Robert Smalls


Robert Smalls escaped slavery posing as the captain of a Confederate ship.

It started on a spring night in Charleston Harbor in 1862.

CSS Planter
CSS Planter

Smalls and six enslaved deckhands waited for their wives, children, and friends to join them aboard the CSS Planter, a Confederate ship they were about to steal.

Smalls and the 15 men, women and children faced either a life of self-determination – if the plan worked – or more violent violations of their humanity – or death – if they failed. But it was worth the risk, they surmised.

 “That was always his fear: that his family would be ripped away from him,” author Cate Lineberry said of Smalls in a CSPAN interview in 2017. Her book, Be Free or Die, details Smalls’ life and his attempt to escape from slavery. “That was really why he was searching so hard for a way to escape, not just for himself but for his family.”

Their chance came May 13, 1862. The haze of the Civil War hung like fog over Charleston Harbor. Smalls planned to lead his 15 shipmates through a harbor of mines, sentry posts and a Confederate army swollen on pride from taking Fort Sumter a year earlier.

Smalls worked aboard the Planter with seven other enslaved deckhands and three white officers, including the captain, first mate, and engineer.

Born in Beaufort, South Carolina in 1839, Smalls was a short, stocky man who couldn’t read or write, but he knew the harbor better than any map. He worked up to the position of wheelman on the Planter after being aboard just a year. Had it not been for his race and enslavement, he would have held the title of pilot. Either way, the position empowered him to learn the harbor, the boat, and the people who worked aboard her. He knew the location of sea mines and the codes and signals to move through the port unencumbered. He would use it in his attempt to escape.

Before the war, the Planter hauled cotton. As hostilities flared, the cargo changed to cannons and ammunition.

The Planter was moored next to a Confederate general’s headquarters the night they planned to take her. She was laden with a shipment of munitions and tended only by the enslaved crew. 

The Planter’s new captain, Charles Relyea, was a short, stocky man who resembled Smalls, a fact Smalls uses in his escape plan. Relyea’s penchant for wide-brim hats and unauthorized shore leave are two other facts Smalls exploits. 

In the hours before night transitions into day, enslaved deckhands scurried about the Planter, lighting boilers, undocking the boat and getting her ready to sail without arousing suspicion. It was the moment of truth. Would wives, children, and friends be at the rendezvous point on time? Would the captain or one of the other officers return early?

 Moreover, could a crew of enslaved deckhands, their wives and children in tow, fool the Confederate navy into letting them escape into the Atlantic Ocean? Laws preventing enslaved black people from gathering without a white person present were enacted to stop excursions like what was about to happen. Surely the absence of a white officer aboard the ship would arouse suspicion and foil the plan. Smalls started the steamer through the harbor at 4 a.m. With all but one deckhand in on the idea (the master had black sentries too), the boat backtracked up the inlet to pick up family and friends.

Daylight just breaking over the horizon, Smalls, short and stocky with a wide-brim hat, did his best impersonation of the captain. Family and friends hid below deck. At any moment he knew one of the garrisons could fire on them, sinking the Planter if not causing her to surrender.

One of the first sentries to see the ship said he thought it was strange her sailing so early. But he didn’t raise the alarm. Challenged at other posts, Smalls gave the right signals and was allowed to pass. But a formidable Fort Sumter stood between the Planter and, 10 miles out in the Atlantic, a Union fleet.

As the Planter approached the fort, Smalls tried to continue his façade even as the rising sun poured daylight on his face. He signaled the garrison and was allowed to pass. But instead of turning its usual route, Smalls headed the ship toward the open sea. By the time the Confederate navy reacted, the Planter, pushing a full head of steam, was out of gun range, but not out of danger. When they reached the Union fleet, one of the ships had guns trained on the Planter, awaiting orders to fire. But the captain held off when he noticed a white beds sheet had replaced the Planter’s confederate battle flag. 

“Good morning, sir. I have brought you some of the old United States’ guns, sir,” Small told a Union captain as he surrendered the cargo of artillery.

The escape is considered one of the greatest in American slave history. That a 23-year-old illiterate deckhand took a 147-foot steamer under the nose of the rebel army and sailed it to freedom through Charleston harbor amazed the world and embarrassed the South.

Smalls went from enslaved deckhand to a celebrated war hero and abolitionist. He was the first African American to captain a ship under Union control. During Reconstruction, he served five terms in the U.S. Congress until a bribery scandal forced him out.

“When I look at this man, I see someone who had incredible courage and perseverance,” Lineberry said. “When I see him – when I look at him, I see a father. He was very concerned that his children have a better life.”

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