Ahaha, um... That's actually kind of complicated, because the simple answer is definitely NO, nope, not even a little bit, he deserved it, nope.
Buuuuuuuuuuut nothing is ever black-and-white, so of course the simple answer isn't really a proper answer.
Does he feel sorry for Pitch, specifically, the guy that tried to kill Sandy AND Baby Tooth? No. That ship sailed about the time Pitch did that whole 'cold and dark' speech in Antarctica. Jack's worldview is very much 'we protect the kids = good, he tries to hurt the kids = bad.' While Jack totally understands the necessity of fear a heck of a lot better than the other Guardians (and why does it always feel strange to try to swear when I'm using Jack's journal?) because fun can be really scary sometimes (think of roller coasters or haunted houses or really awesome sled rides), Pitch took it too far and his fear was hurting people. So Pitch needed to be gone and ten minutes ago, at that.
But. Together with the 'fear is necessary' stuff, Jack also knows pretty darn well what it feels like to be forgotten. Getting walked through is not on his top ten list of ways to spend an afternoon. That, poetically enough, he wouldn't wish on his worst enemy, even if that enemy is Pitch. So while he knows it's the only way to keep the kids safe, it still doesn't quite sit right with him.
So yes, short answer, NO! Longer, more tl;dr answer, he doesn't feel bad FOR Pitch, but he does feel a bit bad.
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I feel bad for Pitch. Does that count?Ahaha, um... That's actually kind of complicated, because the simple answer is definitely NO, nope, not even a little bit, he deserved it, nope.
Buuuuuuuuuuut nothing is ever black-and-white, so of course the simple answer isn't really a proper answer.
Does he feel sorry for Pitch, specifically, the guy that tried to kill Sandy AND Baby Tooth? No. That ship sailed about the time Pitch did that whole 'cold and dark' speech in Antarctica. Jack's worldview is very much 'we protect the kids = good, he tries to hurt the kids = bad.' While Jack totally understands the necessity of fear a heck of a lot better than the other Guardians (and why does it always feel strange to try to swear when I'm using Jack's journal?) because fun can be really scary sometimes (think of roller coasters or haunted houses or really awesome sled rides), Pitch took it too far and his fear was hurting people. So Pitch needed to be gone and ten minutes ago, at that.
But. Together with the 'fear is necessary' stuff, Jack also knows pretty darn well what it feels like to be forgotten. Getting walked through is not on his top ten list of ways to spend an afternoon. That, poetically enough, he wouldn't wish on his worst enemy, even if that enemy is Pitch. So while he knows it's the only way to keep the kids safe, it still doesn't quite sit right with him.
So yes, short answer, NO! Longer, more tl;dr answer, he doesn't feel bad FOR Pitch, but he does feel a bit bad.