Back in April, 1861 when the Civil War began at Fort Sumter, Smalls was assigned to steer the Planter, a lightly armed Confederate military transport under the command of Charleston’s District Commander Brigadier General Roswell S. Ripley. Planter’s duties were to deliver dispatches, troops and supplies, to survey waterways and to lay mines.

In April of 1862, Smalls began planning an escape, discussing it with other slaves in the crew except one, whom he did not trust.

On the evening of May 12, the Planter was docked in Charleston as usual, with its three white officers disembarked to spend the night ashore, leaving Smalls and the crew on board. At about 3 a.m. on May 13, Smalls and seven of the eight slave crewmen made their previously planned escape to the Union blockade ships.

Smalls put on the captain’s uniform and wore a straw hat similar to the captain’s. He sailed the Planter past what was then called Southern Wharf and stopped at another wharf to pick up his wife and children and the families of other crewmen.