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Chapter 19 begins around Christmastime. The inmates will be away from their families, so Mark brings a cake to help cheer them up. At this point Nathaniel, Jimmy, and Patrick have all been transferred to the county jail. Their loss weighs on Mark. In the meantime, the class grows beyond Mark's ability to manage it:
Within a month, the class grew from four to fifteen members. My triage skills proved useless in the face of such overwhelming need […] Naturally, the class lost focus. I spent all my energy moving from one clique to another, trying to get them to stop talking, stop teasing each other, stop picking on Wong, stop pulling the erasers out of my pencils, stop drumming on the table (216).
Mark wants to keep Benny Wong from being picked on, but knows from experience this will only exacerbate things. Unfortunately, Mark still inadvertently ends up making things worse. As things continue to deteriorate, Mark begins to learn that the relative freedom of his classroom has its consequences:
[T]he others all agreed that the class worked because it was the one place where they knew they could express themselves without fear of being judged, and I was the one adult they could count on not to play the role of authority figure (224).
However, with Duane's help, Mark also realizes "the most troubled boys need the class the most" (225), which seems to make playing an authority sometimes necessary, just as Mr. Sills and Mr. Jackson said.
In Chapter 20, Mark visits his father, and in conversation Mark begins to question his own motivations in working at the youth facility, especially compared to his colleagues. In comparison to Sister Janet and Duane, Mark's motivations seem shallow, as one exchange with his father brings out. Mark explains that if he can simply persevere through the negative experiences and outcomes without becoming too pessimistic as to the value of the writing class, it will be worth it. His father challenges him, sardonically: "Can you really do that? And not expect some kind of result, or feel it has to lead to something else? More power to you" (228).
Back at the juvenile facility, Mark attempts to let the students choose their own topic, but is unwittingly led into a trap that lets the boys pick on Benny. Mark is embarrassed and angry, and determined to do a better job leading the class. His experiment—involving more structured time—proves moderately successful. At the end of the day, he receives a note from Benny, which encourages him. In the note, Benny relates his understanding of the others who pick on him, as well as his determination to focus on his future. Mark is encouraged by this display of trust and hope.
Mark learns that Francisco has lost his case. The new student, Dale Jones, rejoins the class, but the students have difficulty focusing: Francisco's predicament has left them uneasy about their own fates. However, after some prompting by a female security guard, Ms. Brigade, the inmates begin to write. Duc and Dale Jones both offer significant essays and stories. Francisco is obviously still despondent, and has difficulty focusing on writing, which seems useless to him. However, Francisco thinks about his brother, and writes to communicate to him not to follow in his footsteps. Later, Duc describes his early days in the facility, while Dale writes a longer essay about his feelings and reflections. Dale's writing describes his anger and frustration with being incarcerated: "Deep down inside this angry person awakens. Another day facing perpetual incarceration behind no mercy walls, as we are inmates […] But living in darkness for so long, you're taught not to express certain emotions" (251). Mr. Sills, who had previously vouched for Dale, questions him about his writing. When Dale reads it for him, Mr. Sills responds positively, saying to both Dale and Mark, "I like those results" (252).
These chapters bring to a head some of the running conflicts throughout the book. These conflicts include: Mark's somewhat selfish motivations for participating in this class, and its value as a whole, in the face of the students' impending jail sentences. Mark is forced to confront his own weaknesses as an educator, and within these, the ambivalence of his commitment to his students. The departures from his class, and the subsequent influx of new students, changes this: Mark has trouble keeping new students in line, and the class as a whole suffers. True to the warnings given by Mr. Jackson and Nathaniel, many of the young inmates take advantage of Mark's relaxed manner. Eventually, Mark realizes that he is obligated to prove students discipline, if only to allow them to express themselves better; this point seems paradoxical, but speaks to the problem at-large. Elsewhere, now that Mark has allowed himself to consider the shallowness of his initial ambitions, he begins to take the conduct of his class more seriously, and with greater responsibility. As he sets firmer guidelines, he begins to notice talent and hard work manifest in his students' writing. Benny's note at the end is the symbol of Mark's growth as a teacher: by realizing he is the "buster" who is constantly taken advantage of and disrespected but can still grow and mature, so can his students.
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