 During the first year of the war, he served as a field officer, initiating several raids.He was an important assistant to John Hunt Morgan, doing a preparatory raid (Hines' Raid) in advance of Morgan's Raid through the states of Indiana and Ohio, and after being captured with Morgan, organized their escape from the Ohio Penitentiary.He was later involved in espionage and tried to stir up insurrections against the Federal government in selected Northern locales.