In 1862, during the Civil War, a 23-year-old enslaved man named Robert Smalls pulled off one of the boldest escapes in American history.

Smalls worked as a pilot on the Confederate transport ship Planter, which carried guns, supplies, and troops in Charleston Harbor. From his position on deck, he carefully studied the ship’s white officers, memorizing every order they gave and the exact hand signals and whistle codes used to pass through checkpoints. He also helped establish a nightly routine that encouraged the officers to feel comfortable going ashore, which gave him the opening he needed. Smalls understood that the slightest mistake could expose him, but when the moment came, he was ready.

One night in May, when the officers left the ship to sleep ashore, Smalls seized his chance. Dressed in the captain’s hat and long coat, he steered the Planter out of the harbor. At each Confederate fort, he gave the correct signals, bluffing his way past guards who thought they were watching their own officers at work.

Before leaving, Smalls had arranged for his wife, children, and several other enslaved families to wait at a rendezvous point. He stopped to pick them up, then guided the ship toward the Union blockade. As dawn broke, he pulled down the Confederate flag and hoisted a white bedsheet his wife had brought on board.

Sailing straight into Union lines, Smalls delivered not only himself and his family to freedom, but also a ship loaded with artillery and intelligence of immense value. 

His daring act freed twelve people and stunned the nation.

Robert Smalls went on to captain the same ship for the Union Navy, meet President Lincoln, and later serve five terms in the U.S. Congress.