John Custis, often called Jack, was the son of John Custis IV and Alice, an enslaved woman. John Custis recognized John as his natural son. John Custis IV’s will bequeathed a “portrait of my Negro boy John” to Ann Moody, a Williamsburg tavernkeeper’s wife with whom he was romantically involved. This is the only documented portrait of a person of African descent as the primary subject (not an attendant) from colonial Virginia.
See: John Custis IV’s Will, Custis Family Papers, Virginia Historical Society; Janine Yorimoto Boldt, “‘Constantly to look at me’: Slavery and the Development of Colonial American Portraiture,” Winterthur Portfolio (Summer/Autumn 2022): 127-166.