Educated Guesses A Blog Full of Guesses

Colson Whitehead’s The Underground Railroad and the Complexity of Freedom


Colson Whitehead’s critically acclaimed and award winning book is an intriguing and a thoughtful fictional account of slavery.

Whitehead reimagines the Underground Railroad – literally – as a series of locomotive stations connected via subterranean tracks.

## Caution this essay contains plot spoilers ##

The book centers around Cora, a young teenager on the Randall plantation in Georgia. Her grandmother Ajarry survived the Middle Passage and found herself as property in a strange new land on the same plantation. Ajarry somehow found some semblance of solace and freedom in a 3 yard square plot of soil near the slave quarters where she slept. This plot of land provided a respite and a repository for her fallow hopes to take root. She passed this on to her daughter Mabel and eventually her granddaughter Cora claimed it as her own after Mabel vanished one night as if into thin air.

This birthright, if you will, was all that Cora had that connected her to her family and as a result she stood her ground to protect it at all costs from fellow slaves who were looking to stake a claim of their own.

One day, Caesar, a fellow slave, approached Cora to ask her if she would join him on his plan to escape. She initially rebuffed him and his plans. She thought that he looked at her as a good luck charm because of her mother’s seemingly successful flight to freedom.

Cora had a complicated relationship with the idea of escape and freedom. Her mother’s escape became the stuff of legend and a source of hope for those she left living in captivity. Simultaneously, she also became a source of shame for the slave owners who feared that the hope would eventually create ripples in their free labor pool. Cora on the other hand could not make heads or tails as to why her mother would leave her behind and choose freedom over her. Cora was very young when Mabel left.

During one of the few celebrations that the slaves were afforded, a birthday party for one of the elders – whose birthday was out of thin air because none of them actually knew what day they were born – Cora stands in the gap for a young boy who is being brutalized by one of the slave owners. The boy accidentally bumped into him while dancing causing him to spill a drop of his drink on his white shirt. The slave owner proceeds to beat the young boy with his cane and Cora falls to the ground to cover him up.

Both are beat mercilessly.

Later both are then subjected to additional punishment for their actions and as an object lesson for the unlearned. Oddly enough, this isn’t what causes Cora to change her mind and take Caesar up on his offer to escape.

The straw that breaks that camel’s back is when the escaped slave Big Anthony was captured and brought back to the plantation by a slave catcher. He was tortured and then eventually hung and burned. Big Anthony’s swinging and smoldering body served as a sadistic talisman of sorts for the slave owner to replace the vestiges of the spirit of freedom that may still be in the air because of Mabel with the stench of recompense.

That was it, Cora decided to make a run for it with Caesar.

Their escape led them to the first stop on their ride on the Underground Railroad , South Carolina, where they both “passed” as freed slaves in the new Southern experiment of dealing with Negro uplift, which ended up being a real experiment on Negro bodies.

The next stop was North Carolina, which landed Cora in the attic of an abolitionist family who had just recently gotten out of the “game” due to the extreme measures that were being adopted against the Negro and Negro sympathizers in the state. Unfortunately, Caesar did not make it out of South Carolina alive.

From North Carolina, Cora ends up in Indiana on a co-op farm full of fugitives.

From there she found herself above ground as an unlikely traveler on the road to freedom trying to put all of the broken pieces of her former self behind her.

There are lots of twists and turns on the tracks that take Cora from station to station on the Underground Railroad, but the overarching theme of the book is freedom. And, throughout the book freedom comes in various forms. It isn’t necessarily a state of being – as property on a plantation or as fugitive in a non-slave state – as much as it is a state of mind.

At the end of the book we find out the details of Mabel’s legendary flight to freedom. She absconded to a small island in the middle of the swamp to take a break on that fateful night.

“She lay on her back and ate another turnip. Without the sound of her splashing and huffing, the noises of the swamp resumed. The spadefoot toads and turtles and slithering creatures, the chattering of black insects. Above—through the leaves and branches of the black-water trees—the sky scrolled before her, new constellations wheeling in the darkness as she relaxed. No patrollers, no bosses, no cries of anguish to induct her into another’s despair. No cabin walls shuttling her through the night seas like the hold of a slave ship. Sandhill cranes and warblers, otters splashing. On the bed of damp earth, her breathing slowed and that which separated herself from the swamp disappeared. She was free.

This moment.”

This moment of freedom no matter how fleeting was enough for her.

“She had to go back. The girl was waiting on her. This would have to do for now. Her hopelessness had gotten the best of her, speaking under her thoughts like a demon. She would keep this moment close, her own treasure. When she found the words to share it with Cora, the girl would understand there was something beyond the plantation, past all that she knew. That one day if she stayed strong, the girl could have it for herself.”

Mabel headed back to the plantation to her baby girl to slide back into her bed undetected before the sun would find her missing. On the way she was bitten by a cottonmouth. She sank to the bottom of the swamp and was never heard from or seen again.

The mythology of Mabel is what motivates the actions of many in this book. Because no one ever knew what happened to her, they were left to their own devices to make up the end of the story. No one settled on the actual truth. Both sides of the racial divide came to the same conclusion. She had escaped. She was free.

But her freedom meant different things to different people. Mabel’s freedom meant hope to some slaves while it was a bridge too far for others. Mabel’s freedom was an existential threat to the Randall plantation and the slave owners reacted accordingly.

Mabel’s freedom represented abandonment to Cora, an abandonment that has stood in the way of her complete emancipation. After Cora arrives at her last stop on the Underground Railroad, she is lost and listless. She happens upon a convoy of carriages traveling on the road. After being offered helped from a couple of the carriage drivers, Cora finally accepts the generosity of the third driver – a black man. She joined him in his wagon where she was offered and accepted some food and a blanket.

“The blanket was stiff and raspy under her chin but she didn’t mind. She wondered where he escaped from, how bad it was, and how far he traveled before he put it behind him.”

With those words we can only hope that Cora one day can put it all behind her so that she can move forward.

Easier said then done.

Along Cora’s journey there is a lot of destruction and human carnage.

Among the carnage are white abolitionists who risked, and others who lost, their necks to help her and others to be delivered from evil. There were also black folks who were complicit in the capture of those who looked like them.

The human condition is complex and Whitehead does a good job of equitably doling out the good, the bad and the ugly beauty among the characters regardless of race.

Slavery is America’s original sin along with the stealing of the land from and the slaughtering of the indigenous people, but that’s a whole other story completely that needs to be continually told.

The mythology or narrative surrounding that sin doesn’t provide much room for the sacrifices that white people made in abolishing slavery. Black folks could not have done it by themselves. While it is true that they did not start it or sign up for it in the first place – the initial capture of the human cargo carried out by fellow Africans notwithstanding – the fact of the matter is that it was a bi-racial effort.

And it is going to take a bi-racial effort to eventually put it all behind us, not for the sake of forgetting it, but for the sake of all of us moving forward together in a way that is equitable to those who still suffer disproportionately from that sin and equally for those who are up to the opportunities that they are not afforded because of it.

Let’s face it, at this point, fortunately or unfortunately, we are all in the same boat as a country.

About the author

Andre Kimo Stone Guess
Andre Kimo Stone Guess

Andre Kimo Stone Guess is a writer and cultural critic from the Smoketown neighborhood in Louisville, Kentucky. He was VP and Producer for Jazz at Lincoln Center in New York and CEO of the August Wilson Center for African American Culture in Pittsburgh. He now runs GuessWorks, Inc. with his wife Cheryl.

Educated Guesses A Blog Full of Guesses