See his smiling face!
Of course he’s happy enslaved!
… Shit, he stole our boat.
History is so full of badass escapes from slavery that it’s hard to pick the most badass, but Robert Smalls’ escape has to be in the running. Why? Let Lonely Island give you a hint.
Smalls was born in South Carolina in 1839. His mother, Lydia Polite, was a slave. Her rapist, Henry McKee, was Polite and Smalls’ owner. Polite made sure that her boy worked in the fields, even though he could have remained as a relatively ‘privileged’ house slave, specifically so he’d see whipping and not get any weird ideas about what slavery was all about. Once he hit age twelve, he was hired out as a labourer in Charleston. Slave owners liked to do this sort of thing, as they could earn money without doing a damned thing and not have to pay for their slave’s upkeep. Smalls got to earn money, too!… A dollar a week. Yay.
Nevertheless, in Charleston, he was introduced to two of his great loves: 1) boats, and 2) Hannah Jones, hotel slave. He learned everything there was to know about the former and married the latter. Smalls had every intention of working to buy the freedom of himself, his wife, his two newly-acquired stepchildren, and his and Hannah’s eventual daughter and son together, but slaves were expensive and Smalls only got to take home a dollar a week, remember. The math just didn’t work out. If his family was ever going to be free, he’d have to be more audacious.
Fortunately, a bloody civil war that pit brother against brother, insert melancholy sound of bugle here, gave Smalls the opportunity to be more audacious.
After the capture of Fort Sumter by Confederate forces (the event that officially kicked off the war), Smalls was placed on the military transport CSS Planter and got to steering it. As he bopped it down and up the coast, he couldn’t help but notice the Union blockade, some seven miles off from Charleston’s harbour. So he smiled and played the part of the happy slave the Confederacy believed was actually a thing while he plotted with his fellow enslaved crew members.
In the wee hours of May 13, 1862, Smalls and Crew made their move. The Planter‘s white officers being asleep onshore, Smalls dressed up as the captain (complete with a convenient straw hat), sailed her off, picked up his and everyone else’s wives and children, and sailed on past the checkpoints. (He’d memorized both the checkpoint signals and the captain’s mannerisms beforehand.) Once they were out of the Confederate’s gun range and approached the Union’s, down went the stars and bars and up went a bedsheet Hannah had packed. They soon surrendered to the United States Navy the following: the Planter, 200 lbs of ammunition, a Confederate code book, a map of all the mines in the area, and all that sweet intel Smalls had stashed in that lovely brain of his. For remainder of the war, he continued to serve with the Navy, raised money and supplies for ex-slaves, and helped persuade Lincoln that hey, maybe it would be a good idea to allow black men to fight for a cause that fundamentally affected them, among other deeds.
After the war? Smalls bought up the seized property of his former owner / sperm donor, and successfully fought off McKee’s attempt to sue for it back. (I imagine he flipped him the bird after the judgement was read.) There, he lived with his wife, children, mother, and McKee’s aged wife. Then he learned to read and write, started up a school, went into business, and became a flippin’ congressman, serving for two terms.
Smalls died of malaria and diabetes in 1915, hyper-competent ’til the end.