Prior to the war, Webster was a friendly, well-spoken writer. He kept most of his cheerful air about him, but as the war went on, he developed a hatred for the Germans, something that was reinforced when Easy Company discovered the concentration camp at Landsberg. During Operation Market Garden, Webster's personality changed into a more deep and depressed manner, probably because he witnessed the death of his good friend, Robert Van Klinken
Webster retained his Private rank throughout his Army career, never advancing beyond it. He never volunteered for missions or tasks, although he actively fought in the war and never let his comrades down. Webster spurned promotion, considering himself a chronicler of war above all else.
Webster was born on 2 June 1922, in Bronx, New York. He was educated at the Taft School in Watertown, Connecticut from 1937 to 1940 and then attended Harvard University in 1940.
World War II
Webster volunteered for the U.S. Army in 1943. He was assigned as a machine gunner to Easy Company, 2nd Battalion, 506th Parachute Infantry Regiment, 101st Airborne Division. He made a jump at Fort Benning and completed training at Camp Mackall and Camp Shanks.
Webster participated and was wounded in Operation Overlord on 6 June 1944. He was evacuated but later requested to be transferred to Easy Company, in order to see more action. Webster returned to duty for Operation Market Garden on 17 September and witnessed the death of his best friend, PFC Robert Van Klinken at Nuenen. He later heard news of another best friend, CPL Donald B Hoobler, at Bastogne. He eventually grew cynical about the war, and wrote to his mother to 'not worry if he got killed'.
Webster participated in the assault on "The Island" (Episode "Crossroads") on 5 October. He assisted in rounding up several prisoners, suffered a leg wound from machine gun fire and was again evacuated, this time for a longer period. Thus, he was absent for the battles at Bastogne and Foy, but returned to his unit at Hagenau in February, 1945. He wrote of how glad he was to be back among his friends, in spite of being initially ostracized by them and regarded as a 'replacement' due to his absence from Bastogne. Eventually, the company welcomed him back more.
During Easy Company's time in Germany, Webster grew more and more contemptuous towards the Germans after the Company liberated a Nazi concentration camp. Shortly after, back in town, he menaced a complaining German baker, asking if he was a Nazi or "even a human being" before being reprimanded by another soldier.
Webster participated in the capture of Hitler's Eagle's Nest and returned to the U.S. after the war ended. After the European Theater of Operations ended, he was 4 points short of the 85 needed to go home and was to be deployed with the rest of Easy Company to Japan; fortunately, Japan surrendered before redeployment occurred and Webster was returned to the US and discharged. He couldn't understand why anyone could stay in the Army.
After the war he completed school at Harvard, and worked at the Wall Street Journal and Los Angeles Daily News. He later married and had three children. Over the years, he became interested in sharks, and studied them.
He eventually wrote a book on sharks called Myth and Maneater. Later, he began to write his memoir, Parachute Infantry: An American Paratrooper's Memoir of D-Day and the Fall of the Third Reich. He wrote many articles for papers, such as The Night Before D-Day, They Ride the Wild Waves and We Drank Hitler's Champagne.
On 9 September 1961, while studying sharks, Webster was lost at sea off the coast of Santa Monica, California. He was never found and presumed dead.