Personally speaking, the Four Species is one of the most downright bizarre and mysterious mitzvos in our tradition. The underlying principle is not stated in the Torah, which concludes the instruction with the general theme of the Chag:

וּלְקַחְתֶּם לָכֶם בַּיּוֹם הָרִאשׁוֹן פְּרִי עֵץ הָדָר כַּפֹּת תְּמָרִים וַעֲנַף עֵץ עָבֹת וְעַרְבֵי נָחַל וּשְׂמַחְתֶּם לִפְנֵי ה אֱלֹהֵיכֶם שִׁבְעַת יָמִים – On the first day, [take the Four Species]; and you should celebrate and rejoice before Hashem for seven days. (23:40)

There is no obvious reason or ethic for doing this, and you won’t find many who can explain it. What significance can saving the Arba Minim have for us?

One of precious few explanations given is that it represents different kinds of Jews. The esrog has a pleasant taste and a pleasant scent, and represents Jews who have knowledge of Torah as well as performance of mitzvah performance. The palm branch, which produces tasty fruit and is itself a food, but has no scent, represents Jews who have knowledge of Torah but are lacking in mitzvah performance. The hadas, the myrtle leaf, has a strong scent but no taste, represents Jews who perform mitzvot but little Torah knowledge. The arava, the willow, has neither taste nor scent, represents Jews who have no knowledge of Torah or mitzvos. We bring all these together to remind us that every one of these four kinds of Jews is important and has their place. And such is life; real community is only found when all types of people can be together. The mitzvah, and society, fails when any part is excluded.

Rabbi Shlomo Farhi notes there is a general principle of hidur mitva, which means that the attitude to any mitzvah should be such that the mitzvah is done in an elegant way. With the esrog, the prescription of the mitzvah is that the mitzvah must be elegant, beyond the general principle of hidur mitzvah. There are people who will spend days on end inspecting their esrog so that the shape and shine are perfect; and this is what the mitzvah actually requires!

Why is this the only mitzvah where we must go above and beyond to search for something perfect, just to fulfil the basic premise of the mitzvah?

Rabbi Farhi explains that the taste and scent allegory applies to ourselves too. There are parts of our practice that we love, understand and are good at, and parts that we don’t like, do, or understand; and everything in between. The part of Judaism that I love, understand, and am good at is something that is worth spending time on, and it should be the focal point. That is worth putting effort into, and being proud of. That is a real achievement. The search for the perfect esrog shows the value we should place on that part of ourselves.

The agricultural element cannot be forgotten either – Sukkos is the harvest festival. The Rambam notes that the Jews complained in the wilderness:

וְלָמָה הֶעֱלִיתֻנוּ מִמִּצְרַיִם לְהָבִיא אֹתָנוּ אֶל הַמָּקוֹם הָרָע הַזֶּה לֹא | מְקוֹם זֶרַע וּתְאֵנָה וְגֶפֶן וְרִמּוֹן וּמַיִם אַיִן לִשְׁתּוֹת – Why have we been taken from Egypt to this awful place, with nowhere to plant, not figs, or grapevines, or pomegranates; nor water to drink! (20:5)

In contradistinction to their ingratitude, taking the Arba Minim, abundant in the fruitful and productive Land of Israel, is a symbolic refutation of their attitude to the care God took of them, and expresses our own gratitude at all we are fortunate to have. The Arba Minim are waved either axis of three dimensional space, vertical, horizontal, and lateral, to signify our awareness that this is the space in which God operates, in a way the desert generation did not appreciate. The plants we take, which require water, are waved at the beginning of the rainy season, as we call on Hashem “Hosha na”, to aid us.

The Rambam’s observation is critical to unlocking what the Arba Minim are. The mitzvah is a rejection of the attitude of the wilderness, and we embrace our reliance on Hashem for all things through it.

The mitzvah of Sukka requires that for 7 days, a large part of living, particularly eating, takes place in a somewhat flimsy hut, with some plant material as the roof. The primary reason is stated in the Torah:

בַּסֻּכֹּת תֵּשְׁבוּ שִׁבְעַת יָמִים כָּל הָאֶזְרָח בְּיִשְׂרָאֵל יֵשְׁבוּ בַּסֻּכֹּת. לְמַעַן יֵדְעוּ דֹרֹתֵיכֶם כִּי בַסֻּכּוֹת הוֹשַׁבְתִּי אֶת בְּנֵי יִשְׂרָאֵל בְּהוֹצִיאִי אוֹתָם מֵאֶרֶץ מִצְרָיִם אֲנִי ה אֱלֹהֵיכֶם – Every resident of Israel will sit in huts for 7 days; so that the generations will know that I had Israel live in huts when I took them out of Egypt. (23:42,43)

What specific import does this have to us, other than recalling an ancient memory?

Arguably, it is a natural progression from Yom Kippur. We profess multiple times on Yom Kippur that we did not act in private the way we did in public. Perhaps the Sukka brings the two into synthesis. The Sukka is closed, yet anyone outside can hear whatever happens within it’s walls; a Sukka is not private. Perhaps sitting in a Sukka is a commitment to acting in private more like we are in public.

The Rambam explains that the exposure to the elements reminds us of the miracles experienced in the wilderness, the stated reason in the Torah. At the beginning of nationhood, when our people’s history began, and before anything remarkable occurred, we were completely looked after – just like we are surrounded completely surrounded by the Sukka. God is good to us just because, without qualification. Sukka reminds us that we are each taken care of in our own, personal way.

The Chagim all have an agricultural element to them, which is somewhat anachronistic today – yet the themes remain relevant. Sukkos is the harvest festival, a time of celebration and plenty – a farmer would literally reap what he had sown, finally seeing the fruit of his labour. Rav Hirsch notes that in this time of achievement, we are to walk away, and remember that in a physically and spiritually barren wasteland, we were helpless, yet cared for nonetheless. We retreat from our comforts and securities to a greater or lesser degree. Sitting in a Sukka is a mitzvah of simplicity.

This was more obvious when everyone had to journey to Jerusalem as part of the mitzvah. They would have to leave wherever they were from, whatever their professions, and the roads would be packed with people doing the same thing. By getting there, away from their busy lives, sharing with people doing the same thing, there would be a strong and shared sense of common identity.

The simplicity of Sukka reminds us that we are each taken care of in our own, personal way, no matter the circumstance or whether we deserve it. This realisation ought to cause a deep sense of gratitude for all the goodness we experience, as well as feelings of modesty and humility. Thinking about all this may even get us to act more like it too!

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.