4 min read

Jacob Told Esau the Blessing Had Cost Him Everything

When Jacob sent word to Esau after twenty years, his message was not diplomatic. He told his brother the blessing had done him no good at all.

Curated by Arthur · Told by Maggid ·
Table of Contents
  1. The Message He Sent Ahead
  2. What He Was Actually Saying
  3. The Gifts That Followed the Words
  4. Buying Down the Danger

The Message He Sent Ahead

Jacob had heard the news about Esau's four hundred men and wept bitterly. Then he composed himself and wrote a message.

It was not the message of a man trying to project power, or of a diplomat managing a dangerous reunion with the careful language of advantage preserved. It was a confession. He told Esau: think not that the blessing your father gave me profited me. For twenty years I served your uncle Laban, and he deceived me, and changed my wages ten times. I labored in cold and heat. I was robbed of what I earned and then earned it again. What I have now is not from the blessing Isaac spoke. What I have is from the work of my hands in a foreign land and from God's mercy at the end of it.

He wanted Esau to understand that the inheritance of Abraham was not a prize that the thief of the blessing got to enjoy while the rightful heir went without. The blessing was words. What became of the words was twenty years of hard use in a country that did not care about his grandfather's covenant.

What He Was Actually Saying

He was telling his brother: you did not miss what you think you missed.

The birthright Esau had sold and the blessing Esau had lost were not the same as the inheritance of Abraham, not the part that manifested as comfort and ease and material reward. They were the calling, the burden, the obligation to carry a covenant through twenty years of Laban's deceptions and produce something worth giving to the next generation. Esau had sold his portion of that work for a bowl of lentils and had gotten, in exchange, twenty years of the life he actually wanted: the sword, the hunt, the freedom from his father's God.

Jacob was not falsely modest. He was making a theological argument under extreme pressure, trying to convince his brother that the robbery had not been what Esau thought it was.

The Gifts That Followed the Words

Then he sent the gifts. He did not only send words. He sent goats and rams and camels and cattle and donkeys, wave after wave of animals with servants between them, each wave arriving before Esau as a separate tribute, each servant instructed to say: these are from your servant Jacob, a gift to my lord Esau. Jacob is coming behind us.

The strategy of spacing out the gifts was Jacob's own invention, preserved in the tradition as a piece of practical psychology. Each wave would soften Esau's anger a little more before the next wave arrived. By the time Jacob himself appeared, Esau would have received so many gifts that the anger might have been drained before the two men faced each other.

Buying Down the Danger

Jacob was not only reasoning with his brother. He was paying for time, buying down the danger with animals, trusting that Esau's resentment could be managed if he received enough of what he had always wanted: recognition, material tribute, his brother on his knees calling him lord.


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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.

Legends of the Jews 6:169Legends of the Jews

Legends of the Jews turns to Jacob Wept and Sent Gifts to Appease Esau's Army.

So, what does Jacob do? He tries to smooth things over. He sends messengers to Esau, hoping to placate him. And the message they carry? It’s fascinating.

The messengers are instructed to say, "Thus speaketh thy servant Jacob: My lord, think not that the blessing which my father bestowed upon me profited me." In other words, "Hey, Esau, don't think this blessing has made me rich or powerful! It's not like it's done me any good."

Then comes the list of grievances. "Twenty years I served Laban, and he deceived me, and changed my hire ten times, as thou well knowest. But did I labor sorely in his house, and God saw my affliction, my labor, and the work of my hands, and afterward He caused me to find grace and favor in the sight of Laban." Jacob is painting a picture of hardship, of struggle. "Look at everything I've been through!" he seems to be saying.

And then, almost as an afterthought, he mentions his prosperity: "And through God's great mercy and kindness, I acquired oxen and asses and cattle and men-servants and maid servants." But immediately, he downplays it, adding, "And now I am coming to my country and to my home, to my father and mother, who are in the land of Canaan. And I have sent to let my lord know all this in order to find favor in the eyes of my lord, so that he may not imagine that I have become a man of substance, or that the blessing with which my father blessed me has benefited me."

It’s a carefully crafted message, isn’t it? A mixture of humility, self-deprecation, and a subtle reminder of God's favor. It's Jacob trying to defuse a potentially explosive situation. He's trying to convince Esau that he's not a threat, that the blessing was just words, and that he’s still the same old Jacob.

