The Torah of Esau

Originally given as a senior sermon at JTS.

As a fellow chef of hearty legume-based soups, who is also named Jacob, you might expect me to identify strongly with the patriarch of this week’s parashah. But truthfully, I’m much more drawn to Esau as a character, and I find that I’m thoroughly on the side of Team Esau.

Since I was a child in day school, I have always been troubled by our patriarch Jacob’s behavior in this parashah. Deceiving his brother, only to top it by deceiving his father–what kind of Jew behaves this way? But I’m certainly not here to denigrate Jacob. Rather, I’m going to leverage my discomfort with his actions to instead force us to take Esau more seriously as an inspiration and dugmah ishit (personal example) for us. I want to lift up the Torah of Esau offered by Parshat Toldot and consider what we might learn from him.

To begin with, Parashat Toldot is not about Jacob, per se. We get our title from the line that terminates the genealogy of Ishmael:


.ואלה תולדת יצחק בן אברהם אברהם הוליד את יצחק

And these are the generations of Isaac, son of Abraham; it was Abraham who sired Isaac. (Genesis 25:19)

This is an odd, repetitive sentence! We only need the first half of it; why say “Abraham sired Isaac,” when that is of course what it means to call Yitzhak, ben Avraham, son of Abraham? Furthermore, for my fellow grammar enthusiasts out there, putting on my Bible M.A. hat for a moment, we have some unusual syntax here, what we call “disruptive word order.” The Torah usually puts verbs first, but here the subject, Abraham, is moved earlier into the sentence, highlighting his role: it was Abraham who sired Isaac.

I think the verse beats us over the head a little bit with the emphasis on Abraham to set up that this next cycle of stories is really about who will inherit and perpetuate Abraham’s legacy. Isaac has now inherited that covenant and assumed the role of patriarch, but this verse sets up the primary drama of this parashah. To whom will Isaac pass on the covenant? That is, who is the true inheritor of the Abrahamic legacy? We can read Esau and Jacob’s ongoing wrestling–literal in the womb and metaphorical in life–as a contest over acquiring that legacy. Who will assume the role of protagonist, of the next patriarch? If we remove our prior knowledge about how this will end, we get the sense that the Torah is intentionally ambiguous about who that inheritor will be.

The sale of the birthright, our first real interaction between the twins, merits a closer read to examine the scene and evaluate Jacob’s tactics. Esau asks Jacob for some soup:

הַלְעִיטֵ֤נִי נָא֙ מִן־הָאָדֹ֤ם הָאָדֹם֙ הַזֶּ֔ה
Serve me some of that very red stuff. (Genesis 25:30)

Jacob replies unflinchingly that he will only do so in exchange for Esau’s selling his birthright. Esau replies hineh anochi holech lamut (Genesis 25:32)–listen, I am about to die from starvation! Jacob proceeds to extort Esau for the firstborn rights before he will feed him lentils, a crop abundantly available at the time in the Ancient Near East. Even if we think that Esau was being dramatic or hyperbolic, it really does not matter: Jacob’s response is appalling!

Can we imagine a greater violation of the Abrahamic ethos? Consider the contrast to the start of Parashat Vayera, where a convalescent Abraham literally jumps at the opportunity to feed complete strangers (Genesis 18:2). Rabbi Shai Held has proposed that this emphasis on hospitality and generosity of spirit is actually the absolute core of the Abrahamic legacy. He reads the test that Abraham’s servant applies to Rebecca—finding someone who offers to water his camels—as a pure test of this kind of generosity (Held 2015, D’var Torah on Parashat Chayyei Sarah: “People are Complicated”). The primary quality needed for someone who wishes to join this family is a concern for the needy and hungry. Yet Jacob, the supposed heir, cannot be bothered to support his own brother. If an ill Abraham fed strangers, all the more so a healthy Jacob should feed his own brother, who, ironically, is only so hungry because he was off getting food for the rest of his family to eat!

