Watkins served as deputy clerk of the county court for seven years. He served as the sheriff of Prince Edward County from 1880 to 1881. He also worked in the cotton business in Birmingham, Alabama, for a short time.[2]
After getting admitted to the bar, Watkins became the senior member of the law firm of Watkins and Brock. In 1886, he became judge of Prince Edward County but resigned that post in 1891 to become prosecuting attorney.[2] Watkins represented Prince Edward County in the Virginia House of Delegates for the session of 1897-1898. He was elected to the Virginia State Senate in 1899, representing Prince Edward, Cumberland, and Amelia counties.[2] Watkins served as town attorney for Farmville from 1898 to his death.[2]
Watkins served as the secretary-treasurer of the board of trustees of the State Normal School (later the State Teachers' College). He served as a trustee of Hampden-Sydney College from 1886 to 1932. He served as trustee of the Normal and Industrial Institute for Negroes (now Virginia State University) in Petersburg for 20 years.[2]
Personal life
On September 2, 1886, Watkins married Nannie Edwards Forbes, daughter of Colonel William W. Forbes and Amonette Cobb Forbes, of Buckingham County.[2] They had eight children: William Forbes, Samuel W., Mrs. Maurice Miller, Frank Nathaniel Watkins, Asa D., Patsy, Nancy, and foster daughter Mrs. Joseph Powell.[2]
Watkins died on April 14, 1938, at his home in Farmville. He is buried at Farmville Cemetery.[2]