Roosevelt Sills is native of Emporia, Virginia. He was born January 25, 1952, the seventh child of James and Louise Sills. He graduated from Greensville County High School. Roosevelt enlisted in the United States Army in September 1970. He attended Basic Training at Fort Campbell, Kentucky and Advanced Individual Training at Fort Sill, Oklahoma. Command Sergeant Major Sills completed Airborne School at Fort Benning, Georgia.

His active duty assignment as a Section Leader with the 5-81st FA (Airborne), 8th Infantry Division, Wiesbaden, Germany. Upon his release from active duty, CSM Sills joined the United States Army Reserve. CSM Sills served in numerous leadership and staff positions in the 78th Division (Training), to include Training NCO, 2nd Bde; Senior Drill Sergeant of CO A, 3-310 Regiment; First Sergeant, Co B-310; Battalion Operations Sergeant, 3-310 Regiment; Operations SGM for 2nd Bde; and as Battalion Command Sergeant Major, 1-310 Regiment.

CSM Sills was ordered to Active Duty during Desert Shield/Desert Storm as the Battalion Sergeant Major, 1-310, 2nd Bde, 78th Division (Training). After completion of the Gulf War, CSM Sills served as Bridge Command Sergeant Major for 2nd Bde, 78th Division (Training) and then as Brigade Command Sergeant Major, 2nd Bde, 76th Division (Training) in Lodi, New Jersey. He assumed his duty as Division Command Sergeant Major from 1995 to 1999. Service was extended in the status of advisory role for one year. He was instrumental in the development of many of the army training programs. He was instrumental in the transformation and transition of Army Reserve Forces and Active Duty Component in “The One Army Concept in the 20th Century.”

His military education includes Airborne School, Drill Sergeant School, United States Army Sergeants Major Academy, Dragon Gunner Course, Senior Non-Commissioned Officer Leadership Courses, Equal Opportunity Course, Front Line Leadership Course, TSO/Trainer Workshop Course, Flag Football Official Course; Master Fitness Course, British Jump School, Shelter Manager’s Course, MAPTOE Course, Air Delivery Course, and the Observer Controller Course.

His awards include the Legion Merit, the Meritorious Service Medal with two Oak Leaf Cluster, Army Commendation Medal with three Oak Leaf Clusters, Army Achievement Medal with three Oak Leaf Clusters, Good Conduct Medal, Army Reserve Components Achievement Medal with Four Oak Leaf Clusters, National Defense Service Medal with Bronze Star, Vietnam Service Ribbon, Armed Forces Reserve Medal, Non-Commissioned Officer Development Ribbon with the numeral 4, Army Service Ribbon, Overseas Service Ribbon, Parachutist Badge, Drill Sergeant Qualification Badge, 9MM Pistol Badge (Marksman), M16 Rifle Badge (Expert), and the British Parachutist Wings.

CSM Sills attended Bergen Community College in Business with Computer Programming Concentration. He retired from Public Service Electric and Gas Utilities Company as a distribution supervisor after 32 years. He attended numerous business courses.

Roosevelt recently graduated from the Ministry Training Academy (MTA) at Covenant Life Ministries Church in March 2017. He currently serves on the Teaneck Senior Citizen Advisory Board and Teaneck Community Scholarship Board. He serves on with the Teaneck Patriotic Board and leadership team of Covenant Life Ministries Church in Teaneck, New Jersey.

CSM Sills and his wife Ramona, reside in Teaneck, New Jersey. They have two daughters, Tiffany and Tikki, one granddaughter, Talia, and two grandsons A.J. and A.D.