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Ironically this chapter is proof enough for me that Guwon isn't some secretly evil dude that just puts on a mask, as some of us theorized. He cried because he believes he's responsible for the outcome of the trail by not being strict enough with his society. He didn't kill out of joy, he killed because that was his job and the people voted for it. His tears were real and he felt empathy is what I think. This honestly made me like him even more because he did what had to be done by fair voting yet he felt sadness over the outcome. I think teacher twink will be some sort of catalyst for Guwon to eventually change the system of the town - but teacher twink will quickly realize that being good in a bad world only makes things worse in their world.