During World War II, after graduating from the Naval Academy in 1941 and being commissioned as a Naval Reserve officer, Richmond 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, Richmond served as a battalion commander at the segregated Camp Robert Smalls. In early 1944, 16 black sailors reported to Great Lakes to undergo a two-and-a-half-month training program to become officers. Richmond devised the curriculum for the black men and supervised their training. They were commissioned in March 1944 and subsequently became known as the Golden Thirteen. After leaving Great Lakes in 1944, Richmond served on the staff of Rear Admiral John L. Hall during the 1945 invasion of Okinawa and later had shore duty in Hawaii and Japan. Following the war, Richmond returned to the Detroit area (where he had grown up) and worked as a stockbroker for 43 years.