Rebels of Black History: The Great Escape of Robert Smalls

Illustration for article titled Rebels of Black History: The Great Escape of Robert Smalls
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Editor’s Note: This week, The Root commemorates Black History Month with a series on little-known or forgotten rebels, celebrating black America’s legacy of defiance.

If you, like me, were raised in the American educational system, your education on black history was that Martin Luther King had one speech and George Washington Carver was this close to making a lightsaber out of peanuts. There are so many great stories in black history that have gone unwritten. Stories that, frankly, dismantle any notion of white people being capable of any form of supremacy.

Today, I’d like to talk to you about one of the smartest, bravest and most badass figures in American history. A man who stole a Confederate warship and delivered himself and 16 others to freedom.


His name was Robert Smalls—and reader, he was nothing to fuck with.

A Life in Bondage

Our story begins on April 5, 1839, when Lydia Polite gives birth to Robert Smalls in Beaufort, South Carolina. She was the property of Henry Mckee, which meant Smalls, too, was his property. He was made to work as a houseboy, tending to McKee’s needs until the age of 12, when he faced one of the harsher realities of slave life; he was sent to Charleston, S.C to earn money for McKee.

Charleston was 75 miles away from Beaufort. While by today’s standards, that’s a quick skirt in the whip, it was no easy journey then. This distance meant Smalls was effectively separated from his mother.

He worked as a server and gas lamp cleaner before finding work as a stevedore on the docks, loading and unloading cargo from the ships. It was on those docks that he would learn some of the skills essential to his escape.


At age 17, Smalls married Hannah Jones, a slave. Her owner gave them permission to wed, based on the sheer fact he liked Smalls. Within two years, Jones gave birth to their first child, Elizabeth. This event only furthered Smalls’ anxiety about being separated from his family. The possibility of coming home from work one day only to find his wife and child had been sent off was too real.

This would be the fuel that drove Smalls in his quest for freedom.

Take Your Freedom

Alright, so we’re two years deep into the Civil War. Things are just a tiny bit heated. The Union has deployed ship brigades at Confederate ports to prevent trade from getting in or out, and the Confederates have built up heavily armed fortresses throughout the islands of South Carolina. Amidst all this, Smalls has found himself as a crewman of the Confederate steamship the Planter.


Smalls was nothing short of a natural when it came to the sea. His time on the docks taught him how to properly build rope lines and sails. He was so good that he gained a reputation as one of the best pilots in Charleston. Occasionally, he was allowed to pilot the Planter when the white officers would visit their families (or just felt like turning up).

Smalls understood that the chaos of the moment could provide the perfect opportunity to escape. One day, when the captain left the ship, the slaves put his straw brim on Smalls. They joked that he could pass for the captain since they shared a similar build and the hat hid his face. This was probably the most significant instance of joke-cracking in history, as it’s where Smalls initially got the idea to steal the Planter.


Over time, he would formulate a plan. It broke down like this:

  1. Convince the crew to jack the Planter.
  2. Make sure the crew didn’t talk about the plan to jack the Planter.
  3. Jack the Planter.
  4. Make it through multiple Confederate checkpoints.
  5. Deliver it to the Union and steal their freedom in the process.

Smalls was pretty much out here plotting GTA: 1862. He had to build a crew, steal a vehicle, successfully evade the authorities and deliver it to the checkpoint. No lie, I would play this game.


On the night of May 13, 1862, it was go-time. Martial law was about to be declared in Charleston in anticipation of a Union attack. This would mean more guards, more guns and zero chance at escape.

If they were going to take their freedom, it was now or never.

They faced a hiccup in their plan when one of the white crew members announced that he was going to sleep on the ship. This didn’t stop them, though, as they quickly decided the man was either getting kidnapped or killed; probably both. Luckily for the crewmember, he decided to head to shore for the night, anyway.


Smalls gathered his crew and boarded the Planter. They picked up their wives and children and only told them of the plan as it was in progress. Understandably, they were scared shitless. This man was not only stealing a Confederate warship but he was flaunting it through multiple Confederate checkpoints on the hope that a hat and some steam would be enough to hide his identity.

After passing through Fort Johnson, they made their approach to Fort Sumter. If they got through here, they were into Union waters and one step closer to freedom. As they were passing through Fort Sumter, the captain of the Planter John Rylea had noticed that his ship just straight-up wasn’t there.


Now, Reader. If I were to find that my ship was gone and none of the crew could be found, I would quickly deduce that I, indeed, had been jacked. Not Rylea though; nah, he decided to ask questions. It was lucky he did, because had he reported Smalls had taken his ship, Fort Sumter would’ve been able to fire on them as they were passing.

Smalls managed to safely make it through the Confederate forts into Union waters. By the time the Confederates realized what happened, the Planter had been dipped. They took down the Confederate flag and rose a white bedsheet as a makeshift flag of surrender.


A Union vessel, the Onward, spotted the ship and was going to fire as it couldn’t see the white flag through the heavy fog. Moments before they were about to start blasting, they saw the white flag and the black men and women celebrating on the ship. They hailed down the Planter and were met by Smalls who greeted them by shouting: “Good morning, sir! I’ve brought you some of the old United States guns, sir!”

Robert Smalls had successfully delivered his family to freedom.

Hubris, It’s a Hell of a Drug

There’s no arguing that Smalls’ skills as a pilot and his intelligence got him to freedom. He observed not only the proper signals for each checkpoint but the captain’s demeanor when giving them. Reports tell of how he so accurately mimicked Rylea’s body language that Confederate guards couldn’t tell it wasn’t him helming the ship.


I’d argue that 95 percent of the plan’s success comes down to Smalls and Smalls alone. Upon learning more about his story and the circumstances of his escape, there was one essential factor that goes overlooked.

White hubris.

If you go through Confederate accounts of Smalls’ escape they all reveal that white folks straight up didn’t believe a slave could pull this off. Literally, it didn’t even register in their minds that this could happen.


When the Planter left the docks of Charleston at an unusually early time, a guard saw it but didn’t even raise the alarm. He just assumed the captain was on board. Instead of signaling for help, Rylea spent his time asking questions because he knew, in his heart of hearts, there was no way this could happen.

I mean, I get it.

It’s absurd to think a man who spent most of his life on the docks, developed a reputation as one of the best sailors in the game and was noted for his innate charisma could ever utilize those skills to obtain freedom. It’s simply preposterous, y’all.


Even after Smalls had successfully escaped, the Confederates refused to believe it. In one of the oddest instances of white people taking credit for a black person’s work, a rumor was spread that a white man helped them plan it. They didn’t know who the white man was, but they knew there was one.

They were so dedicated to the idea of white supremacy that they refused to believe what their eyes were telling them.


His quest for freedom wouldn’t be the only extraordinary act Robert Smalls committed in his lifetime. After escaping, he became a civilian pilot for the Union Navy before becoming the first black captain in the U.S Navy’s history. Post-war, he became a five-term Congressman representing the state of South Carolina and was one of the first black men elected to the House.

The details of Smalls’ life are worthy of at least three HBO miniseries, a documentary on Netflix and a lead role in the next Assassin’s Creed game. My guy went from slave to war hero to trailblazing politician. If you didn’t know his name before, you do now.


He was Robert Smalls; and like I said, he was nothing to fuck with.

The stylin', profilin', limousine riding, jet flying, wheelin' and dealin' nerd of The Root.

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This is one of my favorite stories, needs to be made into a movie for sure!

It is a good thing that crew member decided to go ashore, otherwise he may have had to say, while the escapees were murdering him, “You’re killing me, Smalls!”