1. Wake Up and Celebrate!

—​Rabbi Yisrael Baal Shem Tov

On Sukkot, the Baal Shem Tov would exclaim, “Where is the celebration? Every Sukkot, in the Temple, they would celebrate for seven days, non-stop. Rabban Gamliel would juggle torches, and their eyes never saw sleep. How could it be that we’ve been sleeping all these hundreds of years? Wake up, you sleeping people! Wake up from your slumber!”

You see, since the Temple was destroyed, it’s like the entire Jewish people fell into a deep sleep. When you’re sleeping, you’re still alive, breathing, digesting, pumping blood. But your eyes don’t see, your ears don’t hear, and your mind doesn’t understand anything—it just dreams crazy dreams.

That’s how we have been since the Temple was destroyed. In the Temple, we saw open miracles. We felt we were standing in G‑d’s presence. We understood clearly that there is a G‑d in the world and He is everywhere—within all things and beyond all things at the same time.

So losing the Temple is not just losing a nice building. It’s a deep spiritual loss. At the celebration in our own Sukkahs we are making up for some of that. We’re tapping into a deeper reality to get a tiny taste of what we lost. The celebration is meant to wake us up, so that we won’t be satisfied with life as it is, so we’ll do all we can to repair this world and merit to see the times of Moshiach now!

Keter Shem Tov, siman 345. Torat Menachem, vol. 10, pp. 69–75.​

2. The Awesomeness of Sukkot Celebration

—The Maggid of Mezritch

The Talmud tells us that when Hillel the Elder came to celebrate in the Temple on Sukkot, he would say, “If I am here, everyone is here. If I’m not here, no one is here.”

Now that’s very strange. The Talmud tells many stories about the extreme humility of Hillel, describing how he had the patience for every person and never saw himself as greater or more important than others. But this statement of his seems quite the opposite!

Until we take into account a short passage of the Jerusalem Talmud:

Rabbi Yehoshua ben Levi said, “Do you know why it was called ‘The Celebration of the House of Drawing Water?’ Because from there they drew divine inspiration.”

Rabbi Jonah said, “The prophet Jonah ben Amitai was one of the holiday pilgrims to the Temple. He walked into the Simchat Beit Hashoeva and the divine spirit rested upon him.”

From this we understand that the divine spirit only rests upon a joyous heart. As the verse says, “As soon as the musician began to play music, the spirit of G‑d rested upon the prophet.”

So Hillel came to this celebration and he felt this awesome spirit of divine inspiration. When he said “If I am here, everyone is here,” he meant that if he could feel it, certainly everyone else could feel it.

But what about his next words: “If I am not here, no one is here.” He certainly didn’t mean that if he can’t feel it, nobody else could. That would be a contradiction to what he just said.

So here’s a solution: Consider the way we think about relative wealth. For a person who deals with dimes and nickels, every nickel or dime is significant. But for a person who carries around hundred-dollar bills, there’s no need to bother with dimes and nickels. Nevertheless, for both of them, a precious, flawless jewel makes nickels, dimes, and hundred-dollar bills all seem the same.

That’s what Hillel meant—that the divine spirit there was so awesome, everyone was equally small in comparison. So much so, that if he could not feel it, he couldn’t imagine that anyone else could—because relative to this awesome experience, the smallest and the greatest were all the same.

Ohr Torah, siman 431.​

3. Wine, Water and Happiness

—Rabbi Schneur Zalman, the Alter Rebbe

The whole year long, all the offerings in the Temple were accompanied with wine. Only on Sukkot was water poured on the altar—and then the joy was much greater.

What is the connection between water and such great joy?

The answer is that wine brings its own joy—and that limits how much joy it can provide. Water doesn’t impose any limits.

“Wine,” the Psalmist sings, “gladdens the heart of man.” Wine has intrinsic taste, energy and certain other properties that, when used the right way, can enhance a celebration—some wines more than others.

Water is simple and tasteless. That’s why, unless you are thirsty, you don’t say a blessing on drinking plain water.

Yet it’s that simplicity of water that allows it to carry an even greater joy. Water doesn’t paint that joy any color or squeeze it into any form. So the celebration that goes alone with the pouring of water knows no limits.

That’s the difference between the other festivals and Sukkot. On the other festivals, the joy is mainly according to the person’s understanding. But the joy of Sukkot far transcends comprehension.

That’s also the difference between the joy of doing a mitzvah that’s limited to your understanding of the deep meaning of this particular mitzvah and the joy of a mitzvah done out of the simple knowledge that this is what G‑d wants of you. Understanding is sweet, but the joy carried in simplicity is unbounded.

Based on Likutei Torah, Netzavim 48c, further explained in Likutei Sichot, vol. 2, Sukkot (s’if 17ff).​

4. When Nobody Celebrates Sukkot

—Rabbi Dovber, the Mittler Rebbe

“When someone lowers himself with true humility,” the sages taught, “G‑d raises him up.”

