A Game Called Freedom

A subscriber wants to know about a heroic story of escape.

One of the best things about history is discovering exciting stories you have never heard about. Sometimes, these stories are so far-fetched that you would think they came from the mind of a novelist.

But most times, heroic stories are straight from the souls of brave people.

We take a break from discussing the prison situations of our politicians and instead dive into a story of courage, trust, and determination led by a young man who defied the rebellious government that sought to keep him and his family enslaved.

Joanne, a longtime subscriber, friend, and coworker who takes time to help me format client presentations and memos and even edits my content here at Okay History, brought up the idea for our latest Ask Me Anything segment.

Excellent idea Joanne, so thank you for suggesting it.

Let’s dive in. I’ll make sure to bring my unique literary style.

Robert Smalls was born enslaved in Beaufort, South Carolina, in 1839. As a child, he was well respected, which kept him in the enslaver’s house, along with his mother, Lydia Polite. Lydia did not want Robert to grow up without working in the fields and have a different experience of being enslaved, so she convinced her master to let Robert out of the house.

The oppressor agreed, and soon Robert was being leased out to the people of the city of Charleston by the time he was twelve. Smalls did various odd jobs but eventually landed gigs in the Charleston Harbor. As a deckhand and later pilot, Robert would accelerate his education of the waterways and formulate the potential plan for freedom.

When Smalls turned twenty-three, he had a wife named Hannah and two children –  four-year-old Elizabeth and infant son Robert, Jr.

At twenty-three, I didn’t have a girlfriend, let alone a wife. I had no kids and played a lot of video games.

With two decades of enslavement under his belt, Smalls saw his family’s future in bondage. He hated the idea of his children working in houses or fields; they had to escape for freedom, which, fortunately for them, was just a few miles off the Charleston shore, where the Union Navy sat occupying the waterways to squeeze the south of the world’s resources. Smalls knew he had to get there; it was just a matter of how.

Hopefully, Robert could win his family’s freedom with a few clever joystick moves one level at a time.

But Robert’s life was far from a video game. There was no reset button to try again if you failed to escape. Getting caught meant certain death to Smalls, and the most likely outcome for his family would be that they would be sold off to faraway places, most likely never to see each other again.

The easy choice was to choose a one-player mode because taking everyone complicated the opportunity. Kids tend to slow you down, and although I’m not an expert, I believe infants occasionally cry, which would be unhelpful if you were trying to hide.

The game was stacked against them.

But there was no way Smalls would leave his family behind. He figured out a plan. As a pilot for the CSS Navy boat, the Planter, which is a dumb name for a boat, but the Confederacy was pretty dumb, so it was on brand; Smalls and his crewmates knew every inch of the Charleston Harbor. Smalls planned to pilot the ship through Charleston Harbor with family on board, surrender to Union ships and play a new game called “Freedom!”

The captain of the Planter was Charles J. Relyea, who was 47 in May 1862. I’m currently 47 and captain the desk next to the guest bed in our upstairs bedroom. Relyea also had a wife named Hannah and two children of his own. This must have factored into Relyea's trust for Smalls, that he would defy Confederate orders and leave his boat to be onshore with his family, while Smalls and other enslaved men just sat there and did nothing, like plotting to escape.

Robert worked to convince the other enslaved boatmates that the plan would work. They, too, knew the risks, but when someone else owns you, and you have a chance to try and be free, death is not a terrible alternative. Knowing the rules of the game, they bought in.

Despite never playing the game “Freedom,” Robert had heard of 15 enslaved people taking a boat and escaping to the north not too long before. His cheat code was the fact that Charles J. Relyea also captained that boat. Relyea had left the boat alone with his enslaved crew and then woke up the next day to see them gone. Not really sure why Chuck repeated his same behavior, even I’m not that dumb. I just need occasional formatting and editing help.  

So early on May 13, 1862, Smalls and the Planter crew pressed play.

If you don’t know anything about Charleston Harbor, or the way Small made his escape, I have drawn a map – video game style.

Source: Google Maps and sweet art skills.

The Planter had to navigate by Dummies, also known as Confederate navy men, whose job was to keep an eye on any movement at any given time. Since the Confederacy still employed a guy who had already had a boat stolen, the prospects were good that the Dummies would live up to their names.

Smalls and the crew had to pick up their families waiting for them, then pilot down past Fort Johnson, Fort Sumter, and Fort Moultrie, the trinity of Dumb Confederate forts. Even if Smalls made it through this gauntlet of Dummies, approaching a Union Navy who wasn’t in on the plan and weren’t Dummies themselves could still fire upon the Planter coming towards them.

It was a daunting task. Smalls had to achieve many levels to win the game.

Level 1: Wait for Chuck to head off home, leaving his boat with enslaved people who watched over cannons and ammunition to be delivered the next day to Fort Sumter.

Level 2: Leave at the right time, when it wasn’t too early; even Dummies could figure out that something is up, but also not leave with too much sun because even Dummies can see who is steering a ship during the day.

Level 3: Put on the Dumb straw hat that Chuck used to wear all the time, which mostly covered his face. Dummies only look at the hats other Dummies wear, making them susceptible to being duped by disguise.

Level 4: Pick up his family and the wives of a few other boatmates.

Level 5: Sound the horn with the secret Dummy message at the final checkpoint, convincing the Dummies that it was Relyea and not Smalls steering the boat. Because seeing the hat and hearing the right sounds is good enough for Dummies.

Level 6: Approaching the Union Navy while not getting gunned down.

Get through all six levels, and “Freedom” is achieved.

Remarkably, Smalls did just that. He piloted the Planter with the Dumb straw hat, navigated the Harbor to pick up his family, and tooted his horn correctly. He even swapped out the rebel flag on the mast for a white bedsheet because the Union Navy wasn’t dumb and knew what that meant.

It’s even more remarkable that no one knows this heroic story. But Amazon announced a few years ago that it was making a movie about Smalls, which I’m sure will come out any day now. When it is released, you could even purchase a video game console while watching.  

Hopefully, with the help of, say, the 142 most popular history newsletter on Substack, we can begin to bring Smalls’s story to light over time. But we have already made some progress.

We renamed a battleship after him. The USS Robert Smalls was commissioned earlier this year. It had been named after the Battle of Chancellorsville, which weirdly was a Dummy’s victory.

So I hope this retelling of the story is helpful, Joanne. If you like the story of Robert Smalls, be sure to hit that like button. If you have any interesting topics you would like me to cover, email me at Chris@okayhistory.com. I promise it won’t take me two weeks to reply. I’m looking at you, Uncle Jack. My Bad.

Anonymous and I are hitting the road to Maine tomorrow for the next ten days. I will deliver another Maundy Monday Newsletter because I at least keep track of that.

Have a great weekend.

Okay,

Chris

Blue is ready for his week in Maine with his Maine beer.