17 June 1746–21 Apr. 1815
In 1775 Winston was elected a delegate to the Hillsborough Provincial Congress, where he signed the Continental Association, and he and the county's other delegates were constituted as the Surry County Committee of Safety. In April 1776 he represented Surry at the Halifax Provincial Congress and voted to instruct the state's delegation to the Continental Congress to vote for independence. In 1778 he was made entry taker (register of deeds) for Surry County. This position brought him into close contact with the Moravians (Unitas Fratrum ) of Salem, and he assisted them in acquiring deeds to the Wachovia settlement. Although occasionally at odds with the Moravians, especially in his role as a Patriot militia leader, Winston was on friendly terms with them for the remainder of his life. This gave him a substantial base for a lengthy political career.
Shortly after the 1775 Hillsborough Congress Winston was named second major, then first major of the Surry County militia. In February 1776 he led a group of Surry volunteers to fight Tories at the Battle of Moore's Creek Bridge. Later that year he and his men joined a multistate effort against the Overhill towns of the Cherokee. Winston and his force served under Colonel Martin Armstrong and General Griffith Rutherford in subduing the Indians, and Winston participated in the negotiations that led to the signing of the Treaty of Long Island on the Holston on 20 July 1777.
During the remainder of the Revolution he had several opportunities to protect the peace-loving Moravians from marauding militia groups from both sides and to lead Patriot groups against Tory forces in the Surry County region. In September 1780 Major Winston and sixty Surry County militiamen joined Colonel Benjamin Cleveland and his Wilkes County troops. They met with the over-mountain men and joined in the defeat of Major Patrick Ferguson and his forces at Kings Mountain on 7 Oct. 1780. On 15 Mar. 1781 Winston and his militia served under General Andrew Pickens in the Battle of Guilford Court House. Some accounts report that Winston and his men were among the last Americans to leave the battle, and that Richard Talliferro, serving with Winston, was the last American to be killed. Years later Winston apparently was given the rank of lieutenant colonel in the Stokes County militia. In 1812 the North Carolina legislature presented him an "elegant sword" for his military services.
Winston represented Surry County in the House of Commons in 1777, 1779, 1782, and 1783. In 1788 he was a delegate to the Hillsborough convention to consider the ratification of the proposed U.S. Constitution. He voted with the majority neither to ratify nor to reject the Constitution apparently in hopes of forcing either a new convention or the addition of a bill of rights to the proposed document. Winston was also a delegate to the 1789 Fayetteville convention and voted with the majority to ratify the Constitution.
In 1787–89 he represented Surry County in the North Carolina Senate. He led the movement to divide Surry County and was senator from newly created Stokes County in 1790, 1791, 1802, 1807, and 1812. In addition, he represented the district consisting of Surry, Stokes, Iredell, Wilkes, and Ashe counties in the Third Congress of the United States (1793–1795) and in the Eighth and Ninth congresses (1803–7).
A hardworking state senator, Winston represented the interests of his Piedmont region in a generally Jeffersonian manner. On several occasions he called public meetings to determine the wishes of his constituents on local, state, and national issues. He favored education, limited government, and supremacy of the legislature and opposed the dominance of eastern over western counties. In the national Congress Winston attended and voted regularly, but he served on no important committees and never addressed the body on any issue. He backed the Jeffersonian position on almost every matter on which a vote was recorded. Thus he was an undistinguished but reliable representative. He served twice as a presidential elector, voting for Jefferson in 1800 and Madison in 1812.
In 1784 he became a trustee of the Salisbury Academy, and in 1807 he was tapped by the legislature to serve a six-year term as trustee of The University of North Carolina. In 1809 he was a trustee for the Germanton Academy, located only a few miles from his home.
As early as 1782, Winston owned 980 acres of land and was identified as the enslaver of fifteen people. In 1790, he owned 1,362 acres of land and was the enslaver of eighteen people; on his death, he left a will in which he indicated ownership of 900 acres in Stokes County and 8,000 acres of western lands. He was married twice, first to Jane Dalton in 1769 and later to Minerva Elizabeth Lanier. His children numbered at least twelve, mostly boys. Triplet sons, Samuel L., Lewis L., and William H., moved to Mississippi and Alabama where one became a major general in the War of 1812, another a state supreme court judge, and the third lieutenant governor. Another son, Joseph, remained in North Carolina and also became a major general in the War of 1812.
Winston was buried in the family cemetery near Germanton. In 1849, when Stokes County was divided, the county seat of Forsyth, the new county, was named for him. In 1894 a statue of Winston was erected on the Guilford Court House Battlefield, and in 1906 his remains were moved to the battlefield, now a part of the Guilford Court House National Military Park.