People: Scots of Windsor's Past
Oscar E. Fleming (1861-1944):
"Sober of speech, precise in his statements, prudent in his counsels, delicate in his remarks, he is the very picture of the professional diplomat."
~ Carl Morgan [Birth of a City] 1
Oscar Fleming's paternal grandfather, Daniel Fleming, immigrated to Canada from Scotland in 1824 and settled in Halton County. His son, Samuel, married Sophia Harwood, and the couple set up home in the town of Milton, where Oscar was born. The Fleming family moved to Windsor in 1867, while Oscar was still a young child. He went on to study law at Osgoode Hall and was called to the Bar in 1886.
Two years after setting up his own practice in Windsor, Fleming entered into partnership with E. S. Wigle; J. H. Rodd joined them in 1893. Fleming, Wigle & Rodd made "a strong combination and [the firm] covers every line of practice, engaging in the greater part of the litigation in this part of the country." 2
As a practitioner of the law, Fleming was also naturally inclined to pursue politics. He spent three years on the City Council before being elected mayor. Once in office, he led the campaign to have Windsor incorporated as a city. When his efforts came to fruition the following year, Windsor's residents showed their gratitude by electing him first Mayor of the City of Windsor. He attempted to enter federal politics in 1908, running as the Conservative candidate for the House of Commons in Essex North, but was narrowly defeated by Liberal candidate R. F. Sutherland.
Fleming was also an active businessman: he served as the vice-president for McAlphin Consumers Tobacco Company Limited in Toronto, and was director for both the Standard Paint & Varnish Works Company Limited and the Windsor Turned Goods Company Limited. But his biggest contribution to the community was his work in promoting the St. Lawrence Waterway. From the ideas he presented as a keynote speaker at the 1922 Border Chamber of Commerce conference grew the Deep Waterways & Power Association, of which he was first president. The Fleming Channel in the Detroit River is named in his honour, and a memorial cairn in Alexander Park along Riverside Drive near Strabane Avenue commemorates the work he did to extend the Great Lakes system.
Fleming married Carolina Drake in 1890 and had nine children with her. One son, Kenneth E. Fleming, graduated from McGill University with an electrical engineering degree, and went on to form Confederation Coal & Coke Limited. Oscar's younger brother Harwood meanwhile studied pharmaceuticals in Toronto and returned to Windsor to become the city's leading druggist and pharmacist. Oscar helped Harwood fund the construction of a building for his business at the corner of Ouellette Avenue and Chatham Street, which was named the Fleming Building for the family.