May 13, 2022

Robert Smalls Sails a Stolen Ship to Freedom

Robert Smalls Sails a Stolen Ship to Freedom

May 13,1862. During the American Civil War, a slave steals a Confederate ship and flees with his family to freedom.


Cold Open

It’s the middle of the night on May 13th, 1862. The American Civil War between North and South has been raging for just over a year, and in Charleston Harbor, South Carolina… a small paddle steamer, the Planter, pushes through the low mist coating the water. A wisp of smoke rises from its funnel. A Confederate flag ripples at its mast.

Onboard, a stocky young man named Robert Smalls peers out into the darkness. He wears a captain’s uniform. But he’s not master of this boat. He’s a slave.

Robert has heard that slaves like him can find freedom in the Union-controlled north. So he stole this boat, and he’s driving it out of Confederate territory, with 15 other enslaved passengers and crewmen on board. But first, he has to navigate the steamer out of Charleston Harbor, a heavily fortified rebel naval port.

At that moment, Robert sees a light shining through the darkness from the shore ahead.

He crosses the deck urgently. He opens the door to the pilothouse. And inside, another Black slave mans the wheel. Robert tells him, “We’re coming up on the first fort”.

Robert takes the wheel and control of the boat. Ahead is the first checkpoint. Robert can see a sentry standing on duty in a guard tower. So he slows down.

Robert’s worked as a crewman on this boat since last year. He’s learned the protocols in the harbor. He knows that in order to pass the checkpoint, he needs to send a friendly signal to the guard. So he reaches up and pulls on a cord…

Robert waits for the sentry to reply and give him permission to pass. But he is nervous. If he and the other runaway slaves are discovered, there will be no hope for them. The fort’s guns could blow the steamboat apart in an instant.

But Robert hears the sentry’s shout: “Pass the Planter!

Robert breathes a sigh of relief. And as the Planter glides by the fort, the crewman beside Robert in the pilothouse grins nervously. But Robert knows they’re not safe yet. They have to pass four more checkpoints, then an even bigger danger – Fort Sumter, the last and most heavily armed of all the harbor’s defenses.

One mistake, one wrong signal, one sentry looking too closely, and the whole deception could fall apart, and this daring escape to freedom might meet a violent end. 

Robert Smalls will be successful in his escape from slavery, and his bravery and cunning will help show that Black Americans can join the bitter struggle against the Confederacy. Robert’s example will be a rallying cry for others to join the fight for their nation’s future; and his impact will be felt long after his daring escape from Charleston Harbor on May 13th, 1862.


From Noiser and Airship, I’m Lindsay Graham and this is History Daily.

History is made every day. On this podcast—every day—we tell the true stories of the people and events that shaped our world.

Today is May 13th: The Escape of Robert Smalls.

Act One: The Plot

It’s late April 1862, a few weeks before Robert Smalls leads the crew of the Planter north.

It’s night in the city of Charleston. Robert Smalls and his wife Hannah have just put their two young children to bed. They have a four-year-old daughter and a baby boy who’s just one and still nursing.

Hannah finishes a lullaby and tiptoes away from the sleeping children. Sitting at a nearby table, Robert beckons her over to join him. He says there’s something they need to talk about. And when Robert begins, he speaks in a mere whisper. If anyone overhears what Robert is about to say, if anyone learns what he has planned, they all could be whipped, sold off, or even shot because he is planning an escape. 

Robert was born into slavery in 1839. By the time he was 12, his owner was hiring him out as a laborer. He worked as a hotel waiter, a lamplighter on the streets of Charleston, and then as a dockworker, loading and unloading ships. When he got older, he began working on the boats as a sailor.

Most slaves in Robert’s position would see their owner claim all their wages. But Robert was a favorite of his owner, and as a young man, he managed to strike a deal that was unusual in its time. Robert was permitted to live with his wife Hannah, who was also a slave, and their two young children. He was also allowed to keep a dollar of his wages every week. And bit by bit, Robert saved up for the thing he wanted most in the world – his family’s freedom. It would cost him an enormous amount of money, $800, over 20,000 today. But even if it took decades, Robert was determined that his wife and children would not live out their days in slavery.

