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This paper discusses Robert Smalls’ daring escape to freedom on the morning of May 13, 1862. Smalls was an enslaved worker on the Confederate ship the Planter. Along with other enslaved members of the Planter’s crew, Smalls commandeered the ship and sailed past Confederate forts and ships in the Charleston Harbor until they reached the Union. I argue that the story of Robert Smalls validates arguments that enslaved people were not bystanders in the quest for emancipation; rather, the unique circumstances of the Civil War and the morning of May 13, 1862, allowed Smalls to enact his carefully created plan to seize his own freedom.