Wesley Pennington grew up in Cranston, Rhode Island in a family of five boys and one girl, in which he is the youngest. He graduated from Cranston High School East and went on to study sociology at Western Connecticut State University. Wesley then became a member of the United States Army. He served a tour in Korea and upon coming back from Korea, he was assigned to the prestigious 82nd Airborne Division. During his time with the 82nd, Wesley was in one of the first groups sent to Operation Desert Storm.