I find A’s listing of propositions a bit robotic. For easy reference, I’ll list them again:
(1) it is morally required to give to beggars and immoral to refuse; (2) it is morally salutary to give to beggars, but it is not required; (3) it is morally neutral to give to beggars; or (4) it is morally wrong to give to beggars.
The easy one missing would be: whether it is morally salutary or not to give to beggars changes with time, place, and circumstance. Those old Greeks offer us a way to navigate the arguments offered by A and Bill Goodwin. Plato would say, would he not, that it would be unjust to give to someone anything that would further enable him to harm himself? Donating change or a few bills to the random vagrant who is sure to use said donation to further his substance abuse problem would be morally repugnant. If, on the other hand, the money enables him to nourish himself or is part of a cumulative effort on his part to become a more self-sufficient member of the community then it would be morally salutary (and good for the city, by the way). In other words, donating money does not, ipso facto, contribute at all to his freedom to choose—it can, in fact, do the opposite (giving money to a drunk enslaved to his passions will merely further his enslavement).
I would add that the argument made by A along the lines of: he’ll find the money elsewhere for his habit (whatever it may be) is a complete non-sequitur from the standpoint of the morality of the giver. One’s active participation in the homeless person’s self-abuse is the moral center of the situation; i.e., one’s contribution to or facilitation of self-destructive behavior is what matters, morally speaking.
The morality of the entire enterprise, then, comes down to one’s judgment on whether or not it is fitting to give money to the bum. And in so far as it is nearly impossible even for the most empathetic and perceptive of us to be able instantly to judge the intended use of the panhandler’s gains, I would have to say that in practice the random toss of change or bills into the cup must necessarily only be good by accident, and thus can only be moral by chance—that is to say, not at all. To be sure of the morality of donating to the panhandler would necessitate more interaction and involvement than can be expected in the drop of change by the passerby.
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