These five ‘gangsta’ slaves made some of the most daring escapes we’ll never forget

Robert Smalls

At just 23 years old, Smalls captured a ship in the Charleston Harbor and sailed himself and a small group to freedom. Born a slave in Beaufort, South Carolina, Smalls was hired as a rigger in Charleston and eventually a sailor which led to a job as a deckhand on the Confederate supply ship, the Planter, carrying supplies between forts in Charleston Harbor.

Smalls learned how to navigate the Planter and in the predawn hours of May 13, 1862, in the middle of the Civil War, he and a crew of eight men, along with five women, and three children (including Smalls’s wife and two children), “quietly slipped the Planter out of Charleston Harbor” as white officers and crew slept in the town.

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Smalls expertly navigated the ship through five Confederate checkpoints, offering the correct signal to pass each as he went towards the Union blockade. As PBS said of his expedition, “It was daring and dangerous, and if caught, the crew was prepared to blow up the vessel”.

But Smalls was strategic. When he reached the Union Blockade, he quickly changed the Confederate flag and raised a white bed sheet, signaling surrender. Praised in the north for his courage, Smalls later helped recruit African Americans to serve in the Union Army and would end up as one of the first Black Americans to serve in the United States Congress.