Robert Smalls

Based on Wikipedia: Robert Smalls

The Man Who Stole a Confederate Warship and Sailed It to Freedom

At three o'clock in the morning on May 13, 1862, a twenty-three-year-old enslaved man named Robert Smalls put on the captain's coat and straw hat, took the wheel of a Confederate military transport ship, and sailed it straight past five rebel forts—giving the correct secret signals at each checkpoint—before delivering the vessel, its cargo of artillery, and sixteen enslaved people to the United States Navy.

It was one of the most audacious escapes in American history.

But what makes the story truly remarkable isn't just the daring theft. It's what came before and after. Smalls would go on to personally persuade President Abraham Lincoln to allow Black soldiers to fight for the Union, serve in seventeen major battles, become a ship captain, win election to Congress, and author legislation creating America's first free public school system.

He did all of this before the age of forty.

A Mother's Terrible Gift

Robert Smalls was born on April 5, 1839, in Beaufort, South Carolina, in a small cabin behind the house of Henry McKee, the man who enslaved his mother Lydia Polite. Beaufort sits in the heart of South Carolina's Lowcountry, a region of barrier islands, tidal marshes, and winding rivers where the Gullah culture—a distinctive African-American heritage with its own language, traditions, and deep connection to the sea—shaped daily life.

From the beginning, something set young Robert apart. McKee favored him over the other enslaved people on the property. He was given easier work and better treatment. His mother was allowed to work as a house servant rather than in the brutal cotton fields.

This worried Lydia Polite deeply.

She understood something about human psychology that many parents struggle to grasp: comfort can be a kind of blindness. She feared her son would grow up not understanding the true horror of slavery, that he would become complacent, even grateful for his chains simply because they were lighter than someone else's.

So she made an extraordinary request. She asked McKee to send her young son to work in the fields. She asked that he be made to witness whippings.

It was a terrible gift. She wanted her child to suffer just enough to understand what slavery really was—and to want something better.

Learning the Waters

When Smalls was twelve years old, his mother arranged for him to be hired out to work in Charleston, South Carolina's largest city and one of the busiest ports in the South. This was a common practice: enslaved people could be "rented" to employers who would pay their owners a weekly fee. Smalls earned sixteen dollars a week for his master, of which he was allowed to keep exactly one dollar for himself.

He started at a hotel, then became a lamplighter—one of those workers who walked the city streets at dusk with a long pole, lighting the gas lamps that illuminated the cobblestone roads. But it was the harbor that captured his heart.

Charleston Harbor was one of the great maritime crossroads of the Americas. Ships arrived from Europe, the Caribbean, and ports up and down the Atlantic coast. The waterfront was a chaos of activity: merchants shouting, stevedores hauling cargo, sailors speaking a dozen languages. For a young man who had grown up in the relatively isolated world of a Beaufort plantation, it must have seemed like the entire world had opened up before him.

Smalls worked his way through nearly every job the harbor had to offer. He started as a longshoreman, loading and unloading the endless stream of ships. He learned to rig sails—the complex art of setting up the ropes and pulleys that controlled a ship's canvas. He became a sailmaker, understanding how those great sheets of fabric were constructed and repaired.

Most importantly, he learned to pilot vessels through the harbor's treacherous waters.

Charleston Harbor is not a simple bay. It's a complex system of channels, sandbars, and shifting currents where the Ashley and Cooper Rivers meet the Atlantic Ocean. Islands dot the water. Forts guard the entrances. The depth changes with the tides. A pilot needed to know every inch of it—which channels were deep enough for which ships, where the currents ran strongest, how the wind behaved differently near Morris Island than it did near Sullivan's Island.

Smalls became what was called a "wheelman," essentially a helmsman who steered the ship. Enslaved people weren't permitted the official title of pilot, but Smalls was doing the same job. He could navigate the harbor in darkness, in fog, in storms. He knew the location of every fort, every battery, every defensive position.

He was gathering intelligence that would one day help him steal a warship.

Love and the Price of Freedom

On Christmas Eve, 1856, seventeen-year-old Robert Smalls married Hannah Jones, an enslaved woman who worked as a hotel maid. She was five years older than him and already had two daughters from a previous relationship. Their own first child, Elizabeth Lydia, was born in February 1858. A son, Robert Jr., followed but died at age two.

