Robert Smalls—a 23-year-old enslaved man in Charleston, South Carolina
What’s he known for?
Stealing a Confederate battleship.
In the middle of enemy waters.
Disguised as the captain.
With the crew.
And his family on board.
And delivering it to the Union.
Yeah. Let’s talk about it.
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His situation:
Smalls was enslaved.
But due to his skills, he worked in and around the harbor—eventually as a wheelman aboard the CSS Planter, a Confederate military transport ship.
He listened. He learned.
He watched the captain’s moves.
He memorized signals.
He noticed when guards got lazy.
He bided his time.
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The plan:
One night in May 1862, while the white officers were ashore…
He put on the captain’s uniform and hat.
Used his voice. His mannerisms.
And sailed that damn warship out of Charleston Harbor.
Not just with himself—but with his entire crew of fellow enslaved men. And their families.
He navigated Confederate checkpoints, saluted with the right signals, and sailed straight toward the Union blockade.
At first, the Union ships aimed their cannons—
then Smalls raised a white bedsheet.
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What happened next?
He surrendered the ship to the Union.
Delivered guns, ammo, intel, and the ship itself.
It was one of the boldest escapes in U.S. history.
Lincoln and Congress took notice.
They passed a bill to allow Black men to enlist in the Union army because of him.
Smalls would go on to become:
• A Union naval officer
• A U.S. Congressman (yes, from South Carolina)
• A fierce advocate for education and civil rights
• And a living example of what happens when dignity outweighs fear.
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Final kicker:
Years later, he bought the house he was enslaved in.
And let his former enslaver’s widow live there until she died.
When asked why?
“Because it was the right thing to do.”
