James Monroe Bailiff was born in DeKalb County, Tennessee near Temperance Hall on December 2, 1845. He enlisted in Allison's Battalion of Cavalry, Company A, on February 25, 1863 with his brother, Columbus. He served as a private.

James Monroe Bailiff circa 1865

Monroe fought in the Battle at Chickamauga. He was shot on the second day of that battle. A minie ball from an Enfield rifle lodged in his right side after piercing his cartridge box. He and Columbus, who was suffering from typhoid fever, remained in the area until being captured by Union troops in December. After a brief stay in Nashville, TN, they were transferred to the prison at Louisville, KY, and were released in the spring of 1864. He returned to his home in DeKalb County to recuperate from his wound for the remainder of the war. Monroe married Eliza Jane Foster on October 6, 1865. He and his wife reared nine children on their farm, which remains in the Bailiff family, in the Dry Creek Community. He was active in the Dry Creek Missionary Baptist Church and served as one of its early deacons.

James Monroe Bailiff succumbed to cancer on May 8, 1927, and was laid to rest in the Snow Hill Baptist Cemetery. His wife joined him on January 22, 1928.