In the predawn hours of May 13, 1862, darkness cloaked Charleston, South Carolina, as a salty breeze wafted from the marshes across the silent harbor. The gentle lapping of waves against the wooden wharf, occasionally punctuated by a ship’s bell, was the only sound disturbing the quiet. Moored at the wharf, just miles from Fort Sumter—where the Civil War’s opening shots had rung out a year earlier—lay the Confederate sidewheel steamer Planter. A faint trail of smoke curled from the Planter’s smokestack above its pilothouse. On deck stood Robert Smalls, a 23-year-old enslaved man, his heart pounding with the weight of the moment. In the coming hours, he and his young family—his wife, Hannah; their four-year-old daughter, Elizabeth; and their infant son, Robert Jr.—would either seize their freedom or face death. Smalls knew their fate hinged on his courage and the audacity of his plan.
Like countless enslaved people, Smalls lived with the constant dread that his family could be torn apart by sale, never to reunite. Escape was the only way to keep them together, but fleeing as a family was a near-impossible feat. Enslaved families were often separated, living and working apart, and traveling with young children—especially an infant whose cries could betray them to slave patrols—multiplied the risks. Capture meant brutal punishment: whippings, shackles, or sale to distant owners. Now, Smalls’ moment had arrived. With a plan as bold as it was perilous, he signaled the other enslaved crew members aboard. It was time to take the Planter. Smalls aimed to seize the steamer and deliver it to the Union fleet blockading Charleston Harbor, part of President Lincoln’s strategy to choke off Southern ports after Fort Sumter’s fall in April 1861. Charleston, a vital Confederate hub, relied on blockade runners to smuggle war supplies, food, and goods in exchange for cotton and rice bound for Europe. The Union’s blockade, though imperfect due to the harbor’s many channels, intercepted some of these runners, capturing or sinking them.
The journey from the wharf to the Union fleet, roughly ten miles, was fraught with danger. Smalls would need to navigate past heavily armed Confederate fortifications and shore batteries without arousing suspicion. The Planter’s noisy engine and billowing smoke made stealth impossible, so Smalls devised a daring ruse: under cover of darkness, he would impersonate the ship’s captain.
The plan was riddled with risks. The Planter’s three white officers—Captain Charles J. Relyea, First Mate Samuel Smith Hancock, and Engineer Samuel Z. Pitcher—posed an immediate threat, and Smalls’ crew would need to neutralize them. Guards at the wharf could spot the theft. Smalls’ family and others were hiding on another steamer up the Cooper River, forcing the Planter to backtrack—a move likely to draw attention from sentries. If they successfully retrieved everyone, the group of 16 men, women, and children would then face the gauntlet of the fortified harbor. A single misstep could prompt the forts to fire, obliterating the Planter. Even if they cleared the harbor, approaching a Union ship carried its peril: without quickly proving their friendly intent, the Union crew might assume the Confederate steamer was hostile and open fire.
Smalls, a trusted member of the Planter’s enslaved crew, had earned a reputation as a skilled pilot, though the Confederates denied him the title. The crew of ten included the three white officers and six other enslaved men—engineers John Small and Alfred Gourdine, and deckhands David Jones, Jack Gibbes, Gabriel Turner, and Abraham Jackson. Relyea, the captain, occasionally left the ship in the crew’s care overnight, a violation of Confederate orders requiring officers to remain aboard. This lapse, likely rooted in Relyea’s underestimation of the enslaved crew’s capabilities, was the linchpin of Smalls’ plan.
When Smalls shared his plan with Hannah, she asked what would happen if he were caught. “I shall be shot,” he replied candidly. The men faced near-certain death, while the women and children risked severe punishment or sale. Hannah, resolute, declared, “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.” Convincing the crew was another gamble. Discussing escape in Confederate Charleston was dangerous, but Smalls had no choice. In late April or early May, the crew met secretly and weighed the stakes. Staying meant a life of enslavement, especially if the Confederacy won the war. The allure of freedom proved stronger than fear, and all agreed to join Smalls.
As the moment arrived, Smalls gave the order to depart. The crew raised the Confederate “Stars and Bars” flag and South Carolina’s palmetto flag to maintain the ruse. A Confederate guard 50 yards away watched the Planter pull away but assumed the officers were aboard and raised no alarm. A police detective made the same assumption. Luck held. The Planter steamed to the North Atlantic Wharf to retrieve Smalls’ family and the others. The pickup went smoothly, with the ship gliding into place without incident. With 16 aboard, the women and children hidden below deck, the Planter turned south toward Fort Johnson, leaving Charleston and slavery behind.
At around 4:15 a.m., the steamer approached Fort Sumter’s towering walls. Fear gripped the crew, with some trembling and others praying, but Smalls remained composed. Wearing Relyea’s straw hat, he pulled the whistle cord, signaling the Confederate pass code—two long blows and a short one. A sentry shouted, “Blow the d—d Yankees to hell, or bring one of them in!” Smalls, staying in character, replied, “Aye, aye.” The Planter pressed on, smoke and steam rising as it churned toward the Union fleet. The crew lowered the Confederate flags and raised a white bed sheet to signal surrender. A sudden fog obscured their makeshift flag, heightening the risk that the Union ship Onward, a 174-foot clipper, would mistake them for a hostile vessel.
As the Planter closed in, the Onward’s crew spotted the white flag. Captain John Frederick Nickels hailed the steamer, demanding its name and intent. Smalls’ crew responded, but in their relief or nerves, they missed Nickels’ order to come alongside and began circling the stern. Nickels shouted, “Stop, or I will blow you out of the water!” The warning snapped them to attention, and they maneuvered alongside. Aboard the Planter, jubilation erupted. Some crew members danced and shouted, others cursed Fort Sumter, now fading in the distance. All 16 were free. Smalls addressed Nickels triumphantly: “Good morning, sir! I’ve brought you some of the old United States guns, sir!—that were for Fort Sumter, sir!”