Henry Espy was the Mayor of Clarksdale, Mississippi until 2013.
Espy's grandfather, T. J. Huddleston, Sr., created the first hospital in Yazoo City, MS for African Americans.
Henry Espy was the first African American appointed to the school board in Clarksdale, MS.
Espy is President of Century Funeral Home and Burial Association in Clarksdale and Yazoo City.
The funeral home was created by his grandfather, T. J. Huddleston, Sr. His son Henry "Chuck" Espy, III served in the Mississippi State Legislature, representing the 26th District through 2016, and is the current mayor of Clarksdale (2017–present).