The Arizal (Rav Yishak Luria of Safed, 1534-1572) had the practice of distributing on Ereb Sukkot the money that had been set aside for charity as the "Pidyon Nefesh" before Yom Kippur. This is, indeed, the customary Misva of the day of Ereb Sukkot – to distribute money to the poor.
The money should be distributed while having in mind the Ushpizin – Abraham, Yishak, Yaakob, Moshe, Aharon, Yosef and David, the "guests" who visit us in our Sukkot. The Zohar comments that the Ushpizin do not come to the Sukkot of those who are not hosting needy people at their table, and the commentators explain this as referring to those who had not given charity before Sukkot to assist the poor. The Ushpizin have no interest in joining us if we had not helped the needy before Sukkot, and so before Sukkot, money should be distributed to the poor with the Ushpizin in mind.
The significance of giving charity on Ereb Sukkot can be seen also from the explanation given by the Vilna Gaon (Rabbenu Eliyahu of Vilna, Lithuania, 1720-1797) for why Sukkot is celebrated during this time of year. The Sukka commemorates the "Ananeh Ha’kabod" – the miraculous "clouds of glory" which encircled and protected Beneh Yisrael during their sojourn through the wilderness. The question thus arises as to why this commemoration is held in Tishrei, and not in Nissan, when Beneh Yisrael left Egypt and first received the "Ananeh Ha’kabod" to protect them. The Vilna Gaon answered that on Sukkot we commemorate not the "Ananeh Ha’kabod" themselves, but rather their return to Beneh Yisrael after the sin of the golden calf. G-d was angry at the people after the sin of the calf, and so He removed the special protective clouds, leaving them exposed and vulnerable. The next day, the 18th of Tammuz, Moshe ascended Mount Sinai to beg G-d to forgive the people. Moshe spent two forty-day periods atop the mountain, and G-d finally proclaimed His forgiveness on Yom Kippur. Even then, however, although forgiveness was granted, the relationship between G-d and the people was still strained. In order to fully repair the relationship and restore the people to their previous stature of glory, G-d commanded them to donate materials and construct the Mishkan. The people donated materials during the three days following Yom Kippur – the 11th, 12th and 13th of Tishri – and on the 14th, they brought all the materials to Besalel and the other artisans assigned to build the Mishkan. The work began on the 15th of Tishri, whereupon the "Ananeh Ha’kabod" returned. We therefore celebrate Sukkot at this time by living in Sukkot to commemorate the return of the "clouds of glory."
Developing this idea further, on Yom Kippur, we earn forgiveness for our misdeeds, but on Sukkot, Hashem goes even further, restoring His special love and affection for us. He therefore invites us into the Sukka, which is called the "shade of faith." The numerical value of Sukka is 91, which is the combined numerical value of the two primary Names of G-d ("Havaya" and "Adnut"). The Sukka represents G-d, and on Sukkot G-d lovingly welcomes us to bask in His presence despite the fact that we have sinned. As the Gemara comments, G-d instructs us on Sukkot, "Seh Mi’dirat Keva" – "Leave your permanent residences." The numerical value of "Seh" is 91, alluding to the fact that we join G-d – represented by the number 91 – in the Sukka during this holiday. This concept is also alluded to in the "Ata Behartanu" prayer which we recite on the holidays. The phrase, "Ata Behartanu Mikol Ha’amim" ("You have chosen us from among all the nations") refers to the time of the Exodus, when G-d took us from Egypt so we could become His special nation. The next phrase, "Ahabta Otanu" ("You have loved us") speaks of Matan Torah, when G-d showed us His love by giving us the Torah, the greatest gift imaginable. We then recite, "Ve’rasita Banu" ("You have desired us"), referring to G-d’s continued love and affection for us despite the mistakes we have made.
Returning the Vilna Gaon’s comments, it emerges that the period between Yom Kippur and Sukkot was spent generously donating materials towards the construction of the Mishkan. Therefore, this is a time for generous giving, and it is thus appropriate specifically during these days before Sukkot to distribute charity to the poor and to needy Torah scholars. As was the case in Sinai, we hope and pray that our involvement in generous giving during this time, combined with our repentance during the High Holidays, will render us worthy of Hashem’s ongoing love, compassion, affection and grace, and we will be deserving of basking in His presence and receiving His bountiful blessings.
