The Neushipper Zone

In the second game, Boss is framed as this cruel (perhaps a little pathetic) force that kept the ghosts in the office in an effort to not be alone. He's shown to be withholding the truth from them and lying to them about the truth of ghosts and how evil spirits are formed. Mind you, the secret was that good and evil are subjective and your ghostly form, your shadows, are built on your own guilt and your own perception of good and evil.

Brushing off the fact that I feel like this whole thing is super obvious, Charlie also mentions to Boss that Eugene has become his "puppet" and can't think for himself, make his own decisions, and that he just follows the rules Boss made blindly.

Essentially, Boss is antagonized in the second game, he isn't entirely villainized but he's framed in the wrong for keeping the ghosts stuck with him in the office. I'm not saying that it's not a bad thing to be doing, and had it been in character or made a little more sense to who he is in the first game, then I would have accepted it, but my main problem here is that it doesn't.

Let's see what we're shown of Boss in the first game. First and foremost, he's a sap. In the murderer ending, when Eugene sneaks off (directly disobeying Boss' orders and getting the help of Charlie to kill Jack as an act of justice for the kids and their mother), Boss has known Eugene for three days at most and he cries when he needs to seal the boy away.

One could argue that this relates to him and his whole agenda of keeping the office members close to him so he isn't to be alone, but I feel the need to mention that he drove Eugene away from the office once he realized that extended time with them was tampering with his mental state, making him prefer the underworld over the mortal world. If Boss really wanted to keep people close to him so they wouldn't be able to leave or think for themselves, he would've let Eugene stay. He wouldn't have driven him off and he would've let the boy continue to keep seeing them despite the harm it may cause to him.

In relation to this, if this Boss was the same one in CiU, then in the endings where Eugene dies (as a good spirit) then we wouldn't have the choice to choose between staying with the Underworld Office or passing on. Boss would have framed it as if he had no choice and was meant to stay with them.

Even if we take into consideration that Eugene could only stay in the mortal world if it was with the Underworld Office, we need to take into account that, had it not been for the office, Eugene had no reason to stay. He didn't have family close enough to stay nearby, sure he was friends with Luke but at the time they weren't that close, not close enough for Eugene to consider staying just for him.

This also debunks the "Boss' cute little puppet" comment, because he has given Eugene the freedom to make his own choices. Like in the main ending where Eugene breaks Jack's window. Boss had never told him to do that, hell, he never even told him that he could intervene, Eugene figured it out himself. In the first game, Boss is less of the controlling tyrant and more of a silent guide, only stepping in when absolutely necessary.

Now for his treatment with River. Yes, the hitting of the fan is a little iffy, but I view their dynamic as more of a sibling one and as someone with a sister myself, I get it. I doubt it's doing much harm anyway, they're ghosts.

One could argue that Boss gives Eugene all the freedom required compared to the other ghosts because he's the favorite, but there is a moment when Boss comes to River's defense, that being when Eugene called out for River in the subway and Boss reprimands him for calling her to a place that's sensitive to her. When River mentions calling Eugene newbie, Boss indulges in his own way and opts to call him junior.

In the first game, while we don't see much of the ghosts outside of how they interact around Eugene, it's evident that he cares. (Rivers character is also a little off in the second game too, but I'll delve more into her another time.)

Boss and River are also seen to be close, in the monster ending, once more, River is the one who's brought along to deal with Charlie and Eugene. Of all the people in the office, he chose River (I like to think she's also been with him the longest here). Hayden may have not been an option due to his age, but Joan is fully capable of joining him rather than Boss, and yet he chooses her.

Another inconsistency I would like to point out is his backstory. It doesn't quite make sense compared to what he's said about it in the first game?

In the monster of the underworld ending, Boss says this.

Boss states that he died not caring if he breaks himself if it were for the sake of justice, but in the game? He dies in a means of sacrifice. He puts himself into a portal to the underworld because he was told to do so, not of his own decision. I find it strange and rather anticlimactic for this to be the death of Boss in-game. It just doesn't feel right and it doesn't connect fully to what has been established in the last game.

In short, I believe that Boss (much like the rest of the cast) is mischaracterized in the second game. He's far more softer than he lets on, and I do think his character is drastically different depending on the game.

I'd love to hear your guy's thoughts on this though, I'm always open for discussion and it's good to get opinions regardless of if you agree with my takes or not. Thanks for reading, and don't be afraid to talk to me or ask questions!