When his father got into financial difficulty, Crapsey quit school at age eleven and took a job in a dry good store. When, after two years, his father recovered financially, Crapsey returned to school, but because he was the oldest boy in his class, he felt uncomfortable and quit school again and took a job in a hardware factory. After a co-worker called him "worthless," in August 1862, at age fourteen, Crapsey joined the army during the American Civil War. However, he was given a medical discharge the first winter after his enlistment and sent back to his home in Fairmount, Ohio.