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Sara I know this is late, however hopefully this helps someone else.

1) Why did the author not go into more detail on how Elwood was convicted of that crime? Couldn't he have been absolved by his teacher and others, like his employer?
2) In the very last paragraph in the book, a character is referenced who now owns the diner (Blondie's) who used to read comic books at the Nickel institute. Which character is the author referring to?
3) Did Turner give the letter to Spencer?
4) Would this be acceptable as a high school literature circle book or is it for adults?
5) What is the significance of July 3, 1975?
6) How could do many evil people be in the same place at the same time? How could they all go along with what was happening there, whether they participated or not?
7) Why read this book?
8) How can this have happened? How have we not heard about this before now?
9) Were you aware of Dozier School for Boys prior to reading this book?
10) Is hope worth it? Was there ever going to be a different way for Elwood in this place, in this time?
11) Is it fate rolling the dice, when Elwood finds two rivets broken on his bike chain the first night he is heading to college? Is destiny playing games, when it is a man named Rodney driving a stolen vehicle who stops to give him a lift? Is it something as simple as sheer bad luck that they are pulled over by the police?
12) The Nickel Academy, a state-sponsored reformatory, looks good from the outside but inside, all manner of horrors and crimes are being perpetrated upon these young boys. Wasn't the state of Florida paying attention? Or do they know and just look away? It's not till many years later that the truth starts to come out about what was really going on there all those years. How many knew the truth but never spoke up?
13) What else is being hidden from us? When does it stop? Does George Orwell make a point of this in 1984; he who controls the future erases the past?
14) Any thoughts on the prologue? Did Colson Whitehead do this effectively? Did the discovery of the unmarked grave site on the campus grounds give a feeling of foreboding and the possible violence ahead?
15) Do we applaud Elwood for sticking to his principles or recognize that his inability to bend will bring him a lot of unnecessary hurt and pain in life?
16) The last few chapters of the book alternate between Nickel and New York. For example at the end of chapter 14 Elwood is being dragged off to the White House. But 15 starts with Elwood moving a possessions from a basement to Long Island and complaints about Harlem gentrification. Does this juxtaposition and flow work for you?
17) How did people feel about this unexpected ending?
18) One student, Jaimie, is half-Mexican and constantly shuffled between the "white" and "colored" sections of Nickel Academy. Why do you think the author included a character with Jaimie’s ethnic identity in this story?
19) In the prologue, the narrator observes that after the truth about Nickel Academy comes out, "even the most innocent scene—a mess hall or the football field—came out sinister, no photographic trickery necessary." Can you think of a time in your life when discovering the history of a place (a particular building, a statue, a historical landmark, etc.) dramatically changed your perception of it?
20) One of Elwood’s takeaways from Dr. King’s speeches is the importance of maintaining one’s dignity in the face of oppression. Is Elwood’s decision to escape (and risk the consequences of capture) rooted in the realization that he can no longer maintain his dignity in a place like Nickel?
21) Who do you think was the true "villain" of the story? The teachers? The school itself? Something or someone else?
22) When did you anticipate the true identity of the storyteller? What did that revelation add to you the story for you?
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by Colson Whitehead (Goodreads Author)
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