#which makes s6 contrast SO starkly imo like sorry ms gamble but you were trying to do To Much in one season and lost the plot

[angelsdean]

DEAN Well, whatever. Something turned him into a monster. And you know if you woulda taken out the other one there'd be one less to worry about. SAM I'm sorry, all right? I hesitated, Dean, it was a kid! DEAN No, it was an "it". Not the best time for a bleeding heart, Sam.

Once again, random line at the start of the episode that on the surface level paints Dean as overly-callous, isn't actually abt the person they're talking about and is instead abt Dean's own internal turmoil over what John told Dean before he died, as is the thread throughout this entire episode (and the season at large) which will be made explicit by the end of the ep (and into the next) when dean finally reveals what John told him he'd have to do.

For weeks (months? -- how long has it been at this point) Dean has been grappling with the knowledge of what John wants him to do. He's trying to reconcile with it, trying to understand a world where he could follow through with John's request and actually kill Sam. We know from 2x03 Bloodlust that Dean's already started questioning John's brand of monster ethics. It's Dean, not Sam, at the end of that episode who reflects on the case and how that applies to their lives and their job and it's Dean who wonders how many monsters didn't actually deserve to die. Sam just sweeps it under the rug and gives John the benefit of the doubt, saying he was doing "the best he could," while Dean feels torn up about the whole thing. What John taught them is no longer enough, not when he's got Sam's life in his hands. Not when he has to determine when his own brother is past the point of saving. And the parallel storyline with Gordon and his sister shows us that Dean wouldn't be able to do the same.

Now, in 2x09, we see he's still grappling with this issue. When it comes to monster ethics on this show, it can get dicey. Both brothers flip-flop a lot, depending on the situation, sometimes they fall back on what John taught them, but they both also have their own separate codes they follow. John's brand of monster ethics was very much = a monster is a monster is a monster and shoot first ask questions later. Dean's brand of monster ethics is: a monster is someone (can even be human!) who preys on and kills innocent people. Sam generally I think believes this too, but! he is prone to sympathizing or not sympathizing with certain monsters depending on how he personally relates to them. Max in 1x14 got his full sympathy because Sam related to him and saw him as a victim, whereas Simon in 2x05 gets very little sympathy from Sam despite also being one of the Special Children because Sam is already convinced that he's the "bad guy."

Anyways, point is, while Dean does "shoot first" in the scene they're discussing above, he does it because he sees the man harming his wife. Hurting an innocent person = monster. He's also grappling with the Sam and John stuff. He's questioning his father's ethics but also wondering at what point will Sam stop being his brother if he were to "go darkside." So he's working out these feelings by talking about other people. "It was an 'it'. Not time for a bleeding heart" is more about him telling himself that, in my opinion. It's him trying to convince himself to not let his heart get in the way of his job. Because Dean cares so much. Because Dean is often thee bleeding heart being forced into impossible situations by the narrative. He's always letting himself be vulnerable to hurt and loss. And he knows IF it ever gets to the point where Sam is the thing that's hurting people, he'll still struggle to kill him. So he's telling himself now, letting John's "wisdom" speak through him, to not let his heart get in the way.

But we know, we know it's just words. Because later in this episode when they all think Sam is infected, he can't go through with it. Would rather die himself (and right the "wrong" of him even being alive in the first place) along with Sam than kill his own brother.