When Blackburn passed through Boston sometime around 1760, the Bowdoin family already owned portraits by Joseph Badger, Robert Feke, and others. Nevertheless, James Bowdoin II lost no time in securing Blackburn’s talents to depict young James III and his sister Elizabeth. The result is this unusual double portrait, which is at once a charming portrayal of children and an assertively up-to-date statement of their importance as the rising generation of one of New England’s most prominent families. Indeed, Blackburn subtly alludes to the family’s crest, which includes three birds, through the bird held by the James III and the two in his cap.