Which Slave Sailed Himself to Freedom?

100 Amazing Facts About the Negro: Life took him from a daring sea escape to a stint in Congress.

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At the top of the list is Robert Smalls, a 22-year-old mulatto slave who's been sailing these waters since he was a teenager: intelligent and resourceful, defiant with compassion, an expert navigator with a family yearning to be free. According to the 1883 Naval Committee report, Smalls serves as the ship's "virtual pilot," but because only whites can rank, he is slotted as "wheelman." Smalls not only acts the part; he looks it, as well. He is often teased about his resemblance to Capt. Relyea: Is it his skin, his frame or both? The true joke, though, is Smalls' to spring, for what none of the officers know is that he has been planning for this moment for weeks and is willing to use every weapon on board to see it through.

Background

Smalls was born on April 5, 1839, behind his owner's city house at 511 Prince Street in Beaufort, S.C. His mother, Lydia, served in the house but grew up in the fields, where, at the age of nine, she was taken from her own family on the Sea Islands. It is not clear who Smalls' father was. Some say it was his owner, John McKee; others, his son Henry; still others, the plantation manager, Patrick Smalls. What is clear is that the McKee family favored Robert Smalls over the other slave children, so much so that his mother worried he would reach manhood without grasping the horrors of the institution into which he was born. To educate him, she arranged for him to be sent into the fields to work and watch slaves at "the whipping post."

"The result of this lesson led Robert to defiance," wrote great-granddaughter Helen Boulware Moore and historian W. Marvin Dulaney, and he "frequently found himself in the Beaufort jail." If anything, Smalls' mother's plan had worked too well, so that "fear[ing] for her son's safety … she asked McKee to allow Smalls to go to Charleston to be rented out to work." Again her wish was granted. By the time Smalls turned 19, he had tried his hand at a number of city jobs and was allowed to keep one dollar of his wages a week (his owner took the rest). Far more valuable was the education he received on the water; few knew Charleston harbor better than Robert Smalls.

It's where he earned his job on the Planter. It's also where he met his wife, Hannah, a slave of the Kingman family working at a Charleston hotel. With their owners' permission, the two moved into an apartment together and had two children: Elizabeth and Robert Jr. Well aware this was no guarantee of a permanent union, Smalls asked his wife's owner if he could purchase his family outright; they agreed but at a steep price: $800. Smalls only had $100. "How long would it take [him] to save up another $700?" Moore and Dulaney ask. Unwittingly, Smalls' "look-enough-alike," Captain Rylea, gave him his best backup.

To white Confederates, the Union ships blocking their harbors were another example of the North's enslavement of the South; to actual slaves like Robert Smalls, these ships signaled the tantalizing promise of freedom. Under orders from Secretary Gideon Welles in Washington, Navy commanders had been accepting runaways as contraband since the previous September. While Smalls couldn't afford to buy his family on shore, he knew he could win their freedom by sea -- and so he told his wife to be ready for whenever opportunity dawned. 

The Escape on the Planter 

That opportunity is at hand on the night of May 12. Once the white officers are on shore, Smalls confides his plan to the other slaves on board. According to the Naval Committee report, two choose to stay behind. "The design was hazardous in the extreme," it states, and Smalls and his men have no intention of being taken alive; either they will escape or use whatever guns and ammunition they have to fight and, if necessary, sink their ship. "Failure and detection would have been certain death," the Navy report makes plain. "Fearful was the venture, but it was made."

At 2:00 a.m. on May 13, Smalls dons Capt. Rylea's straw hat and orders the Planter's skeleton crew to put up the boiler and hoist the South Carolina and Confederate flags as decoys. Easing out of the dock, in view of Gen. Ripley's headquarters, they pause at the West Atlantic Wharf to pick up Smalls' wife and children, along with four other women, three men and another child.

At 3:25 a.m., the Planter accelerates "her perilous adventure," the Navy report continues (it reads more like a Robert Louis Stevenson novel). From the pilot house, Smalls blows the ship's whistle while passing Confederate Forts Johnson and, at 4:15 a.m., Fort Sumter, "as cooly as if General Ripley was on board." Smalls not only knows all the right Navy signals to flash; he even folds his arms like Capt. Rylea, so that in the shadows of dawn, he passes convincingly for white.

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