Most of the time when I'm walking through the City I am approached by someone looking for money and from my last experience, they are getting very creative now.
I was in front of Grand Central Station enjoying the beautiful day and the architecture when a man came right up to me and said "Do you speak Hebrew?" I immediately stopped and looked at him. He was, in my judgement, in his late 40's early 50's, dressed casually in a short sleeved polo and jeans pulling a suitcase on wheels. He did not appear to be a beggar.
I responded "No...but I do speak a little Yiddish." He then told me he's from Israel and that he just needed cab money to get to the airport. I gave him 5 bucks, wished him luck and moved along. It seemed a bit strange to me but I let it go until the other day when someone was telling me about the new street begging scam. Specifically how they dress up in nice clothes, carry a briefcase or suitcase and ask for help...
I'm not sure what he did with the money but maybe he found his way to Israel. I hear the street beggars really rake it in over there.