Oliver H. Dockery was born in 1830 in Rockingham, North Carolina, and graduated from the University of North Carolina at Chapel Hill in 1848. He began his career in public service by being elected to the State House of Representatives in the late 1850s. Dockery transitioned from a brief stint in Confederate service to advocating for the Federal Government during the Civil War. He later served as a Republican in the U.S. Congress, where he chaired the Committee on the Freedmen's Bureau. Dockery also participated in the State constitutional convention of 1875 and held diplomatic roles, including serving as the United States consul general in Rio de Janeiro, Brazil, from 1889 to 1893.

Oliver H. Dockery's political identity is marked by an intriguing blend of steadfast commitment to agricultural interests and a willingness to cross traditional party lines. His tenure as a Republican Representative and his later Populist candidacy reveal a penchant for ideological fluidity. Dockery's involvement in the Freedmen's Bureau and his advocacy for the Federal Government during the Civil War, despite his Confederate service, illustrate a complex approach to national unity and regional loyalty. His legal challenges to election results underscore a principled stance against electoral fraud, adding another layer to his multifaceted political persona.