On a Christmas Eve impulse in 1856, Robert Smalls married a thirty-three-year old hotel slave named Hannah Jones. At the age of seventeen, he became a family man, and no one could convince him that he had made a bad decision. By the spring of 1862, the twenty-three-year-old Robert Smalls had small children to support — a daughter, Elizabeth, his son and namesake, Robert, Jr., and a third baby on the way. His wife and family lived on the Coffin Point Plantation, located on the far shore of St. Helena Island. The Philbricks, who managed the plantation for the Gideonites, knew them well.
Robert himself was employed on the side-wheeler Planter, flagship of Brigadier General Roswell Ripley, deputy commander of all Charleston defenses. This shallow-draft boat, 150 feet long and 46 feet wide, supplied Confederate outposts along the coasts because it could carry heavy loads of armaments through the shallow passages of the Sea Islands.
In the days just prior to Hunter's emancipation proclamation, the captain, C. J. Relyea, and his crew of three whites and eight slaves had been helping to evacuate General Hagood's troops from their base on Cole's Island. Smalls was a better seaman than the ship's captain, and often worked in the wheelhouse, actually steering the ship while the captain struck a swashbuckling pose on the deck. Ripley and Relyea trusted Smalls but gravely under-estimated his intelligence. They freely discussed military orders, strategies, passwords, and secret signals in front of the slaves, wrongly assuming they would not understand or remember what they heard.
“Why does yo’ always be sittin’ on de deck whittlin’ ‘way at some piece o’ wood?” one of the other slaves asked him. “Dere’s a good game a’ chance goin’ on below decks.”
“But I can’t hear what the Captain is sayin’ when I’m below deck,” Robert explained.
“What yo’ care what he be sayin’?”
“ ‘Cause he’s telling me how I can steal this ship.”
“Gwan wid’ you. He not be tellin’ yo’ nuttin.’”
“Oh, yes he is, Clem. He just doesn’t know it.”
“Yo never gonna be stealin’ no ship.” Clem shook his head in irritation.
“Yes, I am. And you and the others are going to help me.”
“Shure we is! An den maybe we’s gonna take over de rest o’ de world, too.”
“I’m serious, Clem. Tonight, when we tie up for the night, meet me back of that old bait shed on the dock, and bring the other members of the crew with you. I have a plan that will set us all free and make us heroes.”