Matthew Ashby

Ashby was the son of a Black man and Mary Ashby, a white woman who was an indentured servant. He was born free because in Colonial times a child inherited his or her mother's social status. But under Virginia law, he was also indentured until age 31 and was prohibited from meeting with slaves. Ashby worked as a messenger for Virginia governor Norborne Berkeley and as a carpenter. He acquired material goods, such as a silver watch, books, and candle-making equipment, that seemed out of reach of most Black colonists.

He married Ann Ashby, a slave of a bricklayer, and purchased her and their two enslaved children, John and Mary, in 1769 for 150 pounds. Although he owned them, Ashby had to petition the government to win their freedom. John and Mary attended Williamsburg's Bray School.