The Torah teaches us that we have to dwell in the Sukkah for seven days, so that all generations should know that in the desert, our forefathers sat in huts.
There is a well know argument between Rabbi Akiva and Rabbi Eliezer. Rabbi Eliezer holds that those huts were one spiritual hut of the Clouds of Glory that surrounded us, protected us, and kept our clothes clean. Rabbi Akiva holds that they dwelled in literal huts after leaving Egypt.
The opinion of Rabbi Eliezer makes more sense because it was such a great miracle, it makes sense that we have to remember this every year — especially because it strengthens our Emunah and shows HaShem’s love for us. However, according to Rabbi Akiva, what is the point in remembering that they built and dwelled in huts? What is the significance in this that we have to remember this every year for a whole seven days?
Reb Issac Sher explains that Rabbi Akiva is teaching us that HaShem took care of every single individual personally because how did they get the tools and materials to build the huts besides from HaShem? HaShem provided for every single person with their needs and not just to everyone in a general way. This is what we commemorate. This is what Sukkot is representing. As Rabbi Yosef Albo says in his book Sefer HaIkarim, that there are three main beliefs that our faith is built on: The existence of HaShem, that the Torah is from Heaven, and that there is personal supervision of HaShem. Pesach represents the existence of HaShem, that HaShem creates the laws, that we all know as the laws of nature, and changes them when needed. When we were Egypt, there were the ten plagues, and after by the splitting of the sea. Shavuot of course teaches us that the Torah is from heaven. Sukkot teaches us that HaShem takes care of every single person. This is why it is called “Zman Simchateinu”, a time of our happiness. The way to reach true Simcha is by realizing that HaShem is in our midst, and watches over us that everything is for the good.
May everyone dwell safely and happily in our sukkahs, and recognize that HaShem dwells with us watches over us.
Rabbi Eliyahu Tal