Enlistment Winston enlisted in the US Army on August 8, 1941 from his hometown Shelby, Mississippi. He was around eighteen years old when he enlisted. When he enlisted his civil occupation was a semi-skilled chauffeur, bus driver, taxi driver, truck driver, and tractor operator. In 1941 he was single and without dependents. He was 71 inches tall and 143 lbs.
Service Winston was put into the 3530th Quartermaster Truck Company. Hal C. Pattinson, Brigadier General, outlines the function of the Truck Companies during WW2 in a book titled United States Army in World War 2, The Technical Services, The Quartermaster Corps: Operations in the War Against Germany. The principal Quartermaster function in World War II was to supply items needed by all Army troops, most notably, food and clothing. But the Quartermaster Corps was more than a supply force; it provided many services, such as bath and laundry facilities, necessary to the health and comfort of the troops. The prompt collection and careful identification and burial of the dead and the respectful and suitable disposition of their possessions were essential services that contributed much to the morale of the front-line soldier. While established to serve the Army itself, before the war was over in Europe the Quartermaster organization found it had also to provide minimum support for millions of war prisoners and destitute civilians.
It was very common for African Americans to be put into truck companies like the 3530th. These companies would train recruits to drive supply trucks, help injured soldiers, etc. Winston was one such soldier.
Quartermaster companies are often overlooked because they are supplementary rather than actionary. However, without the Quartermaster companies, soldiers in combat would have likely suffered a great deal more and would probably have suffered heavy losses. In addition, soldiers did not choose which unit to be placed into, so African Americans were often grouped together in Quartermaster companies purely based on race. According to Hal C. Pattinson, However prosaic a history of providing goods and services may seem at first glance, this was an activity of vital concern to the American soldier, and in the Mediterranean and European theaters it was an enormous and highly complicated operation. By the spring of 1945 the Quartermaster organization in the European theater was feeding and clothing and otherwise providing necessities and comforts to more than seven and one-half million people, the largest human support operation by a single organization in all history to that time.