But is Esau buying it? That's the question, isn't it? Does this carefully worded message truly reflect Jacob's heart, or is it just another layer in a long history of family drama? And does it even matter? Sometimes, even the most skillfully crafted words can't undo the past. Sometimes, the past just demands to be reckoned with.

Full source
Bereshit Rabbah 75:11Bereshit Rabbah

Bereshit Rabbah turns to Jacob Hopes Esau Has Repented After All These Years.

Jacob, remember, is about to face his brother Esau, from whom he'd essentially stolen a birthright and a blessing. So, what does Jacob do? He sends messengers ahead. But why?

It wasn't just to announce his arrival. According to Bereshit Rabbah, Jacob was hoping, praying, that Esau might have repented. He wanted to offer Esau a way out, a path to reconciliation before they even met face-to-face. He instructs his messengers to say, "Don't think Jacob is the same impoverished man who left his father's house with only a staff. Tell him, 'I have become two camps!'" (Genesis 32:11). In other words, "I’ve earned everything I have through hard work."

There’s also a subtle, almost heartbreaking, element of appeasement. Jacob calls Esau "my lord" multiple times. And, as the text points out, this act of humility doesn't go unnoticed.

The Holy One, blessed be He, says to Jacob, "You abased yourself and called him ‘my lord’ eight times. As you live, I will establish eight kings from his descendants before your descendants." The passage then references, "These are the kings who reigned in the land of Edom, before the reign of a king for the children of Israel" (Genesis 36:31). In other words, Jacob's deference to Esau will have long-lasting political ramifications. This is a pretty powerful statement about the consequences of our choices, isn't it?

Jacob, though, wasn't just extending an olive branch, he was also prepared for the worst. He tells his messengers, "If you are prepared for peace, I am with you, and if for war, I am with you." He even boasts, "I have warriors, courageous and strong, who say something before the Holy One blessed be He, and He performs their will on their behalf."

It’s a fascinating blend of diplomacy and, well, divine intimidation. Jacob is essentially saying, "I'm ready for anything, and I have God on my side." Which leads the text to quote (Psalm 145:19), "He performs the will of those who fear him."

This situation reminded David of his own trials while fleeing from Saul. As we find in the text, David says, "For behold, the wicked bend the bow" (Psalms 11:2).

And then comes a truly profound question: “If the foundations are destroyed, what can the righteous man do?” (Psalms 11:3). David is asking, if Jacob, the very foundation of the world, is forsaken, what hope is there for anyone? The text equates Jacob with "the righteous man is the foundation of the world" from (Proverbs 10:25).

The passage concludes with the powerful declaration: “Some on chariots and some on horses, but we invoke the name of the Lord our God” (Psalms 20:8). Even when facing overwhelming odds, the Psalmist trusts in God.

So, what can we take away from this? It seems to me that this passage from Bereshit Rabbah is about more than just a tense family reunion. It's about the delicate balance between humility and strength, between seeking peace and preparing for war, and, ultimately, about trusting in something larger than ourselves, even when the foundations seem to be crumbling. It's a reminder that even in the face of daunting challenges, faith, preparation, and a little bit of preemptive diplomacy can go a long way.

Full source
Targum Pseudo-Jonathan on Genesis 32:6Targum Pseudo-Jonathan on Genesis

As Jakob prepared his message to Esau, he did something strange. He instructed his servants to announce that the great blessing stolen years before had, in effect, come to nothing. Of all that in which my father blessed me there is nothing in my hand; but I have a few oxen and asses, sheep, and servants and handmaids; and I have sent to tell my lord that that blessing hath not profited me (Genesis 32:6).

Targum Pseudo-Jonathan keeps the self-effacement intact. Jakob, who was returning with eleven sons, vast flocks, and a heavenly escort, told his brother the blessing had brought him nothing. A few cattle. A few servants. Not the empire Esau had feared.

Why? Because he wanted mercy, not envy. That I may find mercy in thine eyes and that thou mayest not maintain enmity against me on account thereof. A brother nursing a twenty-year grudge needed to hear that the stolen blessing had not crowned Jakob with splendor. It had only tired him.

The Maggid teaches: humility before an estranged brother is not a lie; it is a kindness. Jakob chose to minimize his fortune because the fortune itself was not worth the renewed hatred of a twin. Sometimes you shrink the story of your success to make room for reconciliation.

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