Webb was born November 30, 1919, and grew up in Portsmouth, OH. After high school, he attended Kentucky Military Institute to prepare for enrollment at Virginia Military Institute, but after reading an article about The Citadel in National Geographic magazine he applied for admission in 1939 and was accepted. He became battalion commander for Padgett Thomas Barracks and lettered on The Citadel rifle team. With the rest of his class, he missed final summer ROTC camp in 1942 because the camps were filled with Army recruits. After graduation in 1943, Webb was assigned to officer candidate school at Fort Benning, GA, graduating first in his class. In November 1943 he was commission and assigned to the infantry school cadre, remaining there nine months until sent to the 174th Infantry regiment at Camp Chafee, AR. Two months later he was shipped to Europe as an individual replacement officer and was assigned as a platoon leader in C Company, 48th Armored Infantry Battalion, 7th Armored Division, in charge of roughly 40 men. Immediately sent into combat, he became acting company commander six days after joining the unit, because he was the only remaining officer. After a month in combat, he received a battlefield promotion to first lieutenant and was awarded a Silver Star medal for valor and later received a Purple Heart. Webb said that a first hand account of a war scene cannot be conveyed verbally. “If you could smell it, if you could feel it, if you could taste the food, if you could hear the noises—it’s a very all-encompassing experience.” He continued, “The most horrendous smell I ever smelt was later in the Bulge when I opened the door to a house, and a German soldier had been laying there for two or three days, and the stench was such that your stomach involuntarily vomited.” After being wounded in the Battle of the Bulge, he was treated at a hospital in Paris. Six weeks later he was back in action as a platoon leader, often sleeping in a foxhole in the snow. After the war, Webb returned to Ohio and ran a lumber company for a while, but in 1951 he returned to military service, including a tour in Korea near the end of the war there and two tours in Vietnam. He also served two tours at The Citadel, as tactical officer for several years in the 1950s and as commandant of cadets for six months. After retiring from the Army in 1973, he returned to Charleston, where his wife had grown up, operated an charter fishing business for fifteen years.