The steamship slowly drifted across the harbour, as quietly as the paddlewheels slapping against the water and the chugging and grinding of the engine allowed. A fog helped to hide them, and those on board knew it was imperative to stay inconspicuous. They were on a secret and dangerous journey that dark May night, one that could change their lives – or end them. While there were no officers, a man in the captain’s coat and hat stood on the deck. His name was Robert Smalls, and on this stolen ship he intended to sail himself and everyone below decks to freedom from slavery.


Smalls had been born into slavery 23 years earlier, on 5 April 1839, to a domestic named Lydia Polite in Beaufort, South Carolina. He actually had it easier, relatively, than the other enslaved children – possibly since his master, Henry McKee, may have been his father – but his mother wanted him to understand the horrors faced by black people in the United States. Her harsh lessons included putting him to work in the fields and forcing him to witness a whipping.

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The man planning to commandeer a 150-feet sidewheel steamship, the CSS Planter, was shaped by these experiences. He was also one of the best pilots in the harbour, who knew the waters so well that he could navigate the sandbars and shallows even in the dark. This would be handy as his escape would be in the early hours. While his white officers had refused to call him a pilot, instead using the term ‘wheelman’ for a slave, Smalls was plotting to be the captain on his own voyage. He would be escaping Charleston.

Family commitments

Smalls had been 12 when his master first sent him to the town. Over the years, he worked a number of jobs, from waiter at a fancy hotel to a rigger and stevedore, before being enlisted on the crew of the Planter. Smalls enjoyed being near the water and, what’s more, he was allowed to keep around $1 a week. Showing some entrepreneurial spirit, he also sold fruit, candy and tobacco on the docks, and managed to save $100. He had hoped to use it to buy his freedom.

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Instead, all hopes laid in escaping on the Planter on the night of 12/13 May 1862. It began when the three officers went ashore – despite going against regulations, they did this often – leaving the slave crew alone. Smalls had been waiting for this moment and told the others to be ready. Only two didn’t stay with him. They got the boiler started, but before steaming for open water the ship had to make a pre-arranged rendezvous, which required heading as slowly and quietly as possible in the other direction. There, they would pick up their families, including Smalls’ wife and children.

It was in Charleston that he had married another enslaved person named Hannah and had a daughter, Elizabeth. While permitted to live together, there was a constant fear that any one of them could be sold at any moment and they would be separated. Smalls approached Hannah’s master Samuel Kingman to buy his wife and child himself. The price was $800, and the birth of their second child, Robert Jr, would only make it more expensive. Hannah agreed with Smalls that their best chance of staying together was to escape, declaring, “I will go, for where you die, I will die.”

Close encounters

With a total of 16 enslaved men, women and children on board, the Planter turned around and started the most dangerous leg of its journey. If captured, everyone faced severe punishment, if not death, as runaways. The noise and smoke of the engine negated any chance of getting through Charleston Harbor without being spotted, so Smalls knew the ship had to appear as if on a routine patrol. That meant passing four military checkpoints, plus armed gun batteries on the shore, all capable of blowing the Planter out of the water.

He dressed in the captain's coat and straw hat, and even mimicked his walk so that he could look the part

The reason for this weaponry was that the American Civil War had been raging for 13 months, with Charleston a crucial port for the South. The North had imposed a naval blockade of the whole Confederate coastline, however, so Union ships were anchored just a few miles away. Smalls knew this, since the Planter had become an armed dispatch vessel to carry munitions for the army. At the time of his escape, it had four cannons and 200 pounds of ammunition in its stores.

Smalls therefore aimed to escape from slavery, taking others with him, in the middle of a war and in a ship that he could hand over to the enemy. He had spent the last year learning all he could of how the Planter functioned and what signals he needed for the checkpoints. On the night, he dressed in the captain’s coat and straw hat and even mimicked his walk so that he could stand on deck and, from a distance, look the part.

The Planter passed three checkpoints – Castle Pinckney, Fort Ripley and Fort Johnson – without incident, but the last checkpoint was Fort Sumter: an intimidating fortress on an artificial island with high walls and plenty of firepower.

Castle Pinckney, Smalls' first checkpoint (Photo by Buyenlarge/Getty Images)
Castle Pinckney, Smalls' first checkpoint (Picture by Buyenlarge/Getty Images)

The rest of the crew wanted to take a wide arc around; Smalls argued this would be more suspicious and sailed right towards it. At around 4.15am, he gave the signal and, a few moments later, received the all-clear. As they sailed on by, he gave a burst of the ship’s whistle as a “farewell to the Confederacy”.

