Don’t Give Up On Your Brother

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November 16, 2025

6 min read

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Toldot (Genesis 25:19-28:9)

In this week’s Torah portion we have the enigmatic story of the struggle between Yaakov and Eisav over acquiring the blessings from their aged father, Yitzchak. Yitzchak sets the drama in motion by summoning Eisav and telling him to prepare to receive his blessing.

"See, now, I have aged; I know not the day of my death. Now sharpen, if you please, your gear – your sword and your bow – and go out to the field and hunt game for me. Then make me delicacies such as I love and bring them to me and I will eat, so that my soul may bless you before I die" (Bereishis 27: 2-4).

What was Yitzchak thinking? How is it possible that Yitzchak did not recognize the extent of Eisav’s depravity, and wanted to bless him?

Eisav’s Destiny

It is a mistake to think that Yitzchak was a blind old man, somewhat out of touch with reality, who was easily deceived by Eisav. Yitzchak understood full well how depraved Eisav was – but he also clearly saw his enormous potential and the pivotal role he could play in enabling the Jewish people to accomplish their mission.

The Torah describes how Eisav looked when he was born: “The first one emerged ruddy (admoni), entirely like a hairy mantle; so they named him Eisav” (ibid 25:25). Rashi explains that the fact that Eisav was “admoni” was a sign that he would have the propensity to shed blood (Bereishis Rabbah 63:8). Does this mean Eisav was destined to become a murderer?

The word “admoni” is used in only one other place in Tanach, and that is in describing the young David, whom the prophet Shmuel meets for the first time. “He [David] was ruddy (admoni), with fair eyes and a pleasing appearance. Hashem then said, ‘Arise and anoint him, for this is he!’” (I Shmuel 16:12). How can the same word be used to describe the essence of the evil Eisav and the righteous King David?

David indeed had the propensity to shed blood, like Eisav. But unlike Eisav, he took that innate inclination and channeled it toward good by battling the enemies of the Jewish people and defending Hashem’s honor.

All traits can be used for good or evil. Eisav was not compelled to become a murderer; he could have used his inborn traits to accomplish great things.

Partnership

Yitzchak had a strategy. He wanted Yaakov and Eisav to form a partnership that would combine their inherent strengths to perfect the world. Yaakov would lead the spiritual realm while Eisav would rule the material world, freeing Yaakov to focus on the loftier mission of spreading Hashem’s word to humanity.

Yitzchak never intended to give Eisav the “birkat Avraham,” the spiritual blessing that represents the transfer of the covenant originally forged between Avraham and Hashem, and the inheritance of the Land of Israel. Yaakov was always the intended recipient of this far more important blessing, which Yitzchak gave him at the end of the Torah potion, when he knew that he was blessing Yaakov. “May He grant you the blessing of Avraham to you and to your offspring with you, that you may possess the land of your sojourns, which God gave to Avraham” (Bereishis 28:4).

The blessing that Yitzchak intended to give Eisav – which Yaakov received after he dressed up as Eisav – was for material abundance and political domination. “And may Hashem give you of the dew of the heavens and of the fatness of the earth, and abundant grain and wine. Peoples will serve you, and regimes will prostrate themselves to you; be a lord to your kinsmen, and your mother's sons will prostrate themselves to you…” (ibid 27:28, 29).

The Seforno (ibid 27:29) explains why Yitzchak deemed this blessing appropriate for Eisav, and what his intention was in telling Eisav that he would rule over his brother. He thought it would be best for Yaakov to remain in Eretz Yisrael and not be burdened with the responsibilities of the physical world. Yaakov could then focus all of his efforts on Torah, while Eisav, working toward the same objective, would rule the material world.

Yitzchak was correct in his assessment of Eisav’s potential and the impact that the combined abilities of Yaakov and Eisav could have on the world. His mistake was in strategy. He realized Eisav was immoral, but he thought that if Yaakov would just reach out to him he would be able to set him on a righteous path. Yitzchak thought that forging a partnership between his two sons would force Yaakov to influence Eisav. But Rivka realized that this strategy was terribly mistaken, because empowering Eisav before he did teshuvah, repented, would remove his greatest impetus to change. Once Eisav would have this power, he would never be motivated to face his demons and improve.

Eisav’s Tears

Yaakov’s potential to reach out to Eisav and turn him around sheds light on another curious statement of Chazal. The Zohar (Shemos 12b) says that the prolonged exile of the Jewish people is because of the tears Eisav shed upon discovering that Yitzchak blessed Yaakov. “And Eisav said to his father, ‘Have you but one blessing, Father? Bless me too, Father!’ And Eisav raised his voice and wept” (Bereishis 27:38). The redemption will come, the Zohar says, when our tears (of repentance) will cancel the tears of Eisav.

Why should the Jewish people have lost the Beis Hamikdash, the Holy Temple, and gone through a lengthy, brutal exile due to Eisav’s tears? Eisav was evil, and did not deserve the blessing Yitzchak intended to give him. So why were Yaakov and his descendants punished for the poor choices Eisav made that caused him to be undeserving of the blessings?

The Torah’s answer is that it was not entirely Eisav’s fault. Ultimately, the Jewish people share the blame for Eisav’s conduct, because Yaakov should have reached out to his brother. Had he done so, he would have succeeded in bringing him back to Hashem.

We find the same point made in the Torah portion of Vayishlach, with regard to Yaakov’s preparations for meeting his feared brother Eisav: “But he got up that night and took his two wives, his two handmaids, and his eleven sons and crossed the ford of the Yabbok” (ibid 32:23).

Rashi comments: “And where was Dinah? [Yaakov] put her into a chest and closed it over her, so Eisav would not set his eyes upon her. Yaakov was punished for withholding his daughter Dinah from his brother, for [had Dinah married him] she might have returned him to virtuous conduct. So she fell into the hands of Shechem.”

Yitzchak’s vision of his two sons working in tandem – with Yaakov ruling the spiritual realm and Eisav ruling the physical realm – was indeed correct. And Yaakov is faulted for not doing what he could have to prompt Eisav’s teshuvah. Imagine the consequences for not doing all we can to reach out to our Jewish brothers and sisters who are innocent victims of assimilation and ignorance.

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