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Isaac Held Esau's Head and Prayed and God Said No

Isaac was blind and near death. He took Esau's head in his hands and asked God for mercy. The answer came back without softening.

Curated by Arthur · Told by Maggid ·
Table of Contents
  1. A Father Who Saw Clearly
  2. The Hands Holding the Head
  3. What God Said
  4. Why Isaac Had Gone Blind

A Father Who Saw Clearly

Isaac could not see his son's face. He had been blind for years, the tradition saying that the smoke of Esau's wives' incense offerings had damaged his eyes, or that the tears of angels falling on him at the Akedah had left their mark, or simply that age had taken what it takes. But blindness had not taken his knowledge of his son.

He knew what Esau was. He had watched the birthright go for a bowl of lentil soup. He had seen the Hittite marriages, the women who made daily life in the household a source of grief for both him and Rebekah. He had heard the plan to kill Jacob after he died, had watched Jacob leave for Padan-aram because of it. He was near death himself, and one of his two sons was building a legacy of violence and dismissal.

He prayed anyway.

The Hands Holding the Head

The scene in Pirkei DeRabbi Eliezer is physical and specific: Isaac grasps Esau's head. Both of his hands holding the head of this son, and he pleads with God. He asks mercy for the wicked son who had not learned the Torah's commandments. He does not pretend Esau is righteous. He prays for a wicked man because the wicked man is his child.

His argument was careful. Perhaps, he suggested, Esau's failures came from ignorance rather than defiance. A man who never fully absorbed the weight of what he was supposed to be could not be judged on the same terms as a man who had received Torah and rejected it knowingly. Perhaps the ignorance was a mitigating factor. Perhaps there was still something salvageable in the field-man, the hunter, the son who came in exhausted and sold everything for food.

He even reached for Isaiah: favor will be shown to the wicked, and he will not learn righteousness. He was not pretending the verse proved his case. He was deploying it as a plea, the way a father uses whatever language might work in the ear of someone who holds his child's fate.

What God Said

God said no.

The tradition did not soften the refusal. The divine response confirmed what Isaac had already known: Esau had seen, had known, had chosen. The ignorance argument did not hold because the ignorance had not been innocent. Esau had been in the presence of Torah and covenant his entire life. He had watched his brother and chosen a different road with open eyes. The plea for a mitigating distinction between ignorance and defiance failed because the distinction did not actually exist in Esau's case.

Isaac had made the best argument available to a father who loves a son who has become what Esau had become. The best argument was not enough.

Why Isaac Had Gone Blind

The tradition on Isaac's blindness connected the physical condition to the spiritual situation in ways that were not coincidental. Some accounts said the blindness came from the Akedah: when Abraham bound Isaac on the altar and the knife was in the air, angels wept, and their tears fell on Isaac's eyes. The tradition that followed from this was that blindness was a mercy: Isaac could not look directly at Esau's face and see the wickedness written there day after day. A father blind to his son's face might still reach for him. A father who saw clearly might give up.

Other accounts connected the blindness to Esau's wives and their idolatrous practices, the incense from their foreign altars filling Isaac's house. In this reading the blindness was damage done by cohabitation with what Esau had chosen: the wrong marriages, the wrong altars, the wrong way of life filling the household that Isaac had built on the covenant his father had brought from Ur.

Either way, Isaac prayed in darkness for a son he could not see, holding his head, asking for something he knew even as he asked it might not come.


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The texts this telling draws on, in full. Open a card to read inline, or expand it for a wider, quieter read.

Pirkei DeRabbi Eliezer 39:16Pirkei DeRabbi Eliezer

Our tradition grapples with this question constantly. Take the story of Isaac and Esau, for example. It’s a family drama, a theological debate, and a reminder of the power – and limits – of prayer.

The familiar version gives us the players. Isaac, the son of promise. Esau, his twin brother, often portrayed as the "wicked" one. But what happens when Isaac, facing Esau, chooses to plead for his son's soul?

Pirkei DeRabbi Eliezer, a fascinating early medieval Midrashic (rabbinic interpretive commentary) text, gives us a glimpse into this very moment. It tells us that Isaac, confronting Esau, grasps his head and turns to the Holy One, blessed be He, with a desperate prayer. image for a moment. Isaac, the patriarch, physically holding his son, Esau, and begging for divine mercy.

What does he say? "Sovereign of all the universe! Let mercy be shown to this wicked one, for he had not learnt all the precepts of the Torah, as it is said, 'Let favour be shewed to the wicked, yet will he not learn righteousness.'" (Isaiah 26:10). He argues that Esau’s wickedness stems from a lack of proper learning, a lack of exposure to the wisdom of the Torah. Isaac continues, noting Esau’s "iniquity concerning the land of Israel and the Cave of Machpelah," again quoting Isaiah: "In the land of uprightness will he deal wrongfully" (Isaiah 26:10).

