Depends. I don't think JJ was attending coaching sessions or coach sessions. That to me is where most of that happens. I have never heard of JJ being intimate with the coaching stuff. I have no clue how close or far JJ was to any of this.
In my opinion, there is no way that JJ doesn't know what's going on under Monty. I cannot imagine me not being aware of different theories/ schools of thought within a group I manage. I intentionally stay out of the weeds, but I am very aware of what's going on. I don't believe there is a way for JJ not to know what's going on.
I don't have a strong opinion on Young, but I would not be surprised if the assistants were banging their head against the wall screaming for Monty to do A, B, and C, and Monty ignoring them. I can see Monty being a control freak and "going with his gut."