Why is that? Because if someone truly has that quality of sincere humility, that person can handle greatness without it getting to his head. David, for example, even when he was a great hero and king of Israel, still danced and sang with joy like a commoner when the Holy Ark was brought to Jerusalem.

Or take Hillel the Elder, who was extremely humble. When he came to the Simchat Beit Hashoeva (the Sukkot celebration in the Temple), he declared, “If I am here, everyone is here. If I’m not here, no one is here.” Such extreme haughtiness that would seem to be the opposite of Hillel’s extreme humility.

But in truth, quite the contrary. The only reason he could say this is because he was so humble, so it didn’t affect him.

Hillel felt the intense divine light in this great celebration and felt like nothing before it. What difference did it make if one nobody was smarter than the other nobodies? They’re all still nobodies before the awesome divine presence they felt there.

So he said, “If a nobody like me could be here, then all these nobodies can also be here!”

To say that, you have to really believe you are a nobody.

Shaarei Teshuvah, Shaar Hatefillah, end of chapter 4 (pg. 25c).​

5. The Divine Guests to Our Sukkah

—Rabbi Menachem Mendel, the Tzemach Tzedek

The Zohar tells us that each night a party of seven special Ushpizin—Aramaic for “guests”—come to our Sukkah, each night led by a different member of the party. The order is: Abraham, Isaac, Jacob, Moses, Aaron, Joseph, David.

Who are the Ushpizin, really?

They are the modalities with which G‑d created the world.

When G‑d created the world, on the first day He created with Kindness. On the second day, He created with Judgment. On the third, with Beauty. The fourth day was Victory. The fifth was Splendor. The sixth, Connection. And the seventh was Majesty.

So that on every Sunday, the modality of Kindness reigns. And on Monday, Judgment reigns. And so the week continues, according to that very first week of creation.

The Ushpizin are lofty souls who brought those seven divine modalities of creation into reality in this world during their lifetime. Abraham reflected G‑d’s kindness in the world. Isaac reflected divine judgment. Jacob was all about divine beauty. Moses’ life reflected Victory. Aaron reflected divine splendor. Joseph connected heaven and earth. And David was the embodiment of divine majesty.

On the three festivals, a higher light shines through each of these modalities, a joyous light. But the highest, most joyful light is that which shines through them on Sukkot. It is like the joy of a person who is reunited with a long lost close friend. So too, these modalities of creation are reunited with their source above.

Based on Ohr HaTorah, Sukkot, pg. 1748.​

6. What Makes the Sukkah Such a Happy Place?

—Rabbi Shmuel, the Rebbe Maharash

What’s the great joy of Sukkot? It’s the kind of joy you feel when you meet a close friend you haven’t seen in years, and you run to him and hug him tight. The longer you were apart, the tighter the hug, and the greater the joy.

You see, on Yom Kippur, we did teshuvah. Because there might have been some time in our past when we put the energy of our holy souls into something or some place where holy souls don’t belong. Then we regretted that, and on Yom Kippur, we returned to G‑d with love, and G‑d accepted us and forgave us for everything. That’s one reason for celebration.

But what happens to those wrong things we might have gotten involved with in the past? They return as well. Because everything has some spark of good in it, some purpose for which G‑d created it. Just that some things lose their purpose. It’s like their spark went out, and they became dark and ugly.

But when we return to G‑d on Yom Kippur, the good in those things returns as well. And that’s a very great celebration for G‑d. When we return, well, He expects us to return. But those sparks of goodness are to Him like long lost friends that He had given up on. It gives Him great joy to see the works of His creation return to Him.

The schach of the Sukkah is that hug, brought about by the returning souls and sparks of goodness. We celebrate in the Sukkah, and do the mitzvah of Lulav in the Sukkah, to bring that hug into ourselves.

Based on Hemshech V’chacha 5637, chapter 97.​

7. Unprocessed Happiness

—Rabbi Sholom Dovber, the Rebbe Rashab

What does water have to do with joy? Wine, we understand. But water?

But that’s just the point: Even the water is celebrating here!

You see, wine represents understanding. Wine, it says in David’s psalms, makes people happy. The same with understanding. When you work hard to understand something, and you finally get it, you smile.

But you never really get all of it. The most you can understand is only what can fit within a human mind. The real truth as it truly is, that remains beyond us.

Water represents that kind of truth. Water has no color, no form, no way to grasp it. Water represents the wisdom that is beyond understanding.

But on Sukkot, in the Temple, that wisdom, in its deepest, purest sense, came out into the open, accessible to all. If understanding brings joy, imagine what joy that wisdom brought when it burst into our world.

That’s why all those who came walked away with a spirit of divine inspiration. They soaked up that light of pure wisdom that shone there in that celebration.

And so should we!

Based on the conclusion of the maamar Ushavtem 5669.