Command Sergeant Major (Retired) Gregory Caywood, a native of Greenup, Illinois, enlisted in the Army in 1995 and served for 27 years, retiring in 2022. A decorated veteran, he held leadership roles from platoon forward observer to Brigaide CSM and deployed three times in support of Operation Enduring Freedom. CSM Caywood holds a Bachelor of Arts from Columbia College and two Master’s degrees—in International Relations from Webster University and Secondary Education Social Sciences from the University of West Alabama. After retiring, he taught high school English and served as a substitute teacher before becoming the JROTC Senior Army Instructor at Southern Prep. His awards include the Legion of Merit, two Bronze Stars, six Meritorious Service Medals, and the Combat Action Badge.
