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The Underground Railroad Today: (A Lack of) Progress in the Whiteheadverse

By: Ben Schneider

“It’s always Mississippi in the fifties,” J. Sutter says in Colson Whitehead’s John Henry Days while working in 1996 West Virginia (127). Whitehead’s novels span generations of American history and a wide range of Black perspectives, and a common one is the firm belief that the political system works against Black people. J. Sutter, a jaded New York journalist, makes this remark assuming he will be arrested or hanged for stealing a laptop while his white coworker gets only a slap on the wrist for the same crime. J. thinks the contemporary South is no better off than when Jim Crow laws reigned supreme, and his family history of being enslaved is ever-present on his mind. His circular view of the passage of time reflects Whitehead’s melding of historical events together through anachronism to connect the present and the past, a move Professor Madhu Dubey says, “offers Whitehead a perfect vehicle for defamiliarizing public narratives about race and national history at the turn of the twenty-first century” (“Museumizing” 111). In his meta-slave narrative, The Underground Railroad, Whitehead takes the concept to another level by reusing similar scenes and images from his previous novels within the context of slavery. Cora’s experience as an enslaved teenager living on a Georgia plantation and subsequent escape by train references critical moments from the Whitehead Literary Universe. Showing enslaved people performing the same activities as their descendants decades later creates a dichotomy of pessimism and optimism for the present and future of Black expression. Parallel scenes between The Underground Railroad and Colson Whitehead’s other novels, most notably Sag Harbor, point to a frustration over the lack of racial progress across the decades, but they also indicate that more privileged Black people today can choose to act like their ancestors did with pride by having similar events as their ancestors.

At first glance, the racial violence in The Underground Railroad echoing scenes in Whitehead’s other novels suggests that there has been very little racial progress in the United States. When Cora is whipped for shielding a little boy with her body, she reflects on how the other enslaved people react during a whipping: 

It was customary for slaves to witness the abuse of their brethren as moral instruction. At some point…everyone had to turn away…as they considered the slave’s pain and the day sooner or later when it would be their turn at the foul end of the lash.

(Railroad 46)  

Being whipped by the slave master or field overseer serves as required “moral instruction” for the spectating enslaved people so that they always remember their place at the very bottom of the social ladder. Each person is reminded of their role as a slave even if they are not the ones being punished. As Whitehead emphasizes here, this image is a scene of instruction, a common element in Black literature. These scenes depict Black people, especially younger ones, recognizing the limits imposed on them by white society solely because they have darker skin. Born into slavery, these people are already well aware that they are viewed as inferior, but the Randalls, a family of slaveowners, likes to reinforce the message. Being whipped is tragically not Cora’s worst experience, but it serves as a common instructional one from which every enslaved person learns.  

The terms are different in Sag Harbor, Whitehead’s semi-autobiographical coming of age novel set in 1985, more than a century after emancipation. Ben Cooper looks back on his time as a 15-year-old in an upper-middle class family that spends its summers in Sag Harbor, a Black community in the Hamptons. He recounts an episode from fourth grade when a white student made a racist remark about him and the other kids shot down the remark without incident. Ben’s father, meanwhile, gets quite angry at Ben for not standing up for himself. He assumes that Ben had been afraid of being hit back, so he hits Ben hard to show that bullies cannot do anything worse. Ben concludes that “[the] lesson was, Don’t be afraid of being hit, but over the years I took it as, No one can hurt you more than I can” (Sag Harbor, 164). His family members learn the same lesson because his brother and sister close their bedroom doors knowing Ben is about to be hit, and his mother often backs down from arguments to prevent abuse.  Ben’s scene of instruction growing up mirrors Cora’s because it involves violence from someone more powerful, but his father keeps this a private matter. His father’s lesson is supposed to be the opposite of Randall’s, insisting that Black people should fight back against those who inflict pain. However, Ben takes them to have the same meaning: no one is more powerful than the master of the house and no one else can stand up to the master of the house. Professor Cameron Leader-Picone asserts that because scenes of instruction are so common in Black literature, they work as “[rituals] of group identification,” but Ben’s experience “is filtered through an individualistic lens” (“Post-Black” 438-439). Not only is a scene of instruction collective on behalf of Black writers, but Terrance Randall is teaching a collective lesson to all the people he owns.  The lesson from Ben’s father is specific to Ben because he is not hardened in his upper-class life, but the action is effectively the same. Through this parallel Whitehead shows that the evolution from a slave owner whipping Black people to a Black father hitting his son is no evolution at all.

The parallels between The Underground Railroad and Sag Harbor are more complicated than the continuation of physical violence, as some suggest racial progress seems to be frustratingly slow but still possible. During Jockey’s birthday party on the Randall plantation, the other enslaved people organize a race for the little kids: 

Cora always arranged the children at the starting line, aiming their feet, calming the skittish ones, and graduating some to the older kids’ race if need be…The young slaves and the old slaves gathered on the sidelines of the horse path.

