Like so many enslaved people, Smalls was haunted by the idea that his family—his wife, Hannah; their four-year-old daughter, Elizabeth; and their infant son, Robert, Jr.—would be sold. And once separated, family members often never saw each other again.
The only way Smalls could ensure that his family would stay together was to escape slavery. This truth had occupied his mind for years as he searched for a plan with some chance of succeeding. But escape was hard enough for a single man; to flee with a young family in tow was nearly impossible: enslaved families often did not live or work together, and an escape party that included children would slow the journey significantly and make discovery much more likely. Traveling with an infant was especially risky; a baby’s cry could alert the slave patrols. And the punishment if caught was severe; owners could legally have runaways whipped, shackled, or sold.
Now Smalls’ chance at freedom had finally come. With a plan as dangerous as it was brilliant, he quietly alerted the other enslaved crew members on board. It was time to seize the Planter.
Smalls’ plan was to commandeer the Planter and deliver it to the imposing fleet of Union ships anchored outside Charleston Harbor. These vessels were part of the blockade of all major Southern ports President Abraham Lincoln had initiated shortly after Fort Sumter fell in April 1861. As one of the largest ports in the Confederacy, Charleston was a lifeline for the South. A largely agrarian society, the South depended on imports of war materiel, food, medicine, manufactured goods, and other supplies. With the U.S. Navy blocking the harbor, daring blockade runners, looking to make hefty profits, smuggled these goods into Charleston and carried cotton and rice out of the city for sale in European markets. After supplies arrived in Charleston, the city’s railroad connections delivered them throughout the Confederate states.
Although crucial, blockading such an important port was a staggering task. The many navigable channels in and out of the harbor made stopping all traffic nearly impossible and had led Northerners to refer to Charleston as a “rat hole.” Although many vessels outran and outmaneuvered the blockade, the Union was able to intercept some and either capture or destroy them.
Though the wharf and the U.S. fleet were only about ten miles apart, Smalls would have to pass several heavily armed Confederate fortifications in the harbor as well as multiple gun batteries along the shore without raising an alarm. The risk of discovery and capture was high.