Then in July 1861, at the age of 22, Robert joined the crew of the steamboat called Planter.The vessel carried cotton and passengers between Charleston and Georgetown 70 miles up the coast. Every week, Robert learned a little more about boating, and every week, he set aside a few cents toward freeing his family.

By the spring of 1862, Robert had saved up around a hundred dollars. But by then, the American Civil War was underway. Charleston was under the control of the southern rebels, the Confederates. The Planter and its crew were leased by the Confederate Navy and put to work moving men, guns, and supplies between the defensive forts scattered around Charleston Harbor. The outbreak of the war meant that Robert is now forced to help the people who wanted to keep him and his family enslaved forever. But this moment of crisis also represents an opportunity.

At first, it was to him a joke. One day, while on board the Planter, one of Robert’s crewmates pointed toward the horizon. Robert looked out over the water and saw a fleet of Union ships that was blockading Charleston harbor. Robert’s crewmate laughed that they should steal their steamboat and sail out to join them. The other crewmen chuckled, but Robert saw the idea’s potential.

Now, a few weeks later, in his tiny apartment, Robert tells his wife Hannah what he’s going to do and how he’s going to do it.

The white officers in command of the Planter are supposed to be on board the steamboat day and night, to be ready to leave at a moment’s notice. But they have family in Charleston so they often break the rules and spend their nights ashore.

Robert’s plan is to wait for an evening when these officers are absent, then sneak Hannah and their children onto the Planter, along with the families of the other crewmen. Robert will pose as the boat’s white captain. The two men are about the same size. And Robert hopes that if he stands on deck wearing the captain’s hat and jacket, nobody glancing at the boat from the shore will notice anything’s wrong. Once they’re clear of the harbor, they’ll raise a white flag and head straight for the Union fleet just off the coast.

Robert knows the plan is risky and certainly dangerous. Still, he feels they have to try. But he won’t do it unless his wife gives him her blessing. Hearing the plan, Hannah is silent for a moment, taken aback by her husband’s daring. Then she says, “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.”

A few weeks later, Robert will put his plan into action. He, his wife, and his children will board the Planter under cover of darkness, sail out of Charleston Harbor, and make a dash for freedom.

Act Two: The Escape

It’s just before dawn on May 13th, 1862.

Water churns through the paddlewheels of the steamboat Planter. In its pilothouse, Robert Smalls shifts nervously and stares out over the waters of Charleston Harbor.

The steamboat and the runaway slaves onboard have already passed four Confederate checkpoints. One last fortification stands between them and freedom, but it’s the one Robert fears the most - Fort Sumter.

The man-made island looms out of the waters in the center of the harbor. It was here that the very first shots of the American Civil War were fired. And as the Planter approaches the massive, cannon-studded walls, Robert can sense the prying eyes of the watching guards.

Just then, one of Robert’s crewmen appears beside him in the pilothouse. He urges Robert to steer a wider course, to keep their distance from the walls. But Robert knows their only hope is to act normal and stay the course. That way the guards won’t suspect that anything is amiss.

So Robert follows normal protocols. He slows the steamboat to a halt and sounds the secret signal that the white officers always use. Two long blasts and a short one. Then he waits for the guards to give him permission to pass the fort.

The young slave folds his arms across his chest, mimicking steamboat’s white captain. He’s wearing the captain’s uniform, as well as a wide straw hat to help conceal his face. But dawn is creeping across the sky now. It’s getting lighter. And Robert knows that if they’re delayed here too long, they’re sure to be discovered.

Below deck, the crew’s families hide in the dark among a cargo of guns and ammunition. Robert’s wife Hannah rocks their infant son in one arm as she strokes the hair of her four-year-old daughter, asleep across her lap. Neither is old enough to really understand what’s going on. And Hannah is glad of it. Looking around, she sees the eyes of the other families shine with fear in the darkness.

Up in the pilothouse, Robert is beginning to wonder what’s taking so long. Perhaps an officer from the fort wants to come on board to hitch a ride or check their cargo. Either would be disastrous.

Robert and the other crewman have already decided they won’t take their families back to slavery. They’ll fight, even if it means death.

But then, there’s movement from the fort. Robert tenses as an armed guard waves at them. But then the man shouts - “Pass!” Robert breathes a sigh of relief and quickly gets underway.

