Born in Germanton, 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 1826 to 1830. He was the sixth Lieutenant Governor of Mississippi in 1832 under Governor Abram M. Scott. After Scott's death in October, Winston acted as governor for the last six weeks of Scott's term. He the last to hold the office of lieutenant governor, which was eliminated under a revised state constitution, and was not reinstated until passage of Mississippi's post-Civil War constitution in 1869. Winston served again in the Mississippi Senate in 1833.
Winston died in Natchez, Mississippi on December 1, 1834.