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.