It’s almost tragic that the most bada$$ escaped slave story most people know is Django Unchained. Because in real life, not only did slaves frequently escape, but they often did it without help from free whites, and without murdering several hundred people. Instead, what they had was cleverness and the audacity to try ridiculous plans that by all rights should never have worked.
5. A Couple Cross-Dress Their Way Out of Slavery
In 1848, a slave in Georgia named William Craft hit upon a brilliant plan to escape from his life of bondage: His wife, Ellen, was very light-skinned, and with some forged papers she could easily pass for white. So, why not just pose as her slave and get on a train heading north? There’s no way that plan can turn into some kind of wacky Three’s Company-style farce!
Wait, there was one problem — in those days, it was pretty much unheard of for a white woman to travel alone in the company of a male slave, presumably because white men were wary of the enormous sex party that would inevitably break out in just such a situation. For the plan to work, the dainty Ellen would have to be disguised as a white man (she in no way looked like one of those). So, in true wacky ’80s sitcom style, they wrapped most of Ellen’s face in thick bandages and a pair of tinted glasses. Then, just to make sure that this disguise would attract as much attention as possible, they threw on a huge top hat. Since Ellen couldn’t write, they also put a fake cast on her right arm so she wouldn’t be asked to sign her name.
With Ellen now resembling the invisible man in disguise as a mummy, they boarded a train to Philadelphia, only to find that they would be sitting across from a close friend of Ellen’s master, who had known her for years. Luckily he didn’t recognize them. Unluckily, he kept trying to start a conversation, forcing Ellen to pretend to be deaf to avoid talking to him. She kept this up for the rest of the journey, probably thinking that at any moment somebody was going to spring out and announce that it had all been a practical joke.
Finally, at their last stop in Baltimore, a suspicious railroad employee refused to allow William to board the train to Philadelphia without proof that he did actually belong to Ellen. However, the other passengers were so sympathetic to the thought of the clearly deathly ill “young man” wandering around Philly without his faithful slave to help him, they insisted that both be allowed to board. And with that, they were free.
4. Lewis Williams Is Switched With a Body Double Mid-Trial
As a young boy, Lewis Williams escaped from slavery in Kentucky and grew up free in the abolitionist stronghold of Cincinnati. Things went wrong in his early 20s, however, when he decided to visit a local psychic to find out if a girl he liked was into him. Somehow he also ended up confiding that he was actually an escaped slave. Astonishingly for a woman who made her living ripping people off, the psychic immediately betrayed him to his former owner in exchange for a reward. Williams was seized by bounty hunters and taken before a judge to be extradited to Kentucky.
And they would have gotten away with it, too, if the leader of the black community in Cincinnati hadn’t been a stone-cold bada$$ by the name of Reverend William Troy. No sooner had he heard about the arrest than he was dreaming up a plan so insane that no one would see it coming.
As luck would have it, Troy knew another young man who bore a striking resemblance to Williams. And he also knew that some white people have famously questionable skills in the field of advanced telling black people apart. So when Troy heard that Williams had been seized, he made sure that a crowd of his fellow abolitionists rushed over and packed into the courtroom. Then they simply waited until everyone else was distracted by a dramatic legal argument, at which point Williams and his double quickly switched places and Williams crawled out the door on his hands and knees, hidden behind a wall of hilariously large old-timey women’s skirts.
To give him time to escape, Williams’ lawyers allowed the trial to continue for several more hours before a bailiff finally noticed that the defendant was an entirely different person. Williams’ troubles weren’t over there, though, and the house he was hiding out in was surrounded by suspicious policemen. Again, Troy swung into action with another of his patented wacky schemes. And as in the previous entry, it was cross-dressing to the rescue.
So, Troy disguised Williams as his daughter in petticoats, crinoline, and a large bonnet with a veil. The fugitive walked right out the front door and past the crowd of policemen on the arm of a “gentleman caller.” Another life saved due to the heroic power of shenanigans.
3. Henry “Box” Brown Mails Himself to Freedom
In 1849, Henry Brown was determined to escape his miserable life on a Virginia plantation. But how? Safety was hundreds of miles away, and he wasn’t a young man anymore. Brown decided to get creative. And by that we mean, for the third straight entry, the escapee used a scheme that would seem too ridiculous for a cartoon.
