Sailing to Freedom: The Story of Robert Smalls — Historic America (2024)

When one thinks of the Civil War in Charleston, South Carolina, the mind immediately goes to Fort Sumter where on April 12, 1861 Confederate forces fired the first shots of what became the bloodiest war in American history.

However, just over a year after the war began, Charleston was also the site of an extraordinary act of courage on the part of an enslaved man named Robert Smalls. Many have never heard the story his remarkable story.

Robert Smalls was born on April 5, 1839 into the institution of slavery in Beaufort, South Carolina, located just south of Charleston on the coastal Sea Islands. His mother was an enslaved woman, Lydia Polite. While it is not known who Smalls’ father was, it is believed that his father could have been the man who owned his mother, Henry McKee. Lydia wanted her son to fully understand the brutality and horror of the institution into which he had been born. She had grown up working the fields of South Carolina and had been ripped from her family on the Sea Islands at the age of nine years old. Smalls grew up viewing the constant beatings and whippings of his fellow enslaved people as his mother arranged for him to work in the fields during his youth. Smalls’ great grandchild, Henry Boulware Moore, would later write that “the result of this lesson led Robert to defiance” as the young man would frequently find himself in the local jail.

Slavery was deeply entrenched into the fabric of Charleston as was rebellion against it. Charleston was the port of entry for a third of all enslaved people brought across the Atlantic Ocean in bondage. Just over a decade before Smalls’ birth, Charleston had also been the site of a failed slave uprising planned by free Black preacher and carpenter, Denmark Vesey, in 1822. Born into slavery, Vesey was able to buy his freedom when he was around 32 years old. In June 1822, a month before the revolt was scheduled to take place, Vesey was accused of planning the uprising when one of his co-conspirators gave him up to authorities. On July 2, 1822, Denmark Vesey was executed alongside 34 of his co-conspirators.

The quelling of Vesey’s planned uprising lead to the passage of the first Negro Seamen Acts. South Carolina’s white, slave-owning ruling class feared the implications of Vesey’s failed revolt against their hierarchy and social order. As a result, South Carolina’s legislature passed laws to restrict contact between free Black people and enslaved people as well as to restrict the movement of free Blacks. Among these was the Seamen’s Act of 1822 which required free Black sailors on ships docked in Charleston’s harbor to be imprisoned during the time their ship remained in the city.

This was the background against which Robert Smalls arrived in Charleston’s harbor. Fearing for her son’s safety, Lydia persuaded the McKee family to allow Smalls to work in the port city as a laborer. It was here, at the age of 17, that Smalls met his wife Hannah Jones, an enslaved woman who worked as a local hotel maid. They were married in December 1856 and would go on to have two children together. Smalls attempted to buy his family’s freedom, but could not afford the steep cost. The young couple were all too aware of the fact that their family could be broken up at any time, just as Smalls’ mother’s family had been. The possibility of family separation hung over so many enslaved people, including Smalls because, once separated, enslaved families would likely never see each other ever again. The fact would haunt Smalls for years to come. He knew the only way to guarantee his family’s security was to escape.

Escape from slavery was more easily said than done. It is difficult to comprehend the sheer magnitude of such a task considering that the majority of enslaved people were illiterate, impoverished, and suspected by law enforcement. Despite the well known stories of successful escapees such as Frederick Douglass or Harriet Tubman, the overwhelming majority of enslaved people who attempted to escape were caught. Smalls was well aware of the risks associated with attempted escape, let alone the risks that came with attempting to escape as an entire family unit. Despite this, the dream of freedom would occupy his thoughts for years to come.

By the time the Civil War began Robert Smalls was 22 years old and an experienced Charleston dock worker. He knew Charleston Harbor like the back of his hand. As a result, he was assigned to the Confederate military cargo transport vessel known as the Planter as a member of its enslaved crew. Smalls was one of the thousands of enslaved Black men that were forced to provide support for the Confederate war effort. Despite the fact that Smalls had a reputation as one of the best maritime pilots in the area, his color and enslaved status prohibited him from holding any rank. During his time on the Planter, Smalls was part of a ten man crew that included three white officers: Captain Charles J. Relyea, First Mate Samuel Smith Handco*ck, and engineer Samuel Z. Pitcher. The other six crew members, including Smalls, were enslaved men; they consisted of engineers John Small and Alfred Gourdine as well as deckhands David Jones, Jack Gibbes, Gabriel Turner and Abraham Jackson.

