Mr. Winston is a 1991 graduate of Indiana University with a Bachelor of Science in English Education and will begin his 35th  year in education.  He began his career at Northside High School, in Warner Robins, GA, where he taught for four years.  Most importantly, he met his bride of 33 years, Mrs. Mendi Winston at Northside.  He then taught for 11 years at Attica Jr./Sr. High School and Turkey Run High School in West Central Indiana only to see his career go full circle and end up back at Houston County at Perry High.  Mr. Winston teaches 9th and 10th grade Literature, is the Perry High Bass Team Coach and is an assistant instructor with the PHS JROTC Raiders program..

He and his wife, who also teaches at Crawford County High School, are blessed with three amazing children.  All of their children are graduates of Perry High.  Their son, Zach, is a Staff Sargent in the United States Air Force where he is stationed in Cheyenne, Wyoming.  Their twin daughters, Courtney and Keeley, are 2020 graduates of Mercer University and have both joined their parents as educators.  Courtney teaches 5th grade at Kings Chapel Elementary and Keeley teaches Pre-K at Morningside Elementary. In April of this year, daughter Courtney gave birth to her first child, and Jeff and Mendi's first grand child, Tyler Brock Owens. In March of 2024, Son Zach and his wife Kendahl gave birth to their first child, and Jeff and Mendi's second grand child Emerson John Winston and in March of 2025, Daughter Keeley will give birth to her first child, and Jeff and Mendi's third grandchild, daughter Wrenley Jaye Hagler..  Life is great for the Winston's!