Called “the greatest merchant on this Continent” in his obituary, Apthorp helped transform Boston into one of the key commercial centers in the American colonies. When the fashionable painter Robert Feke came to town, Apthorp commissioned this elegantly tailored and confidently posed likeness of himself. The sailing ship in the distant background symbolizes Apthorp’s deep financial interests in the Atlantic trade, which included not only textiles, wine, and guns, but also enslaved people. In fact, the slave trade and its attendant commerce comprised a significant portion of colonial Boston’s economy until the decades after the Revolutionary War, when anti-slavery attitudes in New England gained momentum.