Oscar Ernest Fleming
Oscar Fleming was the first mayor of the City of Windsor. He was also a prominent lawyer, politician, and businessman who was instrumental in building a seaway which connected the Great Lakes to the Atlantic Ocean.
In 1891 Fleming campaigned for mayor on a pledge that he would turn the Town of Windsor into the City of Windsor. He won, and the city was born a year later. In addition 
to serving as the first mayor of the City of Windsor, as well as the final mayor of the Town of Windsor, he served a member on a number of boards and associations in the municipality, and acted as director of the Kelsey Wheel Company Ltd., the Windsor Truck and Storage Company Ltd., and several other large corporations.
Mr. Fleming was born March 17, 1861 in Milton, Ontario. He was educated in Windsor, and in 1881 began to read law with Windsor barrister Duncan Dougall. Fleming graduated from Toronto’s Osgoode Hall in 1885 and returned to Windsor to practice law. Over fifty years of his life were dedicated to the study and practice of law, during which his name was well known throughout Ontario and was acknowledged as one of the leaders of the bar in Windsor. In 1890 he entered Windsor Town Council, serving as councillor for a year. He also served as a Member of the Windsor School Board from 1887 to 1890, served as Alderman from 1890-1891, and was named a King’s Counsel in 1907. He served as mayor of Windsor from 1891 to 1893. Mr. Fleming helped form the Essex Border Utilities Commission to manage the public services of Windsor, and was a member until its dissolution after the incorporation of the City of Windsor. He was also instrumental in the building of the Metropolitan General Hospital and was chairman of the hospital board for many years. Fleming worked with Adam Beck in the campaign to establish the Ontario Hydro-Electric system. However, Fleming may be best remembered for his work as president of the Canadian Deep Waterways and Power Association. The Association resulted in the development and deepening of the St. Lawrence waterways so that ocean shipping might be brought to the Great Lakes ports. Fleming was the husband to Caroline Fleming Drake, and was father to eleven. He was also an Anglican and an active member of the Church of Ascension in Windsor. Fleming’s other accomplishments included acting as synod member of the Diocese of Huron, being a 32nd Degree Mason, and member of the Scottish Rite. Oscar Fleming died in Toronto age the age of 84 on November 29, 1944.
Sources:
“Ex-mayor O.E. Fleming is mourned.” Windsor Star. Nov 30, 1944.
More, Lauren. “First city mayor remains with us thanks to video.” Windsor Star. Feb. 13, 1992.
Stagg, Ronald. The Golden Dream: A History of the St. Lawrence Seaway. Toronto ; Tonawanda, N.Y. : Dundurn Press, 2010. P. 114.
“Tribute paid O.E. Fleming.” Windsor Star. Dec. 2, 1944.