There was one last danger. The Union blockade could fire on the Planter, an enemy ship, especially if flying the Confederate flag. Smalls had overlooked this. It was hastily lowered and replaced by a white flag made of bedsheets. The Planter then approached the USS Onward and, after a few tense minutes, Smalls was able to explain what was happening to the amazement of the Union sailors. As the other slaves appeared on deck and started celebrating, he turned over the ship with the words, “I am delivering this war material including these cannons and I think Uncle Abraham Lincoln can put them to good use.”

Fort Sumpter, Smalls' final checkpoint (Photo by Heritage Art/Heritage Images via Getty Images)
Fort Sumpter, Smalls' final checkpoint (Picture by Heritage Art/Heritage Images via Getty Images)

Liberation at last

Smalls had delivered more than a ship: he had brought himself, his family and a dozen others from slavery. Newspapers and magazines spread the news of his escape in the North, where he was hailed as a war hero. For capturing the Planter, Smalls received a reward of $1,500. Such was his fame that he met with President Lincoln and may well have inspired the decision to let black soldiers join the Union Army. In the South, a bounty was put on his head.

Smalls’ efforts to escape the Confederate South on board the CSS Planter attracted widespread press coverage across the North (Picture by Getty)
Smalls’ efforts to escape the Confederate South on board the CSS Planter attracted widespread press coverage across the North (Picture by Getty)

This was not the end of Smalls’ story, but the beginning of his life as a freeman. And the first thing he did was to join the Union fight. He served in numerous naval engagements, including when he piloted an ironclad (an armourplated warship) and helped remove the mines that he had been made to lay for the Confederates. Ultimately, Smalls distinguished himself enough to be given, fittingly enough, command of the now-USS Planter, making him the first black captain of a ship in US service.

At the end of the Civil War, he chose not to build his new life in the North. Instead, he returned to South Carolina, where he had been enslaved. Learning to read and write, he became a prominent businessman, set up a store for freed people, established a school for black children, and started a newspaper. He also ended his military career with the rank of major-general in the state militia.

Black soldiers of the American Civil War

Freemen and runaway slaves not only fought for the Union – they fought prejudice within the Union, too

When President Abraham Lincoln issued the Emancipation Proclamation on 1 January 1863, it not only freed more than 3 million slaves in the Confederate South, but it also allowed black men to fight for the North by enlisting in the Union Army. By the end of the war, around 180,000 had joined the army and another 20,000 had joined the navy, forming around one-tenth of Union forces.

Those in the army served in segregated regiments, the United States Colored Troops, and while there were certainly tales of extraordinary bravery in battle – such as the 54th Massachusetts Volunteer Infantry at Fort Wagner – they tended not to be trusted by white officers to be fighting men. There was also the greater risk they faced if captured by the Confederates, as they could be put into slavery or at least treated far worse than their white comrades.

Until an act of Congress in June 1864, black soldiers did not receive equal pay for their service to the Union: they got $10 a month (minus $3 for their uniform) compared to the $13 for white troops. This was a hardship familiar to Robert Smalls, as he was denied a military pension of $30 per month until 1897.

Continuing the fight

The Reconstruction period after the war opened the door to the political arena to black men for the first time, and Smalls was among the first to walk through it. From 1868, he served in the South Carolina House of Representatives, before becoming a member of the Senate in 1870. By then, he had already shown his willingness to fight for black rights: when removed from an all-white streetcar in Philadelphia in 1864, he organised a mass boycott that led to integration on public transport within three years. As a politician, he helped draft a new state constitution, founded the Republican Party of South Carolina, and campaigned for social services and education.

In 1874, Smalls was elected to the US House of Representatives, and served a number of non-consecutive terms. But the promise of Reconstruction that black people could find a place in the US as citizens able to vote – encapsulated in the 14th and 15th Amendments – was shortlived. White southerners stripped away black rights, introduced restrictive laws, and launched attacks on black politicians. Smalls faced trumped-up charges of corruption and bribery for which he was sentenced to three years in prison, although ultimately pardoned.

Disenfranchisement was all but complete by the end of the 19th century, so it was in one of his last acts before losing his political position that Smalls spoke at the South Carolina constitutional convention of 1895. His words: “My race needs no special defence, 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.”

That optimism never deserted him, nor his kindness. What better proof of that than the house in Beaufort where Smalls lived out his days until his death in 1915, aged 75. He had bought it shortly after the Civil War, and he would occasionally have an elderly woman suffering from dementia come to the door believing that she lived there. That house had formerly belonged to Henry McKee, his former master, and that woman, who Smalls welcomed in and cared for, was McKee’s wife. The legacy of slavery in the US is deeply painful and traumatic, but, in more ways than one, Smalls managed to escape.


This article first appeared in the September 2022 issue of BBC History Revealed


Jonny Wilkes
Jonny WilkesFreelance writer

Jonny Wilkes is a former staff writer for BBC History Revealed, and he continues to write for both the magazine and HistoryExtra. He has BA in History from the University of York.