Quote 64
I worried about it for a moment as I held the bottle by the neck, but I wanted to trust her, and so I did. I took a minor sip, and as soon as I swallowed, I felt my body rejecting the stinging syrup of it. It washed back up my esophagus, but I swallowed hard, and there, yes, I did it. I was drinking on campus. (52before.7)
Pay close attention to how Miles describes his first moment of rule-breaking by drinking on campus: he's worried, takes only a teeny sip, rejects it, and only through great effort on his part does he successfully violate the rules. We can see this instance as representative of how Miles feels about rules in general—he doesn't particularly like breaking them, but he can do it if he needs to, especially if that need involves social acceptance. Think about whether his stance changes as he progresses throughout the book.
Quote 65
The nice thing about the constant threat of expulsion at Culver Creek is that it lends excitement to every moment of illicit pleasure. The bad thing, of course, is that there is always the possibility of actual expulsion. (3before.115)
And here Miles explains quite clearly why he breaks the rules: it leads him closer to his Great Perhaps. Also, it's fun. But the reward also has its risk, and the risk comes to a head when Alaska takes one risk too many.
Quote 66
The Eagle looked at me. He was crying, noiselessly. Tears just rolled from his eyes to his chin and then fell onto his corduroy pants. He stared at me, but it was not the Look of Doom. His eyes blinking the tears down his face, the Eagle looked, for all the world, sorry. (thedayafter.23)
We can only imagine what sort of thoughts and emotions are running through the Eagle's head as he announces Alaska's death because we're stuck with Miles as a narrator. It wouldn't be out of the question though, to think that the Eagle, much like Miles, feels responsibility for Alaska's death. If only he had been stricter, if only he had meted out more punishment, if only… To what extent is the somewhat lax enforcement of the rules at the Creek responsible for Alaska's death?