13 Apr. 1839–7 Mar. 1888
Winston's plans for a career in law were cut short by the outbreak of the Civil War. He enlisted in the Confederate army in the spring of 1862 and was commissioned a captain in the Forty-fifth North Carolina Infantry. Wounded and captured at Gettysburg in July 1863, he was sent to Johnson's Island Prison in Lake Erie. There on the night of 31 Dec. 1863 he escaped across the frozen lake into Canada. With the help of a relative in New York, he obtained passage from Canada to Nassau and then ran the blockade into Wilmington, rejoining his regiment in time for the Wilderness campaign. When his commanding officer was killed at Spottsylvania in May 1864, Winston became colonel of the regiment and served with distinction until the war's end.
After being mustered out, he accepted a position as principal of the Memphis Academy in Memphis, Tenn., but he soon left and returned to North Carolina to take up farming. In 1867 he married Marian Long of Caswell County, and the couple had five children. Active in the Granger movement, he obtained the post of master of the New Hope chapter; however, Winston's interests in national finance and currency reform led him in other directions. Believing that the answer to the nation's fiscal woes lay in inflationary measures, he started a correspondence on that topic with farm and labor leaders across the country and participated in the formation both of the National Independent party in 1875 and its successor, the National Greenback Labor party, one year later. At the Greenback's national convention in 1880, he vigorously supported its presidential nominee, James B. Weaver.
Winston also agitated for the Greenback cause on the local level. In 1876 he published an open letter to the residents of his congressional district—the Fifth—urging them to support financial reform, and in 1878 and 1880 he was an unsuccessful Greenback candidate for the district's congressional seat. In 1880 Winston again attempted to organize the party on the state level but failed miserably, attracting only five people to the state convention. He also served as political editor of a short-lived Greenback newspaper, the Greensboro Beacon. Still proselytizing for soft money, Winston ran for Congress in 1882 as a Republican and again in 1884 as a Liberal but was defeated both times. He died four years later at his home near Hycotee post office in Caswell County.