager of eastern lines, 1908 to 1911. In the latter year he became assistant to the Vice-President.