Pennington is a retired educator and former superintendent of both the Indianola and West Tallahatchie school districts. Prior to that he was the Indianola Junior High School principal, teacher, and coach.
Pennington served as executive director of Delta Health Alliance from 2004 to 2008 and currently sits on its board. He’s a former member of the Mississippi Board of Trustees of the Institutions of Higher Learning, the Mississippi Instructional Management Task Force, and the South Sunflower County Hospital. He is a former president of the Delta Council. Additionally, Pennington has served on the Mississippi State Health Board and as Administrative Assistant to the President at Delta State University.