The Trent thing is an addtional bit later on. Tybalt starts out saying the appropriate response is to sue MC, and that he's only been holding back until now because of Jill. He later adds that Trent thinks they should sue MC. But its very clear the lawsuit is coming from Tybalt, and that Trent is gung ho for it.
That's not how I read it. After listing a litany of crimes (some real, some bullshit):
Tybalt: "The only logical way to combat this is to press charges."
Jill: "No, Tybalt! Don't you dare do that to him."
Tybalt: "See, I knew you would side with him and that's why I've been holding back."
Tybalt: "All because of you."
Jill: "And I thank you for it. You're doing the right thing."
Tybalt: "But I talked to Trent and he's not as noble as I am. He says we should press charges."
Jill: "Trent said that?"
Tybalt: "Yes, he's adamant and very petty. So extremely petty! I was shocked!"
Jill: "Let me talk to Trent, I'm sure we can come to an understanding without lawsuits."
Tybalt: "I can handle Trent for you. He'll listen to reason, if I really explain it to him."
I love how Tybalt says that Trent can be extremely pretty. Does that mean he knows his own actions are petty. Does he look in the mirror each night and each morning and cry about what a loser he is? I hope so.
It doesn't seem to me the reaction that any ordinary person, even more so Jill as she was described to us, would have when faced with blackmail.
If Tybalt was the problem, why wouldn't she talk to the other Preps?
Then again, it could be that I don't want to give in to the fact that she's been turned into a complete imbecile eh...
I think Jill honestly believes that Tybalt thinks he's helping her by trying to remove the bad influence that is the MC, and she in turn is trying to help the mc by accepting Tybalt's help.
I don't think Jill thinks Tybalt is blackmailing her. She's a little simple...