What I did notice is that he is consistently comparing himself to his younger brother, to a point where he feels very threatened by the mere thought of having his brother end up working where he is working. This challenge began a LONG TIME ago for him.

Often with an obsessive challenge it can be one little thing that someone says that can mean something significant that is helpful. I have found that to be true for myself. Honestly, I am wondering if this goes all the way back for him and he just has not realized it. My older sister NEVER got over the fact that when she was only two years old, a baby herself my older brother came into the picture and took something from her. This has NEVER changed and she hates it when he comes around all these years later.