In May 1862, an enslaved man named Robert Smalls won renown by stealing the Planter, the Confederate military transport on which he served as a pilot. On a night when the ship’s three white officers defied standing orders and left the vessel in the care of its crew, all slaves, Smalls guided it out of its slip in Charleston Harbor and picked up his wife, their two young children and other crewmen’s families at a rendezvous on the Cooper River. Flying the South Carolina state flag and the Stars and Bars, he steered past several armed Confederate checkpoints and out to the open sea, where he exchanged his two flags for a simple white one—a gesture of surrender to a Union ship on blockade duty. In all, he delivered 16 enslaved persons to freedom.
After serving the Union cause as a pilot for the rest of the Civil War, he returned to South Carolina, opened a general store that catered to the needs of freedmen, bought his deceased master’s mansion in Beaufort and edited the Beaufort Southern Standard.