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 and later territorial Governor of Mississippi.
Winston served as a member of Mississippi Senate from 1827 to 1828 and, most notably, as a sixth Lieutenant Governor of Mississippi (1832) and the last to hold this office, due to constitutional changes (Lieutenant Governorship was reinstates in 1870).
Winston died in Natchez, Mississippi.
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