The Clouds of Glory marked travel movements for the Jews in the desert, and according to Midrash, flattened obstacles, cleared wild beasts, and possibly cleaned their clothing too. The Chag of Succos is dedicated to commemorating them. There is no equivalent display of appreciation for the manna or Miriam’s well, which are all along the same line of supernatural providence for the nation. Why are the Clouds remembered, and not the well or manna?

The Chida explains that food and water are the basic requirements for survival. Taking the Jews into the wilderness of the desert necessarily meant God would provide nourishment from somewhere; what could otherwise be expected? The Jews had their own shelter through tents and huts. But Clouds that protected the camp from the harsh sun, and according to Midrash even more, is far beyond what could have been expected – לפנים משורת הדין.

Secondly, they were a gift that showed God’s love for the people. This is proven by the fact that people outside the camp – such as the Egyptian stragglers and people forced out due to tzaraas – did not benefit.

Thirdly, the Clouds were appreciated far more than the manna and the water. The Jews complained and gave orders regarding the food and drink on offer in the desert – but they never complained about the Clouds. The Clouds were the perfect gift.

The Chida notes that perhaps these are hinted to:

לְמַעַן יֵדְעוּ דֹרֹתֵיכֶם כִּי בַסֻּכּוֹת הוֹשַׁבְתִּי אֶת בְּנֵי יִשְׂרָאֵל בְּהוֹצִיאִי אוֹתָם מֵאֶרֶץ מִצְרָיִם אֲנִי הֹ אֱלֹהֵיכֶם – In order that your ensuing generations should know that I had the children of Israel live in booths when I took them out of the land of Egypt. I am the Lord, your God. (23:43)

לְמַעַן יֵדְעוּ דֹרֹתֵיכֶם כִּי בַסֻּכּוֹת הוֹשַׁבְתי – I gave it to you as a gift; and they were enjoyed perfectly
אֶת בְּנֵי יִשְׂרָאֵל – I gave it to the Jews; not the Egyptian stragglers.
בְּהוֹצִיאִי אוֹתָם מֵאֶרֶץ מִצְרָיִם אֲנִי ה’ אֱלֹהֵיכֶם – I took you out of Egypt; so I fed you, but didn’t have to provide the Clouds.

The Clouds were an incredible, and totally unwarranted display of affection to the Jews. This is commemorated on Succos.

On the kiddush of the festivals, we say the following:

דַּבֵּר אֶל בְּנֵי יִשְׂרָאֵל וְאָמַרְתָּ אֲלֵהֶם מוֹעֲדֵי ה’ אֲשֶׁר תִּקְרְאוּ אֹתָם מִקְרָאֵי קֹדֶשׁ אֵלֶּה הֵם מוֹעֲדָי
שֵׁשֶׁת יָמִים תֵּעָשֶׂה מְלָאכָה וּבַיּוֹם הַשְּׁבִיעִי שַׁבַּת שַׁבָּתוֹן מִקְרָא קֹדֶשׁ כָּל מְלָאכָה לֹא תַעֲשׂוּ שַׁבָּת הִוא ה’ בְּכֹל מוֹשְׁבֹתֵיכֶם – Speak to the Children of Israel, and tell them these are the Festivals that they shall keep holy. For six days, work may be performed, but on the seventh day, it is a complete rest day, a holy occasion; you shall not perform any work. It is a Sabbath to the Lord in all your dwelling places. (23:2,3)

Why is Shabbos inserted into the middle of the Festivals?

The Vilna Gaon explains that on all the Festivals certain types of food related activity are permitted, whereas on Shabbos all melachos are forbidden. However on one Yom Tov no melacha is permitted – Yom Kippur – which is also known as שַׁבַּת שַׁבָּתוֹן – the same terminology that the Torah uses for a regular Shabbos. Thus the pasuk can be rendered:

שֵׁשֶׁת יָמִים תֵּעָשֶׂה מְלָאכָה – On six days melacha is permitted – the first and last days of Pesach (2), one day Shavuos (3), one day Rosh Hashana (4), one day Succos (5), one day Shmini Atzeres (6).
וּבַיּוֹם הַשְּׁבִיעִי שַׁבַּת שַׁבָּתוֹן מִקְרָא קֹדֶשׁ כָּל מְלָאכָה לֹא תַעֲשׂוּ
However the seventh is the holy of holiest – no melacha is permitted – Yom Kippur!

The Mishna in Pirkei Avos (4:28) warns of characteristics that portend man’s downfall:

רבי אליעזר הקפר אומר, הקנאה והתאווה והכבוד, מוציאין את האדם מן העולם – Rabbi Eliezer said: jealousy, lust, and pride, remove man from the world.

The Chiddushei Harim explains that the Chagim, the Shalosh Regalim seek to address these shortcomings.

Pesach makes up for lust, as we eat matza, the poor man’s bread – the simplest, most base of all foods. Despite seeming undesirable, it is all we eat for a week, demonstrating how we are capable of subduing our passions and desires in pursuit of closeness with God; precisely the step the Jews took by blindly following Him into the wilderness.

Shavuos addresses jealousy, or prying eyes. The Torah was given without casting glances at what uncomfortable obligations were required. They unilaterally accepted the Torah, simply because God was offering it, with perfect trust. This demonstrates the ability to subdue jealousy and self-interest.

Succos atones for  pride, commemorating our reliance on the clouds Hashem surrounded us with in the desert. A sukka literally has to be a flimsy little shelter, subject to the elements, under the open sky – showing how small man is. By stepping into a sukka for a week, we demonstrate the capability of deflating our egos, and being humble, relying solely on God.

The Chiddushei HaRim notes jealousy, lust, and pride relate respectively to the soul, heart, and body. Yirmiyahu chastises people for stumbling in these areas:

כֹּה אָמַר ה אַל יִתְהַלֵּל חָכָם בְּחָכְמָתוֹ וְאַל יִתְהַלֵּל הַגִּבּוֹר בִּגְבוּרָתוֹ אַל יִתְהַלֵּל עָשִׁיר בְּעָשְׁרוֹ – So says Hashem: “Let not the sage rejoice in his wisdom; nor the mighty in his strength; nor the wealthy in his riches.” (Yirmiyahu 9:22)

Wisdom and jealousy relate to the soul, might and lust relate to the heart, and wealth and pride relate to the body. The prophet warns not to rest on our laurels, even if we think we’ve made it. We must always work on them, and tellingly, it is a year round endeavor that encompasses all seasons.

After developing all three aspects the prophet discusses, Sukkos ends, and Simchas Torah begins. After אַל יִתְהַלֵּל עָשִׁיר בְּעָשְׁרוֹ, wherein we recognise our humanity, fallibility, shortcomings, and how reliant we truly are, we can say that אתה הראת לדעת כי יהוה הוא האלהים אין עוד מלבדו – we have been show that Hashem is truly unique.