First of all, Dean initially wasn't planning on giving Sam the Lucky Charms. He knew Sam would want them, so he lied and told Sam they were out.
I’m not criticizing Dean. He hadn’t had any yet, and the implication is that Sam had. He didn’t want to deal with Sam being difficult, so he hid the box for himself. Something parents and older siblings do all the time when they have a
So Dean wasn’t going to give Sam any damn Lucky Charms, although he knew Sam would want them. But Sam found out, and gave Dean puppy dog eyes, and Dean caved.
Does that mean little Dean is unable to say “no” to the puppy face? (“You know, my brother could give you this puppy dog look, and you’d just buy right into it.”) Little Sam certainly seems to think that his puppy dog eyes will do the trick. Maybe this has happened before?
Maybe young Dean can’t say “no” to adorable little Sam. Is that why he hid the Lucky Charms? On the other hand, we see a few years later, in a AVSC, that Dean has no problem screaming in Sam’s face when Sam brings up their mother. He's not moved by Sam then. But of course, Dean is torn between Sam and John. Sam is asking questions. John doesn’t want Sam to know the answers. Dean’s lashing out is in part about feeling trapped between those two very willful individuals, and his loyalties to both of them. Maybe it's different with the Lucky Charms, where John is out of the picture.
But maybe Dean can say no to Sam's puppy dog face. Maybe what’s going on in is more complicated. Maybe Dean hands over the Lucky Charms not because he can’t handle Sam’s cuteness, but because he knows if he doesn’t Sam will badger and badger and badger him until he does. We all know what Sam’s like. If child Sam wanted something, he went after it. To quote Dean himself, “You’ve always known what you want. And you go after it. You stand up to Dad. And you always have. Hell, I wish I—anyway….I admire that about you. I’m proud of you, Sammy.” Perhaps Dean's choice was about anticipating a war that Dean wasn’t up for fighting.
If Sam wanted that cereal, he had to fight for it, like he had had to fight for everything else in his life, from knowledge of the supernatural to acting in a high school play to going to college. Lucky Charms was far from something that was good for Sam or that he needed, but Sam as a young child did not know that. And Sam as a young child could not trust the older child and adult in his life to get him what he wanted and needed. If Sam wanted it, he fought for it. He was five. He couldn't distinguish between "something I actually have a right to" and "more than my fair share of cereal".
In this light, Dean’s choice is not one of sacrifice or selflessness. It’s a move of pure exhaustion. I cannot deal with this kid today. It’s the act of a parent who doesn’t discipline their child because they are fucking tired - except Dean isn’t a parent. He’s a ten-year-old. He’s a little boy trying to be the good soldier and mature man his daddy wants him to be.
And Sam was a child who only got his needs met when he fought for them. And so he fought for them. Every damn second of every damn day.
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