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Reuben Wells Leonard was born in Brantford, Ontario, and attended the Royal Military College in Kingston. After graduation, he worked for the Canadian Pacific Railway doing survey work. His work with the CPR was interrupted only briefly when he served in the Northwest Rebellion.

In 1911, Leonard became Chairman of the National Transcontinental Railway Commission and was responsible for overseeing the construction of a railway from Moncton, New Brunswick to Manitoba. He was also active as a professional engineer and was at one time President of the Engineering Institute of Canada. He also served as the President of Coniagas Mines Ltd. from 1906 to his death in 1930.

Reuben Leonard was a philanthropist and made monetary donations not only to Queen's but also to the Girl Guides, Boy Scouts, the University of Toronto, the Art Gallery of Ontario, and many other organizations. He also established the Leonard Foundation in 1916 to provide financial assistance for children of ministers, soldiers, teachers, and engineers.

It was Leonard who donated what is now known as Leonard Field to Queen's in 1923 in recognition of the services of its graduates and students in the First World War (see Wartime at Queen's).

Leonard Hall is also named in his honour.