Background
Bailey was born on May 6, 1825 near the town of Pennsville in Morgan County, Ohio.
Bailey was born on May 6, 1825 near the town of Pennsville in Morgan County, Ohio.
He earned a civil engineering degree at the University of Illinois.
He moved to Kilbourn City, where he successfully engaged in lumbering and in engineering construction. At the outbreak of the Civil War he raised a company in the 4th Wisconsin Regiment. Of this company he was appointed captain and was mustered into federal service, July 2, 1861. With his regiment, he was sent immediately to Maryland, and, in the following spring, to New Orleans with Benjamin Butler's expedition. The remainder of his war service was along the Gulf. He was promoted major of his regiment, May 30, 1863; lieutenant-colonel, July 15, 1863; and colonel, May 3, 1864. During much of this time he was on detached service and, owing to his engineering skill, was successively engineer 2nd division, 19th corps, distinguishing himself at Port Hudson in July 1863, chief engineer defenses of New Orleans, and military engineer 19th corps. It was in 1864, on Banks's Red River expedition, that Bailey rendered his outstanding service. The army marched overland accompanied on the river by a fleet of light-draft gunboats and transports which, aided by high water, passed upstream without difficulty. When, however, the retiring army reached Alexandria on April 26, the water had subsided and the fleet could not pass over the falls. In this emergency, Bailey, then engineer 19th corps, recommended construction of wing dams to raise the water in the river high enough to permit the boats to pass over the falls. He executed this task with such skill and energy that in twelve days the entire fleet, thirty-three vessels all told, had cleared the obstruction. More than $2, 000, 000 had been saved to the government. For this act Bailey was granted the thanks of Congress, was brevetted brigadier-general June 7, 1864, and was presented by Admiral Porter with a sword. Participating later, with distinction, in the reduction of Mobile, he was appointed, on November 10, 1864, brigadier-general of volunteers and on March 13, 1865, major-general by brevet for gallant and meritorious services in the campaign of Mobile. Resigning on July 7, 1865, he settled in Vernon County, Mo. In the fall of 1866 he was elected sheriff, and on March 21, 1867, was murdered, near Nevada, by two bushwackers whom he had arrested and who, while returning to the county seat, shot him in the back of the head.
Bailey married Mary Spaulding in 1846.