Boss is a great, textbook grey character. I often see the term “grey character” applied to characters who are, like... A light grey. Mostly good but had to take one tough decision that the protagonist doesn’t like, but it’s also kind of subjective.
Boss isn’t represented as 100% evil, and yet, has done horrendous things. The scene of her and two other Executioners killing the civilians was nightmarish, and she’s at the origin of this decision... but it makes sense. It bores me whenever someones says something to the extent of Boss bad bad evil ugly bad and refuses to even talk about her, because what she did was cruel, but also revealed her incredible intelligence and efficiency.
In a real-world scenario, what she did would have most likely worked. And if Sagishi weren’t so determined (and Hacker a literal genius), it would have in Akudama Drive. She efficiently put an end to the civilian uprising, and legally got away with what she did.
The first introduction to Boss’ intelligence was her decision to force Executioners to work in duos. She showcases her observation skills, but also her knowledge and understanding of the human mind, by taking a decision that undeniably works and makes sense. And that image of her intelligence is a rather positive one, that makes her appear to care for human lives and feelings.
And is it fair to say that she turns out not to care? She does take the decision to kill a group of innocents, so there is a good chance that she does not. But why does she take that decision? To her, putting an end to this uprising was saving Kansai and its inhabitants. So did she take that decision out of caring for the majority? It’s hard to tell, and I think it’s an interesting conversation to have, so I think Boss shouldn’t be excluded from the conversation just because of the atrocities she has committed.
I mean, I would exclude her if she were trying to have a conversation with me, but being that she’s not, in fact, real-- I don’t think any harm would be done to the victims by wondering why Boss does the things she does.
If I had to give an even hotter take - at that point in time, I personally feel like we have no canonical reason to believe that Pupil is any better of a person than her Boss, as she doesn’t question her orders. So why talk about one, but not the other?