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...why does it bother you so much?

FWIW, I'm avoiding making any value judgments. The fact is, it does bother him. And it's his estate to leave to whomever he chooses. Notice in the subject heading the use of the word "angst". So, to be fair to him, it does bother him. In fact, it bothers him in TWO ways. First, enabling what he considers irresponsible behavior. And, second, unequal disbursement because he still loves his son despite everything that has happened (or at least, it sounds like that is the case).

It sounds to me like this is the "Goofus/Gallant" psychology conflict.

Plus we don't know why he was in prison. Drug use? Assault? Murder? We have no idea (and it's none of our business). If it were me, the reason for the imprisonment would affect my attitude. If he was in for rape? I wouldn't leave him a dime (for example).

I don't think there is a right/wrong answer. It's just right or wrong for him, and it seems both options are right AND wrong, hence the "angst".

I'm just being a sounding board. Giving options. Not trying to make value judgments for him because I think his values are different than mine.
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