If at the end of the day he is really stuck and in need (regardless of the causes), and you are able to help him financially, then yes you should. However, you can put pressure on him to work by reducing the assistance a little such that he realizes it’s serious. So don’t stop completely helping him out, but do so in a way that pushes him to work. But at the end of the day, as long as he is in need, you should help him out. Allah will reward you and compensate you for that.