During the Spanish–American War, Bailey served at Fort San Jacinto, Texas, as commander of Battery G, 1st Artillery Regiment, and then at Fort Preble, Maine, where he commanded a battery of the 7th Artillery Regiment. He was promoted to captain in 1899.[4]
From 1911 to 1913, Bailey commanded the 1st Provisional Coast Artillery Regiment at Fort Crockett, Texas.[2] In 1913 he was assigned to command the coast defenses of Puget Sound, Washington, after which he returned to Fort Totten as commander of the North Atlantic Coast Artillery District.[2] From 1914 to 1917 he commanded the coastal defenses of Manila and Subic Bays in the Philippines.[2]
In 1918, he was assigned as commander of the 81st Division, which he commanded in France from 1918 to 1919.[2]
Post-World War I
In 1919, Bailey was selected to command the Middle Atlantic Coast Artillery District at Fort Totten, and returned to his permanent rank of brigadier general.[2] He assumed command of Department of the East at Governors Island, New York on October 13, 1919.
In 1885, Bailey married Mary M. Dodge.[4] They were the parents of two daughters, Omira and Merry.[4] Omira Bailey was the wife of Army Colonel Alexander Wheeler Chilton, and Merry was the wife of Army Colonel Charles Lewis Gandy.[4]
Bailey's first wife died in 1923. In 1924, he married Elizabeth Hegeman Bailey.[5][6]
Death and burial
Bailey suffered a hip fracture in a fall in July 1945 and never fully recovered. He died on September 21, 1946, at his home in Jamestown, New York.[1] Bailey was buried at Lake View Cemetery in Jamestown, New York.