A shoemaker by trade, Enoch Crosby joined the Continental army in 1775. His accidental discovery of a Tory conspiracy, however, indicated his talent for intelligence, and he was soon charged with infiltrating British lines to spy on their operations. Following the war, an attempt was made to reward Crosby financially for his many life-risking ventures into the enemy camp, but Crosby refused the gift, claiming that he had not served his country for mere gold. Nevertheless, a tribute that he could not avoid came to him in 1821 with the publication of James Fenimore Cooper's The Spy, a novel said to have been inspired by Crosby's exploits.
When The Spy became a play in the late 1820s, curiosity about Crosby was awakened, and this portrait-commissioned by the son of one of Crosby's wartime superiors-was a reflection of that interest. On the picture's reverse, Crosby testified that the likeness was an "accurate" record of his features and signed himself "Enoch Crosby, Secret Agent of the Committee of Safety in the Revolutionary War."