Born in Roswell, New Mexico, Drew volunteered for the U.S. Army Air Forces in May of 1942. He was sent to England where he was assigned to the 561^st Squadron, 388^th Bombardment Group in the Eighth Air Force. Drew flew ten missions as a B-17F Bomber co-pilot. He was shot down on his eleventh mission. With the help of French partisans he escaped through France to Switzerland, where he met and married a local girl. Willingham ended his service as a captain in December of 1945. He later worked as a sales representative, homebuilder, and business consultant.