Rubuta ci gaba ga wannan sakin layi - A cikin matasansa, ya shirya wani kamfani na doki na yau da kullum da aka sani da Mountain Rangers, wanda ya zama wani ɓangare na 7th Virginia Cavalry ("Ashby's Brigade"). Da barkewar yakin basasa, an sanya Ashby da sojojinsa zuwa rundunar 'yan bindiga ta Virginia ta Colonel Thomas J. "Stonewall" Jackson. (Mutumin da ya fi kowa ƙarfi) Ko da yake Jackson ta Valley yaƙin neman zaɓe
Ashby ya zargi Jackson saboda rashin horo da horo na mutanensa. A lokacin da aka kashe Ashby, ya jagoranci mutanensa a yakin Good's Farm kusa da Harrisonburg, ya karbi tauraronsa. Duk da haka, ana kalubalantar matsayin Ashby na hukuma kamar yadda ba a tabbatar da haɓakawa ba har sai bayan mutuwarsa.