Born in Germantown (Stokes County, North Carolina) as a son of the Representative Joseph Winston. He was also a brother of Louis Winston, future Mississippi Supreme Court justice and brother-in-law of Robert Williams, another North Carolina Representative.
Winston served as a member of Mississippi Senate from 1827 to 1828 and, most notably, as a sixth Lieutenant Governor of Mississippi (1832) under Governor Abram M. Scott and the last to hold this office, due to constitutional changes (Lieutenant Governorship was reinstated in 1870).
Winston died in Natchez, Mississippi.
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