Wilson Caldwell was born on February 27, 1842, in Chapel Hill, North Carolina. His parents were Rosa Burgess, who was enslaved by UNC President David Swain, and November Caldwell, who was enslaved by North Carolina Governor Caldwell and worked as a college servant at UNC for 30 years. As his mother was enslaved by President Swain, Wilson Caldwell was also enslaved by Swain at the time of his birth. Before the Civil War, he worked at UNC as a gardener and a waiter in the dorms and laboratories.
After the Civil War, Caldwell held a number of positions. Following the inauguration of Governor Holden, he held the office of Justice of the Peace for a year. In 1869, Caldwell began operating a school for Black children in Chapel Hill and later became the principal of a school near Elizabeth City. Following the reopening of UNC in 1875, he resumed his former position as waiter. He left the university in 1884 to go to Durham, hoping to earn more money for his family, but he quickly returned to Chapel Hill and spent a year farming. He would later say, “Durham is not a place for a literary man!” He returned to work at the University and became the curator of South Building and the head of the labor corps. In 1886, Caldwell was elected to the Board of Commissioners of Chapel Hill, to a seat reserved for a member of the University. He was married to Susan Kirby and they had 12 children, one of which was the doctor Edwin Caldwell.
Caldwell passed away in 1898. The UNC class of 1891 had a monument dedicated to UNC’s first president, Joseph Caldwell, moved to Wilson Caldwell’s grave and rededicated to him, along with his father, November Caldwell, and David Barham and Henry Smith, two other Black university servants.