Oscar Ernest Fleming was born March 17th, 1861 in Milton, Ontario, the son of Samuel Fleming and Sophia M. Fleming (nee Harwood). He moved to Windsor at about age 6. He became a prominent lawyer, politician, and businessman. He was Mayor of Windsor from 1891-1893: the last Mayor of the Town of Windsor and the first Mayor of the City of Windsor. He was also involved in the construction of the St. Lawrence Seaway. In 1890, he married Caroline Maud Fleming (nee Drake) and they had 11 children together. He died November 29th 1944.