It’s a powerful plea. Isaac acknowledges Esau's flaws, his failings, but still seeks compassion for him. He seems to be suggesting that perhaps Esau’s actions are a product of ignorance rather than inherent malice. Maybe, just maybe, there's still a chance for him.

But what happens next? Does Isaac's prayer work?

Pirkei DeRabbi Eliezer delivers a stark answer: "The Holy Spirit answered him, saying: As I live! he shall not see the majesty of God."

Wow.

That's a pretty definitive rejection. Despite Isaac's heartfelt plea, the divine decree stands. Esau, in this telling, is beyond redemption. He will not experience the fullness of God's presence.

This passage raises so many questions, doesn’t it? Is Esau's fate sealed? Is Isaac’s prayer ultimately futile?

Perhaps the story isn't about whether Esau can be saved, but about the unwavering love of a parent who tries to save him. It’s about the enduring hope that even the most wayward soul can find its way back. But it's also a sobering reminder that choices have consequences, and that sometimes, despite our best efforts, some paths lead away from the divine.

This brief but powerful scene in Pirkei DeRabbi Eliezer leaves us pondering the nature of free will, the limits of divine mercy, and the enduring power of a parent's love. What do you make of it?

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Bereshit Rabbah 65:10Bereshit Rabbah

The ancient rabbis grappled with these questions constantly, poring over scripture for answers. One particularly poignant example comes from Bereshit Rabbah 65, as it tries to understand why Isaac, a patriarch, a man of God, went blind in his old age. "His eyes dimmed from seeing" – that’s the verse from (Genesis 27:1) that sparks this whole exploration.

Rabbi Elazar ben Azarya offers one perspective: Isaac’s blindness stemmed "from seeing evil – from seeing the evil of the wicked one," meaning his son, Esau. The idea is that God, in his infinite mercy, shielded Isaac from the pain of witnessing his son's wickedness firsthand. Imagine Isaac walking through the marketplace, people whispering, "That's the father of that awful Esau!" To spare Isaac that shame, God dimmed his eyes. As (Proverbs 28:28) says, "With the rise of the wicked, a person should hide."

This idea connects to a broader principle: "Anyone who produces a wicked son or a wicked student, ultimately his eyes will dim." It's a harsh idea, isn't it? But it speaks to the profound disappointment and pain that comes from seeing someone you nurtured stray from the righteous path. The text even brings up examples. Aḥiya the Shilonite, whose eyes dimmed because of his wicked student Yerovam, as described in I (Kings 14:4). And then there's Isaac himself.

The rabbis don't stop there. They offer another, more mystical, interpretation. "From seeing [mereot] – as a result of that sight [re’iya]." This refers to the Binding of Isaac, the Akeidah. Remember that harrowing scene? Abraham, commanded by God, prepares to sacrifice his son Isaac. According to this interpretation, the ministering angels wept at the sight. Their tears, the Bereshit Rabbah tells us, fell into Isaac’s eyes, and those tears, filled with divine sorrow, eventually caused his blindness. "Behold, their angels cry out outside." (Isaiah 33:7). Can you picture it? A cosmic sympathy, the grief of the heavens impacting a mortal man.

And there’s yet another layer. Again, linking Isaac's blindness to the Akeidah, the text suggests that Isaac, in that moment of profound crisis, "directed his eyes heavenward and looked at the Divine Presence." It was too much. It's like a parable the Rabbis share: A king is strolling by his palace, and sees his friend’s son peering at him through the window. It was forbidden to look directly at the king. The king thinks, "If I kill him, I'll upset my friend. Instead, I'll just decree that his windows should be sealed."

Similarly, when Isaac looked at the Shekhinah, the Divine Presence, God couldn’t bring himself to punish Isaac directly, knowing the pain it would cause Abraham. So, instead, he "sealed" Isaac's eyes, causing them to dim with age. It’s a powerful image, isn’t it? Isaac's spiritual vision, his yearning for God, paradoxically leading to his physical blindness.

So, what do we take away from all this? Is Isaac’s blindness a punishment? A divine shielding? A consequence of witnessing the divine? Perhaps it's all of the above. The Rabbis, in their wisdom, offer us multiple perspectives, reminding us that the mysteries of faith are rarely simple, and often invite us to confront complex and sometimes uncomfortable truths. And maybe, just maybe, by wrestling with these questions, we can find a little more light in the darkness.

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Book of Jubilees 26:27Book of Jubilees

The story of Jacob and Esau is one of sibling rivalry, deception, and destiny. a pivotal moment: Isaac unknowingly blessing Jacob instead of Esau, as recounted in the Book of Jubilees, chapter 26.

