The Big Confrontation – Jacob & Esau Meet


Esau & Jacob Meet after 20 Years

Jacob remained alone. A man wrestled with him until dawn
– This week’s Torah portion, Genesis 32:25

During the night of Exile, the nations of the world and the kingdom of Edom (Esau) wrestle with Jacob, until the dawn of redemption
– Midrash Lekach Tov on the verse

Esau told Jacob: I will travel alongside you. My lord you know that the children are weak and I have responsibility for the nursing sheep and cattle. If they are driven hard for even one day, they will die…Please go ahead of me… I will lead my group slowly, following the pace of the work ahead of me, and the pace of the children. I will eventually come to you, my lord, in Seir [Edom]
– Genesis 33:12-13

And when will he [Jacob] go [to Seir]? In the days of Moshiach, as it says (Ovadiah 1:21) Redeemers will ascend Mount Zion to judge the Mount of Esau, and the kingdom will be G-d’s
– Rashi

The stage is set. Jacob is returning to Israel after 20 years of exile. Twenty years previously he fled from his brother Esau who, furious at the fact that Jacob “stole” his birthright and blessings from him, wanted to kill him. During his years in exile, Jacob built a strong home and large family. He matured extensively during his twenty year tenure under his complex and cunning uncle and father-in-law, Laban.

The big day has come. What will happen when Jacob meets Esau after all these years? Has Esau’s anger waned? Has he forgiven what Jacob did to him?

Jacob and Esau represent “two nations” in a perpetual struggle (see previous weeks’ articles) – the battle between matter and spirit, between body and soul, between the G-dly and the mundane, between religion and science, between the religious and the secular. In personal terms – the battle between selfishness and dedication to a higher calling.

What happens when Esau and Jacob finally confront each other? What does it teach us about dealing with our own challenges, our own version of the Jacob/Esau confrontation? Can peace be achieved between matter and spirit, body and soul – G-d and the universe?

So, this week’s parsha is a critical one being that in it we learn about this momentous/archetypal confrontation, which teaches us about all confrontations to come – up to and including the confrontations of our present today.

Many lessons can be derived from this week’s story in dealing with and conquering adversity. Here are some of them.


Before confronting Esau, Jacob first sends messengers to scout out what lies ahead and to meet Esau. The first step in facing an adversary is to understand their intentions, assess their strengths and review all your options.


You must be well prepared. Jacob’s message to Esau was: “I have lived with Laban, and have delayed my return until now.” Even while living with the corrupt Laban “I remained committed to the 613 mitzvahs,” and maintained my relationship with G-d. Jacob’s words teach us that before facing the harsh realities of life we must build a secure home base, firmly standing on the pillars and foundations of faith, spirit and a strong value system and ideals.


The only way to complete the transformation of the material world is by imbuing others with energy to carry the spirit further. Our work in refining the “Esau’s” and “Edom’s” of our life includes inspiring others to become ‘messengers’ that carry the power. It is not enough to do the work alone; the barometer of our own success is our ability to affect and influence others in the same spirit. We are social creatures; our lives affect and are affected by other people. In life you have two and only two choices: Either you influence others or they influence you.


Jacob prepares to face Esau by covering all his bases: He prays to G-d; he prepares gifts to appease him; and he prepares for battle.

Prayer: Speak to G-d and implore Him to help you. Faith and prayer connect you to your higher purpose. This connection to above gives you the fortitude and persistence to face any challenge, the confidence to face any adversary.

Appeasement: When confronting any challenge in the material world around us, it is critical to study and analyze the ‘enemy’ and learn what ‘speaks’ to it, what can reach and perhaps change his mind.

War: As a last resort you must prepare to fight the enemy.

The ultimate objective is not to destroy but to transform the enemy. Not to annihilate the material world but to shape it into a channel for the spiritual. To do so effectively, you need to begin with prayer, to access G-d’s strength to succeed in facing your challenges. Then you need to assess the challenge and find a way to win it over, to speak to and persuade it on its own terms to reconcile with you. Finally, if all else fails you must be ready to go to war and confront your enemy.


In preparation for encountering Esau the following day, Jacob ferries his family across the Yabbok stream, but he remains behind “alone,” to retrieve some “small jars” of his that were left behind. There, “a man wrestled with him until dawn.”

