7 Most Audacious Prisoners Escapes in History

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Smalls Escaped Slavery

Robert Smalls was a slave, and a skilled sailor in May, 1862. The son of a slave mother and a white father, he was only 22 when he planned his daring escape. The Union Blockade had, for some months, been accepting runaway slaves, so Smalls knew he only had to reach the Union ships. He had already decided that he would not be retaken alive, planning to fight and sink the ship if his plan failed.

He served as part of a slave crew on a ship, the C.S.S. Planter, with only a white captain and two white mates. On May 13, 1862, the Captain and two mates were off the ship. Smalls and the other members of the crew sailed the heavily armed cotton steamer out of the Charleston dock, and stopped to pick up waiting family members at a pre-set rendezvous point. Smalls, wearing the Captain’s wide-brimmed hat, navigated the ship out of Charleston Harbor. Smalls’ resemblance to the Captain in build and features had been noted, and likely helped his disguise. The ship crossed Confederate waters, with Smalls giving the correct coded signals at various checkpoints, including Fort Sumter. It was only after the C.S.S. Planter was out of range of rebel guns that forces at Fort Sumter realized that all was not well.

In less than four hours, Smalls and his crew reached the Union Blockade. They raised a white flag of surrender, a bedsheet brought on board by Smalls’ wife. He had brought 17 others, including nine men, five women, and three children with him to freedom. Eight of those were members of the original slave crew. Smalls wife and children were among those he rescued.

As the first Union ship reached the C.S.S. Planter, Smalls stepped forward and said, according to eyewitnesses, “Good morning, sir! I’ve brought you some of the old United States guns, sir!”.

Following their escape, Smalls and his crew received half of the value of the Planter from the U.S. Congress. During the war, Smalls served the Union. Smalls went on, after the war, to purchase his owner’s old home, and to serve in the South Carolina Assembly and Senate, and then in the U.S. House of Representatives.

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  • AnnaDulder
    • Michelle Powell-Smith

      There were so many good ones to choose from–I read this one, but it didn’t make the final cut. My extras could make up a post on their own!

  • Steven Simon

    Very good article.

  • Richard Snell

    That spance they ran across was mined. And they still ran.
    With guards in the towers shooting and being blown up by a mine if they stood on It. They still had the resolve to run.
    This is one of the worst.