Live Free or Die Free: The Thrilling Escape of Robert Smalls

Robert Smalls 1862

Robert Smalls in 1862. (Hagley Museum and Library)

Robert Smalls was born on April 5, 1839, in Beaufort, South Carolina. His mother, a slave named Lydia Polite, gave birth in a small shack tucked behind the comfortable home of her master Henry McKee, who may very well have been Robert’s father.

Lydia taught her son about the true evil of slavery from an early age, taking him to a local jail to see a slave woman whipped mercilessly and to a slave auction to see human beings – children among them – bought and sold like cattle. She had been ripped away from her own family at age 9, and she was determined to prepare her son for a difficult and dangerous future. Robert took her teaching to heart. He remarked later in life, “Although born a slave I always felt that I was a man and ought to be free, and I would be free or die.”

Charleston Slave Badge

A Charleston slave badge. (National Museum of American History)

In 1851, at age 12, he was sent away to Charleston, South Carolina. Contracted out to various employers, he worked for wages that went into his master’s pocket. Like all hired-out slaves in Charleston, Smalls had to wear a medal identification badge at all times. After spending time as a hotel waiter and as a lamplighter, he found himself loading and unloading cargo ships at the city docks. Working around the water, he developed skills that would serve him well later.

During his time in Charleston, Smalls met and fell in love with Hannah Jones, a slave owned by a man named Samuel Kingman. Legally, slaves were prohibited from marrying. Most owners, however, allowed unofficial weddings, in part because a slave with a family was believed less likely to run away. By agreeing to pay Kingman $5 every month, Smalls gained permission for such a marriage with Hannah.

At age 22, several months into the Civil War, Smalls was hired out to work about the Planter, a privately-owned steamship contracted by the Confederate military to carry messages, troops, and supplies. (This wasn’t unusual. While African Americans did not willingly fight for the rebellion as soldiers, despite Neo-Confederate lies to the contrary, hundreds of thousands of slaves were forced to support the Confederate military as laborers.) As a skilled boat pilot, Smalls was an invaluable addition to the crew, which consisted of three white officers and six other slaves.

Confederate authorities required officers to remain with their vessels overnight. Over time, however, the Planter’s captain Charles J. Relyea and his white colleagues became complacent, occasionally leaving the vessel in the care of her enslaved crew. On one such occasion, Relyea left behind a straw hat he typically wore when out on the water. Trying it on, Smalls realized that by disguising himself as the captain, he might, with the help of his fellow slaves, be able to commandeer the Planter and sail to freedom.

Desperate to save his family from a life of bondage, he brought his plan to Hannah. When she asked what would happen if they were caught stealing the ship, Smalls didn’t mince words. “I shall be shot,” he said. Sharing her husband’s courage, Hannah responded, “It is a risk, dear, but you and I, and our little ones must be free. I will go, where you die, I will die.”

On May 12, 1862, Smalls put his daring plan into motion, knowing he would probably only get one chance. Several days earlier, authorities had announced that Charleston would be placed under martial law at noon on May 13, after which security would be much tighter and escape likely impossible.

Everything depended on perfect timing. Charleston’s harbor was guarded by the powerful guns of Fort Sumter, weapons that could blow the Planter out of the water with ease. If the Planter passed Sumter too early, it would arouse suspicion. If it passed by too late, visibility would be better and Smalls would be unable to keep up his disguise.

As the day wore on and Smalls and his co-conspirators steeled their nerves, the Planter’s white first-mate added a new complication, announcing that he intended to spend the night on the vessel. Hiss uncharacteristic caution may have been a result of the fact that the Planter was carrying a shipment of munitions and heavy artillery, scheduled for delivery to Fort Ripley on the morning of May 13. One of the guns on board the Planter had belonged to Fort Sumter before the war.

With martial law on the horizon, Smalls couldn’t afford to wait. He planned to lock the first-mate in his cabin, or if necessary, kill him. Luckily the first-mate changed his mind and went ashore, sparing Smalls from having to cause a commotion that might have alerted authorities.

Later that evening, the families of the Planter’s enslaved crew arrived at the docks for what seemed to be a routine visit. While Hannah had been involved in the plot since the beginning, the other relatives had been kept in the dark. Smalls now briefed them on the plan, then sent the women back ashore. To avoid arousing suspicion, it was critical that they been seen leaving the Planter. Smalls had arranged for them to hide aboard a different steamer, the Etiwan, further up the Cooper River.

Finally, several hours after midnight, the Planter got under way. Slipping away from the wharf, Smalls turned up river to rendezvous with the Etiwan. Once that was accomplished, he turned towards Charleston Harbor. His goal was the Union blockading fleet, several miles off shore. To reach those ships, the Planter had to pass by multiple Confederate batteries and fortifications bristling with powerful guns. At any point, a close examination would reveal that the vessel had been commandeered by slaves.

With that risk in mind, the escapees came to a decision. If their ruse was discovered, there would be no surrender. If the worst should happen, they vowed to jump overboard holding hands. Either they would live free or they would die free.

Years later, Alfred Gourdine, a shipmate of Smalls during the escape, described the Planter’s nerve-wracking journey to freedom in a newspaper interview. “Once clear of the wharf and headed down the bay, we ran at slow speed, Smalls in the pilot-house and steering by the compass,” he said. “Smalls held her right down channel, flying the Confederate flag as usual.”

After passing a picket boat, Smalls called for more steam. “I could hardly stand,” recalled Gourdine, “and it was the same with all others except Robert Smalls. If he lost his nerve for a single minute no one noticed it. We passed a gunboat at anchor and Smalls saluted her with the whistle. We ran close to a brig with two barges behind her, and he shouted something about the fog to the man in the brig’s pilot house.”

Charleston Defenses 1863

This map of Charleston and its defenses shows a failed Union attack a year after Smalls escaped and gives a good sense of what he was up against. (Library of Congress)

The greatest danger came from Fort Sumter “We feared that our appearance at such an early hour might excite distrust,” Gourdine remembered. “There was danger, too, that a boat might put off to us on some legitimate errand if such a thing happened and we refused to stop, we could count on all the big guns being turned loose on us. When we drew near the fort every man but Robert Smalls felt his knees give way and the women began crying and praying…Smalls kept the steamer right on her course, and when she was opposite the fort he saluted with the whistle, and added an extra toot as a farewell to the Confederacy.”

When the Planter finally got out of range of the Confederate’s guns, the free men and women on board began celebrating. “There was more weeping and praying and singing of hallelujah songs,” said Gourdine.

As the Planter approached the Union fleet, Smalls called out a greeting to a shocked Union captain. “Good morning, sir!” he said. “I’ve brought you some of the hold United States guns, sir!—that were for Fort Sumter, sir!”

Robert Smalls

Robert Smalls and the Planter. (Library of Congress)

Robert Smalls’s life story is incredible. Fictional and legendary heroes pale in comparison. Odysseus? Batman? Luke Skywalker? Frodo Baggins? Robin Hood? Compared to Smalls, those guys are boring wimps. Truth isn’t just stranger than fiction, it’s also cooler.

I’ll return to the further exploits of Smalls another time. His adventures did not end with his escape. Over the next few years he used his skills to serve the Union cause. After the war he became one of the first African Americans to serve in the United States Congress.

-P. Sicher

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