Jessi E. Sterwart was born 19 March 1935 in Truman, Arkansas and attended public schools in Pointsette and Craighead Counties. He graduated in 1957 from Arkansas State University with a B.S.A. degree in agriculture education. A distinguished military graduate, he was commissioned as a second lieutenant in the U.S. Army. During the next 26 years, he held various command, staff, and diplomatic assignments in the United States, Africa, Europe, and Asia. Colonel Stewart recieved the following awards: Legion of Merit, Silver Star, Distinguished Flying Cross, Bronze Star, Meritorious Service Commendation Medal, Army Commendation Medal with oak leaf cluster, Vietnam Cross of Gallantry with Palm, Unit Citations for combat actions in Vietnam, Service Medals for world wide assignments including Vietnam. Colonel Stewart was infantry, aviation, airborne, and Army staff qualified. He attended the Basic and the Advanced Infantry Course at Fort Benning, Georgia, the Command and General Staff College at Fort Leavenworth, Kansas and the Army War College at Carlisle, Pennsylvania. Colonel (then Major) Stewart commanded the 170th Assault Helicopter Company, 52nd Aviation Battalion, 1st Aviation Brigade during the battle of Dak To (1967) and the Tet Offensive (1968) in the Republic of Vietnam. He was awarded the Silver Star for gallantry in action during the Battle of Dak To.
On 9 November 1967, Major Jessie E. Stewart, Commander of the 170th Assault Helicopter Company, personally spearheaded aerial combat assaults under intense enemy fire during the Battle of Dak To. The Silver Star Citation for gallantry in action reads in part: "Major Stewart distinguished himself while serving as mission commander by voluntarily making sorties into a very small landing zone that was under intense enemy fire. On four different occasions, the fighting grew so intense that the helicopters had to be pulled back until the fighting was reduced Despite the mortar and automatic weapons fire, he steadily pressed on until the battered and bloodied troops were extracted out of the landing zone. Becasue of his valrous action, the wounded troops were saved and the dead did not fall into enemy hands. Major Stewart's actions and willingness to lay his life on the line to save his fellow soldiers were in keeping with the highest traditions of military service and reflect great sredit upon himself, his unit, and the United States Army.