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.

Once aboard, Robert took to the helm while the others went to their places. As he navigated slowly away from Charleston and out to sea, his heart stopped at least a dozen times. His plan was to make it to the Union fleet, but to do this, he’d need to pass not 3, not 4, but 5 Confederate checkpoints at sea. What choice did they have, though? Robert and everyone else on board the Planter was ready to risk everything and had made a pact to sink the ship and go down together should they be discovered. When discussing his plan to escape them all to freedom, Hannah said this:

“It is a risk, dear, but you and I, and our little ones must be free. I will go, for where you die, I will die.”

They managed to pass each Confederate blockade with luck, fog, and the dark of night on their side. Years of working on this plan provided Robert with all the tools he needed to impersonate the Planters’ captain; hat, hand gestures, coat, and all. Once they approached the Union Navy, they had to act fast. If the Union saw a Confederate flag coming toward them, they’d blow them all to shreds. The USS Onward spotted the approaching vessel and yelled at them to retreat, or they’d fire. But Robert kept sailing. He was so, so close. If he turned back now, the Confederates would be on to them and they’d all be gone. In the knick of time, Hannah quickly exchanged the Confederate flag for a white sheet which she’d been saving for this moment.

In The Negro’s Civil War, James McPherson quotes the following witness account:

“Just as No. 3 port gun was being elevated, someone cried out, ‘I see something that looks like a white flag’; and true enough, there was something flying on the steamer that would have been white by application of soap and water. As she neared us, we looked in vain for the face of a white man. When they discovered that we would not fire on them, there was a rush of contrabands out on her deck, some dancing, some singing, whistling, jumping; and others stood looking towards Fort Sumter, and muttering all sorts of maledictions against it, and ‘de heart of de Souf,’ generally. As the steamer came near, and under the stern of the Onward, one of the Colored men stepped forward, and taking off his hat, shouted, ‘Good morning, sir! I’ve brought you some of the old United States guns, sir!'” That man is Robert Smalls, and he and his family and the entire slave crew of the Planter are now free.”

And just like that, at 23 years old, Robert managed to pull off one of the most complicated and risky escapes in Civil War history. They’d done it. They’d left Charleston as slaves and arrived in Fort Sumter as free people. Was it true? Could any of them believe it? Probably not. But no longer was he haunted by the long and callous life of a slave. No longer did he dread the same for his children. He and his family were finally free.



Post Enslavement

Now, you may be thinking this is the part where Robert, Hannah, and their kiddos make it to Canada, settle down on a few acres, get a dog and sip whiskey in the evenings. But that wasn’t the case – Robert Smalls was far from done with the United States. Almost immediately, President Lincoln was inspired by his escape and authorized freedmen to join the Union, which had previously been forbidden. Robert wasted no time enlisting in the Union Navy and went on speaking tours all across the north to recruit black men to join the Union and their cause. He conducted a total of 17 Union missions in an around Charleston and inspired countless freedmen to serve.

After the war, Robert purchased the very property on which he was a slave, opened a general store, a newspaper, and even a small school for African American children. Jane McKee had fallen on hard times in a post-Confederate world and was suffering from dementia. One day she wandered into the house where she once lived. Robert greeted, welcomed her, and allowed her to stay until her death. Proof that at his core, Robert was as kind as he was fearless. He eventually traveled around Philadelphia where he learned to read and write while also creating fundraisers to help establish former slaves.

His lengthy resume as a former slave, Confederate escapee, sea captain, Union soldier, and now businessman eventually led him into politics. He started by serving as a delegate to the state’s constitutional convention and was later elected to both the South Carolina House of Representatives and the State Senate. He personally worked on laws and regulations that guaranteed protection of African Americans, introduced the Homestead Act, and even had a hand in the Civil Rights Bill of 1866.

He dedicated the rest of his life to the advancement of freedpeople and his family until he passed away peacefully in his home at the age of 75. His legacy of bravery can be seen in many other heroes that came later, such as Ida B. Wells, Du Bois, MLK, and beyond. Who knows what the lives of him and the others he sailed to freedom would’ve been like without him? Would his children have been sold off to Arkansas to till away in the July heat? Would his wife be shipped off to a new master’s house for God knows what? Would his stubbornness eventually grant him death sentence? We’ll never know, and that’s all thanks to his undying bravery and insatiable quest for freedom. He was a fighter, a leader, a lion-hearted hero who burst at the seams with fearlessness, but most of all, he was free.