One must wonder; how could the Torah describe Sukkot so negatively? It is almost as if the Torah predicts us to fail. After all the uplifting davening and teshuva process of Rosh Hashanah and Yom Kippur, the Torah reassures us that the first thing we will do when we sit down in the sukkah Yom Tov night is to tell a juicy piece of lashon hara. How could the Torah, which is always so supportive, corrective, and inspiring, have turned so negative and cynical? Furthermore, how does the portrayal of Sukkot as a time of ראשון הוא לחשבון העוונות fit together with it

being זמן שמחתנו?

Rabbi Levi Yitzchak of Barditchev offers an incredible insight into this midrash (Kedushas Levi Parshas Ha’azinu). The Gemara explains that there are two kinds of teshuva. One is a Teshuva M’Yirah as a result of which זדונות נעשה לו כשגגות, our intentional sins, are reconfigured as unintentional and less severe. Another form of teshuva is Teshuva M’Ahavah, which transforms our sins into merits, זדונות נעשה לוכזכיות (Yoma 86b).

Following the Ahavah-Yirah model, the Kedushas Levi then describes the progression of the month of Tishrei using the verse, “שמאלו תחת לראשי וימינו תחבקני” (Shir HaShirim 2:6). In Chassidic thought, the left is associated with severity and fear while the right is associated with loving, kindness, and joy.

Accordingly, this verse captures the difference between Rosh Hashanah and Yom

Kippur on the one hand, and Sukkot on the other. Called the Yamim Noraim, Rosh Hashanah and Yom Kippur are defined by awe, a sense of seriousness, and reckoning as we stand before our Creator and He judges us for the coming year. Sukkot, however, is entirely different. The festival, which we call zman simchateinu in our davening, is a time of boundless joy, to the extent that Chazal

say that he who has not witnessed the simchat beit hashoeva, one of the feature

events of Sukkot, has not ever witnessed joy in his life (Sukkah 51a). Additionally, the Sukkah recalls how Hashem cared for us in the desert by enveloping us in the ananei hakavod and expresses how the Shechinah presently surrounds us in Its loving embrace (See ibid. 11b, Shulchan Aruch O.C. 625:1). Thus, while the Yamim Noraim are defined by yirah, Sukkot is defined by ahavah.

Now we can understand why Sukkot is called “ראשון הוא לחשבון העוונות.” What we are able to achieve during the Yamim Noraim is Teshuva M’Yirah, which only dims the stain, so to speak, left by an avierah. But during Sukkot, a time of simcha and ahavah, we can achieve Teshuva M’Ahavah, which not only erases the stain entirely, but even transforms it into a beautiful adornment. So, we say that Sukkot is “ראשון הוא לחשבון העונות” not because it is the first moment we sin anew; on the contrary, it is the first moment that we can return to those once considered sins and count them as merits.

This idea is carefully reflected in two minhagim of Rosh Hashanah and Sukkot that revolve around water. On Rosh Hashanah it is customary to do tashlich, the practice by which we go to a body of water and throw away our sins as the verse states, “ותשליך במצולות ים כל חטאותם” (Micha 7:19). On Sukkot there is a special

libation called nisuch hamayim in which water is drawn from the Gichon spring,

danced up to the Temple Mount, and poured on the mizbeach. One must wonder, why is it that the very water into which we disposed of our sins we now draw from and offer on the mizbeach? How can water tainted with our sins possibly be a fitting offering for G-d? The answer is that on Rosh Hashanah, a time when we

can only reach Teshuvah M’Yirah, the only thing we can do is get rid of the sins

that have been turned into shegagot, inadvertent acts. But on Sukkot, a time when we achieve Teshuvah M’Ahavah, those sins have been transformed into zechuyot and are now perfectly fit to be included in an offering on the mizbeach.

Let us tap into the positive and simcha-filled energy of Sukkot and in so doing get the new year of 5783 started off the right way.

Shabbat Shalom, 

Rabbi Avi Berman