Marriage among enslaved people existed in a strange legal twilight. Southern states didn't recognize these unions as legally binding—enslaved people were property, after all, and property couldn't enter into contracts. But the social reality was different. Enslaved communities developed their own wedding traditions, their own understandings of commitment and family. Masters often permitted and even encouraged these unions because stable families were less likely to attempt escape.

Smalls loved his wife and wanted desperately to free her. Under certain circumstances, it was possible for an enslaved person to purchase the freedom of family members. Smalls learned the price: eight hundred dollars.

That's roughly twenty-eight thousand dollars in today's money. And remember, Smalls was allowed to keep only one dollar a week from his labor. Even if he saved every penny, it would take him fifteen years to accumulate that sum—and that assumed prices wouldn't rise, that he could maintain his health, that nothing would go wrong.

He had managed to save one hundred dollars. Seven hundred more to go.

Then, in April 1861, everything changed.

The War Arrives

The American Civil War began in Charleston Harbor itself, with Confederate forces bombarding the federal garrison at Fort Sumter. Smalls would have heard the cannons from his position in the city. He would have seen the smoke rising from the island fortress. The war that would eventually free four million enslaved people had begun in his own backyard.

Within months, Smalls was assigned to pilot the CSS Planter, a Confederate military transport ship. The name "CSS" stands for Confederate States Ship, just as "USS" denotes United States Ship. The Planter was lightly armed—it wasn't a warship in the traditional sense—but it was essential to Confederate operations. Its job was to survey waterways, deliver supplies and troops, and most significantly, help lay underwater mines throughout the harbor.

These mines were called "torpedoes" at the time, a term that would later shift to mean the self-propelled underwater missiles we know today. In the 1860s, a torpedo was simply an underwater explosive device anchored to the seabed or floating just below the surface, waiting for an unsuspecting ship to strike it. Smalls helped position these weapons throughout Charleston's waters.

He was, quite literally, learning where the Confederate defenses were weakest and where they were deadliest.

Meanwhile, the United States Navy had established a blockade around Charleston. The strategy was straightforward: prevent goods from entering or leaving Southern ports, strangling the Confederacy economically. From the deck of the Planter, Smalls could see the Union ships sitting seven miles out in the Atlantic, an entire fleet representing freedom just beyond his reach.

Sometime in April 1862, he began to plan.

The Conspiracy

The Planter carried a crew of nine enslaved men in addition to its three white officers. Smalls approached his fellow crew members one by one, feeling each man out, testing their reactions before revealing anything that could get them all killed.

One crew member he never approached at all. Smalls didn't trust him. This small detail reveals just how calculated the conspiracy was. One wrong word to the wrong person would mean death—not just for Smalls but for everyone involved.

The plan was elegantly simple in concept but terrifyingly complex in execution. The three white officers had developed a habit of sleeping ashore while the enslaved crew remained on the boat. If Smalls could get the boat moving during those night hours, if he could navigate past five Confederate forts using the correct signals, if he could then survive the approach to Union warships that would assume any vessel leaving Charleston was an enemy—then he would be free.

If any single element failed, he would be executed. And not quickly. The punishment for an enslaved person attempting such a spectacular act of rebellion would be designed to send a message.

On May 12, 1862, the opportunity arrived.

The Night of the Escape

The day began with routine military logistics. The Planter traveled ten miles southwest of Charleston to Coles Island, where a Confederate outpost was being dismantled. There, Smalls and the crew loaded four large artillery pieces onto the ship—heavy guns that would need to be transported to fortifications elsewhere in the harbor.

Think about that for a moment. The Confederates were literally loading their own weapons onto the ship that would soon carry them to the enemy.

Back in Charleston that evening, the crew added two hundred pounds of ammunition and twenty cords of firewood to the cargo. The Planter was docked at its usual spot, just below the headquarters of General Roswell Ripley, the Confederate commander of Charleston's defenses.

Then the three white officers did what they always did: they went ashore for the night.

Before leaving, Captain Relyea granted Smalls permission for the crew's families to visit the boat—a privilege that was occasionally allowed. The families arrived, and for the first time, the women and children learned what was about to happen.

They did not take it well.

Hannah Smalls, who had known her husband longed for freedom, was taken aback to learn that an actual plan existed and was about to be executed that very night. But she recovered quickly. "It is a risk, dear," she told him, "but you and I, and our little ones must be free. I will go, for where you die, I will die."

