As I read more of Joseph Telushkin's A Code of Jewish Ethics, Volume 2: Love Your Neighbor As Yourself,
 I thought about charitable giving to beggars and how I have handled it 
in the past.  Telushkin told two stories that caught my eye.
One
 story was about how Rabbi Shmuley Boteach gave a dollar to a beggar, 
even though Rabbi Boteach suspected that the beggar might use that money
 for alcohol.  Rabbi Boteach told the beggar to use the money for 
something good, and Rabbi Boteach said that the beggar was too smart to 
spend the money on alcohol.  When the beggar left and Rabbi Boteach's 
family asked why Rabbi Boteach gave money to the beggar, when the beggar
 was obviously going to spend it on booze, Rabbi Boteach responded that 
he had compassion on the man because the man had been reduced to 
begging, and that he was attempting to respect the beggar's dignity by 
talking to him as a person.
Another story was about a rabbi who 
was collecting money to buy wood for the poor so that they could be warm
 during the winter.  When the rabbi came to a rich guy's house, he made 
his request to the rich guy----and he made the request quite 
lengthy----while they were both standing in the cold right outside of 
the rich guy's door.  The rabbi's purpose in doing this was so that the 
rich guy could see what it is like to be cold, and thus the rich guy 
would give more so that the poor could keep warm during the winter.
When
 I lived in Boston, New York, and Cincinnati, I came across beggars.  
Many times, I've ignored them.  Many times, I've given them a little 
money so that they'd get off my case.  Sometimes, I would add to my 
giving a little sermon to the beggar about how he should be looking for 
work and not spending money on alcohol.  Many times, I've bought beggars
 a meal.  In doing so, either I order it myself, or I watch the beggar 
order it, making sure that my money is being used for food rather than 
booze.  And then there have been times when I have bought the beggar 
lunch and sat down to eat with him.
I probably sound 
insufferable.  I mean, if I were reduced to begging, I wouldn't want 
someone giving me a little sermon about how I should work and not drink 
alcohol.  I wouldn't want someone monitoring me to see that I bought 
food rather than booze, as if I were some kind of criminal.  Probably 
the best thing that I did was eat with the beggars and talk with them 
like people rather than as objects of my magnanimity.  My problem with 
that, however, was that then some of them would try to hustle me for 
more money.
I remember when I was walking with a friend one snowy 
Thanksgiving, and my friend bought a newspaper from a homeless person.  I
 scoffed at what my friend was doing, but my friend replied, "Look, that
 guy was standing in that blizzard!"  The lesson that I learned from 
that is that, whether a beggar is from the "worthy" poor or the 
"unworthy" poor, he still does not deserve to be standing in the cold.
I've
 appreciated some of the lessons that I've learned from beggars: about 
trusting in God to meet one's daily needs (as beggars, of course, wonder
 where their next meal will come from, and one of them told me that God 
provided), and about what it's like to be homeless and to try to find 
work.  One time, I gave a beggar money to buy a sandwich.  I asked him 
what kind he wanted, and he replied that he desired a large sandwich.  
So I have him money for a large sandwich, and he requested a small 
sandwich while pocketing the rest of the money, right in front of me!  
At the time, I was upset that he saw me as a chump, even though I didn't
 say anything at the time.  Nowadays, I don't blame him for trying to 
save money and to make it go further.  I try to do that myself.
 
 
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