The Underground Railroad

Chester is a young boy who lives on Randall. Cora takes a liking to him because, like her, he is a “stray” (an orphan). When Terrance forces the enslaved population to dance, Chester accidentally knocks Terrance’s wine onto his shirt, causing both Chester (and Cora, who defends him) to be brutally whipped. After this point, Chester never speaks to Cora again.

Chester Quotes in The Underground Railroad

The The Underground Railroad quotes below are all either spoken by Chester or refer to Chester. For each quote, you can also see the other characters and themes related to it (each theme is indicated by its own dot and icon, like this one:
Family, Heritage, and Home Theme Icon
). Note: all page numbers and citation info for the quotes below refer to the Doubleday edition of The Underground Railroad published in 2016.
Chapter 10: Indiana Quotes

How could such a bitter thing become a means of pleasure? Everything on Valentine was the opposite. Work needn't be suffering, it could unite folks. A bright child like Chester might thrive and prosper, as Molly and her friends did. A mother raise her daughter with love and kindness. A beautiful soul like Caesar could be anything he wanted here, all of them could be: own a spread, be a schoolteacher, fight for colored rights. Even be a poet. In her Georgia misery she had pictured freedom, and it had not looked like this. Freedom was a community laboring for something lovely and rare.

Related Characters: Cora (aka Bessie), Caesar, Chester, Molly
Page Number: 272
Explanation and Analysis:
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Chester Character Timeline in The Underground Railroad

The timeline below shows where the character Chester appears in The Underground Railroad. The colored dots and icons indicate which themes are associated with that appearance.
Chapter 2: Georgia
Family, Heritage, and Home Theme Icon
Endurance vs. Rebellion Theme Icon
Value, Ownership, and Commodification Theme Icon
Brutality and Violation Theme Icon
...sets up the children’s race at Jockey’s feast. She looks out for a boy called Chester, who is also a stray. He is already tall and strong, and Connelly, the overseer,... (full context)
Family, Heritage, and Home Theme Icon
Endurance vs. Rebellion Theme Icon
Death and Freedom Theme Icon
Value, Ownership, and Commodification Theme Icon
Brutality and Violation Theme Icon
History, Myth, and Fantasy Theme Icon
...with vigor and joy that they do not really feel. Suddenly, Terrance roars in anger; Chester has bumped into him and splashed wine on his shirt. Terrance lifts his cane to... (full context)
Endurance vs. Rebellion Theme Icon
Death and Freedom Theme Icon
Brutality and Violation Theme Icon
...He was interrupted in the middle of raping an enslaved woman, and he whipped both Chester and Cora three days in a row, ordering that their wounds be doused in pepper... (full context)
Chapter 9: Caesar
Family, Heritage, and Home Theme Icon
Endurance vs. Rebellion Theme Icon
Death and Freedom Theme Icon
Value, Ownership, and Commodification Theme Icon
Brutality and Violation Theme Icon
History, Myth, and Fantasy Theme Icon
...he knows she will say yes even before she does. The fact that Cora shielded Chester during the incident at the dance further proved that she would be essential to Caesar’s... (full context)