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TorahAnytimes Newsletter Sukkot-Chol Hamoed

Oct 11, 2025 • Parshat Sukkot-Chol Hamoed

Compiled and Edited by Elan Perchik

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Rabbi Moshe Donnebaum

Rav Chaim's Decision

The great gaon and tzaddik, Rav Chaim Kanievsky zt”l, was entirely devoted to his sefarim. Writing them was not merely an intellectual exercise; it was his life’s calling, his avodas hakodesh, his means of spreading Torah throughout Klal Yisrael.

Rav Chaim was not a Rav of a community, nor was he a Rosh Kollel, a Rosh Yeshivah, or a regular rebbe. His sefarim were his way of spreading Torah to the world.

Among his many works, his final major project was the monumental Derech Emunah, a five-volume commentary on the Rambam’s Seder Zeraim (the laws of agriculture in Eretz Yisrael), written in the style of the Mishnah Berurah. It became a beloved classic among the Jewish community across the spectrum. Following its success, Rav Chaim began a similar work on Seder Kodshim (the laws of sacrifices and the Beis Hamikdash), titled Derech Chochmah. It was meant to span five or six volumes, but he completed only one. Not due to frailty or waning strength, but by choice.

The question is why. Why did Rav Chaim, after seeing the tremendous need and success of Derech Emunah, stop writing Derech Chochmah?

Chazal teach that each of the Four Species taken on Sukkos represents a different segment of Klal Yisrael.

The esrog, which has both taste and fragrance, represents Torah and good deeds, the spiritual elite. The lulav, from the date palm, has taste but no smell, reflecting Torah without deeds. The hadas has fragrance but no taste, referring to good deeds without Torah. The aravah has neither, representing the simple Jew.

Yet, when we recite the blessing on the arba minim, we specify the Lulav—“Al Netilas Lulav.” Why the lulav and not the esrog, the most distinguished of the four?

The Gemara (Sukkah 37b) explains that the lulav is gavoha mikulam, the tallest of them all. But what does height have to do with holiness? Greatness in Torah is not measured in inches. Many of the gedolei Yisrael were small in stature, but towering in spiritual stature.

The answer is profound. The lulav is “gavoha” not in size, but in spirit. The lulav willingly binds itself together with the hadas and aravah; those who lack its taste and fragrance. It humbles itself to join the others, to elevate them, to teach, to inspire, and to carry them. The esrog, though greater in intrinsic holiness, stands alone. The lulav, by contrast, becomes greater through unity; through its willingness to give of itself for the sake of others. That is true greatness.

A similar idea appears during the creation of the world, when Hashem separated the upper and lower waters. The upper waters remained above, basking near the Kisei HaKavod (Throne of Glory), while the lower waters were sent below into this physical world. The lower waters cried out, “It is not fair! Why should we be distanced from Hashem in Heaven?”

Hashem comforted them with two mitzvos: melach (salt) and nisuch hamayim, the water libation offered on the Mizbeach during Sukkos. Through these mitzvos, the lower waters would also ascend spiritually. But what truly satisfied them was the realization that their descent had purpose; that they were helping others serve Hashem. By being here on earth, they enabled korbanos, tefillah, and avodah. They achieved holiness not by being close to Heaven, but by uplifting others on earth.

Rav Chaim Kanievsky embodied this lesson. He once explained why he discontinued Derech Chochmah. Letters were pouring in from all over the world and people were coming to him, asking for guidance, for halachic rulings, for clarity. He realized that answering these questions — helping others — had become his new figurative Derech Chochmah.

Even though he deeply loved writing and understood the Torah value of completing the sefer, he made a deliberate choice. He put aside his own spiritual project to lift others. He would respond to hundreds of letters a day, all while maintaining his schedule of finishing Kol HaTorah Kula (the entire Torah) each year.

He chose, like the lulav and the lower waters, to bind himself to the people.

The Chasam Sofer writes in his introduction to Yoreh De’ah that one who helps others, even at the expense of his own spiritual growth, will not lose out. Hashem grants him the merit of what he could have achieved on his own, and more.

So too with Avraham Avinu. Though he was not on the prophetic level to be shown the destruction of Sodom, Hashem said, “I will reveal it to him, for he is busy with My children, guiding them, teaching them, uplifting them.”

Likewise, Rav Chaim was granted siyata d’Shmaya far beyond measure. By sacrificing personal accomplishment for the sake of others, he reached the highest level; the greatness of the lulav and the mayim tachtonim. And that is true greatness.

Rabbi Yaakov Asher Sinclair

A Whisper from Heaven

I once heard a remarkable story from someone named Shragi.

Shragi had been listening to a lecture from Rabbi Ephraim Wachsman, who told the story of a man who used to drive into Manhattan every day. Each day, he was confronted with challenges to guarding of the eyes; maintaining moral and spiritual discipline in a world filled with temptation.

