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Reginald Hayward was born in Victoria, the son of Charles and Sarah Hayward. In 1908, he took over the family business, the B.C. Funeral Company. Hayward also served in public life, first as a school trustee (1913) and then as an alderman (1922) and mayor (1922-1924) for the municipality of Victoria. Following his term as mayor, he became Victoria's Conservative Member of the Legislative Assembly, a position he held for 11 years. He also gave his time to a number of private organizations including the B.C. Protestant Orphan's Home and the Native Sons of British Columbia. Reginald was married to Isabella Morrison Jaffrey, with whom he had three sons, Charles, William, and Reginald Jr.