Rabbi Naftali Zvi Horowitz,
Zera Kodesh, Ropczycer Rebbe, d. 1827
In Succot the Children of Israel dwelt
So we find that our teachers read that the shade of the Succah is the shade of faith [tsela dhimanuta], and we are forced to say that the word tzel only applies to one who doesn't sit right under the shady thing but rather at a little distance from it. One who sits right next to a tree and the shade of the tree is spread out over him; it's not the same as one who sits under a tree. So too here as one says, 'underneath the Succah' and this is to teach us something based on what our teachers said 'God is your tzel' just as every action of a person is also acted out by his tzel,it also appears that every action of a person awakens something Above.
And this is the idea of the Succah we make; it is a paradigm of the upper Succah. And this is the idea of the upper Succah of the very, very Upper Aboveness; the Upper nezTZELet mimaTZIL, May God's Name Be Blessed. And there is no screen distinguishing between that and the maTZIL of the light of the Blessed Ain Sof. For there is nothing between the Creator and the Created.
And the light which comes from the aspect of the Upper Succah which is only a little different from the light of the Ain Sof, as mentioned above, which can be seen from underneath that Succah. And in this way we make a Succah and it is like the tzel from the Upper Succah which is roofed with a schach which is not entirely thick like the ceiling of a house, and it's not a screen which entirely separates off from the air of the heavens like the ceiling of a house. Rather it's like a screen that makes a partial separation so the stars and the air of the heavens can be seen from it. And the remez that the stars should be visible through the schach is that star [כוכב] has the same Gematria as 26 + 22, for the Name is the inner aspect of the letters through which revelation occurs.
Yehudah Aryeh Leib, the Second Gerer Rebbe (1847 – 1905)
The Sukkah is like a Chuppah, marking the marriage of man and wife, 'For I caused Israel to dwell in sukkot when I took them out of the Land of Egypt' [Lev 23:43]. At the Exodus from Egypt Israel were mekudeshet to God as it says, I am the Lord who sanctifies [nikdashti] you, who brought you forth from the Land of Egypt to be your God.' [Lev 22:32]
There is a claim to be made against this: why should Israel be selected from among all creatures to be God's own possession? 'For all his possessions he made succot' [Gen 33:17, referring to Jacob]. It is also written 'who spreads out [pores] a sukkah of peace' [Liturgy]. The word pores also means 'to divide' or to 'choose a portion.'
God is wholeness itself. Why then did He choose a fragment of something? Scripture answers, 'I dwell with the lowly and those of humble spirit' [Isaiah 57:15]. The Zohar adds that a person with a broken heart is indeed whole [shalem]. This in fact is to be said in God's praise, wherever He dwells there is wholeness, He makes a whole out of a half.
This is the real meaning of 'who spreads a sukkah of peace.' The inner point that is everywhere wholeness, Israel represents this among God's creatures. On Sukkot 70 bullocks are offered for the seventy nations. The water libations are also interpreted by the Talmud to mean that Israel should pray for God's Kingdom to spread over all Creation. This is the meaning of 'Do not be life a servant who serves the Master only to receive a reward.' [Pirkei Avot].
Mordechai Yosef Leiner, The Ishbitzer Rebbe, d. 1854
And Moses commanded them, saying, At the end of every seven years, in the time of the year of release, in the Feast of Booths, when all Israel has come to appear before the Lord your God in the place which he shall choose, you shall read this Torah before all Israel in their hearing.
It is said in the Gemara, RH 12b, 'What does the festival of Succot have to do with the Shmitta year? Succot, following Rosh Hashanah is already in the eighth year?! Yet all the produce that has grown during the seventh year, you treat it the same way in the eighth as you would have in the seventh.' [i.e. you have to tithe in the eighth year according the size of the harvest in the eighth year, you can't knock off some of the tithing because you weren't farming the crop in the Shmitta year.]
This is according to the verse, 'The heavens are the heavens of God and the earth was given to bnei adam.' This is just the way it seems. But it is well-known that all the actions of a person, even though the power of choice was given to humanity, are as insignificant as a peel of garlic. This is why we say on the first day of the week 'the earth is God's and its fullness' [Psalm for the day on Sunday]. The point of the Sabbath is to know that humanity has no real power, for the 39 forms of work created in the world, with which a person can do what they want are prohibited on Shabbat. But when the weekdays start, and work is again permitted, God forbid that a person say, 'my strength and the power of my hands have got me this wealth' (Deut 8:17). Therefore our sages established that say immediately after Shabbat, 'the earth is God's and its fullness.'
So too with Shmitta, the Torah commands that the earth is God's and all its fullness. Then when the eighth year comes, ploughing and sowing again becomes permitted. In order that we can reap from the land without saying, God forbid, 'my strength and the power of my hands have gained me this wealth,' the produce that was not brought as a tithe in the seventh year, 'you treat it also in the eighth year as you would have in the seventh,' in order to remember that, 'the earth is God's and it's fullness.'