depends on his/her history and depends on what kind of connection we have. but generally i will help him with the amount that i'm not expecting to be paid back.
There are so many factors that have to be considered before people start helping someone in the world of gambling. Definitely if you know the individual personally and know he or she is really in trouble, you will try to go even out of way for helping them because it is a social service as well. But if someone is not willing to change and is simply trying to gather money for more gambling, no one would help him.