William Sherman Jennings was born near Walnut Hill, Illinois. After graduating from Union College of Law (now Northwestern University School of Law) in Chicago he moved to Brooksville, Florida. He served as lawyer and judge in Hernando County. William met his future wife May Mann at her father’s house near Brooksville. Austin Mann, May’s father had just won election to the state house of representatives. Austin was a former Florida Senator.
William courted May and they married and moved into the William Sherman Jennings House at 48 Olive Street in Brooksville (It is currently forsale). The couple had a son, Sherman Bryan Jennings.
William ran for and was elected governor of Florida in 1900. While serving as governor William introduced the statewide primary election system, which replaced the nomination of candidates at a convention. He also worked to drain and develop the Everglades by cutting the natural rock dams in the rivers of south Florida.
After serving as governor William Jennings moved to Jacksonville, where he started a successful law firm. He split his time between Jacksonville and his farm in near Middleburg in Clay County.
The Jennings were a politically prominent family. William’s brother served as a lawyer and state attorney. He was also a first cousin to William Jennings Bryan a former Presidential candidate.