National Portrait Gallery, Smithsonian Institution
In the early hours of May 13, 1862, Robert Smalls made a dramatic escape from slavery by commandeering a Confederate ship and delivering it safely into the hands of the U.S. Navy. As an enslaved worker in Charleston, South Carolina, Smalls became a skilled deckhand and wheelman aboard the Planter, a cotton steamer that was converted into a Confederate transport vessel in 1861. Determined to make a bid for freedom, Smalls and his enslaved shipmates absconded with the Planter after the ship’s white captain and crew went ashore for the night. Under cover of darkness, Smalls and his men picked up several family members before guiding the Planter safely past Confederate positions and handing over the vessel to the commander of the Union blockading squadron, positioned just outside Charleston Harbor. Hailed as a hero in the North, Smalls received a monetary award from Congress and later served as the Planter’s pilot after it became a Union gunship.