For the enslaved people in Charleston and across the Sea Islands, the Union presence offshore represented a possibility that had not existed before. Some enslaved people had already made their way to Union-held territory; the Union commanders had not returned them, and a legal question was developing in real time about the status of enslaved people who reached Union lines. The answer was not yet the full legal emancipation that would come with the Emancipation Proclamation in January 1863. But the direction was legible to anyone paying attention.
Smalls was paying attention. He had been thinking about escape for some time before the spring of 1862. The question was not whether to try but how. And the how was determined by what he had: access to a vessel, knowledge of the harbor, and the confederacy of other enslaved crewmen who were willing to take the risk.
Around April 1862, Smalls began discussing the plan with the other enslaved crew members. According to the NPS account, he discussed it with seven of the eight enslaved crewmen aboard. The eighth was one he did not fully trust with the plan — an understandable precaution when a single person’s disclosure could end everything. Those who were brought into the planning knew what it meant to succeed and what it meant to fail.
The plan took shape through the month of May. Smalls waited for the right night: one when the white officers would be ashore, when the timing of tides and the position of the harbor’s patrol vessels would give them the best window, and when conditions would allow for what came first — the pickup of the families who were not yet aboard.