helmsman, though enslaved people were not permitted that title. As a result, he was very knowledgeable about Charleston Harbor. At age 17, Smalls married Hannah Jones, an enslaved hotel maid, in Charleston on December 24, 1856. She was five years his senior and already had two daughters. Their own first child, Elizabeth Lydia Smalls, was born in February 1858. Three years later they had a son, Robert Jr., who died at age two. Robert aimed to pay for their freedom by purchasing them outright, but the price was steep, $800 (). He had managed to save up only $100. It might have taken him decades to reach $800. Civil War Escape from slavery In April 1861, the American Civil War began with the Battle of Fort Sumter in nearby Charleston Harbor. In the fall of 1861, Smalls was assigned to steer the CSS Planter, a lightly armed Confederate military transport under the command of Charleston's District Commander Brigadier General Roswell S. Ripley. Planters duties were to survey waterways, to lay mines, and to deliver dispatches, troops, and supplies. Smalls piloted the Planter throughout Charleston harbor and beyond, on area rivers and along the South Carolina, Georgia and Florida coasts. From Charleston harbor, Smalls and the Planters crew could see the line of federal blockade ships in the outer harbor, seven miles away. Smalls appeared content and had the confidence of the Planters crew and owners, and at some time in April 1862, he began to plan an escape. He discussed the matter with all the other enslaved people in the crew except one, whom he did not trust. On May 12, 1862, the Planter traveled ten miles southwest of Charleston to stop at Coles Island, a Confederate post on the Stono River that was being dismantled. There the ship picked up four large guns to transport to a fort in Charleston harbor. Back in Charleston, the crew loaded of ammunition and of firewood onto the Planter. On the evening of May 12, the Planter was docked as usual at the wharf below General Ripley's headquarters. Its three white officers disembarked to spend the night ashore, leaving Smalls and the crew on board, "as was their custom." (Afterward, the three Confederate officers were court-martialed and two convicted, but the verdicts were later overturned.) Before the officers departed, Smalls asked Captain Relyea if the crews’ families could visit, which was occasionally allowed,