Real Booths or Clouds of Glory?
The reason for the mitzva of dwelling in a sukka is stated explicitly in the Torah:
You shall dwell in booths seven days; all that are home-born in Israel shall dwell in booths. So that your generations may know that I made the children of Israel to dwell in booths, when I brought them out of the land of Egypt; I am the Lord your God. (Vayikra 23:42-43)
No explanation, however, is given as to why we must remember that we dwelled in booths at the time of the exodus from Egypt. The Tannaim disagree about this matter:
"For I made the children of Israel to dwell in booths." These were clouds of glory; these are the words of R. Eliezer. R. Akiva says: They made for themselves real booths. (Sukka 11b)
The commentators also disagree about the plain meaning of the biblical text. While Rashi, the Ramban, and the Aramaic translations understood the booths as references to the clouds of glory, the Rashbam and the Ibn Ezra understood the verse as referring to real booths.
The authors of the piyyutim for Sukkot tended to accept the view that the reference is to clouds of glory:
The shade of the clouds I will remember.
In each and every generation I will make mention of it.
Remember the loving acts performed for David.
(Yotzer for the first day of Sukkot)
With the beauty of Your clouds You covered the redeemed.
The canopy of Your glory You spread over them so that they be high. (Ma'aravit for the second day of Sukkot)
He covered His laden ones with clouds, for I made the children of Israel to dwell in booths. (Yotzer for second day of Sukkot)
On the face of it, we are dealing here with a theoretical matter that need not be decided. Surprisingly, however, the Shulchan Arukh issued a clear halakhic ruling about it:
Regarding the booths that the verse says He made us to dwell in – these are clouds of glory with which He surrounded them, so that they not be struck by heat and the sun. (Orach Chayim 625:1)
It turns out that the matter has practical significance. The Bach explains that the mitzva of dwelling in a sukka is different from all other mitzvot, in that one who does not have in mind the purpose written in its regard has not fulfilled his obligation.
Since it is written, "That your generations may know," one has not performed the mitzva in the proper manner if he does not know the objective of the mitzva of sukka according to the plain sense of the verse. Therefore, he [the Shulchan Arukh] explains according to the plain sense of the text that the primary intention of dwelling in the sukka is that one should remember the exodus from Egypt… One must have in mind when dwelling in the sukka the reason of the mitzva. (Bach, Orach Chayim 625:1)
This is why the Shulchan Arukh rules on this disagreement – so that one who dwells in the sukka will know whether he must have in mind that his dwelling in the sukka serves as a reminder of our having dwelt in real booths or as a reminder of our having dwelt in the shade of the clouds of glory.
The Difference between a Real Booth and Clouds of Glory
According to R. Eliezer, we must remember on Sukkot God's acts of kindness toward the people whom He took out of Egypt and the high level that they achieved during the period of their wandering in the wilderness. God sent down the clouds of glory in order to house His people in them in the wilderness. In this way, He protected them from enemies and beasts, from the roasting sun, and from the dust and from the wind, and in this way He also caused His Shekhina to rest upon them:
It turns out that there were seven clouds… four on the four sides, one above and one below, and one that went before them. Whatever was low, it raised, and whatever was high, it lowered… And it would strike snakes and scorpions, and sweep and sprinkle before them. (Mekhilta Beshalach, petichta).
There is, in fact, an explicit source in Scripture for a "booth" made from clouds of glory:
And the Lord will create over the whole habitation of Mount Zion and over her assemblies, a cloud and smoke by day and the shining of a flaming fire by night; for over all the glory shall be a booth. And there shall be a pavilion for a shadow in the day-time from the heat and for a refuge and for a covert from storm and from rain. (Yeshayahu 4:5-6)
According to R. Akiva, on the other hand, we must remember how difficult it was for the people of Israel in the wilderness. They sat in the roasting sun and in sandstorms in simple booths. We must remember this in order to appreciate all the good that God provides us with today, giving us a good land and houses full of all things good. Thus writes the Rashbam:
"You shall keep the feast of Sukkot seven days, after you have gathered in from your threshing-floor and from your winepress" (Devarim 16:13) – When you gather in the produce of the land and your houses are filled with all things good, grain, wine and oil. So that you remember that I made the children of Israel to dwell in booths in the wilderness for forty years, without settling and without an inheritance. Because of this you will give thanks to Him who gave you an inheritance and filled your houses with all things goods, and you will not say in your hearts: "My power and the might of my hand has gotten me this wealth" (Devarim 8:17). (Rashbam, Vayikra 23:43)
It seems that according to R. Akiva, the most important part of the holiday is the eighth day – Shemini Atzeret – when we come in from the sukka, from seven days of living in a temporary dwelling, into our warm and comfortable homes that God has given us. According to R. Akiva, it is clear why a person who dwells in his sukka on the eighth day transgresses the prohibition of bal tosif, adding a mitzva (Rosh Hashana 28b), for he lengthens his period of exile. On the contrary, it falls upon us to re-enter our homes and thank God for the opportunity.
