Born deaf and mute to a respected physician in Connecticut, John Brewster began his study of painting in adulthood with a provincial master. Brewster eventually became a successful portraitist and is today acknowledged as one of the most gifted of the early New England itinerant painters.

Billy Emerson (1765–1835) of Topsfield, Massachusetts, was a merchant and extensive property owner, and this portrait captures his charming bravado. Portraits by Brewster of Emerson’s parents, are also in the Athenæum’s collection.