The other women were less composed. They cried. They screamed. The men struggled desperately to quiet them, terrified that the noise would attract attention from Confederate soldiers nearby. Only later, once the shock had worn off, did the women admit they were glad for the chance at freedom.

At some point during the evening, three crew members pretended to escort the families back home. Instead, they circled around and hid everyone aboard another steamer docked at a different wharf. The plan required picking up the families at that location once the Planter was underway.

At three in the morning, Smalls made his move.

Sailing Past the Enemy

Eight enslaved men—Smalls and seven others—fired up the Planter's boilers and cast off from the wharf. Smalls put on Captain Relyea's coat and straw hat. He would need to be visible from shore and from the forts. He would need to look, from a distance, like a white Confederate officer.

The Planter moved through the dark water to the second wharf, where the families waited. Quickly, quietly, they came aboard. The boat now carried sixteen souls: the eight crew members, Smalls's wife Hannah, his two children, and five other women and children.

Now came the dangerous part.

The Planter had to pass five Confederate forts to reach the open ocean where the Union fleet waited. Each fort required the correct steam-whistle signals—a specific pattern of blasts that identified the ship as friendly. One wrong note, one moment's hesitation, and the guns would open fire.

Smalls gave the signals perfectly. Fort after fort let them pass.

The most heavily armed fortification was Fort Sumter itself, the very place where the war had begun. It was manned by suspicious soldiers who took their job seriously. As the Planter approached, everyone aboard felt their knees weaken. The women began crying and praying. Some of the men urged Smalls to give the fort a wide berth, to minimize the time they were under its guns.

Smalls refused. Unusual behavior would arouse suspicion. He kept the ship on its normal path, moving slowly, as though he were simply enjoying the early morning air. He gave no sign of urgency.

When Fort Sumter flashed its challenge signal, Smalls responded with the correct hand signs.

There was a long pause.

Everyone on the Planter waited for the thunder of cannon fire that would end their lives. Smalls later said that in those seconds, he expected to be shredded by grapeshot at any moment.

Then the fort signaled that all was well. The Planter sailed on.

The White Bedsheet

Once past Fort Sumter, Smalls faced a different kind of danger. He was now approaching the Union blockade fleet—warships whose entire purpose was to destroy any vessel attempting to leave Charleston. From the perspective of the Union sailors, the Planter was an enemy ship making a suspicious run in the pre-dawn darkness.

Instead of turning east toward Morris Island, which would have been the normal Confederate course, Smalls steered directly toward the Union fleet. He hauled down the Confederate flags and ran up a white flag of surrender.

Or rather, a white bedsheet. Hannah Smalls had brought it specifically for this moment.

The USS Onward spotted the approaching vessel and prepared to fire. Sailors moved to their battle stations. Gun crews loaded their weapons. In the darkness, the white sheet was almost impossible to see.

Just as the number three port gun was being elevated to fire, someone cried out: "I see something that looks like a white flag!"

The gun crew held their fire. As the sky brightened with the approaching sunrise, they could finally make out the sheet flapping from the Planter's mast. They could also see that no white faces appeared on deck.

Instead, as a Union sailor later recalled, "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."

"Contraband" was the term Union forces used for formerly enslaved people who had escaped to their lines. It had originated as a legal fiction—since the Confederacy claimed that enslaved people were property, Union generals argued they could seize this "contraband of war" without returning it to its owners.

As the Planter pulled alongside the Onward, Robert Smalls stepped forward, removed his hat, and called out: "Good morning, sir! I've brought you some of the old United States guns, sir!"

The Intelligence Windfall

The capture of the Planter was more than a symbolic victory. Smalls had delivered an extraordinary intelligence haul.

In addition to the four large artillery pieces from Coles Island and two hundred pounds of ammunition, the ship carried something far more valuable: the captain's code book containing all of the Confederate signals, and a detailed map showing the location of every underwater mine in Charleston Harbor.

Smalls himself proved even more valuable than the documents. He had spent years piloting vessels throughout the Charleston region. He knew the depth of every channel, the location of every fortification, the strength of every garrison. When Union officers questioned him, they were stunned to learn that their intelligence estimates were wildly wrong. They had believed Charleston was heavily defended. Smalls told them that most Confederate troops had been sent to Tennessee and Virginia. Only a few thousand remained.