According to R Eliezer, the sukka is a continuation of the four cups of wine drunk at the Pesach seder, which is a sign of freedom. According to R. Akiva, it is a continuation of the maror and a remembrance of the servitude.
Both Opinions Are Correct
Do R. Eliezer and R. Akiva disagree about the fate of the people of Israel in the wilderness? In our opinion, this is not necessarily the case. It is possible that during the first year and the beginning of the second year, the people of Israel enjoyed the elevating and pampering providence of clouds of glory. But after the sin of the spies and the decree that "your carcasses shall fall in this wilderness" (Bemidbar 14:29), the Shekhina departed from them. The clouds of glory disappeared and the people remained exposed in simple booths that they built for themselves to protect themselves from enemies, wild beasts, and the desert winds, until the fortieth year when the clouds of glory returned by virtue of the merits of Aharon.
Consider this: Rashi argues, based on the plain sense of the verses, that during the thirty-eight years of their punishment, the people of Israel were censured and the Shekhina did not rest with affection and illumination even upon Moshe:
During these entire thirty-eight years during which the Israelites were lying under God's censure, the Divine utterance was not specially vouchsafed to him in affectionate language, face to face, and tranquility of mind – to teach you that the Shekhina rests upon the prophets only for Israel's sake. (Rashi, Devarim 2:16)
If even Moshe was under God's censure until the fortieth year, why would clouds of glory rest upon Israel? Rather, the clouds undoubtedly departed, and only later in the fortieth year did they return and once again protect the people of Israel.
The Affection of Your Youth
According to the opinion that the booths were clouds of glory, the mitzva of dwelling in the sukka surely comes to remind us of God's acts of lovingkindness to us, as we explained above. According to the opinion that they were "real booths," we find a view among the Rishonim that the sukka comes to remind us not of God's acts of lovingkindness toward us, but on the contrary, of the great virtue of Israel. Rabbeinu Bachya writes as follows:
According to the opinion that they made for themselves real booths, this is the reason that we were commanded to make sukkot like them – to reveal and publicize through the mitzva of sukka the great virtue of Israel in the wilderness. For they walked with all those men, women, and children in that place, where it is not in man's nature to live. As the verse testifies: "a land barren and desolate" (Yoel 2:20); "it is no place of seed, or of figs, or of vines, or of pomegranates" (Bemidbar 20:5). (Rabbeinu Bachya, Vayikra 23:43)
Real booths are the handiwork of man, whereas clouds of glory are heavenly "messengers." According to Rabbeinu Bachya, this distinction accords with what the sukka is supposed to remind us of: Clouds of glory are meant to remind us of God's lovingkindness toward Israel, whereas real booths bring to mind the people of Israel's following after God, which is described by the prophet as an act of affection performed, as it were, for the sake of God:
And the word of the Lord came to me, saying: Go, and cry in the ears of Jerusalem, saying: Thus says the Lord: I remember for you the affection of your youth, the love of your espousals; how you went after Me in the wilderness, in a land that was not sown. (Yirmeyahu 2:1-2)
In the Zikhronot blessing recited on Rosh Hashana, we recite these verses in order to remind God of the days of Israel's love of espousals in the aftermath of the exodus from Egypt. At that time, the entire nation entered the desolate wilderness – men, women and children – based on their trust in God. Manna fell from heaven, but it was forbidden to leave over any of it for the next day; a well accompanied the people, but it was forbidden to store water. The people of Israel marched off in the wake of God with strong belief, and centuries later the prophet Yirmeyahu recalls this conduct as Israel's great merit.
