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.
Most times we just have to face the truth about gambling. Because a lot of people just don't realise how dangerous it can be if you become too attached to gambling. I don't loan out money to someone whom I know very well as a notorious gambler, even if it's a family member. If you have something more important to use with money aside gambling I can offer, but the chances of such person using the money you gave them to do something aside gambling would be very low because they would be greedy to want to double the little they have. I'll rather just buy some important stocks for them at home..
You make a point and I agree with you that such a chronic gambler who has not refrained from his unworthy gambling habits will want to rebound to gamble with the money even when had some other things to do with the money as requested because it is no more fun for such gamblers rather than greeds.
Putting OP's term of expression, I will be interested to know what the relative needed the money for and even if I find it excuse reasonable, there is still an extend I will ignore the gambling relative because he needed to learn his lessons with the hardest experience.
Then I know what he/she would need most is food and medications which I can afford to help. Aside that I don't give a damn.