The officers of the Planter would often leave the ship in the care of its enslaved crew members whenever they docked in Charleston so that they could see their families. While it is possible that Captain Relyea trusted Smalls and the other enslaved crew members, it is far more probable that as a Confederate officer, he believed that enslaved Black men lacked the ability to commandeer the vessel without the guidance and supervision of the white officers.

It was 1862 - a year since the war had begun in the very same harbor in which the Planter was docked. Since that time, President Abraham Lincoln had ordered a blockade of all major Southern ports by the Union navy. Having served on the Planter for the past year, Smalls knew that Union vessels stood outside the mouth of Charleston Harbor. It was his plan to commandeer the Planter and deliver it into the hands of the Union blockade, thereby delivering his family from bondage. The plan was incredibly dangerous: Smalls would have to steer the vessel through the heavily guarded harbor and avoid arousing the suspicion of Confederate forces stationed throughout the area. Furthermore, since the Planter was a Confederate vessel, Smalls faced the additional risk that the Union blockade ships would likely view his ship as a threat and fire upon it. However, when Smalls told his wife Hannah about the idea she responded:

In the dark, early morning of May 13, 1862 - the now 23-year-old Robert Smalls put his plan into action. The white officers had left the Planter for the night. At 2:00 a.m., Smalls put on Captain Relyea’s straw hat. His resemblance to the captain was strong, and Smalls intended to use this to his full advantage. Around the same time, the crew hoisted both the flag of South Carolina and the Confederate battle flag to further the illusion that the ship’s Confederate officers were moving the vessel. Soon after, the Planter eased out of the dock. Stationed less than a hundred yards away, Confederate guards did not suspect a thing, fully believing that the ship was being steered by its Confederate captain.

At around 3:25 a.m., Smalls and his crewmates neared the North Atlantic Wharf where Smalls’ family members were waiting. They hurriedly boarded the vessel. At 4:15 a.m., the ship approached Fort Sumter and its rebel garrison. While the Planter’s fugitive crew and passengers sat fearfully, Smalls remained calm by pulling the ship’s whistle - his experience aboard ship had taught Smalls the correct navy signals to use when passing Confederate fortifications. He even kept his arms folded in the same manner as Captain Relyea, furthering the deception.

As Smalls piloted the Planter towards the Union blockade - stationed just ten miles outside of Charleston’s harbor - the crew took down the Confederate banner and hoisted a white bed sheet which Hannah had brought with her - an improvised banner of surrender. They were now out of the range of the Confederate guns. The sight of the Confederate steamer startled acting Volunteer Lieutenant J.F. Nichols, commander of the U.S. vessel the Onward. The sun was rising as Nichols and his crew first caught sight of the Planter. Just as they prepared to fire upon the Confederate vessel, the white flag of surrender was spotted. Nichols cried out “Stop, or I will blow you out of the water!” prompting the crew aboard the Planter to maneuver the ship alongside the Onward. Having successfully delivered eight men, five women, and three children - including his own family - Robert Smalls stepped forward and proclaimed to Nichols:

In the aftermath of his brave escape to freedom, Smalls was awarded half the value of the Planter (he had previously saved $800 to buy his wife’s freedom, yet now his entire family was free and richer by $1,500). He went on to meet with President Abraham Lincoln as well as Secretary of War Edwin Stanton and successfully lobbied the federal government to allow Black men to serve in the Union army. Smalls himself took up the role of pilot for another Union vessel, the Crusader. He later became captain of the same ship he used to escape to freedom - the Planter. This made Smalls first Black man to command a United States ship.

Following the Civil War, Smalls purchased the home in which he had been enslaved in his youth and served in both the South Carolina State Assembly and Senate. He went on to serve in the U.S. House of Representatives from 1874 to 1886. While Smalls was witness to slavery as well as emancipation, he also bore witness to the rise of Jim Crow laws in his later years. Unsurprisingly, he stood firm & brave against Jim Crow - just as he had stood upon the deck of the Planter thirty years prior. In an impassioned address to the South Carolina state legislature Smalls said:

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