Determined to overcome his struggle, the man made a small but powerful resolution. He placed a tzedakah box in his car, and every time he resisted temptation and looked away, he would put one dollar into it. Day after day, dollar after dollar, he built a quiet treasury of self-control.

When Chanukah arrived, he opened the tzedakah box, and found two thousand dollars inside. Two thousand moments of victory. Two thousand times he had chosen holiness over impulse, mastery over desire, eternity over the fleeting.

With that money, he bought himself a beautiful silver menorah. And that Chanukah, as its candles shone in the window, their light told his story; the story of two thousand triumphs of the neshama.

Shragi was deeply moved. Inspired by the idea, he decided to do something similar. He placed a glass jar in his car. Each time he was tested and chose to look away, he dropped a quarter into the jar.

By the time Sukkot came, he had collected $40 worth of quarters — one hundred sixty moments of victory. With that money, he bought himself the finest myrtle branches (hadassim) he could find.

The Sages teach that the myrtle represents the eyes, as its leaves are shaped like the human eye. Each of those branches symbolized one of those 160 times that Shragi had looked away, 160 moments of spiritual strength, 160 times he had turned his eyes from desire toward Heaven.

Throughout Sukkot, Shragi was filled with joy. Each time he lifted his lulav and looked at those hadassim, he felt the holiness of every small battle he had won.

As the festival drew to a close, he felt a touch of sadness. The mitzvah of the hadassim was ending. Then he remembered a teaching from our Sages: “Objects used for one mitzvah should be used for another.”

So after the holiday, he gathered his hadassim and used them as spices for the Havdalah ceremony that marks the end of Shabbat. There was only one problem: his spice holder was an old plastic container. So he decided that soon he would buy a beautiful crystal and silver spice box, something worthy of the mitzvah.

Shortly after Sukkot, his in-laws returned from Israel. They invited him over, saying they had brought back gifts for the grandchildren.

The children were delighted with their presents of shirts, toys, and souvenirs. Then his in-laws turned to him and said, “Shragi, we have something for you, too.” They handed him a neatly wrapped box. Inside was a black velvet case. He opened it, and there it was: the most stunning crystal and silver spice box he had ever seen.

He stood there speechless.

Sometimes G-d doesn’t show us how precious our mitzvot — our acts of holiness — are to Him. But once in a while, He lets us see a glimpse, a Divine smile, a quiet sign of affection.

Every Saturday night, when Shragi holds that spice box during Havdalah, he feels a surge of joy. It reminds him of those 160 moments of inner strength and self-mastery. It reminds him that G-d saw, G-d cared, and G-d responded.

And that crystal spice box now shines as a testimony that when we overcome our lower urges, when we choose restraint over desire, Hashem sends us a light of His own.

A whisper from Heaven that says, “I saw. I’m proud. And I smile.”

Rabbi YY Jacobson

Not Stingy with Love

I have a dear friend, Rabbi Mordechai Farkash, who once shared with me a story he heard first-hand from the person himself.

This man lived in Israel. For many years, he had been a successful businessman. But over time, things began to unravel. His finances collapsed and his debts mounted, and with that his anxiety, fear, and sense of failure grew unbearable. Eventually, his isolation and depression became so heavy that he simply couldn’t bear the weight anymore. In his despair, he decided that he would end his life.

That morning, he planned that on his way to work, he would stop on one of the bridges outside the city and take his own life, ending what felt like endless pain.

As he was leaving the house, his wife called out to him. “Could you do me a small favor?” she asked gently. “Our son is learning in the Chabad Yeshiva. I prepared a small package of some snacks, some food, a little gift. Could you please drop it off for him on your way?”

For a moment, he hesitated. But then he thought to himself, “What kind of father would I be if I couldn’t even do one last favor for my wife — for my son — before I go?” He took the bag, got in his car, and drove toward Jerusalem.

He arrived at the Chabad Yeshiva and asked to see his son. The mashgiach, the spiritual supervisor, greeted him warmly and said, “Your son is learning right now with such focus. I’d rather not interrupt him. If you’d like, I can give him the package myself.”

The father nodded and handed it over. But before he could leave, the mashgiach looked at him and asked, “Tell me, are you a delivery man, or are you the father of the boy?”

“I’m his father,” he replied quietly. The mashgiach smiled. “Then I want you to know something,” he said. “This entire yeshiva could have been created just for your son. You have no idea what a diamond of a boy you have. His sincerity, his diligence, his humility, I can’t even describe it. You and your wife must have tremendous merit to have raised such an extraordinary young man. You should have endless nachas — endless pride — from him.”

The mashgiach went on for a few more moments, praising the boy, overflowing with warmth and sincerity. Then he said, “Thank you for bringing the package. I’ll make sure he gets it. Have a beautiful day.”

The father left the yeshiva and walked slowly back to his car. His heart was pounding. He thought to himself: “I just heard what kind of son I have. What kind of pain would I bring him if I ended my life today? How could I do that to him — to leave him forever with the knowledge that his father took his own life?”

