Henry Watterson (Feb. 16, 1840 - Dec. 22, 1921), Jeffersontown's most famous resident, was the founder and editor of the Louisville Courier-Journal. In 1894 he bought the Joseph Hite property, which consisted of 100 acres and a four-room house about a mile from the square in Jeffersontown. Watterson transformed the house and property into a grand estate he named Mansfield, after the childhood home of his beloved wife, Rebecca Ewing.

Practically every day, Watterson could be seen traveling the one and a quarter mile driveway (now called Watterson Trail) he had built from his home to the town square in order to board the Interurban Rail Line for work in Louisville. He retired in 1919, passing away two years later while visiting Florida. His wife remained at Mansfield until her death in 1929. 

The estate deteriorated over the years, and was purchased by a developer in 1975. Amid much controversy, the mansion mysteriously burned in 1976. It was later demolished, and a new subdivision called Watterson Woods was developed on the estate.