Even more actionable: the Confederate fortifications on Coles Island, which Smalls had visited just the day before, were being abandoned. They were completely undefended.

Exactly one week later, on May 20, Union forces captured Coles Island and its string of artillery batteries without firing a shot. The Union would hold this position for the remaining three years of the war, giving them a crucial foothold on Charleston's southern flank.

Flag Officer Samuel Francis Du Pont, commander of the blockading fleet, was so impressed that he wrote to the Navy Secretary in Washington describing Smalls as "superior to any who have come into our lines—intelligent as many of them have been."

Convincing Lincoln

Smalls became an instant celebrity in the North. Newspapers and magazines reported his daring escape. Congress passed a special bill awarding prize money to Smalls and his crew for the captured vessel—fifteen hundred dollars for Smalls alone, equivalent to nearly fifty thousand dollars today. It was far more than the eight hundred dollars he had needed to buy his wife's freedom. Now they were free, and wealthy by the standards of formerly enslaved people.

Meanwhile, in the South, newspapers demanded harsh punishment for the three Confederate officers whose habit of sleeping ashore had allowed the theft. Two were court-martialed and convicted, though the verdicts were later overturned.

But Smalls wasn't content with personal freedom. He wanted to fight.

At this point in the war—May 1862—Black men were not permitted to serve as soldiers in the Union Army. President Lincoln worried that allowing Black troops would push the border states (slave states that had remained in the Union, like Kentucky and Maryland) into secession. Several Union generals had attempted to recruit Black soldiers on their own authority, and Lincoln had countermanded their orders each time.

Smalls believed this was a mistake. He had proven that formerly enslaved people would fight for their freedom. He had proven they possessed courage, intelligence, and military capability. In August 1862, Smalls traveled to Washington, D.C., accompanied by a Methodist minister named Mansfield French, to personally advocate for the enlistment of Black soldiers.

They met with Lincoln and Secretary of War Edwin Stanton. What exactly was said in these meetings has been lost to history, but the result was concrete: shortly afterward, Stanton signed an order permitting up to five thousand African Americans to enlist in the Union forces at Port Royal, South Carolina.

These men were organized into the 1st and 2nd South Carolina Regiments (Colored), among the first Black military units in United States history. Their example would pave the way for the more famous 54th Massachusetts Infantry Regiment, whose assault on Fort Wagner in July 1863 would be immortalized in the film "Glory" more than a century later.

Smalls didn't just advocate for Black soldiers. He served alongside them. By his own account, he was present at seventeen major battles and engagements during the Civil War.

Captain of the Planter

After his escape, Smalls worked as a civilian pilot for the Union Navy. He knew the waters better than anyone, and he knew exactly where the Confederates had placed their underwater mines—because he had helped put them there. Now he helped remove them.

The Planter, after repairs, was pressed into Union service. Smalls eventually returned to pilot his old ship, now flying the Stars and Stripes instead of the Stars and Bars. He also piloted several other vessels, including the ironclad USS Keokuk during an attack on Fort Sumter in April 1863. The Keokuk took ninety-six hits during the engagement and sank the next morning, though Smalls and most of the crew survived.

On December 1, 1863, Smalls was piloting the Planter when Confederate batteries opened fire. The white captain, James Nickerson, panicked and fled the pilothouse, hiding in the coal bunker below decks.

Smalls faced a terrible choice. If he surrendered, the African American crewmen would almost certainly be killed. The Confederacy had announced that Black soldiers and sailors captured in Union service would be treated not as prisoners of war but as slaves in rebellion—subject to execution.

Smalls refused to surrender. He entered the pilothouse, took command, and piloted the Planter to safety under fire.

For this action, General Quincy Adams Gillmore reportedly promoted Smalls to the rank of captain, making him one of the first Black men to command a United States military vessel. He served as captain of the Planter for the remainder of the war.

After the War

When the Civil War ended in 1865, Robert Smalls was twenty-six years old. He returned to Beaufort, South Carolina—the town where he had been born into slavery, where his mother had asked that he witness whippings so he would understand what bondage truly meant.

He bought the house at 511 Prince Street.

It was the house where he had been born. The house behind which stood the cabin where his mother had given birth to him. The house where Henry McKee had once been his master.

McKee had died during the war. His wife, still alive, had lost her mind. When she saw Smalls in what had been her home, she didn't recognize the historical transformation that had occurred. She simply saw a familiar face from before the war and took comfort in his presence. Smalls allowed her to remain in the house until her death, caring for the woman whose family had once owned him.

