In 1886, Taylor ran for governor against his younger brother, Democrat Robert Love Taylor (1850–1912), in a memorable campaign known as the "War of the Roses." Canvassing the state together, the brothers often engaged in light-hearted banter and played fiddles, in contrast to previous gubernatorial campaigns, which involved fierce debates. Taylor ran for governor again in 1910, but lost his party's nomination to Ben W. Hooper. He was victorious in 1920 due in large part to divisions within the Democratic Party over taxes and women's suffrage.