Sometimes it might help to save a friend's life when not having some earnings from real life as well.
I wouldn't do that, I'll encourage him to look for a job instead of convincing him to gamble. I might be part of his misfortune if I'm the one encouraged him to gamble while he doesn't have a stable source of income.
Gamblers that doesn't have stable source of income will literally depend in gambling if they see a chance that they can make it as part of their lives. But I think that's not how it should go, I just can't feel it to encourage one person to gamble if I see the possible result.
Honestly, a good friend should always be there to encourage in doing good things and not something that would affect the friend's life negatively which in this situation is what I am seeing the OP doing if he peradventure ends up or ended up doing something like this.
Not everyone can think straight and there are some people who actually do have chicken brain enough to not be able to think for them-selves, and in a case where you are compelling and convincing someone like that to go the gambling lane is more like purposely trying to push the person in front of a speedy train. Who actually does that, if not a terrible friend?