On May 12, 1822, the whaling schooner Industry sailed past Brant Point under the command of Captain Boston, the first African American captain to sail a whaler with an all-black crew. Boston was an established Nantucket landowner and a leader of the island's African American community. He later ran a "public inn," and was also a founder of the African School at the corner of Pleasant and York Streets. When African American pupils Eunice Ross and Boston's own daughter Phoebe Ann Boston were denied access to Nantucket's public schools because of their color, Boston initiated a successful legal action against the town, resulting in one of the earliest integration victories in the country.

This remarkable portrait of Boston is attributed to a painter from the Prior-Hamblin School (named for William Matthew Prior and Sturtevant J. Hamblin), one of many itinerant artists who visited coastal communities like Nantucket throughout the nineteenth century.