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The real issue is that Monty is stuck in his childhood, and he doesn't know it. Everyone comes to a point in life, where they need to stand up and be their own. Monty failed to do this when he was 18. Now, he is still exhibiting a childlike behavior by measuring his success by emotions. This is a dangerous road, and many people are taken heavy meds for they have never found happiness down it.
If I were a Division I school coach, and I read what Monty said to J.O. about feelings, I'd pass on him in a heart beat. My guess is Monty will be heading to a division II school, and he will regret his decision. Live and learn! But, there's a lot of common sense from the collective human experience that is sound and worthy of reflection in one's personal life.
Selfishness in this case is wisdom; you must learn to take decisions into your own hands at the proper age and find a place where you are at ease.
Montgomery has exhibited considerable unease through most of his time at Cal, at least from up-close, according to several sources, and it seemed he was paying out his parents' wishes rather than following his own. This is the biggest step in a kid's life, to gain his independence and the confidence to follow his own path, regardless of the disapproval it brings.
As for Division II...uhh, no, I can't see a starred recruit landing at California of Pennsylvania. Montgomery has a good shot to land at Oregon or Washington, maybe even the Florida schools. He is still well-regarded and could very well make a difference at a strong Division I school.