Esav’s Tears and Our Tears

Vayisa Esav kolo va’yeivk (Bereishis 27:38)

Parashas Toldos revolves around Yitzchak’s twin sons, Yaakov and Esav. After Yitzchak grew old and blind, he decided to bless his older son, Esav, but his wife Rivkah overheard his plan and arranged to substitute the more righteous Yaakov to receive his father’s blessings. When Esav realized what had transpired and that the blessings intended for him had been cunningly taken by Yaakov, he began to cry. The Zohar Hakadosh (Vol. 2, 12b) teaches that the tears shed by Esav as a result of his intense pain over not receiving his father’s blessings enabled his descendants to send Yaakov’s offspring into galus (exile). The Zohar adds that when the tears shed by the Jewish people wash away Esav’s tears, they will be redeemed from exile.

Harav Shmelke of Nikolsburg questions this statement. Throughout the generations, suffering and afflicted Jews have cried millions of tears. Why haven’t they been sufficient to eliminate the few tears shed by Esav so many thousands of years ago? He answers that the Gemara (Chullin 98b) teaches that “min b’mino eino batel” — it is only possible to nullify an item by combining it with a more numerous item of a different type, but an object cannot be nullified by adding to it more of the same. Therefore, the tears cried by the Jewish people lack the ability to cancel out Esav’s tears. However, this reasoning is difficult to understand. How is it possible to say that the tears shed by Esav and those shed by the Jewish people are considered the same type of tears? Do we really cry for the same reason as Esav?

Rav Shmelke explains that Esav cried over the loss of the blessings that Yitzchak gave to Yaakov, which were clearly materialistic in nature (27:28–29). From the fact that our copious tears throughout the generations have been unable to wipe away his, it must be that our tears are also for mundane and earthly issues, and for this reason they are considered comparable to Esav’s tears and unable to nullify them. If we would only begin to cry not over our unfulfilled physical needs, but our spiritual yearnings, then our tears would no longer be classified as the same type of tears that Esav shed and would be able to nullify them, which would bring us the long-awaited fulfillment of the Zohar’s promise for our redemption from galus with the coming of Moshiach, may it be speedily in our days.

Q: What is the significance of the fact that this week’s parashah is named Toldos, and why is it specifically read at this time of the year?

Why did Yaakov bring his father wine to drink (27:25) when his mother only commanded him (27:17) to give him bread and meat, and from where did he get the wine?

A: 1) Harav Moshe Wolfson, shlita, explains that this week’s parashah is called Toldos because it is the only parashah in the Torah in which all three of the Avos are living simultaneously, albeit for a mere three verses (25:26–28). Shlomo Hamelech teaches (Koheles 4:12) that a 3-ply rope is not easily severed. The Gemara in Bava Metzia (85a) teaches that if a man, his son and his grandson are all Torah scholars, the Torah will never cease from their offspring. The simultaneous coexistence of our three forefathers formed such a strong foundation for the Jewish nation that they guaranteed a future for their toldos — descendants. It is no coincidence that this parashah is read in the beginning of the month of Kislev, as it represents our guarantee of victory over the attempt of the Greeks to make us forget the Torah. In fact, the verse immediately following the three verses in which all of the Avos are alive begins (25:29): “Vayazed Yaakov Nazid — Yaakov cooked a stew.” The first letters of these three words spell Yavan — Greece — to hint that although Avraham had died, the indestructible three-ply string had already been established to protect his descendants from the Greeks.

2) The Chizkuni explains that Yaakov’s goal was for the alcohol to slightly confuse his father so that he wouldn’t pay so much attention to determining his true identity. The Tosefes Brachah suggests that the wine was for reasons of health, as the Gemara in Shabbos (41a) teaches that it is unhealthy to eat without drinking. The Torah L’Daas suggests that if the meat was from the korban Pesach (Rashi 27:9), then Yitzchak needed wine for the four cups that are consumed during the Seder. Alternatively, just as many mitzvos are done with a glass of wine, Yaakov reasoned that so, too, the blessings he would receive from his father should be given with a glass of wine. As for where Yaakov got the wine, the Daas Z’keinim writes that the angel Michoel brought it to him from Gan Eden (perhaps that was the aroma of Gan Eden that Yitzchak smelled when Yaakov entered the room — Rashi 27:27).


Originally from Kansas City, Rabbi Ozer Alport graduated from Harvard, learned in Mir Yerushalayim for five years, and now lives in Brooklyn, where he learns in Yeshivas Beis Yosef, is the author of the recently-published sefer Parsha Potpourri, and gives weekly shiurim. To send comments to the author or to receive his Divrei Torah weekly, please email