Despite being born a slave in the low country of South Carolina, Robert Smalls never learned that there were certain things he just couldn’t do because of his color.

Maybe it was because his owner, John McKee, might also have been his father. The McKee family certainly favored Robert Smalls over the other slave children, so much so that his mother worried he would reach manhood without fully grasping the “peculiarities” of the institution into which he was born. To educate him, she even arranged for him to be sent to the fields to work and to see other slaves at “the whipping post.”

This education only led Robert to further defiance and more than once he found himself in the Beaufort jail. Fearing for her son’s future, his mother asked her master to send Smalls to Charleston to be rented out to work. By the time Smalls turned 19, he was earning one dollar a week (his owner took the rest) and he was receiving another education on the waters of Charleston harbor.

By the second year of the Civil War the Union Navy had set up a blockade and the Confederates were dug in defending Charleston and its coastal waters. The C.S.S. Planter was a first-class coastwise steamer which was used to supply the various blockaded island points. It was heavily armed with a 32-pound pivot gun, a 24-pound howitzer and 200 rounds of ammunition, and Robert Smalls was the “wheelman” on board.

On the afternoon of May 12, the Planter returned to the Charleston docks to resupply. It was due to go out again the next morning, but that evening the white officers on board decided to take a break for the night — either for a party or to visit family — leaving the crew’s eight trusted slave members behind.

At 2:00 a.m. on May 13, Robert Smalls donned the captain’s wide-brimmed straw hat to help to hide his brown face and ordered the Planter’s crew to fire up the boiler and hoist the South Carolina and Confederate flags. Easing out of the dock, in full view of the Confederate headquarters, they paused at the West Atlantic Wharf and picked up Smalls’ wife and children, four other women, three men and another child.

At 3:25 a.m., the Planter picked up steam. From the pilot house, Smalls sounded the ship’s whistle while passing Fort Johnson and at 4:15 a.m. passed Fort Sumter, “as cooly as if General Ripley was on board.” Smalls not only knew all the correct signals to flash; he even folded his arms just so, so that in the shadows he passed convincingly for the Planter’s captain.

“She was supposed to be the guard boat and allowed to pass without interruption,” Confederate Aide-de-Camp F.G. Ravenel explained defensively in a letter to his commander. It was only when the Planter passed out of Fort Sumter’s gun range that the alarm was sounded — the Planter was heading for the Union blockade!

At sunrise, Smalls ordered his crew to strike the Palmetto and Rebel flags and hoist a white bed sheet.  Not seeing the “white” flag, Lt. J. Frederick Nickels of the U.S.S. Onward ordered his sailors to open her ports and prepare to fire. Just as the No. 3 port gun was being elevated, someone cried out, “I see something that looks like a white flag!”

True enough there was something flying on the steamer that might once have been white. The Planter neared the blockade, and the Union sailors scanned its deck and assessed its threat.

When it became apparent that the Union ship would not fire, a rush of black men, women and children spilled out onto her deck – dancing, singing, whistling, jumping…

As the C.S.S. Planter steered under the stern of the U.S.S. Onward, the man piloting the boat stepped forward, took off his hat, and shouted, “Good morning, sir! I’ve brought you some of the old United States guns, sir!”

That man was Robert Smalls, and he and his family and the entire slave crew of the Planter were now free.

Source: Henry Louis Gates “The African Americans”