Could be wrong about this . . . but I am thinking two things:

1) What would it feel like if he WERE to give you a "special" rate and were not just following the rules that he has for his financial empire for all clients? Would it be possible that you would feel like you then owed him something, and that might be super squicky because that models a dynamic from somewhere in your past?

2) You are such an incredibly competent person and it has always sounded like you are also a competent professional as a lawyer. To offer a lower rate to someone can imply that said competent/well respected professional is not so much. Perhaps he worries that it would feel insulting to offer you a lower rate.

Oops, now I have three things. My social life is full of professionals, and what people charge and whether they do any pro bono or partially pro bono work is very individual. But I do think it ultimately boils down to the professional, not the client. I really respect those who do reduced and no fee cases of all kinds. But I also respect professionals who never do, because I think they value themselves and their time appropriately. Short version of this point, one I think you know-- this fee issue is about him, not you.