The True Blessings of Jacob and Esau: A Yom Kippur Reflection

The rivalry between Jacob and Esau is one of the most enduring tales of the Torah—a conflict born in the womb that echoes through generations. It is a story of inheritance and separation, blessing and loss. There is much to ponder in this story, and Yom Kippur, with its themes of return, forgiveness, mortality, and encounter with the divine—gives us the perfect invitation to revisit it. Perhaps there are hidden messages behind the concept of "blessing" that might give us clues to the roots of our own divisions, and the promise that awaits when we transcend them.

Jacob and Esau: Right and Wrong

At its core, the story of Jacob and Esau is a tale of family rivalry. Twin brothers stand on the threshold of inheritance, but the younger, Jacob, seizes an opportunity when the elder, Esau, is weary and impulsive. He trades Esau his birthright—his share of the inheritance—for a bowl of stew. Later, Jacob deceives their blind father, Isaac, by pretending to be his brother at the moment when he was prepared to give Esau his soul's truest blessing. When Esau learns of this betrayal, his fury forces Jacob to flee for his life.

Now, because the history we follow traces Jacob’s lineage, we tend to think that Jacob was the rightful inheritor. He was the true heir to his father’s sacred land and spiritual responsibilities. But is it possible that we think he was the rightful one because he was the actual one? He got it; so we assume he deserved it. 

As the story goes, God speaks to his mother Rebekah while she is pregnant, and tells her that her younger son will be the mightier one. Many years later, the mother tells Jacob to steal his elder brother's blessing. Maybe she told him that because God said it would happen, or maybe God said it would happen because he predicted that she would say this. Either way, our midrash supports her decision, by saying Jacob was the better character. And Esau—not a good man. Jacob was good. And the tradition accepts this.

But if we invite ourselves to question it, we can’t really avoid that Jacob lied to own father. He stole from his own brother. So was he really the one of the two who had unquestionable character? And even if a person has some good qualities, does that give them the right to harm another? 

Yom Kippur is a day when we are asked to question our ideas about rightness, and to look at our wrongs. We are asked to look at the evidence we are avoiding, and the biases we’ve formed, and the perspectives we’ve adopted simply because we were told to believe them. And sometimes we find that “rightness” is a decision we made because we, consciously or unconsciously, believe a narrative. 

We might believe that Jacob is the better and more deserving son. And we might believe that it is God’s plan for him to have his father's property. But we might just as soon believe that Esau was wronged, tricked, and overpowered by his cunning brother. If we believe the first, then we justify Jacob’s lying and cheating. And if we believe the second, then we justify Esau’s vengeance and his willingness to take the life of his brother out of spite. 

Yet from a higher vantage point we can see that they’re both a little right, and a lot wrong, and two wrongs don’t make a right. In fact, two wrongs make more wrongs. And their mother knows this, as when she sends Jacob away for his safety, she says to him: “Why should I be bereaved of you both in one day?” Rashi, a medieval commentator, tells us that Rebekah says this because if Esau killed Jacob, Jacob’s other relatives would kill Esau. The death of one would be the death of the other. Because violence begets violence. 

Other midrash tells us that Esau’s morality would have died and then he’d be capable of even worse. Either way, one wrong leads to another, and there is no end to that story.

Imagine, then, what happens over time. There is a threat of great loss when Jacob leaves, but that threat grows exponentially when Jacob returns 20 years later, with 4 wives and 12 children, plus many others in his retinue. And he hears that Esau is coming to meet him with 400 in his clan. Jacob is prepared for the worst. Not just his own death but that of his entire family, as certainly revenge would lead to revenge. If violence were the way forward, we might never have heard their story.

And yet, this isn’t what happens. What happens instead is what I find to be one of the most beautiful and poignant moments in the Torah. 

God and Duality

I want to pause here to point out that when we have major acts of aggression and violence in the Torah, it is often incited by God. For example, God told the people to leave Egypt and at the same time, hardened Pharaoh’s heart, leading to great suffering on all sides. This was God’s design. In Deuteronomy God tells the people to take conquest of the land of Canaan. He turns these pastoral people into an army. 

