Photo Credit: Jewish Press

One of the most urgent segments of our Rosh Hashanah and Yom Kippur liturgy is the proclamation we say with great feeling, “Us’shuvah us’filah u’tzedakah ma-avirin es ro-ah hagizeirah – And Repentance, and Prayer, and Charity remove a bad degree.” As we are getting closer to the Judgment Day, it behooves us to arm ourselves heavily with these three ingredients to ensure that nothing unpleasant, chas v’shalom, happens to ourselves and to our loved ones during the upcoming year.

Today, I would like to zoom in on the third of these powerful weapons, namely tzedakah. The Rambam in the tenth perek of Hilchos Matnos Aniyim makes a truly incredible statement. “Chayavim adam l’hizaheir b’mitzvas tzedakah yoseir mikol mitzvas asei sheb’Torah – A person is required to be careful with the commandment of charity more than with any other positive precept in the entire Torah. Wow!! Bear in mind that amongst the 248 positive mitzvahs in the Torah are such heavyweights as learning Torah, keeping Shabbos, wearing tzitzis and donning tefillin. All of these mitzvahs are complex and necessitate supreme precision to fulfill them properly. Yet, the Rambam says that even more care is needed for the mitzvah of tzedakah.


The Rambam then proceeds to prove this remarkable point from the verse describing why Hashem chose Avraham Avinu as the father of the Jewish nation. There the posuk states, “Ki yidativ lamaan asher yitzaveh es bonov v’es beiso acharov v’shomru derech Hashem laasos tzedakah… – I loved him because I know that he would instruct his children and his household after him in the way of Hashem to do charity…” Thus, the Rambam concludes that the number one reason to choose Avraham as our first father is his dedication to tzedakah. This puts the mitzvah of tzedakah on a very lofty spiritual pedestal. Take note that the Rambam doesn’t simply state how important charity is. Rather he highlights how careful we must be to fulfill this mitzvah properly.

Let me shed some light on one of the demands of this lofty mitzvah. The Gemara relates that after the destruction of the Temple, Reb Yochanan Ben Zakkai was taking a walk during a time of severe famine and he noticed a Jewish woman of noble bearing and regal carriage bending down and picking out barleycorns from the dung of animals. Moved by this sad sight, he asked the woman who she was. She answered that she was the daughter of Nakdimon Ben Gurion, one of the wealthiest men in pre-destruction Yerushalayim. She said to Reb Yochanan, “Rebbe, do you remember my kesuvah?” “Yes,” he exclaimed, “you were promised a dowry of one million golden dinarim. My daughter,” he continued, “what happened to all of your father’s wealth?” “He lost it all because he didn’t give proper tzedakah,” was her response.

The Maharsha is quick to explain that Nakdimon Ben Gurion definitely gave charity. The Gemara reveals to us that when he would go to the study hall, servants would roll out fresh carpets for him to walk upon. After he entered the study hall, he would command his servants to leave these carpets behind for the poor to take. Nevertheless, says the Maharsha, Hashem took away his wealth because he didn’t give charity in the correct proportion to his great wealth.

What a scary thought! Many wealthy people comfort themselves with the fact that they give move charity than the average person. At times, their conscience might gnaw at them saying that they could give even more. But their guilt is assuaged when they tell themselves that they give more than their fellow man which by itself affords them ample protection. This Gemara is a wake up call that this is a wrong way of thinking. Nakdimon Ben Gurion certainly gave more than the average man to tzedakah but his daughter was condemned to pick out barley from feces because he didn’t give enough.

In a similar vein, we are taught in Masechtas Kallah that Rebbe Akiva noted that Rebbe Tarfon was not giving sufficient charity according to his ability. Rebbe Akiva approached Rebbe Tarfon and asked him if he wanted to invest in a great real estate opportunity. As you can imagine, any venture that was suggested by the great Rebbe Akiva was extremely attractive and Rebbe Tarfon readily acquiesced, handing over to Rebbe Akiva the large sum of 4,000 golden dinarim. Rebbe Akiva took the money and promptly gave it to the poor. A while later, Rebbe Tarfon asked Rebbe Akiva to show him his investment. He was curious to see what Rebbe Akiva had bought for him; a farm, a vineyard, a bank!!! Rebbe Akiva surprised him by taking out a Sefer Tehillim and showing him the verse in Number 112, “V’tzidkoso omedes lo-ad – Your charity remains forever,” and informed him that this was his investment. And, as the Chofetz Chaim embellishes, the comment about real estate was not a white lie at all. Rather, Rebbe Akiva was helping Rebbe Tarfon invest in real estate in his Afterlife, for charity remains forever. Once again we see that Rebbe Akiva was helping Rebbe Tarfon to give the rightful amount of charity, commensurate with his wealth.

How often there is an appeal in shul and everyone answers with the same one hundred or one hundred and eighty dollar response. It is incumbent upon us to realize that we must give according to our success and not just according to the amount that everyone else is giving. It is only then that we can truly merit the full protection of the third ingredient or Repentance, Prayer, and Charity.

The Rambam assures us that no one will ever become poor from giving. Then he goes even one step further and assures that no bad will ever come upon a person from his charitable activities. That tzedakah is linked to our health is also absolutely clear. The Kitzur Shulchan Orech cites the famous Medrash for Shir HaShirim, “Tira d’lo tiftach l’anya, tiftach l’asya – The door that doesn’t open up for the poor will open up for a doctor.” And of course the Gemara teaches us in Baba Basra, “Tzedakah tatzil m’mavesTzedakah saves us from death.”

In preparing our defenses for the Day of Judgment, we have many weapons. Saying “Amein, y’hei shmei rabba,” can tear up an evil degree. Learning Torah can ward off retribution. Doing teshuvah and petitioning Hashem with meaningful prayer are also extremely potent. There is something however truly unique with the mitzvah of tzedakah: While all of the other weapons at our disposal can save us from leaving this world before our keitz, our designated time, one of the only ways to actually add years to one’s keitz is through the mitzvah of tzedakah, as the Gemara teaches us in Baba Basra [11], Hashem added twenty-two years to the life a Benyamin HaTzadik for taking care of a woman and her seven children during a time of famine.

May it be Hashem’s will that we have the smarts to give generously according to our ability and in that merit may we be zoche to a Kesiva v’chasima tova u’mesuka, always being able to give and never needing to take.


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Rabbi Moshe Meir Weiss is now stepping-up his speaking engagement and scholar-in-residence weekends. To book him for a speaking circuit or evening in your community, please call Rabbi Daniel Green at 908.783.7321. To receive a weekly cassette tape or CD directly from Rabbi Weiss, please write to Rabbi Moshe Meir Weiss, P.O. Box 658 Lakewood, New Jersey 08701 or contact him at Attend Rabbi Weiss’s weekly shiur at Rabbi Rotberg’s Shul in Toms River, Wednesday nights at 9:15 or join via zoom by going to and entering meeting code 7189163100, or more simply by going to Rabbi Weiss’s Daf Yomi shiurim can be heard LIVE at 2 Valley Stream, Lakewood, New Jersey Sunday thru Thursday at 8 pm and motzoi Shabbos at 9:15 pm, or by joining on the zoom using the same method as the Chumash shiur. It is also accessible on Kol Haloshon at (718) 906-6400, and on To Sponsor a Shiur, contact Rav Weiss by texting or calling 718.916.3100 or by email RMMWSI@AOL.COM. Shelley Zeitlin takes dictation of, and edits, Rabbi Weiss’s articles.