Ali - It may be he has that "blood is thicker than water" attitude about his family. You know, family is family no matter what. You stick with them through thick and thin. Maybe he doesn't want to share the problems with you because he doesn't want to hear your "tough love" answers.
Stopping enabling someone (taking the money away) doesn't mean you don't love them. If you are doing it out of love because it is what is best for them. Once they are standing on their own two feet again they realize it was out of love.
I hope he can one day see he's not doing them any favors.