And here we have something similar. God interferes and creates duality, friction, tension, drama. He creates scarcity by saying one piece of land is more special than any other, and he gives it as a birthright and a blessing that only one brother among brothers can have. Thus he creates superiority which inevitably leads to class struggle, boundaries, and conflict. These concepts get passed on for generations. We feel the ripples of this even today. 

But, we ask, why would God set up scenarios like this? And why is there all this suffering in the world if God is powerful enough to stop it? Doesn’t God want us to have peace, harmony, and unity? Isn’t that his promise? If so, then why does he create all of these difficult conditions? 

Many traditions give us answers to these questions. They ask: how would we grow if everything was easy? We want our own children to develop their character, to go out into the “real” world and discover their gifts; why wouldn’t God want the same for us? What gifts would we discover if we had no one to give them to?

Many spiritual traditions explain that duality is not the highest expression of the divine, but it serves a divine purpose. Like any game that is worth playing, life is more interesting when we are given good challenges. And, at the same time, we are given tools that we have to learn to use. These include holy days, where we are commanded to reflect and repent and look at how we ourselves have reinforced limited ideas.

Clearly, if God created Yom Kippur, he doesn’t want us to simply be perfect. He wants us to become perfect. To not just be who we are, but to enact who we are, and to affirm it with our own will. And the best way to become who we are is to see who we are not. The best way to know what is right, is to do what is wrong, and honestly reflect on what happens.

On this day we are said to have a rare interface with the truth of God, in the holiest of holies, and we are given a description of that God: compassion and tenderness, patience, forbearance, kindness, awareness. Yes, our God is also the creator of vengeance and war. He is the origin of the good and the bad, the light and the dark. But we are reminded again and again, once each year, that the true God, the innermost God, is the God of love. And the question of creation is put to us: which face of God are you going to worship?

Defying Fate

Something incredible happens the night before Jacob faces off with his brother. He takes on God in a hand to hand combat. A wrestling match by the riverside in the middle of the night. Is Jacob’s own will any match for God’s will? 

Incredibly, he prevails. 

This is a wrestling match that occurs on the eve of what could have been a disaster. And while the Torah reveals very little about it, we see that when Jacob wins, something completely unprecedented happens. He is no longer subordinate to the ever-unfolding drama of duality, but he is now an active player, affirming unity, transcending separation, and deciding his own fate.

Midrash tells us that the emissaries Jacob sends to bring gifts to his brother, the Melachim, were actually angels in human disguise. So now Jacob is commanding the divine forces himself—no longer subordinate to them, no longer playing out their play.

The story that fate had given him, the part he was designed to play out, was written in his stolen blessing. That blessing said:

Let peoples serve you,

And nations bow to you;

Be master over your brothers,

And let your mother’s sons bow to you.

That night, Jacob makes a decision to defy this blessing—and the narratives, and the dramas, that go along with it. He doesn’t demand that his mother’s sons bow to him. He bows to them.

“He himself went on ahead and bowed low to the ground seven times until he was near his brother.”

And what happens next?

“Esau ran to meet Jacob and embraced him; he threw his arms around his neck and kissed him. And they wept.”

This scene always brings tears to my eyes. This is t’shuvah: Return. This is reconciliation—the whole purpose of our holiest day. To humble yourself before someone you have wronged. To forgive one who you believe wronged you. To reveal what love is really hiding beneath the facade of separation. 

“Then Esau looked up and saw the women and children. “Who are these with you?” he asked.”

Jacob answered, “They are the children God has graciously given your servant.”

Your servant. “Let peoples serve you,” the blessing had said. But Jacob now offers himself, his flocks, and his family in service instead. Every one of his wives and children prostrates themselves before Esau and calls themselves his servants.

And then Esau asks about all the messengers with gifts that Jacob sent. “What do you mean by all this company which I have met?” 

And Jacob answers, “To gain my lord’s favor.”

And the man Esau, who we are told to believe is rough, uncultured, a lesser man, says the following: “I have enough, my brother; let what you have remain yours.”

Esau—who just showed us an act of mercy perhaps more courageous and humble and noble than any of us could claim to ever have committed, does not even require repayment for what was taken from him. There goes our narratives.

