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This paper addresses the accomplishments of the slave Robert Smalls and his absconding with the valuable Confederate steamship, the Planter, from the Charleston, South Carolina harbor in the early morning hours of May 13th, 1862. Smalls went on to become a pilot and eventual captain of ships for the Union contributing substantially to the Civil War effort. After the war, Smalls became a Congressman. Through his contributions, Robert Smalls left an indelible mark on the history of the United States.