Sorry this is late. I wanted to take some time to look over the first version so I could see where you made changes and had a full MS dropped in my lap this week and yeah, I have more excuses, but you probably don't want to hear them. On to the evil critique!
Thoughts While Reading:
I don't remember you using blurbs to start your chapters before. Is this something you are going to do every time? Otherwise it is going to look odd to do it here.
By the thieves actions (kicking a leg and tugging at his boot), I would guess they either were planning on waking him or not very bright and I am leaning towards the later at this point.
You're ruining the irony of the situation (a kid trying to threaten Kale) by over explaining it. By the end I wasn't smiling, I was going "I get it already, move on."
"But he had to do it; there couldn’t be anyone left to reveal his position to the patrolling Helmsmen."
What about the parents watching?
He didn’t look used to pulling a knife on someone, even if he had the mouth of a mercenary.
You already showed us this, so you don't need to tell us.
There is no way I am buying that he didn't notice a hood sown into his neck before the jailer mentioned it. I mean, your neck really isn't all that thick (that's were we trach people for a reason) and it is mixed into the whole breathing and talking that he is doing now without any apparent difficulty.
I like how he ripped it open, but immediately following that I need some indication of his surroundings. How much can he see? And if he is wandering around there for days, is he in a barred cell where he can see out to a hallway or other prisoners or is it stone or something else? Is he trying anything to get out? And where was the jailer hanging out this whole time they were talking, because if he's in the cell with him I'd guess it would get violent a lot sooner.
Okay, unless he is trying to stay awake on purpose, he's going to fall asleep at some point and it would probably be better for him if he had.
No, I won’t kill for the sake of it, I won’t.
Since when? It thought that was what Kale did best.
I liked the last bit of dialogue with the jailer.
Overall impression:
Well, I am not going to give you too much grief about your overall plot or Kale's characterization or any other issues I usually bring up in your work because I don't know where all your rewrites are and such, but just focusing on this scene, there are some improvements. You seem to be trying to get inside Kale's head more and work out his motivations which is very good step to take to make him more sympathetic (if that is what you want), but I wouldn't put so much of it or at least try to organize better so it flows and doesn't contradict itself within the same scene as others had said. Grammar/punctuation needs a look over, especially around the dialogue. I am curious about the jailers, but I am a bit confused by some of their actions/methods, so I want their reasoning to be good and I want to know at least some of it soon. Keep working, it
is getting better and has some really good moments.