Ashley has served in a number of VFW positions at multiple levels of the VFW organization and is currently serving as the Post 4548 Judge Advocate, the Arkansas VFW State Chief of Staff, and the National VFW Deputy Chief of Staff.  His military service was in the United States Army from 1989 to 1993, earning his VFW eligibility by serving during Operations Desert Shield and Desert Storm. In recognition of his service, he received the Army Commendation Medal with two oak leaf clusters, Army Achievement Medal with four oak leaf clusters, Good Conduct Medal, National Defense Service Medal, Southwest Asia Service Medal with three bronze campaign stars, Multinational Force and Observers Medal, Saudi Arabia Kuwait Liberation Medal, Kuwait Liberation Medal, Combat Infantry Badge, Expert Infantry Badge, and the Air Assault Badge.