The test is to offer to take him to a restaurant or buy him food in a supermarket on condition that he give you all of his cigarettes. If he agrees (and he might not – my grandfather a”h once offered to take a beggar to a restaurant and he said that he wanted money) and then you see him smoking again he is probably not deserving (although you never know – maybe someone gave him cigarettes). This, BTW, is also true regarding wearing nice shoes, etc. Maybe someone gave them to him. However, if one’s tzedaka ability is very limited IMHO he should pick and choose his beneficiaries.