Understanding what exactly transpires here rests on clarifying a clever Biblical wordplay that pervades the parashah. The word b’chorah—firstborn status and inheritance—and b’rachah—blessing—have just one letter switched. Verse 34 says that the lentils episode is how Esau forfeited his b’chorah. By the rules of Biblical primogeniture (firstborn inheritance), the firstborn son inherits a double portion of all of his father’s assets, whereas all other sons split the remaining assets equally. The Spanish commentator Abarbanel has this detail in mind when he notes that the plainest sense of the verse suggests that Jacob is negotiating here purely with respect to material wealth (Peirush Abarbanel alHaTorah, comment on Genesis 25:31. In other words, without that birthright, only 1/3 of Isaac’s wealth, nothing would stop Jacob from carrying on the covenant! The Torah actually highlights for readers the profound irony of Jacob obsessing over the literal birthright of his ancestors while missing the essential symbolism of that very birthright.

Let’s turn from Jacob’s deceit of his brother to his deceit of his father. If Esau’s sale of his birthright were a recognized legal transaction, why would Jacob and Rebecca need to trick Isaac? Couldn’t Jacob have just point out what he’d done? I suspect that Jacob has the decency to be ashamed of himself! He is unwilling to confess to extorting his brother on a matter of life and death. But let’s keep in mind b’chorah vs b’rachah. Jacob now has the legal status of firstborn, meaning that he will inherit more, but that evidently has no bearing on who will receive the superior blessing. Esau even makes this distinction, as he will later separate the two in saying,
אֶת־בְּכֹרָתִ֣י לָקָ֔ח וְהִנֵּ֥ה עַתָּ֖ה לָקַ֣ח בִּרְכָתִ֑י
He took my birthright and now he has taken my blessing (Genesis 27:36).

Esau is under no illusion as to the loss of his firstborn status, but he is unbothered! For decades Esau has known that he will get half of the assets of his younger brother upon their father’s blessing, and he accepts that. But the minute his brother gets a superior blessing, an elevated spiritual status, he is instantly triggered. He becomes a broken man. He begs Isaac:
הַֽבְרָכָ֨ה אַחַ֤ת הִֽוא־לְךָ֙ אָבִ֔י בָּרְכֵ֥נִי
Do you only have one blessing, my father? Bless me as well! (Genesis 27:38)

This is a powerful and gentle reprimand from Esau, a reminder that there is surely enough blessing to go around for everyone. He doesn’t care about the birthright, but he refuses to be deprived of blessing, of a spiritual inheritance. If we lower our guards, our fear of Esau inherited psychologically from how Jacob views his brother, we can appreciate that Esau is, in this moment, not at all menacing. He lets out a tz’akah g’dolah u’marah (Genesis 27:34)—an enormous and bitter cry. I imagine that bitterness is something like a man sobbing so uncontrollably that he tastes the bitterness of his own tears. The Torah directs our sympathies to Esau; he is pathetic, devastated, heartbroken.

The juxtaposition is quite damning of Jacob. He misses the forest—the immense blessing of perpetuating the unique Abrahamic covenant—for the trees, the considerable assets held by his family. He has obsessed over the material when the spiritual was equally on the table for him the whole time. We ought to be troubled that Jacob insists on the b’chorah at the expense of b’rachah. But we can certainly have some empathy for him—how easy is it to get caught up in the material, mundane world and to forsake spiritual priorities?

It is Esau who can easily let go of the material but refuses to relinquish the spiritual life. What would it look like for us to learn from Esau and focus on lives of spiritual plenty, moving through the world with an eye to maximize our spiritual assets? Esau appropriately recognizes that we are called by God to live lives of spiritual, not material, plenty.

I am well aware that this charitable reading of Esau is far from the mainstream direction of Rabbinic opinion. Esau is epitomized as pure evil; the enemies of the Jewish people in each generation—from Rome to medieval Christendom—have been labeled “Edom”. But if we strip away the heavy Rabbinic overlay, the Torah does not actually seem to have an altogether negative view of Esau! Moses reminds Israel in one of his Deuteronomic speeches:

לֹֽא־תְתַעֵ֣ב אֲדֹמִ֔י כִּ֥י אָחִ֖יךָ ה֑וּא
Do not despise the Edomite, for he is your brother! (Deuteronomy 23:8)

What a remarkable and blunt instruction. The Torah recognizes the instinct we might have to resent the extended family of the Israelite nation who have not continued the covenant with God But that sort of attitude is simply not on the table. Esau is a core part of the family. Holistically, I think that there is a reading of Esau available to us that is much more positive than the one we’ve traditionally adopted it. We cannot spurn Esau, the Torah says. So why not embrace him and learn from him?

