Winston Carter (post-war name: Jackson) was born into slavery around 1836 in Albemarle County, Virginia. Carter was a slave of John Coles Carter, who migrated from Virginia to Missouri in 1852 and owned 126 slaves on multiple properties by the eve of the war. On December 10, 1863, at the age of 26, Winston Carter enlisted in the Union army for a period of 3 years. Carter mustered into the 65th USCT Infantry Regiment as a private in Company A on December 18 near St. Louis, Missouri. His service record describes him as 5 feet, 5 3/4 inches tall, with black hair, black eyes, and a mulatto complexion.

The 65th USCT was responsible for garrison duty around Morganza and Baton Rouge, Louisiana. Carter worked on detached service building a bridge from August to October 1865. While his unit never fought in any battles, it suffered multiple casualties due to disease. Carter himself faced hospitalization for bronchitis, diarrhea, and smallpox. Carter, however, survived through the war and mustered out due to the expiration of his term on December 17, 1866. 

After the war, Carter moved to McDonough County, Illinois, where his father was living. He went by the name Winston Jackson, as that was his father's name. He married Mary Smith Jackson on November 21, 1876, in McDonough County. Together they had five children: Harriet A., born May 13, 1877; James B., born December 27, 1880; Henry W., born December 23, 1882; Mary F., born November 29, 1885; and Jessie, born July 15, 1890. He began receiving a pension of $6 a month in 1888. Carter died on July 9, 1891, in Macomb, Illinois, due to complications from heart disease. Following his death, his widow Mary Smith Jackson successfully applied for a pension of $12 a month for herself plus an additional $2 a month for her minor children. In 1892, Mary applied for Carter's accrued pension and was able to receive it in 1898.