(Railroad 23-24)

 This innocuous scene is eerily similar to one at the end of Sag Harbor, when the community gathers for their Labor Day festival: “The boys lined up to race. They double-knotted their shoelaces… They nosed their sneakers as close to the line as possible…they ran for their parents, who did or did not watch from the sidelines” (307-309). The two racing scenes both occur in a celebratory context with little kids sprinting while their families watch close by. On a rare evening where the enslaved people are allowed to relax, the only thing for the older people to do is enjoy the races or to help set up the races. In Sag Harbor, the kids are more sure of themselves and require less help to organize the event. On a street filled with cookouts and parties, the parents have other things they could do besides watch their kids. The overlapping scenes bring up the question: why do the wealthy people of Sag Harbor participate in the same activity their ancestors did with far less options? Perhaps this suggests that the situation of Black Americans has not improved at all. However, it is also possible the two scenes stand for a shared sense of self-expression. The people in Sag Harbor can do whatever they want the whole summer, but they are free to follow in the footsteps of those who suffered in slavery. They might not be aware of their ancestors’ free-time activities, but Whitehead is, given that a celebratory sprint is a unique scene to write. Rather than being trapped in the same pattern, they are honouring the meaningful perseverance of their ancestors while celebrating their own economic success. The kids in Sag Harbor race freely because their ancestors could not, therefore the activity is more meaningful. Even so, it is off-putting to see the race reframed in the context of slavery, where the scene concludes with Cora being beaten. Whitehead shows Black people can move forward and express themselves, but the expression is rooted in the history of slavery.

The main question of The Underground Railroad is how to move forward as a society and face the history of slavery, an issue Whitehead has previously addressed.  The issue is at the forefront of the Valentine farm, a stop on the railroad in Indiana where Black people support themselves. Lander, a great orator born free, advocates for saving everyone, while Mingo, a formerly enslaved man who bought his family’s freedom, calls for staying put and closing the doors to runaways like Cora. His logic is as follows: “The parade of famous visitors spreading the farm’s renown made the place into a symbol of colored uplift—and a target…It always ended in violence” (Railroad 253). Lander’s ideals are appealing to many on Valentine, as Cora and other escapees want to help more people like themselves. However, Mingo’s grim pragmatism ends up being justified as white rioters burn down the farm during a town hall and kill many of the residents. Mingo thinks runaways drag down the farm and bring unnecessary attention to Valentine. He sees racial violence as a guarantee, and his predictions come true so soon they cannot even conclude the town hall. The rioters cannot stand having self-sufficient Black people near them, so they destroy the “symbol of colored uplift” as Mingo predicted.  

The debate between Mingo and Lander intersects with the debate between pioneers Goode and Field in Apex Hides the Hurt. A nomenclature consultant living today is hired to rename the town of Winthrop, which was first settled by former slaves in the 1860’s and now is home to a tech entrepreneur who wants the new name to reflect the current market. With the support of the clan, Goode originally named the settlement Freedom to embody their dreams, while Field wanted the name to be Struggle after their constant reality. Lander is somewhat more realistic than Goode, but the two debates run along the same lines: focus on the current nightmares or reach for the highest aspirations. The pioneers met both aspects head on when their first settlement was burned down by rioters, like Valentine, but they persevered and built another home. Cora, on the one hand, is all too familiar with the nightmares of slavery; she still believes in helping as many people as possible reach freedom. In her world, museums reinforce slavery instead of showing its true nature. The consultant, on the other hand, thinks that Field resonates so much he renames the town Struggle. The locals are ready for the next wave of capitalist development, but he forces them to acknowledge the roots of their town and identify with it: “I live in Struggle and come from Struggle…I will die in Struggle” (Apex 211). Just like Mingo and Field, he wants everyone to fully grasp that the struggle of Black existence lasts a lifetime. Aspirations are only useful if people work to achieve their goals, and sometimes that requires hard sacrifices. In both cases, Whitehead presents idealism and blunt pragmatism as legitimate points of view, but the pragmatists are violently proven correct.