In that moment, something shifted. He changed his plans. He did not go to the bridge. He went home.

Soon after, he left Israel, began rebuilding his life in another country, and eventually shared this story with Rabbi Farkash. The story of how a few kind words had saved him from the brink of death.

That mashgiach will probably never know what he did that day. He didn’t preach. He didn’t lecture. He simply noticed, cared, and spoke from his heart. He wasn’t stingy with his love.

And those few sentences — those words of warmth, of belief, of encouragement — saved a man’s life.

Never hold back words of love. Never assume someone already knows how much they matter. Because you never know, the small kindness you give, the simple words you speak, may reach deeper than you can ever imagine.

Sometimes, all it takes to bring someone back from the edge is one person who chooses not to be stingy with love.

Rabbi Dovid Orlofsky

Two Brothers, One Destiny

In Parshas VZos Ha’Bracha, Moshe Rabbeinu blesses each of the twelve tribes. But when he blesses Yissachar and Zevulun, he pairs them together:

“Rejoice, Zevulun, in your going out, and Yissachar, in your tents” (Devarim 33:18).

Rashi explains that Yissachar and Zevulun entered a partnership. Zevulun engaged in business and supported Yissachar’s Torah study. And in return, they shared the spiritual reward.

But why only these two tribes? Why not any other pairing between any of the other Shevatim?

If we look back to Parshas Vayechi, Yaakov’s blessings show no hint of partnership. Zevulun is blessed to live by the seashores and engage in commerce, while Yissachar is compared to a strong-boned donkey, bearing the burden of Torah and responsibility. They are two entirely different roles.

Years later, Moshe declares: “It is not across the sea that you should say, ‘Who will cross the sea for us?’” Chazal teach that this Pasuk is referring to Torah, and teaching that Torah is not usually found among those constantly traveling for business.

Now just imagine this. Zevulun hears this and realizes, “That’s me. My blessing puts me on the sea, and far from the beis midrash” So he turns to his brother and says, “You have the gift of Torah. Let’s make a partnership. I’ll support you, so that together we’ll both share in its reward.”

This was not charity; it was clarity. Zevulun knew who he was, and he accepted his role with purpose.

There’s a profound lesson here: to serve Hashem fully, one must know their place and fulfill it completely. Rav Chaim Pinchas Scheinberg, zt”l arranged for someone to learn on his behalf during hours he knew he couldn’t. Why did he do this? Self-awareness. It’s honesty when one recognizes their limits, but refuses to be disconnected from Torah.

A genuine Yissachar–Zevulun partnership requires total commitment. If Yissachar learns and Zevulun supports him, both share equally in the reward. The businessman’s effort is spiritual labor no less than Torah study itself.

Rav Henoch Leibowitz zt”l one recalled how a supporter entered the Chofetz Chaim Yeshiva and found the study hall half empty. “A lot of the students have a bad cold,” he was told. “A cold?” the businessman replied. “When I have a fever, I still go to work!”

If only we learned Torah with the same seriousness as we pursue business — with passion, integrity, and constancy — imagine what Klal Yisrael could become.

That’s the lesson of Yissachar and Zevulun: two brothers, two callings, one destiny. One learns, one supports, but both lift the world.

Rabbi Moshe Don Kestenbaum

Permanence in Impermanence

The essence of the Sukkah is that it is a diras arai, a temporary dwelling. By stepping into it, we are reminded that our stay in this world is also temporary. The Sukkah, fragile and fleeting, becomes a living metaphor for life itself.

Rav Moshe Feinstein zt”l explains that most of our spiritual failings come from forgetting this truth. We become ensnared by the material world—its comforts, ambitions, and illusions of control—because we treat them as permanent. We act as though our possessions, our titles, and our egos are lasting realities. In that delusion, we lose sight of what truly endures.

But imagine, says Rav Moshe, if a person knew they only had a short time left to live. Wouldn’t their priorities transform instantly? Wouldn’t they focus on what truly matters—on growth, love, repentance, and closeness to Hashem?

That is the transformative power of Sukkos.

Sukkos awakens us from the illusion of permanence. It pulls us out of our solid homes and places us in a structure that is open to the wind and rain. There, we are taught that the only true stability in life comes from Torah, mitzvos, and the eternal neshama.

And here lies the paradox: we live in a temporary dwelling, yet we live in it as if it were permanent. “Teishvu ke’ein taduru—Dwell in the Sukkah as you would dwell in your home.” We bring in our chairs, our tables, our meals, our families and guests. Even in a transient space, we live with the sense of permanence, with serenity and rootedness.

The message is profound: The things of this world are fleeting. The meaning we bring to them is everlasting.

Money, homes, and success—on their own—fade with time. But when they are used for kindness, for Torah, for holiness, they acquire eternity. When we sit in the Sukkah, even if its walls tremble in the wind, we are grounded in the permanence of a life connected to G-d.

 

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