Vayishlach | Is Reconciliation with Esav a Good Idea?
Summarized by Shmuel Fuchs
Translated by David Strauss
Two parashot, Parashat Toldot and Parashat Vayishlach, are largely devoted to the relationship between Yaakov and Esav, and in between them is Parashat Vayetze, in which Yaakov runs away from Esav and leaves the country.
The two parashot present completely different pictures of the relationship between the brothers. Parashat Toldot, from beginning to end, tells the story of the conflicts between them, beginning with their birth – "And after that came forth his brother, and his hand had hold on Esav's heel" (Bereishit 25:26) – continuing with the sale of the birthright, and concluding with the stealing of the blessings.
Parashat Vayishlach, on the other hand, leaves us with a totally different impression. Despite his fear of Esav, Yaakov tries to establish a relationship with him – he sends him messengers and gifts, and then even meets him face to face, presenting himself as subordinate to Esav. The change is not one-sided, but is evident on Esav's side as well; after a warm reunion with Yaakov, he proposes that they continue together, on the same path, and that contact be maintained between their two camps in one way or another. What lies behind this difference? What changed between Parashat Toldot and Parashat Vayishlach?
It seems that the difference between the parashot should be understood in the context of a broader change in Esav. In other words, the description of Esav during his encounter with Yaakov seems to characterize a more general process of improvement in Esav’s ways, to one degree or another.
Allusions to this change for the better are evident in the account of his wives. Esav first gets married in Parashat Toldot, when it is stated:
And when Esav was forty years old, he took to wife Yehudit the daughter of Be'eri the Chittite, and Basmat the daughter of Eilon the Chittite. And they were a bitterness of spirit to Yitzchak and to Rivka. (Bereishit 26:34-35)
His parents’ distaste for Esav’s choice in wives is further detailed at the end of the parasha:
And Rivka said to Yitzchak: I am weary of my life because of the daughters of Chet. If Yaakov takes a wife of the daughters of Chet such as these, of the daughters of the land, what good shall my life do me? (Bereishit 27:46)
On the other hand, in the framework of the account of "the generations of Esav" in Parashat Vayishlach, we get quite a different picture:
Esav took his wives of the daughters of Canaan: Ada the daughter of Eilon the Chittite and Oholibama the daughter of Ana, the daughter of Tzivon the Chivite, and Basmat the daughter of Yishmael, sister of Nevayot. (Bereishit 36:2-3)
Yehudit the daughter of Be'eri is not mentioned here at all, and we meet a new woman – Oholibama – of the daughters of the Chivites (rather than the Chittites, like the first two wives). In addition, Esav's marriage to the daughter of Yishmael is first reported at the end of Parashat Toldot, but here she is called Basmat, and not Machalat (Bereishit 28:9) – whereas the original Basmat, "the daughter of Eilon the Chittite" (Bereishit 26:34) is referred to here as Ada (Bereishit 36:2). What is the meaning of all this?
It seems that in the wake of his parents' displeasure, Esav decided to distance himself from his previous wives: he divorced Yehudit the daughter of Be'eri, but the daughter of Eilon had already given birth to his firstborn, Elifaz – he could not send her away, but she ceased being his main wife named Basmat, and was thereafter called Ada, that is, “she who was removed from her place.” At the same time, Esav takes a wife from Avraham's family and calls her Basmat, in order to show that she is now his most important wife. So too, Esav leaves the Chittites who live in the land, and joins instead with the Chivites, who live on Mount Seir.
Yaakov: On Reconciliation and Surrender
This explains the change in Esav. But what can we say about Yaakov's actions? We find contradictory attitudes in the words of Chazal. On the one hand, there are midrashim that criticize Yaakov harshly – both for the very meeting with Esav, and for the excessive submission with which he conducts himself:
"Yaakov sent [messengers before him]" – Rabbi Yehuda ben Rabbi Simon began: "Like a muddied spring and a ruined fount, so is a righteous man who falls before the wicked" (Mishlei 25:26): Just as it is impossible for a spring to be muddied and for a fount to be ruined, so it is impossible for a righteous man to fall before the wicked. And like a muddied spring and a ruined fount, so is a righteous man who causes himself to fall before the wicked. The Holy One, blessed be He, said to him: He was going on his way, and you sent to him, saying: "So said your servant, Yaakov."
Rav Huna began: "Like one who grasps the ears of a dog, so is a passerby who is angered over a quarrel not his" (Mishlei 26:17). So the Holy One, blessed be He, said: He was going on his way, and you sent to him, saying: "So said your servant, Yaakov." (Bereishit Rabba, Vayishlach 75)
Yaakov's very submissive attitude toward Esav emerges from the wording of the Torah itself:
And you shall say: Moreover, behold, your servant Yaakov is behind us. For he said: I will appease him with the present that goes before me, and afterward I will see his face; perhaps he will accept me. (Bereishit 32:21)
And Yaakov said: No, I pray you, if now I have found favor in your sight, then receive my present at my hand; forasmuch as I have seen your face, as one sees the face of God, and you were pleased with me. (Bereishit 33:10)
Yaakov turns to Esav as if he were God (as he explicitly states); the criticism of Rabbi Yehuda ben Rabbi Simon in the midrash concerning "a righteous man who causes himself to fall before the wicked" is certainly understandable.
On the other hand, there are those who explained Yaakov's actions in a positive manner. Thus, for example, we read in the Zohar on our parasha:
Rather Yaakov said: I know that Esav reveres Father and has never troubled him. And I know that since Father is alive, I need not fear Esav. Therefore, while Father is alive, I wish to appease him. Immediately: "And Yaakov sent messengers before him.” (Zohar, Vayishlach 166a)
Not only does the Zohar not see Yaakov's actions as mere flattery (even if legitimate), but it seems that it views them as a worthy effort, because it is his responsibility to appease his brother over his theft of the blessings.
In addition to the words of the Zohar, we can also talk about other good things that came out of Esav. In this context, note the statement of Chazal that Esav's head is buried in the Makhpela Cave (Sota 13a), as well as the vast Torah of Rabbi Meir, one of the greatest Tannaim, who descended from Esav (Gittin 56a).
What then is the correct attitude towards Esav? Was Yaakov’s reconciliation with Esav positive, or was it an unnecessary surrender? What is the solution to the contradiction between the midrashim?
The Solution: Reconciliation Without Surrender
It stands to reason that there is no contradiction here at all, and one simply has to distinguish between two different matters: reconciliation in itself is good, a blessing – but obsequiousness is problematic and shameful. It is proper and desirable that Yaakov and Esav reconcile, but the reconciliation should not happen out of submission and seeking forgiveness.
These issues also have ramifications in today's reality. With the miracles that God performed for us with the rise of the state and its establishment, many Christians of various stripes have changed their attitudes towards Judaism and the State of Israel, and they offer us recognition and respect, if not actual enthusiastic support.
The process in itself is good and desirable, and we welcome the long-awaited reconciliation between Israel and Edom. However, we must make sure that it happens not out of our submissiveness and obsequiousness, but with pride and confidence, and with the recognition and blessings of the angel of Esau.
[This sicha was delivered by Harav Yaakov Medan on Shabbat Parashat Vayishlach 5781.]
 For this meaning of the word, see Iyov 28:8 and the commentaries ad loc.