And now this gets even deeper. The following words by Jacob are:

“No, I pray you; if you would do me this favor, accept from me this gift; for to see your face is like seeing the face of God, and you have received me favorably.”

The face of God. This is a major theme of our holiday. Lifnei adonai titharu—you shall be cleansed of your shortcomings in the face of, in the presence of, God. The word lifnei comes from the word panim, which means face. Today, we come before the true face of God. 

Could it be that the holiest face of God is the face of our “enemy” who has forgiven us? Is the true face of God, which we see only a day of repentance, the face of love remembered after it has been forgotten?

Perhaps we too find ourselves on a riverbank at night, contemplating what is at stake in our own decisions. And we too must decide if we are going to wrestle for the truth that we know in our souls. We are faced with a decision—whether to believe what we are told, to follow the orders we’ve been given, to reinforce the concepts we’ve been passed down, and to play our part in the story of endless duality and darkness—or to wrestle the hand of fate and affirm our deepest, holiest truth? We cannot comprehend the ways that God can test and push us. But it is up to us whether or not we will rise to the challenge.

That night, the God Jacob defeats gives him the name “Israel”. It means one who has striven with divine beings and prevailed. This name is not a part of his inheritance. It is an honor that could only be earned through a triumph over fate. The name is given to Jacob when he decides that he isn’t going to do what the human story instructs him to do any longer. He isn't going to be a puppet in the play. He has found his way out of the illusion through humility, love, and sacrifice. And that is what Israel means—standing for unity when your father, your story, and even your God challenges you to do otherwise.

The True Blessing

So what are we to make of Jacob's blessing? After all, we might question: is it really a blessing to be better than everyone else? To be bowed to, revered, and feared? Doesn’t a king get bored after a while—being seen by everyone as a resource, an opportunity? It’s not so easy to find real friends when everyone is bowing to you all the time. 

In the eastern traditions, they say that God created the universe for one purpose. If you are the only one who exists and you have everything there is to have, there is one thing you don’t have, and that is: relationship. God wants others. The whole purpose of creation is to know love. But the highest love doesn’t come from your subordinates; it comes from your equals. Those who choose you because of who you are, not because of what you can do for them, or what they are afraid you might do to them. 

In Judaism we have traditions that suggest that God also desires a more equal, more human connection. And that is available at this time of year because “The King is in the field.” God comes off the throne to a place where the ordinary folk are—to experience a more intimate connection than his superior position affords him. 

And so, we must ask, is being better than everyone else really a blessing? 

Before Jacob pretends to be his brother and presents himself before his old, blind father to receive the blessing, he says to his mother, “But my brother Esau is a hairy man and I am smooth-skinned. If my father touches me, I shall appear to him as a trickster and bring upon myself a curse, not a blessing.” I wonder, maybe Isaac was not so blind, or so naive, after all.

Maybe Isaac was also a trickster who wanted his son to understand the pitfalls of his greed. Maybe he gave Jacob what he wanted, knowing that it would never satisfy him, but that it would provoke him to earn his blessing—the hard way.

Now in his adulthood, Jacob figures out that a true blessing is the genuine love of your brother. And true holy place is a place of peace, not a battleground.  There is no blessing greater than the knowledge that all are blessed. Now that Jacob has learned this, he has to lay his life on the line if he is going to right his wrongs.

Our tradition tells us that it is on the day of atonement that the future is decided and sealed. Through forgiveness, we have a chance to change our fate. And this year we are upon is not an ordinary year. We have everything to lose, or everything to gain. It is a year where if we bow down to the powers that be, and pursue the superiority we think we deserve, we might live to regret it. Or, if we bow to the ones we’ve wronged, we just might bring about a reconciliation even more profound than that of our forefathers.

Let this day be a day of encouragement and empowerment. A time to remember together that our true God is the God of love and compassion—before we have to stand up for that love and compassion in a stronger and more courageous way than we have ever stood for it before. 

They say that Yom Kippur is a day to sing for your life. I say every day this year may be a day that you have to sing for your life. May your song be strong. May your words be clear. May you sing a song of peace. May you know that this is the wrestle that you have been preparing to wrestle. And the outcome is up to us.

G’mar chatima tova.