[See my previous lengthy treatment]
Many times such giving (money on the street) is enabling substance abuse. What is best to do is to personally take the person out to eat and preach the gospel and Catholicism. Then you know he or she is gettin' both physical and spiritual food.
Our parish -- the priest -- used to tell us not to give to anyone who asks near the church door, for this reason. But the parish distributes food. So there are various ways to assist those who may be squandering resources irresponsibly and to fulfill our obligation to be charitable. In other words there are more choices than:
1) Give to anyone without question.
2) Don't give at all.
Those ain't the only two choices. To care about the giving being most "efficacious" and not squandered is part of charity, too: desiring the best for the person: not that they do things that don't help their sad situation.
Of course you can give the money and not think anything else about it. No one can call that "bad" in and of itself. But I think we can take it further in order to assure that it is put to the best use: which is a charitable thing, not uncharitable.
Homeless shelters operate, of course, on a similar principle. They don't just hand out money: the homeless go there: get a bed, roof over their heads, warmth on a cold night, and food. Thus, nothing is possibly wasted in that arrangement.
Just giving to a guy with a cardboard sign on the side of the road: not so. We wouldn't give someone drugs or a drink if they have those problems. So we shouldn't give them money if there is a plausible likelihood that the money will be traded for same. We can make sure that the person is receiving good things rather than possibly bad ones. And again, that's charity, not lack of same.
Someone asked: "playing devil's advocate here, where in the Gospels does Christ say to get verification before giving alms?"
That's no disproof of anything I'm saying. We can and should use wisdom and prudence in intelligently applying the principle of giving with a cheerful heart and being our brother's keeper. The Bible teaches that we give to those who have need: it doesn't spell out in exhaustive detail how we go about that. As always in Scripture (especially with Jesus) it goes back to our heart's disposition and attitude. I'm not disagreeing with giving itself: only talking about the best way to go about it.
So I appeal back to my example: everything the homeless shelter does is verified to be good, with no bad result from it, which is clearly not the case (in whatever percentage) in handing out money to someone on the street. Also, there are passages in the Bible having to do with wise use of resources, such as the parable of the talents.
The article about John Stossel's opinions doesn't indicate whether he advocates giving in other ways than money on the street (perhaps he does). That's the difference between his analysis and mine. I'm saying, "by all means give, but try to make sure the resources are not abused in the enabling sense."
The article seems to presuppose the false dichotomy I noted above: either give cash to the beggar without question or don't give at all. There are many other choices in addition to those two, to help people in need (homeless shelters being one example of what I am advocating).
Substance abuse is very prevalent among the homeless. See these three articles (one / two / three).
Obviously, it's imperative, if we really want to help these people, to get them into drug rehab, too. It's the equivalent of teaching a man to fish rather than giving him a fish. We have to attack the root of the problem (if it is substance abuse), rather than continually putting temporary Band-Aids on it without resolving underlying root causes.
Someone else said: " if I were that poor fellow, down on his luck, I could probably use the occasional stiff drink."
If not an alcoholic, sure. If an alcoholic, this is the worst thing for the person. Many homeless have substance abuse problems, which is precisely the point. Giving someone like that cash on the street is thus often enabling behavior.