Rosh Hashanah — giving even to the undeserving

By Bryan Opert

We all pray to be given a good inscription on Rosh Hashanah (while fantasizing about the brisket and creamy parev ice-cream.) 

What secrets have the Sages given us to achieve this?

We are bombarded all day by people collecting charity, whether organisations or beggars. Many of them appear to have dubious claims. 

The Gemara says that we must also give to those people who collect money as if they are poor, since if not for them we would be punished for not giving charity. Bizarre! How can giving money to those who don’t deserve it be considered a mitzva? The answer that is given, is that these people create the ultimate challenge — we can all ‘slip out’ of giving charity, even to the needy, by using these tricksters as defense of our stingy behavior. How many times have people not given because ‘the beggar will only use it on drugs or booze anyway’? 

Jeremiah even davened to Hashem that He should only send unworthy beggars to the people who persecute him. Rav Zushya of Anipoli asks how could Jeremiah who loved and cared so deeply for humanity ask for such a terrible thing from Hashem?

He answers that Hashem pays us measure for measure. If we, who were facing destruction, would act mercifully only with people who really deserved help, then Hashem would also only save those people who really need it. What then would become of the sinners who persecuted Jeremiah? His solution was to have them give charity to undeserving people, this way he can daven to Hashem that just like they pitied undeserving people, so too Hashem should pity them. This shows true love!

We don’t want Hashem making ugly faces when we come around asking for something, so why not show Hashem that one need not be deserving to get a smile and some change from us?

It would be foolish to look at someone and judge their integrity. Somehow, I don’t think we’d want to switch lives with anyone who ever came to collect. Wouldn’t it be foolish to not give a little, to everyone who asks, on the off-chance of missing out on a great mitzva? Look at it as investing. If you give 10 times, even if nine are a waste of time, the 10th can be worth millions! Sounds like a great investment to me.

May we all be blessed with a year of blessing to be able to give.

• Published in the September 2022 Rosh Hashanah Digital Edition – Click here to read it.

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