First, he had a carpenter friend make up a wooden box 3 feet long by 2 feet wide, which the 5-foot-8-inch, 200-pound Brown somehow squeezed himself into as though he was playing some sort of horrifying human Tetris. Then he had two other friends carry the box down to the offices of the Adams Freight Company and have it “conveyed as dried goods” to Philadelphia. Seriously, you read that right. Henry Brown mailed himself to freedom.
Of course, it wasn’t quite that easy. The biggest problem came when postal workers ignored the large “This Side Up” signs plastered all over the box and stacked Brown with his head facing down. Since Brown couldn’t let anyone know he was in the crate, he was forced to remain standing on his head like that for 20 minutes, until he could be sure he was alone. Brown later claimed that the experience almost killed him and that he was barely able to cling to consciousness long enough to save himself, which does tend to overshadow the equally impressive fact that he somehow managed to right himself without getting out of the box.
Not one to miss a chance to rub it in, Brown immediately adopted “Box” as his new middle name and embarked on a hugely lucrative lecture tour while supporters of slavery fumed impotently. This also infuriated prominent abolitionists like Frederick Douglass, who wanted Brown to keep the details of his escape a secret so they could encourage other slaves to escape the same way. So while we’ve got to give Brown props for his badassery, we can’t quite forgive him for potentially depriving us of the past where the Civil War never happened because every slave in the South simply mailed himself to liberty.
2. Eliza Harris Leaps Across the Ice
In 1838, a woman subsequently known as Eliza Harris escaped from slavery with her baby grandchild. Racing on foot through the snow, she could hear the barking of dogs behind her as her pursuers gained ground. Reaching the Ohio River, she was forced to pause. Despite the vicious cold, the river was not frozen solid, but was chock-full of thin, fast-moving ice floes.
This was the point where most people would give up and turn back, or, accepting their fate, perhaps would pick up one of the smaller ice chunks and attempt to throw it like a Frisbee. Fortunately, Eliza Harris was not most people. Instead she strapped the baby to her back, climbed out onto the ice, and leaped from floe to floe across the river like it was a goddamned Mario level.
And when we say ice floe, if you’re picturing big, stable icebergs like a polar bear might frolic on during a breath mint commercial — think again. This was more like trying to jump from a bucking surfboard onto a moving shark if both those things were made of wet ice. Eliza slipped several times during her crossing and would have been swept away if not for a fence post she was carrying to steady herself. She eventually made it to the other side. It was so badass that a slave catcher who had been lying in wait for her on the other side just helped her up and pointed her in the direction of safety.
Now when you’ve just done something so awesome that one of the worst human beings in the world decided to help you out, you could probably be forgiven for taking it easy for a while. Eliza, on the other hand, simply headed straight back South and, despite the huge reward that had been put on her head, succeeded in liberating her other five grandchildren. Her incredible story eventually made it back to the writer Harriet Beecher Stowe, who based the climactic scene in her famous anti-slavery novel Uncle Tom’s Cabin on her escape across the ice. The book’s heroine is named Eliza in her honor.
1. Robert Smalls Hijacks a Confederate Ship
In 1862, the Confederate naval vessel Planter cast off from its mooring in Charleston and expertly navigated through the heavily mined harbor. Passing beneath the guns of Fort Sumter, the Planter’s captain, in his trademark white naval jacket and straw hat, cheerfully waved to the guards before giving the secret signals that prevented them from blowing his ship out of the water.
The same guards were probably a little surprised when the ship carefully waited until it was out of reach of the guns before immediately turning north and heading for the Union. You see, the man in the captain’s uniform waving to the guards was, in fact, a slave named Robert Smalls. And he was stealing the shit out of the Planter.
At the start of the war, Smalls had found himself as one of the many slaves forced to work in the Confederate Navy. Not missing the bitter irony that he was somehow expected to fight against his freedom, he immediately began planning how to escape in the most audacious manner possible. First, he took the opportunity to memorize the signals needed to get past the fort. He also made sure to remember where the mines were in the harbor, which wasn’t hard because he’d laid most of them himself. And of course, he also stole every single Confederate naval secret he could lay his hands on.
Amazingly, Smalls managed to keep from cackling hysterically during all this, because his white crew mates were so taken in with the deception that they decided to trust him to stay alone on the boat while they went to get drunk. Smalls immediately gathered 12 other slaves and their families and staged his famous defection to the Union, who were grateful enough to give him permanent command of the Planter, making him the only black captain of the war. He became a hero in the North and played a big part in persuading Abraham Lincoln to allow slaves to join the armed forces.
Read more here.