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1
In your opinion, why does Colson Whitehead make the Underground Railroad a literal railroad? What function does this play in the novel?
The physical reality of a literal railroad amplifies the colossal effort of those who used the real Underground Railroad. Cora dwells on the immensity of the labor it must have took to build the railroad. Thousands of former slaves undertook back-breaking work, carving tunnels out of mountains, digging holes in the ground underneath all of America. The labor of others, she thinks, is redemptive; with it, they have been transformed, and without it, she would never be free. Thus the transformation of the Railroad into a literal engine gives Whitehead the opportunity to directly commemorate the courage of the real men and women in history who operated the network and used it to flee.
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2
How do different characters regard the American Dream in the novel?
For Ridgeway, both the founding principle and the driving engine of America are comprised of a simple principle: if you steal property and keep it, it is yours. This brutal, stable reality is the American Dream. In contrast, Elijah Lander describes the American Dream is a shifting uncertainty, in fact a grand “delusion.” These are perhaps the two opposite poles of belief in the central myths of America. Perhaps Whitehead's point is made by the protagonist, Cora, who oscillates somewhere in the middle. Sometimes she she thinks America is just “a ghost in the darkness,” nothing real at all. At other times, she is unsure, “stirred” by the idea of expansion and progress. In the end, she is aligned with those Americans seeking to cash in on the American Dream, moving out west to reap the rewards of the frontier.
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3
What effect does the structure of the novel's chapters have on the development of the plot?
While being transported in chains through Tennessee, Cora reflects on how the peculiar institution has made her a keeper of lists. In a column in her head, she logs everyone who has impacted her journey, honoring them even as she must move on without them. The novel's structure functions in much the same way. Whitehead alternates between chapters depicting Cora's story, and chapters telling the stories of secondary characters. The first such chapter, giving context for Ajarry's life, functions as an exposition and mood-setting for the entire novel. Later, several characters are featured after their deaths—for example, Ethel, Caesar, and Mabel—and so their chapters function as memorials. Other characters—Ridgeway and Stevens, for instance—provide ideological counterpoints to Cora's story, juxtaposing her struggle with the ideas of white supremacist America. In total, these chapters form a list of characters who have impacted Cora, mimicking the list she keeps in her head.
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4
What role does the character of Mabel have on Cora's story?
In some ways, Mabel is the driving force behind Cora's story. When Mabel escapes the Randall plantation, she leaves behind a vegetable garden that reminds Cora of the promise of freedom. Cora grows to resent her mother for leaving her behind to suffer. Throughout the novel, as she makes her way through a hellish landscape in search of the freedom she believes her mother attained, she pictures Mabel in freedom, perhaps in Canada. Cora's struggle is shaped by Mabel in another way too: Ridgeway, the slave catcher, takes it as a personal insult that he never found and recaptured Mabel. This old grievance drives him to capture Cora at all costs. More than just his job, his pursuit of Cora is a personal and thus much more dangerous vendetta.
In an ironic twist at the end of the novel, however, the narrator reveals that Mabel never made it to freedom. She died on her way back to Cora, in the swamp just outside the Randall plantation. Thus the driving impetus of Cora's story falls apart, and it turns out Cora made her escape all on her own.
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5
How does Ridgeway's character develop over the course of the book?
In the third chapter, Ridgeway's back story describes him as a formidable opponent. Tall, cold-hearted, and extremely violent, he makes the perfect antagonist. As time goes on, however, cracks begin to show in his steely persona. Cora learns the odd story of how he recognized a kindred spirit in a young black slave, Homer, whom he freed and befriended. The relationship between the ten-year-old boy and Ridgeway remains an enigma throughout the novel, but there seems to be clear affection there. Thus the slave catcher is not as hard-hearted as he initially seemed. Ridgeway is then severely diminished by the confrontation with Royal and Red in Tennessee. From that point on, his pursuit of Cora borders on the obsession of a mentally unstable man. When he finally catches up to her for the last time in Indiana, he seems unkempt and disheveled. Thus over the course of the novel, Ridgeway's relentless pursuit of Cora appears to weaken him. He eventually unravels while Cora continues on to freedom.