James E. Bailey was born around 1827 in Connecticut to Richard and Amy Bailey. His father was a laborer. He married Emily Bassett on January 1, 1855, and they had at least six children: Edwin, born around 1858; Eva, born around 1861; Louisa, born around 1866; Mary, born around 1869; Amy, born around 1870; and George, born around 1873. They lived in Providence, Rhode Island, and Bailey worked as a harness maker. By 1860, he owned $500 of personal property.
In the spring of 1861, he received a commission as a 2nd lieutenant in Company B of the 1st Rhode Island Infantry. He was promoted to 1st lieutenant on June 4, 1861. The regiment took part in the First Battle of Manassas, and he mustered out on August 2, 1861.
He rejoined the Union army soon afterward, receiving a commission as a captain in Battery E of the 3rd Rhode Island Heavy Artillery. The regiment took part in the siege of Charleston. He was promoted to major on January 1, 1863, and he mustered out on August 27, 1865.
He lived in Pawtucket, Rhode Island, after the war, and he resumed his work as a harness maker. He applied for a federal pension in May 1891 and eventually secured one. He died of “cancer of the face” in Providence on December 23, 1896.