Whitney

I don't think it's what Chuck is actually capable of but more what he thinks he's capable of. I feel like this situation is going to be one that just spirals out more and more. Once Jack plants the seeds their insecurities are going to spill out and ruin a lot. I doubt Jack says this to Chuck and he's like okay absolutely. I think something else has to push him. Perhaps, Chuck tells Blair about Jack's ridiculous command and she's willing to play along at first. This immediately plants in Chuck's head (maybe Jack says I'm sure Blair wouldn't mind, I've had her before, plays on Chuck's jealousies beforehand). Chuck immediately begins to wonder why Blair would ever consider this. He begins getting paranoid and shuts down on her. Blair is just thinking of scheming but starts to realize this is a bad road. She's still willing to do it for Chuck. She begins to wonder why he would let her though. I think it's a test for both of them. She's testing him. He's testing her. They're both going to fail. Jack is going to win. This is probably why he's going to die.