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Positively Speaking: Robert Smalls


By Toby Moore

For Capital Region Independent Media

Toby Moore

Robert Smalls was born into slavery in South Carolina in 1839.

From a young age, the plantation sent him away to work in Charleston, eventually finding work on the docks of Charleston Harbor. Despite the grueling work and long hours, Robert was determined to rise above his circumstances.

Years passed as Robert worked tirelessly to gain the respect and trust of those around him, but Robert’s ambition went beyond just climbing the ranks on the docks. He had a dream, a burning desire to be free.

In 1856, Robert fell in love and married. With his new wife by his side, his dream of finding freedom for himself and his family became an obsession.

When the Civil War broke out, the Union sent several warships to blockade the harbor; and Robert saw an opportunity. He secured work as a deckhand on a Confederate steamship that traveled between ports and laid mines in the heavily fortified harbor. Robert learned everything he could about the ship, gaining the trust of his officers and waiting for the perfect moment.

That moment arrived in 1862 when Robert devised a daring plan to seize control of the ship and escape. All this time, Robert had been playing the role of a dutiful slave, lulling the Confederate officers into a false sense of security. One night, he convinced the officers that the ship was safe with him and that they could leave for the evening. They did, which gave Robert complete command.

Immediately he sent word to his and the crew’s families to rendezvous at the ship before dawn.

As Robert’s wife boarded the ship, his heart raced as he braced for her reaction. It was the first time she’d heard of his plan.

She stood in shock, overwhelmed by the danger of their situation.

A tense silence hung between them as Robert waited for her final decision. He could not imagine leaving without her, and he would not.

With a determined look, she finally spoke the words that would seal their fate: “I will go with you; wherever you will die, I will die.”

With their families on board, Robert dressed as a captain so as not to arouse the suspicion of the Confederacy. Carefully, they made their way out of the harbor and encountered five different checkpoints, each potentially threatening their escape. Using his knowledge of the secret Confederate Codebook, Robert hand-signaled the first four checkpoints correctly, but the most dangerous moment of their escape was yet to come.

As they approached Fort Sumter, Robert’s nerves were on edge. Sumter was the most heavily armed of the Confederate forts. One wrong move and Robert’s ship would be blown to bits. 

One of Robert’s crew later recounted, “When we drew near the fort, every man but Robert Smalls felt his knees giving way, and the women began to cryin’ and prayin’.”

With his straw hat tipped to cover his face, he gave the correct hand signal to the fort, but when no response came, the crew braced for the worst. After an agonizing wait, they were given clearance. Robert set the ship at full speed, straight toward the Union blockade.

Raising a white bedsheet as a flag of surrender, Robert approached the blockade as quickly as possible. They had a problem; the white flag wasn’t visible as the sun was not yet up. The union forces began preparations to destroy Robert’s ship, but just as the cannon was being raised and the fuse almost lit, a Union sailor shouted, “I see something that looks like a white flag!”

When Robert’s family and crew realized the blockade wouldn’t destroy them, they began singing, dancing and praising the heavens for their safe passage. What a sight it must have been!

Robert boldly declared to the commander: “Good morning, Sir! I brought you some of the old United States’ guns!”

With those words, Robert Smalls pulled off one of the most daring escapes in American history.

Robert Smalls so inspired Abraham Lincoln that Lincoln allowed Black people to serve in the military for the first time. Robert went on to serve as a congressman and focused much on African-American civil rights issues.

What would have happened had Robert not followed his dream?

Toby Moore is a columnist, the star of Emmy-nominated “A Separate Peace,” and the CEO of Cubestream Inc.

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