After graduation, he joined the U.S. Army and deployed to Korea with the 187th Regimental Combat Team. After his deployment, he was accepted (after rigorous training) into the newly created Army Special Forces "Green Berets".
Assigned to the 5th Special Forces, SFC Ashley deployed to Vietnam and earned a Congressional Medal of Honor during the Battle of Lang Vei. During an assault to rescue American troops and create openings for continued attacks, SFC Ashley led five charges, creating enough of an opening to allow the rescue of the survivors of Camp Lang Vei. He died of his wounds on February 7, 1968, and rests in Rockfish Memorial Park in Fayetteville, North Carolina.