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.