The Book of Nechemia records that after the Jewish nation was exiled to Babylon, Persian, and Media for seventy years following the destruction of the first Bet Hamikdash, many Jews emigrated from Babylon back to Israel after King Darius II permitted them to rebuild the second Bet Hamikdash.
At the time, although there were many righteous individuals in the Jewish nation, many Jews treated the Mitzvot laxly and even transgressed severe prohibitions because of the length of the exile and persecution they were subjected to.
On their first year back in Jerusalem, Ezra the Scribe, leader of Israel, gathered the entire Jewish nation on the first day of Rosh Hashanah to the Gate of Water in Jerusalem. The entire nation stood around Ezra, who stood elevated on a special wooden podium built for this event, at which point he began reading from the Sefer Torah.
When the nation heard the Torah being read, they began weeping bitterly as they came to the realizing that they were grossly lacking in their observance of the Torah’s commandments. This was preordained by Heaven that they hear scathing words of rebuke being read from the Torah and this served to atone for their sins as if they had actually been punished.
However, Rosh Hashanah is a holiday during which crying is forbidden, as we do not even recite confessional prayers on Rosh Hashanah. Therefore, Ezra turned to the Jewish people and consoled them, as follows:
“And he told them: Go, eat fatty foods, drink sweet beverages, and send portions to those who do not have them, for this day is sanctified to our Lord; do not be sad, for the joy of Hashem is your fortitude.”
Indeed, even the Levi’im that stood next to Ezra placated the nation, as the verse states: “The Levi’im quieted down the nation saying, ‘Be silent, for this day is holy and do not be sad!’ The entire nation went to eat, drink, send portions, and to partake of great happiness, for they understood the matters told to them.”
Following this gathering, there was an event that had possibly never occurred before (or after): Every member of the Jewish nation who had married a non-Jewish woman who had not undergone a proper conversion in the diaspora dissolved their marriage; these men then repented and returned to leading a life replete with sanctity and purity along with the rest of the Jewish people.
In any event, we see that Ezra had commanded the nation to send portions of food and drink to their less fortunate brethren in honor of Rosh Hashanah. This served as a merit for the Day of Judgment and made them even more beloved before Hashem.
Indeed, the Poskim write that throughout the month of Elul, especially on Erev Rosh Hashanah, one should distribute as much Tzedakah as possible, especially to those who toil in Torah study, for “Charity saves from death.” The proper way to behave is to preempt the judgment with acts of repentance, prayer, and Tzedakah, well before the verdict is issued. One should therefore begin giving Tzedakah from now as much as possible and not remain complacent.
The Sefer Seder Ha’Yom (Month of Elul) writes this explicitly, in that acts of repentance, prayer, and charity should begin from Rosh Chodesh Elul and continue through Erev Rosh Hashanah, as was the custom of Hagaon Peri Chadash (see his work, end of Chapter 581).
Our Sages taught (Midrash Rabba, Shofetim), that Tzedakah is greater even than sacrifices, for sacrifices usually only atone for inadvertent sins while Tzedakah atones even for advertent ones.
Maran Ha’Chida (in his glosses on Sefer Chassidim, Chapter 31) quotes Rabbeinu Efraim who proves this point based on the numerical value of “Kessef” (Hebrew for “money”) when spelled in its fullest form is 305, the same numerical value as “Seh” (Hebrew for “sheep”).
