How we cite our quotes: (Chapter.Paragraph)
Quote #1
"I was subject to fits of feeling unworthy, somehow deeply at fault." (2.13)
We never learn why Jack feels this way, so we can probably assume that it's an internal thing, brought about his circumstances or his anxieties rather than someone telling him he's a bad boy.
Quote #2
"To her, I was just another boy doing some dumb boyish thing. But I began to feel that she knew all about me, and that a good part of her life was now given over to considering how bad I was." (2.14)
Interesting that Sister James—who never really lands on Jack the way Dwight and other people do—can elicit the biggest feelings of guilt in him. He feels worse about what Sister James thinks about him than anyone except maybe his mother.
Quote #3
"I was a thief. By my own estimation, a master thief." (7.18)
This is the opposite of guilt: it's pride… a complete lack of guilt. Could that maybe be his attempts to turn his guilt around and make a viable identity with it? "Master thief" sure sounds cooler than "shoplifting punk," which is probably a lot closer to the truth.
Quote #4
"Even more than his anger, his righteousness scared me to the point where my stomach cramped up." (9.14)
"Righteousness" can possibly be translated as "willingness to blame Jack." That may suggest that Jack is less afraid of guilt than he is of getting blamed by other people… regardless of whether or not he did what they accuse him of. (Though in this case, he kind of did.)
Quote #5
"Dwight's bill of particulars contained some truth. But it went on and on. It never ended and before long, it lost the power to hurt me." (11.20)
Blame, it seems, can only go so far in Jack's world. If you use it too much, it just rolls off his back. That may be part of why Sister James' occasional "disappointment" hits him much harder than Dwight's constant badgering.
Quote #6
"In the past, I had been ready, even when innocent, to believe any evil thing of myself. Now that I had grounds for guilt, I could no longer feel it." (15.11)
Again, the guilt fails to seep in after being applied so thickly.
Quote #7
"One night he kissed me, or I kissed him, or we kissed each other. It surprised us both. After that, whenever we felt particularly close, we turned on each other." (18.17)
Here's a little pre-teen homophobia to spice things up. The fact that Jack isn't sure who started the kiss means that the boys can side-step their guilt by blaming the other boy.
Quote #8
"When I think of Chinook, I have to search for the faces of my friends, their voices, the rooms where I was made welcome. But I can always see Dwight's face and hear his voice." (25.15)
We're more "blame" here than guilt, but the message is still clear: when the blame gets through, it does more damage than all of the good times and good feelings of his teen years can overcome. It stays with him forever.
Quote #9
"I knew that Mr. Bolger would see through me and be disgusted." (26.8)
Here's another case where a religious person, soft-spoken and not especially inclined to throw his fists around, ends up causing more guilt than Dwight and his thumpings ever could.
Quote #10
"I didn't need to see the tears in Mr. Welch's eyes to know that I had brought shame on myself." (26.42)
Jack distances himself from Mr. Welch's reaction here: he knows what he did wrong and he can feel bad without seeing any tears. Could this be a kind of self-empowerment, a "nobody makes me feel guilty but me" kind of thing?