Straw Hat to Freedom: Robert Smalls and the Commandeering of the CSS Planter

Posted on June 23, 2015 Updated on May 13, 2019

By Ken Zurski

The guards on lookout at Fort Sumter had little to worry about on the morning of May 13, 1862. The sun was just coming up, and a ship moving through Charleston Harbor at that early hour, likely on orders, was not an unusual sight. They knew the CSS Planter well. There was no alarm. But there was a protocol to follow. The soldiers waited. Then two loud steam blasts came from the ship’s whistle. A closer look at the pilothouse would confirm it. The man at the wheel was a wearing a straw hat. The sentinel boys urged the steamer on by waving their hats in salute.

“Blow them damn Yankees, to hell,” they shouted as the Planter continued out to sea.

Once safely out of view from the fort, the man in the straw hat ordered the crew to take down the confederate flag. In its stead, a white flag was raised, a signal of surrender. The ship reached the Union blockade just outside the harbor. The crew aboard the blockade ship, Augusta, especially the commanding officer, was skeptical at first. A Rebel steamer heading towards them from enemy waters was suspicious. But the wayward ship offered no resistance. Once on board, they found eight black men on the deck and in the hold, five women and three children. The commanding officer demanded to know their intentions. The man in the straw hat stepped forward. He was also wearing a captain’s uniform. His name was Robert Smalls. “I’m a slave,” he said, “and I want to be free to serve the United States Navy.”

Just days before in cramped room near the boat’s dock, the plot was hatched. One of the Planter’s slave workers mentioned how careless the rebel crew of the ship had become when going ashore on leave. At least one rebel soldier needed to stay behind and guard the ship, but oftentimes the whole lot would abandon the vessel, leaving it unattended, a clear violation of policy. Perhaps they were too trustworthy of their black counterparts. But, as one man suggested, perhaps their carelessness was an opportunity.

Robert Smalls was one of the enslaved workers, and the most skilled. He knew the waters around the harbor well and oftentimes piloted the boat. Plus it was suggested he looked a lot like the captain. That may have been in reference to his diminutive size – or in jest. Regardless, Smalls had a plan.

Smalls was born into slavery in Beaufort, South Carolina in 1839. He was short and stout, perfect for working on the docks. When the war began, Smalls was hired out by his master to work in the shipyards. Smalls eventually studied maps and taught himself enough navigational skills to become a good pilot. He was sent to work on the Planter, a former cotton-bale boat now used to transport supplies to Rebel troops. Smalls would work and his master would get paid. In return, Smalls family could stay with him. But freedom is what Smalls wanted for his family, not a compromise.

When the slave crew members agreed the plan could work, it was just a matter of time. They tucked away provisions in the hold of the ship, alerted others to be ready when called, and waited. In three days an opportunity presented itself. That day was Tuesday, the thirteenth of May.

Most of the white crew on the Planter had gone ashore on leave and the ship was left docked, alone and unguarded. Before sunrise, and still under the cover of darkness, Smalls would gather the men.

Harper’s Weekly’s later described the story:

At length, on Monday evening, the white officers of the vessel went on shore to spend the night, intending to start the following morning for Fort Ripley, and to be absent from the city for some days. The families of the contrabands were notified and came stealthily on board.

Smalls would pilot the ship. His figure would be seen first by the soldiers at the fort, so he put on the captain’s uniform and pulled the straw brimmed hat down over his face.

At about three o’clock the fires were lit under the boilers, and the vessel steamed quietly away down the harbor. The tide was against her, and Fort Sumter was not reached till broad daylight. However, the boat passed directly under its walls, giving the usual signal—two long pulls and a jerk at the whistle-cord—as she passed the sentinel.

Smalls kept his head low below the brim. The fort’s sentinel were familiar with the straw hat. The captain of the Planter always wore it with his uniform. The steamer’s whistle blew and the soldiers waved and cheered the ship onto battle. That was the last time they would see the Planter carrying the colors of the confederate flag.

Once out of range of the rebel guns the white flag was raised, and the Planter steamed directly for the blockading steamer Augusta. Captain Parrott, of the latter vessel, as you may imagine, received them cordially, heard their report, placed Acting-Master Watson, of his ship, in charge of the Planter.

Smalls, a former slave and black man, could only serve as a volunteer in the Union Navy and eventually the Army, but he fought in 17 battles and continued to serve on the Planter, now a federal ship. Smalls never wavered from danger. In one incident, the Union commander had ordered the Planter beached when enemy fire was too strong. But Smalls knew they were doomed if they went ashore. He took the wheel and piloted the boat to safety. That earned him a captain’s distinction.

After the war, Smalls got into politics eventually serving as a U.S. Congressman from South Carolina. He is still celebrated in his hometown of Beaufort and recognized as a hero, just as he was after the daring escape. Among his many admirers was Abraham Lincoln. Upon hearing of the Confederate ship’s confiscation and its contraband, the President sent a telegram to his subordinates in the field to immediately send Smalls to Washington.

At the White House, Lincoln personally thanked him for his bravery.