According to Rabbeinu Bachya, the mitzva of sukka comes "to reveal and publicize through the mitzva of sukka Israel's great virtue in the wilderness." "I made the children of Israel to dwell in booths" – but still they did not complain, but rather they trusted in God. By bringing to mind the days of Israel's wandering in the wilderness, dwelling in the sukka strengthens our belief in God and at the same time it reminds God of the virtues of Israel.
Booths of War
Thus far, we have assumed that "real booths" are the booths in which the people of Israel lived for most of the years of their wanderings in the wilderness. But this is difficult: If those booths were so important, how can it be that the Torah makes no mention of them anywhere in the five books of Moshe? What was so unique about those booths that a holiday was established because of them for all generations?
Owing to this difficulty, R. Eliezer of Worms – one of the great Ashkenazi Rishonim – explains that these were not ordinary booths, but rather booths of those going out to war:
Some explain that when they laid siege on the land of the Emorites of Sichon and Og and on the cities in the land of Canaan – this is when Israel dwelled in booths, as it is stated: "The ark, and Israel, and Yehuda are dwelling in booths"… This is the meaning of "I made the children of Israel dwell in booths" – when they laid siege to the nations… And this is "that your generations may know that I made the children of Israel to dwell in booths" – that they should not think that we were living in the land from the time of our forefathers, Avraham, Yitzchak, and Yaakov, but rather they should know that they left Egypt and laid siege to the cities, and God gave them into the hand of Israel. (Roke'ach 219)
The Roke'ach's view is supported by various verses in Scripture, in which it is explicitly stated that soldiers who went out to war dwelt in booths. Thus, it is stated, for example, about David's soldiers who laid siege on Amon:
And Uriya said to David: The ark, and Israel, and Yehuda, abide in booths; and my lord Yoav, and the servants of my lord, are encamped in the open field… (II Shemuel 11:11)
It is very possible that when the people of a fortified city prepared themselves for an enemy threatening war against them, they would build booths for their soldiers in the fields that surrounded the city. These booths provided comfortable quarters for the soldiers who were waiting for the enemy army, and at the same time they were well camouflaged by what was growing in the fields. Thus, we find:
Will you hunt the prey for the lioness or satisfy the appetite of the young lions, when they couch in their dens and abide in the booth to lie in wait? (Iyov (38:39-40)
In the fortieth year following Israel's exodus from Egypt, the inhabitants of the land prepared themselves for war against Israel. To that end, the Canaanites established battle booths and set ambushes against the people of Israel. The people of Israel overpowered the Canaanites and defeated them. It is possible that afterwards, they dwelt in the very booths that the Canaanites had built to fight from them against Israel. In this way, God's promise to Israel by way of Moshe was fulfilled in those who took possession of the land:
And it shall be, when the Lord your God shall bring you into the land which He swore to your fathers, to Avraham, to Yitzchak, and to Yaakov, to give you – great and goodly cities, which you did not build, and houses full of all good things, which you did not fill, and cisterns hewn out, which you did not hew, vineyards and olive-trees, which you did not plant, and you shall eat and be satisfied. (Devarim 6:10-11)
The mitzva of sukka comes, then, to remind us also of Israel's dwelling in the battle booths, following their victory over the Canaanite inhabitants of the land. In remembrance of this victory, a holiday was established for all generations, and Israel was command to dwell during that holiday in sukkot. While we are in the sukka, we are reminded of the help that God provided our forefathers at the time of the conquest, and we know that it is only by virtue of God's assistance that we merited to take possession of the land.
(Translated by David Strauss)
 According to the rules of halakhic decision-making, in disputes between R. Eliezer and R. Akiva, the law follows R. Akiva. Nevertheless, in this dispute, the law was decided that our sukkot serve as a reminder of clouds of glory. This implies that the halakhic codifiers had the reading found in the Midrash Halakha (Sifra 17:11), where the opinions are reversed: According to R. Eliezer the people of Israel dwelt in real booths, whereas according to R. Akiva they dwelt in the shade of the clouds of glory.
 The continuation of Rabbeinu Bachya's words implies that the sukka is meant to remind us of God's acts of lovingkindness toward Israel, as he brings the words of the prophet Yirmeyahu: "Have I been a wilderness to Israel? Or a land of thick darkness?" (Yirmeyahu 2:31), and he explains: "I did not show Israel that they were in a wilderness, a land of thick darkness. For in that very place I prepared for them all their needs, and they lacked nothing."
 See R. Osher Tabibi, "Chag Ha-Sukkot," Alon Shevut 168.