The premise of the Valentine farm also calls into question the long-term viability of Black spaces like Sag Harbor. By nearly all accounts, the farm is a successful venture. Mr. Valentine capably runs his agriculture business, and he makes enough money that he can financially afford to bring in more runaways and pay them to work, with more funds left over to build housing and a school. The crux of Mingo’s perspective is that Valentine will be targeted because the farm is successful, not merely because it exists. Free Black people and abolitionists around the country know the farm is the model of self-sufficiency. As a kind of safe haven, Valentine resembles Sag Harbor, with some crucial differences. Black people can afford to spend their summers in Sag because they are financially successful. Like Valentine, they are proud of themselves for establishing a community of their own amidst a racist system, as Ben and his friends still wonder if white passersby are friendly or hostile. But Sag Harbor is only open to wealthier people and not the lower-class equivalents to Cora. Mingo would fit right in. It would be a shock if Sag Harbor was burned down, but they face the less-obvious contemporary equivalent: Adult Ben repeatedly mentions how the neighbourhoods have changed over the years due to gentrification. The consultant sees that the same thing will happen in the town he is naming, as the influx of workers are buying houses in the historically Black area because “[it’s] a little cheaper on that side of town” (Apex 157).  Prices will almost certainly go up within a few years as the tech industry dominates local business. White people take over the Black area again, but they do so slowly without physical violence. The utopia of Valentine is doomed to fail, but Sag Harbor might not survive, either.

If Valentine finds a utopian equivalent in Sag Harbor, then the Randall plantation finds a dystopian equivalent in the Nickel Academy. The Nickel Boys, Whitehead’s companion to The Underground Railroad, follows the idealistic Elwood and cynical Turner sentenced to suffer through a reformatory school’s blatant racism and abuse.  Many of the boys are forced to work the field all day like slaves, and the state of Florida makes Nickel their official printing press to take advantage of the free labour. All boys are beaten in a white shed, and the “black boys called it the White House because that was its official name and it fit…The White House delivered the law and everyone obeyed” (Nickel 66). Administrators generally apply harsher discipline to black boys at Nickel than white boys, and their small-scale system of injustice is part of a large system run by the nation’s highest office that has upheld  white supremacy since the country’s founding. Professor Derek C. Maus aptly observes that the “symbolic linkage of local and national power intimates that their shared purpose is not law enforcement but rather force enlawment” (Understanding 141). The same is true in The Underground Railroad with the Fugitive Slave Law, which was passed by Congress but enforced by local authorities. Contrary to the popular Civil Rights Movement and abolition movement in the two periods these novels are set in, the national government implicitly or explicitly sides with the racist status quo. The brutal “force enlawment” is the reason escape seems so daunting. Like Cora’s scene of instruction, Terrance Randall roasts Big Anthony alive in stocks for trying to escape to tell the rest of the enslaved people what their punishment will be for running away. Nickel boys caught running away are similarly “[taken] out back” to be killed with their hands in constricting rings (Nickel 103). In his follow-up book, Whitehead lays bare the line from slavery to imprisonment. The threat of brutal death is horrifying in these two dystopias, but they are based on real events, not imagined worlds. One can easily imagine Turner echoing J. Sutter: it is always Georgia in the eighteen fifties.

Colson Whitehead reuses scenes and images from his other novels in The Underground Railroad to show a lack of racial progress over time and the potential for Black self-expression. The perpetuation of violence within the Black community is no better than racial violence on the plantation, but wealthier Black people today can reclaim the actions of their ancestors in slavery. The reality of a Black sanctuary is possible, but destruction is a near certainty. No matter how many years go by, there will still be remnants of the past in the present. In his satirical piece “Picking a Genre,” Whitehead makes fun of Black authors writing a “Southern Novel of Black Misery” who “investigate the legacy of slavery that still reverberates to this day” (“Picking”). However,  Whitehead becomes one of them with The Underground Railroad. The key to his investigation is that slavery reverberates in each period of American history in different forms. From the predatory labour practices in John Henry Days and corporal punishment in The Nickel Boys to domestic violence in Sag Harbor and capitalist expansion in Apex Hides the Hurt, Whitehead addresses the spectrum of racial issues that originate in slavery. With a new book out and no signs of slowing down, it will be interesting to see how Whitehead reuses his imagery going forward.

Works Cited

Dubey, Madhu. “Museumizing Slavery: Living History in Colson Whitehead’s The Underground Railroad.” American Literary History, Dec. 27th, 2019, 10.1093/alh/ajz056. Accessed Nov. 21st, 2021.

Leader-Picone, Cameron. “Post-Black Stories: Colson Whitehead’s Sag Harbor and Racial Individualism.” Contemporary Literature, vol. 56, no. 3, 2015, pp. 421–449, 10.3368/cl.56.3.421. Accessed Nov. 18th 2021.

Maus, Derek C. “The Underground Railroad and The Nickel Boys.” Understanding Colson Whitehead. Columbia, University of South Carolina Press, Apr. 2021, pp. 120–147. Accessed Nov. 21st, 2021.

Whitehead, Colson. Apex Hides the Hurt. Anchor Books, 2006. 

—. John Henry Days.  Anchor Books, 2001.

—. The Nickel Boys.  Anchor Books, 2019.

—. Sag Harbor. Anchor Books, 2009. 

—. “What to Write Next.” The New York Times, Nov. 1st, 2009, 2009/11/01/books/review/Whitehead-t.html.—. The Underground Railroad. Anchor Books, 2016.