Isaac, old and blind, knows his time is near. He calls for his elder son, Esau, a skilled hunter, a man of the field. He asks Esau to prepare a savory dish from his game, so that Isaac may bless him before he dies. A simple request. But Rebecca, Isaac's wife and mother to both Esau and Jacob, overhears this. Favoring Jacob, she arranges a plan. She instructs Jacob to fetch two young goats from the flock, which she prepares into a dish that will taste like Esau's game. She then dresses Jacob in Esau's clothes and covers his hands and neck with goatskin, to mimic Esau's hairy skin. (Book of Jubilees 26).

Jacob, hesitant but ultimately obedient, follows his mother's instructions. He approaches his father, Isaac, and presents himself as Esau.

"And he said: 'Art thou my son Esau?' and he said: 'I am thy son.'"

Isaac, suspicious, asks him to come closer. The text continues, "and he said, 'Bring near to me that I may eat of that which thou hast caught, my son, that my soul may bless thee.' And he brought near to him, and he did eat, and he brought him wine and he drank."

Still unsure, Isaac asks Jacob to kiss him. "And Isaac, his father, said unto him: 'Come near and kiss me, my son.'"

"And he came near and kissed him. And he smelled the smell of his raiment, and he blessed him and said: 'Behold, the smell of my son is as the smell of a (full) field which the Lord hath blessed."

That scent! The earthy aroma of Esau's clothes, carefully placed on Jacob by Rebecca, sealed the deception. Isaac, convinced, bestows the blessing meant for Esau upon Jacob.

The implications? Profound. This blessing, a sacred pronouncement of prosperity and dominion, changes everything. According to later interpretations, this single act set the stage for the lineage of Israel to descend through Jacob, not Esau. (See Genesis 27 for a parallel account).

But what does it all mean? Was it fate? Was it Rebecca's manipulation? Was it Jacob's ambition?

The story, found not only in Jubilees, but also in Genesis and alluded to throughout Jewish tradition, continues to provoke questions about identity, destiny, and the power of words. It forces us to consider the consequences of our actions, the complexities of family dynamics, and the enduring search for meaning in a world filled with both blessings and deception.

What do you think? Was Jacob right to deceive his father? Or was Rebecca overstepping her bounds? Let's discuss!

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Book of Jubilees 26:40Book of Jubilees

The story of Esau is a masterclass in that feeling.

The familiar story centers on Jacob and Esau. The twins. Jacob, the trickster, ends up getting the birthright and the blessing intended for Esau. But what happens after? What was left for poor Esau? The Book of Jubilees, an ancient Jewish text that retells and expands upon the stories in Genesis, gives us a glimpse into that moment.

In Jubilees 26, we find Isaac, the father, having just bestowed the crucial blessing upon Jacob. Esau, understandably distraught, confronts his father.

Isaac says to Esau, "Behold, I have made him thy lord, And all his brethren have I given to him for servants, And with plenty of corn and wine and oil have I strengthened him: And what now shall I do for thee, my son?"

Ouch. Can you feel the sting? Isaac is essentially saying, "Sorry, son, I gave it all away. Nothing left for you." It's a gut-wrenching moment of paternal disappointment.

Esau, in his raw despair, pleads, "Hast thou but one blessing, O father? Bless me, (even) me also, father." And then "Esau lifted up his voice and wept."

Imagine that scene. The weeping. The utter hopelessness. This isn't just about material wealth; it's about legacy, about a father's love, about a sense of belonging.

And what does Isaac say? "Behold, far from the dew of the earth shall be thy dwelling, And far from the dew of heaven from above."

That’s… not exactly comforting, is it? "Far from the dew…" In other words, your life will be harsh, barren, and lacking divine favor. Some translations interpret this as a prophecy of Esau's descendants living in arid lands.

Now, you might be asking: why this bleak pronouncement? Was Isaac being cruel? The Book of Jubilees doesn’t explicitly say, but we can infer some things. Perhaps Isaac felt he had no choice, having already made the irrevocable blessing to Jacob. Perhaps he saw something in Esau that made him believe he wouldn’t use a blessing wisely.

Whatever the reason, it’s a stark reminder that words have power. Blessings, curses… they carry weight, especially within a patriarchal society like the one depicted in the Bible and the Book of Jubilees.

It leaves us with a question: What do we do when we feel like Esau? When we feel like we've been passed over, cheated, left with nothing? Maybe the answer isn’t to weep in despair, but to find our own blessings, even in the "far from the dew" places. Maybe Esau's story isn't just a tragedy, but a challenge to create our own destiny, even when it feels like everything is stacked against us.

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