He was an active IRA brigade staff officer and occasionally acted as brigade commandant of the West Cork III Brigade during the War of Independence. Dick also managed to organise fund raising activities for the purchasing of weapons and comrades on the run. In July 1920, following the arrest of the Cork III Brigade Officer in Command Tom Hales and Quartermaster Pat Harte, Dick was appointed Brigade quartermaster. He was arrested on 22 March 1921 and imprisoned in Cork jail, later being sent to Spike Island, County Cork.