We are predisposed to view Edom unfavorably because of Isaac’s promises that they will live
וְעַל־חַרְבְּךָ֣ תִֽחְיֶ֔ה (Genesis 27:40) sword the by.

There are several variations on the midrash that Edom was initially offered the Torah before Israel. However, upon hearing the prohibition on murder, they were forced to refuse the Torah, replying to God that they were destined, as Isaac said, to live by the sword, and that they would be unable to uphold this commandment (Mekhilta deRabbi Yishmael, BaChodesh 5:8, Avodah Zarah 2b, and Pirkei Rabbi Eliezer 41:2, inter alia). But we need to reckon with the fact that Isaac’s lesser blessing, really more a curse than anything, was foisted upon Esau against his protests in pursuit of a real blessing! What he wanted in his own lifetime, more than anything, was to fulfill God’s covenant with his father by receiving a blessing and becoming his own source of blessing. I suspect that a key factor in our tradition’s consistent denigration of Esau is the need to contrast Jacob favorably with him. We need to resist a zero-sum approach, to refuse to treat every warm remark toward Esau as somehow redounding against our patriarch Jacob. Could we pause that agenda, though, and just do our best to learn from the characters on their own merits, in their own context? If we set that need aside, I think we will find the case for raising up Esau instead.

It’s perhaps unusual for us to learn from Esau, but it is also what our tradition would demand of us. The famous mishnah in Pirkei Avot teaches:
איזהו חכם, הלומד מכל אדם
Who is wise, one who learns from every person (Mishnah Avot 4:1).

I will leave you with my own commentary on this verse borrowing from the midrashic tradition:
Al tikri adam, ela edom – eyzehu hacham, halomed mikol edom.
Do not read adam, a person, but rather read it as Edom, Esau. Who is wise? The one who
learns even from all that Esau did.

JTS has helped me to solidify a two-fold mission statement for my rabbinate: l’hagdil Torah u’lehaadirah, to magnify Torah and to beautify it, and to help others be a source of blessing. The former, I’ve learned over the last almost 5 years, means forcing ourselves to be open to Torah from anywhere and anyone it might emerge, even those, like Esau, with whom we have real qualms. The latter means taking after Esau, recognizing that our core inheritance as children of Abraham is to strive always after blessing above all else and to be a blessing to others. Halomed mikol Edom—may we all merit to yearn for a life of blessing, just like Esau.

Author

  • Jacob Lipkin is graduating in May 2026 from the Jewish Theological Seminary with rabbinic ordination, an M.A. in Hebrew Bible, and a certificate in Spiritual Care and Counseling. He serves as the rabbinic intern at Congregation Shomrei Emunah in Montclair, NJ. He has previously served as the rabbinic intern and educator at the Jewish Association Serving the Aging, Camp Ramah in Northern California, Nativ, and Cornell Hillel. Prior to JTS, Jacob worked at DOROT connecting tween and teen volunteers with older adults as the Facilitator of Intergenerational Programs. He lives on the Upper West Side with his wife Shira and his ever-growing Judaica library.

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Author

  • Jacob Lipkin is graduating in May 2026 from the Jewish Theological Seminary with rabbinic ordination, an M.A. in Hebrew Bible, and a certificate in Spiritual Care and Counseling. He serves as the rabbinic intern at Congregation Shomrei Emunah in Montclair, NJ. He has previously served as the rabbinic intern and educator at the Jewish Association Serving the Aging, Camp Ramah in Northern California, Nativ, and Cornell Hillel. Prior to JTS, Jacob worked at DOROT connecting tween and teen volunteers with older adults as the Facilitator of Intergenerational Programs. He lives on the Upper West Side with his wife Shira and his ever-growing Judaica library.

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