Leonard Rutledge Woolsey was born in Penzance, Saskatchewan in 1922 to Hulbert and Barbara Woolsey. Leonard Woolsey served in the Navy during World War Two and was a member of the crew of the HMCS Athabaskan, which was disabled by a German air attack in August 1943. He also served at sea on the HMCS Chaudiere. He received a commission, ending the war attached to the Royal Navy as a Fleet Air Arm Fighter Controller. After the war, Woolsey attended the University of Saskatchewan where he graduated from Mechanical Engineering in 1949. He worked as a senior executive with Gulf Oil. Leonard Woolsey died in 2008.

Barbara (Mitchell) Woolsey was born in 1898. Barbara immigrated to Canada from Scotland in 1906. She married Hulbert Woolsey in 1915 and together they farmed at Penzance, Saskatchewan. Barbara and Hulbert had two daughters and ten sons. Barbara was an active member of the United Church and the Ladies Auxliary to the Legion. Her husband died in 1968. She moved to Regina in 1971 to enter a nursing home. She died in 1981.