Sukkot
Provisioning for the Entire Year
The Maggid of Trisk would say that during the High Holy Days—Rosh Hashanah and Yom Kippur—he would prepare fear of Heaven for the entire year. And during the festival of Sukkot, which is rich in mitzvot performed with affection and love, he would prepare love of G-d for the entire year.
As Long as I Sit in the Sukkah
Rabbi Fishel of Strikov would sit in the sukkah even when it was raining. They asked him, “But it is stated in the Shulchan Aruch: ‘If it rains, one should enter the house,’ and the Rema adds in his glosses: ‘And anyone who is exempt from the sukkah and does not leave it, receives no reward and is merely a simpleton.’” He replied, “It is better I will be a simpleton, as long as I can sit in the sukkah.”
Where is the Distress?
The reason one is exempt from the sukkah if it rains is because it is considered a form of distress. However, if a Jew is more distressed by not being able to sit in the sukkah, then he is consequently obligated to sit in it. (Beit Yaakov)
Who Can Feel Distress?
Rabbi Menachem Mendel of Kotzk would sit in the sukkah even when it was raining. He would say: A Jew who can feel the rain in the sukkah and be distressed by it, is truly not worthy of sitting in it...
Settled Lights
One of the special qualities of the mitzvah of sukkah is that it draws down "encompassing lights" (orot makifim). The meaning of "tishvu" (you shall dwell) is that by dwelling in the sukkah, one draws these encompassing lights inward, where they are absorbed in a "settled" (hit'yashvut) manner. (the Rebbe Rayatz)
Heavenly Guests
On the Festival of Sukkot, every Jew merits hosting seven distinguished guests in their sukkah: the three Patriarchs — Abraham, Isaac, and Jacob; in addition to Moses, Aaron, Joseph, and David. These holy ushpizin (guests) descend from the Garden of Eden directly to the sukkah, and in the language of the Zohar: "Heavenly guests make their dwelling with him."
The reason the ushpizin appear specifically on Sukkot (and not on Passover or Shavuot) is as follows: It is more difficult to serve G-d during the winter than during the summer. In the winter, the sun doesn't shine as brightly. The sun symbolizes the name Havayah, which represents light and revelation (as it is written, "For a sun and a shield is Havaya Elokim" — the name Havayah is likened to the sun and the name Elokim to a shield that envelops it). Therefore, the ushpizin come to us on the Festival of Sukkot, to give us strength and encouragement in our service of the Creator for the coming winter days. (From a discourse of the Rebbe on the Festival of Sukkot, 5712. Torat Menachem 5712)
And His Right Hand Will Embrace Me
The Festival of Sukkot is likened to the verse, "And His right hand will embrace me." Just as a person embraces a friend out of great love and doesn't want to let go, so too on Sukkot, the sukkah's roof, the sechach, and four walls are like an embrace from G-d, surrounding and encompassing us from all sides, and not allowing us to be "separate" from Him. (the Alter Rebbe, Likkutei Torah – Discourses for Sukkot, 79b)
A True Leader
Once, the Baal Shem Tov made a sukkah that was full of halachic questions, which the great scholars of Mezhibuzh were inclined to deem invalid. The Baal Shem Tov argued with them to validate it, but to no avail. The Baal Shem Tov rested his head on his hand, and a note descended from heaven: "The sukkah of Rabbi Yisrael is valid." The note bore the signature of the angel Metatron.
As explained by the Rebbe: The Baal Shem Tov built a sukkah for himself, the validity of which was questionable, because he was the "head" of all the Jewish People, including all those Jews who were on the level of "your woodcutters and water drawers." Therefore, he built a sukkah that was not in accordance with his true spiritual level. He did this so as to elevate the sukkahs of the simple Jews, thus making their sukkahs fit to receive the Heavenly radiance that is drawn down into the sukkah.
And this is what the Baal Shem Tov showed and taught the great scholars of Mezhibuzh: A true leader is one who is willing to forgo his own beautification of a mitzvah if he knows that by doing so he will help another Jew, even one from the simplest of people. (Adapted from a discourse on the second day of Sukkot, 5727)
The Sechach Does Not Like Anger
Once, the servant of the Rebbe Maharash entered the sukkah while he was in an angry state. The Rebbe said to him: "You must behave with respect before the sechach; the sechach does not like anger." (Sefer HaSichot 5704, p. 12)
One should begin the “Simchat Beit HaShoeva” right away, even before the Kiddush of Yom Tov. They may pause to make Kiddush over the wine—the joyous wine—and to eat the Yom Tov meal with happiness. After that, they should continue the “Simchat Beit HaShoeva” in such a way that “we have not tasted the taste of sleep.” ... a dance with great joy, to the highest level possible—the true and complete redemption through Moshiach. And so it will be for us—immediately—we will continue to celebrate the “Simchat Beit HaShoeva” in our Holy Land, in Jerusalem the Holy City, in the Third Temple, all the way to the Holy of Holies... immediately! (the Rebbe, first night of Sukkot 5749—1988)
