Soldier, lawyer, banker.
Born in Columbus, Ohio on 27 April 1843, son of Edward Bailey, he served in the American Civil War. Discharged in 1865, he worked at various jobs then took education at Bethany College in Virginia from 1871 to 1875. He began law practice at Marysville, Ohio, and was admitted to the Bar in 1877. Later that year, he moved west and established a real estate, loan, and law office in Wichita, Kansas. In failing health, he sold the business in 1880 and spent the next two years traveling through Mexico, California, and other Pacific states, returning to Ohio in early 1882.
Hearing of a land boom in Dakota and Manitoba, he arrived at Winnipeg in July 1882 and opened a private bank at Gladstone in partnership with C. P. Brown, under the name of Lockhart, Bailey & Company. Within a year, Bailey bought the assets of the company, converting it into W. S. Bailey & Company which he operated until 1900 when he closed the business. He traveled through Europe for much of that year then returned to Gladstone to operate a money-loaning business.
He died at Gladstone, unmarried, on 23 January 1916. His remains were returned to the United States for burial.