Even he's my friend, I'll not give any single cents to him/her. It's his fault and should face the consequences of being aggressive in gambling. I don't have a problem with gambling but I have problems with those people who keep wasting their funds. They don't have discipline and control then it's not my problem and it'll serve as a lesson for them.
The first loss should be the first and the last mistake, slap him into the reality that gambling isn't really for profit-making. The only people should waste their money on gambling are those luxurious people who think gambling is for entertainment only.
I understand this. But it won't really hurt you to help once and tell that person to change or try to be a better person. At least you warned and reminded him so he knows there won't be a second chance of help from you.