The “small jars” represent the last ‘containers’ that we need to elevate and refine in fulfilling our Divine mission in spiritualizing the material world. Each person is allocated an allotment of ‘Divine ‘sparks’ (spiritual energy) that is embedded – as energy in ‘containers’ – in our material possessions and property. Everything that comes your way in life contains these ‘sparks’ – your home, relationships, furniture, work, car, food, entertainment, activities, travel destinations. You are charged with the responsibility to discover and reveal these sparks by directing all your activities to a higher, spiritual purpose.

Jacob teaches us that our work must not only consist of the ‘big things’ in life, it must include all aspects, even the ‘small jars.’ Nothing should remain neglected. Every part of our lives can and needs to be redeemed.

“Jacob remained alone.” – The spiritual journey is often a lonely one.

At times you may feel that you are all alone in your work of redeeming the ‘small jars.’ People around you may be involved in all types of glamorous pursuits, and you could feel isolated in your spiritual search. Your search may pale in comparison to what’s ‘happening’ out there. Even then you must remain steadfast in your mission. Your integrity is at stake even when its unpopular.


The spiritual journey is often a lonely one. It includes many challenges and battles. Standing alone you will encounter forces with which you must wrestle. And this wrestling will occur during the night, when it is dark and desolate, as Jacob wrestles with Esau’s angel. This “wrestling” represents the cosmic struggle between matter and spirit, and Jacob’s victory empowers us to prevail over any adversary we face.

In truth, you are never really alone. It only appears that way especially in the cover of night. When you wrestle with an adversary and don’t run away, you realize that you have power. Sometimes that power is just enough to make it through the night, to see it through difficult times. But then when dawn breaks, you see that you have prevailed.


Indeed, the next day when Jacob finally meets Esau, Esau’s heart opens to his brother.

Esau ran to meet him. He hugged [Jacob] and throwing himself on his shoulders, kissed him. They [both] wept.”

After all Jacob’s work and preparation for this encounter with Esau – his 20 years with Laban, building his home and family, his prayer and gifts, his angel wrestling – he is able to face him and reconcile. The two nations and worlds, the two cosmic forces that are Esau and Jacob, have both matured to the point where they can begin to coexist with each other.

The sages argue whether or not this was a complete and sincere reconciliation. The argument reflects the difficulty of integrating the two. Either way the process of resolution between matter and spirit has begun.


Witnessing their reunion, Esau suggests to Jacob that they come together and join forces. However Jacob wisely recognizes that their reunion was only a good beginning.

My lord you know that the children are weak and I have responsibility for the nursing sheep and cattle. If they are driven hard for even one day, they will die… Please go ahead of me… I will lead my group slowly, following the pace of the work ahead of me, and the pace of the children. I will eventually come to you, my lord, in Seir.”

Jacob is telling Esau and all of us that there is much work to be done in resolving the inherent tension between the material and the spiritual. And this work must be done with complete focus. Jacob rejects even Esau’s offer to help by putting “some of my people at your disposal,” even that poses too great of a risk. “Just let me remain on friendly terms with you,” Jacob tells Esau.

Today, after 3571 years of work, the world has become refined and the reconciliation can be completed. Jacob can finally fulfill his promise to Esau, “I will eventually come to you,” and the world can be united under one G-d, with each nation serving in its own unique way.

Each of us must ask ourselves the question: Is my ‘Jacob’ ready to meet and make peace with my ‘Esau’? Is my material life aligned with my spiritual one? Have I integrated what I do with who I am?

The final frontier is upon us. As Esau, Jacob, Ishmael confront each other, they are challenged to embrace the G-d of their father Abraham – a G-d who wants to be at peace with the universe. A peace that can only be achieved when we do our part in revealing the G-dliness in everything we do.

And so this week’s Torah portion closes the chapter of Esau. Just as the portion of Chayei Sarah concludes with the chronicles of Ishmael, and the portion of Toldot concludes with Esau’s marriage to Ishmael’s daughter, this week’s portion concludes with the chronicles of Esau. It details Esau’s family line and the leaders and nations that would descend from him, concluding with Magdiel, founder of Rome.

The seeds have been planted for the confrontations to come. The question today is: Do we understand the message?


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1 year ago

The Rabbi gifting us with his Wisdom and his Humbleness.
Thank You, Chag Orot Sameach,

The Meaningful Life Center