Well I don't know how this question will look like but I have to ask, because I need people's ideas in this situation that am in right now.
So here is my question, If you have a family member or a friend with gambling problem, as in he or she is so addicted to gambling to an extend what he or she thinks about is nothing but gambling, if he or she ran into financial problems and come to you to loan he or her money. are you going to loan the person the money?
Remember it's tough for a family member and a friend to watch their person with gambling problem run into financial problems and refuse to help.
And am also having this thought that if you bail a family member or friend with gambling problem, that they don't have to face the financial problems and they will continue to gamble, adding to future problems.
You are talking about a difficult situation with your family. I would try to help him quit gambling and leave his addiction behind because I would not want to let someone I am close to end it on their own. I would help him meet his basic needs financially but I would never give him cash to gamble with.
The cash you give him will be of no use, it is impossible for your cash to come back to you and you are not helping the person you are close to. I would also refuse if he asked for a loan, no matter when.