Based on a Naaleh.com shiur by Rabbi Beinush Ginsburg.
Why did Hashem command us to celebrate Sukkot in Tishrei, during the fall season? In addition why is their a special mitzvah of simcha on this holiday? The Sefer Hachinuch writes that it is the time of chag haasif-the ingathering of the harvest. There is natural joy at finally enjoying the fruits of one’s labor. Therefore Hashem, in an expression of love, gifted us with an easy mitzvah on a ?silver platter?. Our natural joy is elevated to simcha shel mitzvah. Similarly, Rav Nebenzhal adds that there is a Torah mandated mitzvah to eat on erev Yom Kippur. We will be eating anyway in preparation for the fast. Here too, Hashem lovingly gives us an extra merit to help tip the scales of judgment in our favor.
The Tur offers another explanation. Sukkot in Tishrei, at the beginning of the rainy season, clearly shows the world, that we are moving outside in order to follow Hashem?s command, not to enjoy the pleasant outdoor air. Rav Karlenstein adds that there is a clear connection between Sukkot and the non-Jews. The Gemara states that the 70 sacrifices on Sukkot corresponded to the 70 nations. In addition, Rabbeinu Bachya in Kad Hakemach says that the measurements of the sukkah -10 tefachim high X 7 tefachim long= 70 nations. Sukkot is about bitachon and about trusting in Hashem who provides for all and governs the world. This concept applies to the gentiles too. The Rambam writes that Hashem?s ultimate plan was for all the nations to recognize Him. This will happen through the Jewish nation. The mitzvah of Sukkah is one of the few mitzvoth d?oraysa that we do in public. In essence, we are proclaiming to the world that we are fulfilling Hashem?s command and that our trust in Him remains eternal.
Another reason why Sukkot is in Tishrei is because Hashem wanted it to be a culmination of Rosh Hashana and Yom Kippur. The simcha of Sukkot is supposed to build on and take strength from the kedusha and tahara that we achieved during the days of awe. Sin creates a barrier between us and Hashem. Rav Soloveitchik writes that the illusion that the world functions automatically is a direct result of sin. Without sin we would sense Hashem in every rhythm of life. The boundless joy of Sukkot is the purification from sin and the ultimate closeness to Hashem that we achieved on Yom Kippur.
Rav Karelenstein explains that we say the psalm, L?dovod Hashem from Rosh Chodesh Elul through Shemini Atzeret. Medrash Rabah writes that each Yom Tov is hinted at in the psalm. Ori is Rosh Hashana, Yishi is Yom Kippur, and Ki yitzpineni b?sukkah is Sukkot. On Sukkot we celebrate Simchat Bais Hashoeva which commemorates the water libation ceremony. One of the sources for this practice is the verse in Yeshaya, ?Ushavtem mayim b?sasson mimaynei hayeshua. The simcha of the drawing of the water stems from ?maynei hayeshua?, the root word connected to ?yishi?-the purification that we reached on Yom Kippur.
In Kabalistic language, the Sukkah is called, ?tzila d?hemnusa?-the shadow of Hashem. The Shechina is in our sukkah, hovering above us. There is a unique closeness to Hashem that every Jew can connect to. This is the tremendous simcha of Succot.
May we merit to hold on to the sanctity and simcha achieved during these days throughout the coming year.
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