During World War II, after being commissioned as a Naval Reserve officer, Dille was involved in the training of new recruits at the Great Lakes Naval Training Station north of Chicago. In 1942, with the influx of thousands of black sailors among the recruits, Dille volunteered to be involved in their training and served as a battalion commander. In early 1944, 16 black sailors reported to Great Lakes to undergo a two-and-a-half month training program to become officers. During that time when the black men were under a great deal of pressure, Dille served as a mentor and a source of moral support and encouragement. They were commissioned in March 1944 and subsequently became known as the Golden Thirteen. They chose Dille as an honorary member of the group and in later years attended reunions with them. After leaving Great Lakes in 1944, Dille served at an ammunition depot in Hawaii and later as an information officer to publicize the achievements of black sailors in the war effort. Following the war, Dille worked for the National Newspaper Service and later became publisher of The Elkhart Truth, a newspaper in Elkhart, Indiana, and owner of radio and television stations.