As the steamboat passes beneath the fort’s high walls, the guard gives a cheerful shout: “Blow the damned Yankees to hell or bring one of them in!” Robert’s mouth is dry, but he manages to bellow back across the water: “Aye, aye!”

And then they push into the open ocean.

Still, it’s no time for celebration, not yet. Now, they must find and make it to the Union fleet. Once the Planter is beyond the range of Fort Sumter’s guns, the crewmen eagerly haul down the Confederate flag. In its place, they hoist up a grubby bedsheet – an improvised white flag of surrender.

But as the sun rises, fog rolls in all around them. Robert looks up at the mast. He can barely make out the sheet in the thickening mist.

Ahead, Robert sees the masts of the Union fleet tower like great trees lingering above the fog. If the lookouts on the Union ships miss the Planter’s white flag, they may think a Confederate attack is underway and blow the steamboat out of the water. But Robert has no choice. Turning back is not an option. So he heads straight for the nearest ship.

The minutes crawl by as the Planter splashes noisily toward the Union fleet. The closer they get, the more nervous Robert becomes. All he can do is pray they’ve seen the flag of surrender. And as they close in, the nearest Union ship veers around, presenting a broadside bristling with guns. As Robert braces, he hears a friendly shout from the Union sailors who’ve spotted his white flag.

They are within hailing distance, so Robert shouts out who they are. They’re told to pull alongside. Soon, the commander of the Union ship comes on board the Planter. Robert steps away from the pilothouse, pulling off his straw hat disguise, he declares: “Good morning, sir! I’ve brought you some of the old United States guns!”

Robert’s wife Hannah, their two children, and all the crewmen’s families emerge from below deck. They join their husbands and fathers in dancing and cheering on deck as the white flag, that dirty bedsheet, is pulled down and the Union Stars and Stripes rises on the mast. For the first time in their lives, Robert, Hannah, and the rest of the enslaved persons on the Planter are free.

Their daring escape from Charleston will be national news, causing elation in the north and recriminations in the south. It won’t just make a hero out of Robert Smalls, however, it will also change the course of the American Civil War.

Act Three: The Hero

It’s April 14th, 1865. Almost three years have passed since Robert Smalls escaped slavery and he is back in Charleston Harbor, on the deck of the Planteronce again.

But this time Robert isn’t hiding anything. He is not anxious and there is no disguise.

A special ceremony is taking place today. The Stars and Stripes, the flag of the Union, is being raised over Fort Sumter after years of occupation by the now-defeated Confederacy. Dignitaries and guests have come from all over the country, gathering to mark the end of the Civil War in the place where it began.

Among the ships given the honor of ferrying guests from Charleston out to the fort is the steamboat Planter and its captain, Robert Smalls.

His escape from Charleston made Robert a hero. And he soon put his newfound fame to good use, encouraging the politicians and generals he met in Washington to allow other Black Americans the chance to show their bravery, to let them enlist in the US Army. That wish was granted in early 1863. Within months, thousands had joined up to help win victory over the Confederate rebels.

By then, Robert Smalls had returned to the Planter as its pilot. He served the Union throughout the rest of the American Civil War, taking part in 17 major battles and engagements. After repeatedly proving his intelligence and bravery under fire, he was finally promoted to the rank of captain. So today, Captain Smalls is in Charleston to celebrate the end of a war that not only brought his freedom but ended slavery in America forever.

Robert Smalls went on to buy the home of his former owner in South Carolina. Later he entered politics, serving as a Congressman for nine years. He died in 1915 at the age of 75. On his tombstones are the words of a speech he gave. It reads, “My race needs no special defense, for the past history of them in this country proves them to be the equal of any people anywhere. All they need is an equal chance in the battle of life.”

Robert Smalls showed true and rare bravery in the battle of his own life; And with it, he freed his family and many others from slavery when he piloted the steamboat Planter out of Charleston Bay on May 13th, 1862.


Next on History Daily.May 16th, 1975 Junko Tabei, a Japanese mountaineer, author, and teacher, becomes the first woman to reach the summit of Mount Everest.

From Noiser and Airship, this is History Daily, hosted, edited, and executive produced by me, Lindsay Graham.

Audio editing and sound design by Mollie Baack. 

Music by Lindsay Graham.

This episode is written and researched by William Simpson.

Executive Producers are Steven Walters for Airship and Pascal Hughes for Noiser.