Richard B. Rutledge was one of the 290 men who enlisted for technical training in the ground crew of the 99th Pursuit Squadron when it was formed by the Army Air Corps in early 1941. He was one of the 41 men from the 2nd Army Corps Areas of Delaware, New Jersey and New York. He enlisted at Mitchell Field in Farmingdale, Long Island, on April 1, 1941. He was transferred to the U.S. Army Air Corps Technical Training School at Chanute Field in Rantoul, Illinois, where he was trained as an Airplane Mechanic and then sent to Maxwell Field, Montgomery, Alabama, and then on to Tuskegee Army Air Field.

After the Japanese bombed Pearl Harbor on December 7, 1941 and World War II was declared, the name was changed from Pursuit Squadron to Fighter Squadron and additional Squadrons were formed and trained at the Tuskegee Army Air Base. They later became a part of the 332nd Fighter Group which was commanded by Brigadier General Benjamin O. Davis, Jr. They became famous as fighter escorts to bombers over Europe, when in over 100 missions they never lost a bomber!

During the two-year interval, 1941-1943, while the 99th Fighter Squadron was training and before it left Tuskegee Army Air Field for North Africa in April 1943, Rutledge worked in the Message Center at Headquarters and was transferred to the 318th Air Base Squadron. He was promoted through the ranks from Private to Private First-Class, Corporal, Sergeant and Staff Sergeant He was one of the first 5 black men commissioned in the U.S. Army Air Corps as Warrant Officers (Junior Grade) in January 1943.

After the 99th Fighter Squadron departed Tuskegee for North Africa, he was transferred as an Administrative Officer to Fresno Army Air Base in Fresno, California, then to the 1887th Engineer Aviation Battalion at March Field, Riverside, California. He served with them as the Adjutant of the Headquarters Company. They were shipped overseas to Pearl Harbor, at Oahu, Hawaii, and as part of Admiral William F. "Bull" Halsey, Jr.'s Armada of over 200 battleships, destroyers, cruisers and LSTs, were a part of the invasion of Peleliu Island, one of the Palau Islands in the Southwest Pacific chain of Mariana Islands.

The men of the 1887th Engineer Aviation Battalion were all black, except for the Engineer Officers, who were all white. The mission of the 1887th was to repair and rebuild the airfield on Palau (the nearest island to the Philippines) from which General Douglas McArthur could return to the Philippines. When the Atom Bomb was dropped on Japan, the War ended and after 20 months overseas, Richard B. Rutledge returned to the United States, was Honorably Discharged at Fort Dix, New Jersey on March 26, 1946, one week short of five years of service in the United States Army Air Corps.