Bailey moved to Nemaha County, Kansas, in 1879, and became a successful farmer, rancher, and banker. He and his father founded the town of Baileyville, Kansas in 1880.[2] He served as member of the Kansas House of Representatives from 1888 to 1890. He was president of the Republican State League in 1893. He served as member of the Kansas State Board of Agriculture from 1895 to 1899.
In 1902 Bailey won the Republican gubernatorial nomination and the general election and served as Governor of Kansas from 1903 to 1905. During his tenure, construction on the state capitol was completed, railroad commissioners and the office of state printer became elective positions, and a law banning gambling devices was sanctioned.[3]