 He served as a judge on the fifth circuit court from 1873 to 1888, when he resigned after thinking he was elected to the U.S. Congress in a very close race with Republican Charles Brooks Smith.Although Jackson presented credentials as a Democratic Member-elect to the Fifty-first Congress and served from March 4, 1889 until February 3, 1890, Smith, successfully contested the election and served the final year of the term before being defeated for re-election by Democrat James Capehart.West Virginia legislators then elected Jackson as a judge on the criminal court for Wood County, where he served from 1891 until his death.