It is not going to help if you tolerate him and you still lend him some money even if you understand the situation and it's okay for you that you have the idea that guy might not be able to pay.
It is not compassion if you're going to help him get some money so that he can continue to gamble. A real friend won't tolerate that but instead will educate the addicted gambler to stop it.
Whether he'll get love or hate from that addicted gambler, at least you have expressed and said the right thing to do.
If I was a friend to an addictive gambler and I am in a shoe to advise them to stop gambling, I won't hesitate or stop doing that at any minute I got the opportunity to do so. I have oftentimes try to relate the addiction of gambling to that of drug abuse, permit me if that's not true in your opinion, hence it's very difficult to survive it whenever you're an addict.
I have a friend who was a drug addict and another one who was an addict in gambling. The only difference between them was that the gambler was able to leave gambling in the long run, whereas the drug addict had to pass through rehabilitation before he stopped but they almost behave the same. Like, when they are broke, they still try to go into the practice even when it will require them to borrow money from people around them. And even after they have promised to stop, they can still hide and go back.
So, if I was a friend to an addicted gambler, I won't stop to advise and encourage him to stop, part of which is denying him the funds to play the gamble even when I have it.
We shouldn't tolerate friends like them because we're not helping them at all. I know that some friends really have soft heart and they can be taken as advantage by that addicted gambler.
If you can't help yourself but to help them still, give them food or anything in kind but not money because they will reason out that they need this and that.
But in reality, they're only making a reason so that they can still have funds to gamble. You know, an addicted gambler will do anything in their capacity and reasoning.