In 1771, John Singleton Copley briefly interrupted his busy Boston portrait practice to visit New York, where he painted some of city's most important citizens. Among them was Miles Sherbrook. Born in Britain, Sherbrook immigrated to the colonies and during the late 1760s achieved prominence in New York as a partner in a London-based import firm. Seated at a table, dealing with his business affairs, Sherbrook is portrayed without a wig. He is dressed simply, in business clothes: russet breeches, waistcoat, and frock coat. His cheek is scarred with pockmarks, possibly from a bout of smallpox.
During the two decades preceding the American Revolution, Copley emerged in Boston as the most distinguished of colonial artists. His many portraits of influential New Englanders were remarkable for their craftsmanlike polish and clarity of design. With them he captured the simple strength and moral idealism of the emerging American republic.