User blog comment:JacobKyleF/Critical Review Proposal: Kai Chisaki (Overhaul)/@comment-24097388-20200109192028/@comment-24097388-20200113013257

It's not absurd though. If Chisaki truly did not care about the boss whatsoever, then he would not be doing any of this to begin with. He's doing this as a way for him to return the kindness that his boss offered him. If Chisaki really didn't care about him, he would have just killed him right there, but instead he decides to put him in a coma. He even says right after that scene that he'll fix him up once he's accomplished his goal.

But just because he respects the guy doesn't automatically mean he's going to agree with everything the man says. He's doing this as a means to bring the Yakuza back into the market, back to their glorious days. So for his boss to tell him no, there's obviously going to be conflict between them.

The problem is that he's clearly mentally ill and because of that, he tends to not feel any sign of remorse or guilt to his actions because emotions are almost nothing to him. That's one of the reasons why he treats Eri harshly. The other is that he despises the nature of her Quirk, but at the same time, sees it as an asset that will help fulfill his goal.