This detail says something important about Smalls's character. He was capable of both fierce resistance and extraordinary compassion. He had risked his life to destroy the Confederacy, and then he cared for an old Confederate widow because she was a human being who needed help.

Political Career

The period following the Civil War, known as Reconstruction, represented an unprecedented experiment in American democracy. For the first time, African Americans in the South could vote, hold office, and participate fully in political life. Smalls threw himself into this new arena with the same energy he had brought to stealing Confederate warships.

He was elected to the South Carolina state legislature, where he authored legislation establishing the first free and compulsory public school system in the United States. Before this, education had been largely a private matter, available mainly to those who could afford it. Smalls believed that education was essential to making freedom meaningful—that formerly enslaved people needed literacy and learning to fully participate as citizens.

He was a founder of the Republican Party of South Carolina. This requires some historical context: in the 1860s and 1870s, the Republican Party was the party of Lincoln, the party of abolition, the party that had fought to end slavery. The Democratic Party, by contrast, was the party of the Confederacy, of white supremacy, of resistance to Black political power. These party alignments would gradually shift over the following century, but in Smalls's time, a Black Republican was voting his interests.

Smalls won election to the United States House of Representatives, serving five terms between 1875 and 1887. He represented South Carolina's 5th congressional district—and would be the last Republican to hold that seat until 2010, when Mick Mulvaney won election during the Tea Party wave.

That's a gap of 123 years.

The reason for that gap is the violent end of Reconstruction. After federal troops withdrew from the South in 1877, white supremacist groups used terrorism, fraud, and eventually legal mechanisms like poll taxes and literacy tests to strip Black citizens of their voting rights. Smalls himself was the victim of electoral fraud during this period, and he was briefly jailed on trumped-up bribery charges that were later pardoned.

By the 1890s, Black political participation in the South had been essentially eliminated. It would not recover until the Civil Rights Movement of the 1960s.

Final Years

Robert Smalls died on February 23, 1915, at the age of seventy-five. He had lived long enough to see much of what he fought for dismantled. The free Black citizens who had elected him to Congress had been disenfranchised. The schools he had helped create had been segregated. The promise of Reconstruction had given way to Jim Crow.

But he had also lived to see the world transformed in ways he could never have imagined. He had been born into slavery, forbidden to learn to read, valued as property. He had died a free man, a war hero, a former congressman, a homeowner. His children had been born free. His grandchildren would never know what it meant to be owned by another human being.

His grave is in Beaufort, South Carolina, marked by a monument that commemorates his service to the Union and his leadership in peace. The house at 511 Prince Street—the house where he was born a slave, which he later purchased and owned as a free man—is now a National Historic Landmark.

In 2004, the United States Army named a transport vessel after him: the USAV Major General Robert Smalls. It seems fitting. The man who stole a Confederate transport and delivered it to the Union Navy is now memorialized by a ship that bears his name.

What His Story Means

The story of Robert Smalls resists easy categorization. He was not simply a victim of oppression, though he certainly suffered under slavery. He was not simply a hero, though his escape from Charleston Harbor was heroic by any measure. He was not simply a politician, though he served in Congress for over a decade.

He was all of these things, and something more: a man who understood that freedom must be seized, not given.

His mother understood this too. That's why she asked for her son to witness the cruelty of slavery, even though she could have let him live in comparative comfort. She knew that comfortable slaves rarely become free. She knew that understanding the horror of bondage was the first step toward breaking it.

Smalls never forgot that lesson. When he saw the Union fleet from the deck of the Planter, he didn't wait for liberation to come to him. He went to get it, sailing past Confederate guns with his wife and children aboard, betting everything on a white bedsheet and his knowledge of the waters.

And when he was free, he didn't rest. He fought for others to share that freedom. He testified before Lincoln. He served in battle. He wrote laws creating public schools. He ran for office and won, again and again, until violence and fraud finally stopped him.

The arc of his life suggests something important about how change happens. It doesn't come from waiting. It comes from people who refuse to accept that the way things are is the way things must be. People who study the terrain, gather intelligence, build alliances, and move when the moment is right.

Robert Smalls moved at three in the morning on May 13, 1862. By sunrise, he was free. The ripples from that moment are still spreading.