I empathize with you here because you want to be there for your family and see them grow into the person you think they should be: responsible, ethical, strong, etc. The problem is that people rarely change and in this case you are probably just enabling him by giving him money.
I recommend making him work for any money he wants to borrow from you or your mom. He'll learn there isn't any more "easy money," and you will have done everything you can to help him.
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