Robert Smalls and the Never Ending Quest for Freedom



Early Life

In the spring of 1839, a boy named Robert Smalls was born into slavery in the McKee family of Beaufort, South Carolina. Like so many other enslaved children, he spent a lot of time asking questions and searching for freedom. In his afternoons tending to the McKees, he often dreamt of a life where he and his mother were people instead of property. A life where they could make their own living instead of someone else’s, a life where they could work toward their goals and live out their years full of purpose, opportunity, and passion.


By the time Robert was 12, his slaveholder had begun outsourcing him to Charleston, where he had started laboring on the waterfront as a rigger. Sunup to sundown was spent in the heat of the Carolina sun, working away on the piping hot sea mast surrounded by the squawks of seabirds and thick salty air. Over the years, he slowly worked his way up to a sailmaker, foreman, and though slaves were not allowed the title, a sailor.

As fate would have it, he eventually met an enslaved hotel maid named Hannah Jones; she was five years his senior and already had a child of her own. The pair fell in love and married but not before an undignified and humiliating permission from his master. It was then that he became more determined than ever to escape to freedom. After all, he had a family of his own now. His first thought was to buy their freedom – but how can someone who makes just 50 dollars a year ever have the capacity to save up to purchase freedom, which went for around $1,000? The odds were eternally stacked against any enslaved person looking to free themselves “legally,” and that wouldn’t change for quite some time.

The Planter & The Great Escape

After the start of the Civil War, Robert was sent to labor as a deckhand on a Confederate ship known as the Planter. Eleven years on the shores of Charleston and more than 20 years living a life of slavery gave him both the knowledge and the motivation to risk it all. For the next two years, he did just that. He studied the capitan very carefully, learned all the ins and outs of the Planter, kept a close eye on protocols at checkpoints, and eventually devised a plan to escape. Freedom was just around the bend.

In the early morning hours of May 13, 1862, the white officers and crew members slept like babies on the Charleston shore. Robert, along with ten other enslaved men, five women, and children, including Hannah and their two children, snuck quietly aboard the Planter. The fear was deafening; one child’s cry, one dropped compass, one anchor splash would send them all to their deaths.