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Mathew Ashby was in 1727 born to a black slave father and a white mother who was an indentured servant in York county Virginia. Mathew had one brother called john. He was born free according to Virginia law that allowed children to assume their mother's legal status.  Even though he was born free, Mathew remained indentured until he attained the age of 31, a requirement for every child born of an indentured female servant. He earned a living both as a carter and carpenter in the Williamsburg area. He also worked under Governor Botetourt as a messenger. Due to his hard work, he was able to amass more wealth compared to any common slave or servant (Powers, 1).

According to The Colonial Williamsburg Official History (1), Mathew married a slave by the name Ann who was owned by Samuel Spurr, a local bricklayer. Ann was mother to two children namely, John and Mary. The two children were educated at the bray school where they were able to learn catechism according to the Church of England among other subjects. Mary, their daughter, was baptized at Bruton parish church whose entry described her as a 'free mulatto'.

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Mathew Ashby worked so hard and was able to buy his wife and children from Samuel Spurr at an estimated cost of $150 in the year 1969. His quest for his family's freedom did not stop there as he petitioned the council to set his wife and children free (Powers, 1).  His claim that his wife had been faithful and industrious throughout their marriage was accepted by the council which accorded them immediate freedom on the 27th of November 1769. There were reports of Ashby harboring a runaway slave called Sam in 1769 leading to speculation that he was in contact with the larger community of African Americans.

Two years after freeing his family, Mathew Ashby died on 15th April 1771. He left his wife a considerable estate which included laundry equipment and luxurious items like a tea board and a silver watch. Ann was later remarried to George Jones but the marriage only lasted a short while. The whereabouts of Anne and her children is unknown but the Ashby family legacy survives in the Williamsburg area through his brother john (The Colonial Williamsburg Official History, 1).

Mr. Mathew Ashby is perhaps the most notable and extraordinary example of a man who managed to escape from the bondages of indentured service and slavery successfully.

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