May's husband, William Sherman Jennings, served as Florida's 18th governor. The Jennings lived in Brooksville before moving to the Governor's mansion in 1901. Mrs. Jennings was active in civic work and politics. After her husband died in 1920, she headed the Florida Federation of Women's Clubs and was co-founder of the Florida League of Women Voters. She campaigned for women's suffrage, prohibition, better treatment of children and prisoners, education funding, historic preservation, Seminole Indian reservations, fence laws and highway beautification. Mrs. Jennings died in Jacksonville at the age of 90.