William Duguid, a Scottish immigrant textile importer based in Boston, is the subject of this engaging portrait. In 1773 he sat for Prince Demah, a painter of African descent, who was the “property” of merchant Henry Barnes. Impressed with his talent, Barnes took him to London in 1771, where he studied briefly with artist Robert Edge Pine, who later immigrated to Philadelphia. Demah’s story is extraordinary—he is the only enslaved artist working in colonial America whose paintings are known to have survived. To date, three portraits by him have been identified. When the Loyalist Barnes family fled to England in 1775, the artist remained in Boston, identifying himself as “Prince Demah, limner” and a “free Negro.” He enlisted in the Massachusetts militia in 1777 to fight against the British but died of an unknown illness the following year.