BTW, Chuck knowing that Victoria is a whore shouldn't be a surprise if you recall Edwin's conversation with Abel:
Abel:
"By the way, have you ever wondered if he knew your mother?" (...) "How many videos did she shoot? How big do you think the porn industry of Morehead Hills is?"
Which again paints Victoria
as a selfish woman.
The thing is Grace didn't
"cross the line" or
"messed up" as far as Chuck is concerned. So far the only "bad" thing she did was threatening Victoria that she would tell the truth about her (so it wouldn't even be slander/defamation but a simple truth),
the question remains whether she would have gone through with this and tell everyone that Vicky did porn or if she was bluffing hoping that Vicky would be persuaded. This question can only be answered by TD but until proven otherwise Grace did (almost) nothing wrong.
More importantly though, the reason why I say that Chuck favours Grace over Ian is this bit that you've mentioned yourself:
"When it comes to small favors, I always listen to my little sister's requests. You should pick up the phone when she calls, lad."
and this one:
"That's your mother and my sister, lad. Be more respectful."
I'm pretty certain that if Chuck thought that Ian working with his father was Grace's wish and not her husband's he would have tried to persuade Ian himself, although it's clear we see this scene differently (you see it as some gentle request, I see it as a strong suggestion).
What makes me think that? It's really simple, Chuck is a sick fuck and he considers whores human trash (but not only whores, anyone mundane is human trash for him) and in general has no scruples. Some examples that show that:
1) Using a whore as a piece of furniture (when he was playing go -
"Fine memories on the back of others' hardships").
2) Letting patrons beat whores bloody or worse (that was the case with Grenier who raped one of the house girls with a beer bottle which injured her significantly).
3) He doesn't even know whores' names (they're just whores to him).
4) He wasn't too happy when Edwin asked him to give Emma a night off. He also called her a bitch and later stopped himself from calling her a whore (
"why do you give a damn about one of the wh--") even though he knew what Warren did to her.
5) He didn't give a shit about Rose and the only reason he decided to help her was because Olivier roughed him and Ian up.
6)
"Charles Kohler made a fortune on war profiteering, bribery, falsification of documents, state-sanctioned smuggling."
7) His "disgusting dealings" (as said by a nazi, so it must be pretty bad) with golf instructor, bowling teacher or shuffleboard coach also suggest that Dr. Charles doesn't have any empathy towards people (other than those closest to him). He
broke them permanently (we can only imagine what that might mean).
Chuck might also be a war criminal and at the very least he has no problems associating and joking with war criminals (that COO of Hoarfrost Risk Managment)
so excuse me if I find it hard to believe he would even consider what Grace did as "crossing the line" when that line for Chuck is a light year further.
Why would he think that, what's your reasoning for that? Chuck creeps Victoria out and the only interactions he had with Victoria (that we know of) were of the awkward kind. And knowing that Chuck knows what Victoria did, no way in hell does he think that she was a better mother figure to Ian than his beloved sister. Chuck literally said:
"you know she truly loves you right? I wish you two could get along" to which Ian replies
"Maybe we could, if it wasn't for Dad." which suggests that Ian also loves her but it annoys him that she doesn't let him do what he wants (like Chuck does or
Vicky).
That is somewhat true and I'll get into that but let me recall this line first:
"Honestly, it's my nephew. Having no children of my own, I have a soft spot for Ian and he asked me to hire you."
The phone call in the prologue suggested they haven't spoken in quite a while and that formal "Sir" spoken towards Chuck also suggested that they weren't that close. Chuck liked Edwin and was his
"mentor" but the fact that they haven't been in touch the moment Edwin lost contact with Ian suggests that (there's also "
It's so good to see you, lad. It's been quite some time.").
So until 3 weeks ago they haven't spoken in a long, long time. Now they're starting to bond and Chuck sees how much more happy Ian became. That still doesn't mean much because they've barely started interacting with each other. Until their squash game they haven't been much closer than in high school. Also, imagine Ian asking Chuck to let Emma go earlier or to help Rose - do you think he would answer the same way as he answered Edwin?
Regardless, him liking Edwin is one thing, Grace blackmailing Vicky is another. Considering the above (points 1-7) wouldn't you agree that Chuck doesn't give a damn about her? And wouldn't you agree that he considers Grace as someone much more precious to him than Edwin? Personally I don't see how a person like this would even consider reprimanding her sister for what she did.
Nowhere in the game has been stated that Chuck was Edwin's favourite teacher (the word "mentor" was used) and there was definitely no mention that Edwin was Chuck's favourite student. What was stated however is that Chuck always liked Edwin and that he was the only one of Ian's family who spoke to him warmly but the fact is they weren't that close (see my response above).
