This past shabbos, I was thinking about the fascinating encounter between Yakov and Esav
Yakov had been gone for 20 years, and Esav very likely felt guilt over it. It was a combination of Esav’s threat on Yakov’s life and Rivka’s pretext about marriage that sent him away. And even if Rivka’s pretext has truth (see that Esav immediately responds by marrying “from the family” i.e. Yishmael’s daughter), Esav likely feels some guilt that Yakov ran in a hurry, without the entourage and gifts his grandfather sent to bring his mother. Esav might feel that he caused Yakov to run to Charan with nothing, and significantly hampered his ability to find said wife, coming to down with no money for a dowry. And yet Yakov returns with a huge family: not just one wife, but two, with two concubines on top of that; 11 boys and a girl; and massive wealth. Esav is relieved and genuinely happy to see that Yakov is successful.
Moreoever, he’s happy to see his brother, with genuine love and wanting to reconcile.
But there’s another element underlying the happy reunion. Esav must remember the brachos from Yitzchak, the ones he perceives were intended for him but went to Yakov. Yakov’s family and massive wealth can surely be seen as a fulfillment of the bracha he got from Yitzchak, and form the undercurrent of the interaction. Esav tells Yakov to keep his gift, “Yesh li rav” – I have a lot – meaning, “Father blessed me with material wealth, I don’t need sheep from you.” What’s not said, is what Esav DOES need from Yakov. And Yakov sticks a dagger in right away. Implicit in Esav’s words are a recognition that with the material blessings fulfilled, the other part of the bracha is fulfilled as well: Yakov has essentially been put in charge of the family. Despite being the older brother, Esav is subordinate to Yakov. What’s fascinating to me is that he knows it, and accepts it. And Yakov knows it to. Yakov’s response to “I have much” is “I have everything” – “yesh li col.” As if to say “yes, I know you have material wealth, and a strong army, but so do I, and I have one more thing: father’s designated leadership.
And then this proceeds one step further. Esav acknowledges Yakov’s leadership, and essentially asks to be maintain his status as part of the family. Let us live together, come with me. Let me have a part of our ancestral. divinely gifted homeland. And Yakov rejects him. He makes up an excuse that’s easily deflected (“ok, no problem, we’ll *all* travel slowly”) and tells Esav to be on his way. Fascinatingly, Esav submits to Yakov’s will. Esav wants to be part of the Abrahamic tradition, the chosen family, and Yakov says no, and Esav accepts this!
To me, Esav shows both tremendous maturity and strength at this, as well as further evidence of his fatal flaw.
Esav is frequently demonized in the rabinnic literature as the evil diametric opposite of saintly Yakov. The text, however, doesn’t usually bear this out. Esav submits to his father’s will and allows his brother take the leadership role and sole proprietorship of the Abrahamic family. There is a certain strength to acknowledging and accepting the will of the leadership.
However, to me, Esav’s fatal flaw (and perhaps the reason he was excluded from the family?) is that he, perhaps, is *too* willing to accept “fate” or “destiny.” Aside from this episode, when perhaps Esav should have protested, or insisted to Yakov to allow him into the family, or gone to Yitzchak and Rivka (still alive at this point) and, having conceded leadership, begged to at least remain part of the family. But he doesn’t. He moves on, moves out and goes away. There’s another episode where he does a similar thing. When the boys are younger, at the story of the sale of the birthright. Esav has sold his birthright, and even the most favorable reading of the story (that he truly was starving, and the initial bargaining was under duress), faults Esav for failing to protest the sale afterward. Having recovered from his imminent doom, and being fed and revived, it was incumbent on Esav to protest the sale, unwind the transaction as being under duress and reclaim his birthright. But he doesn’t. He accepts his fate and walks away. And it is only at that point that Torah describes him as despising his birthright.
Why is this so important? Let’s think back to the actions of the father of the family Esav seeks to maintain status in: Avraham. Though there are instances where Avraham acquiesces (the akeida being a famous example) to the word of God, perhaps the story most indicative of Avraham’s caring for others and his general world view is his “negotiation” with God over the fate of Sodom. He doesn’t accept fate; he fights back. He “argues” with God, going back and forth for six rounds of negotiating (50, 45, 40, 30, 20, 10).
This is Avraham’s central quality: acquiescent to the word of God at times, but unwilling to accept fate at others. There are times when it is right to fight (even if the the fight is a losing cause). Esav, despite his description as a hunter and man of the field, may have been just a bit too passive when it came to matters of spirituality and the family future. It was thus that he could not serve as leader, ceding the role to Yakov, and it was thus that he even gave away his place in the family.
The Noy G Show 
Super interesting but wondering where the impression that Esav had any good intention towards Yaakov comes from? I’m not sure Esav felt any guilt about Yaakov fleeing as much as he felt regret and anger at not having received Yitzchak’s blessing, despite the fact that he himself sold it by failing to properly recognize its significance. I think bringing 400 troops along with you to greet your brother is no way of showing that you’d like a happy reunion.
This past shabbos my Rav spoke about the Esav/Yaakov relationship In the beginning of the parsha, Yaakov davens to Ha-shem to save him from “achi, et Esav” Why does he have to explain to Ha-shem which brother he’s talking about, especially since he only has one?
I don’t remember the source, but my Rav noted the two characteristics of Esav/Edom. Their attack is twofold – one effort is made to befriend Yaakov (de Jews) and “attack” them spiritually and when that doesn’t work, the use of force is what they turn to (see Europe celebrating Jewish intellectuals as the generation’s best minds followed by the Holocaust as a recent example).
Yaakov was essentially asking for both spiritual protection and physical protection, both of which he got. When Esav asked to join Yaakov’s clan I don’t think he intended to suddenly do teshuvah and live as Avraham did – the fact that he still held this deep grudge to the extent that he wanted to murder his brother after a 20 year abscence might be an indication.)
As a complete sidenote when Yaakov tells Esav that he would journey to Se’ir, do you think that’s the first instance in history of ditching someone? (“Umm…yeah…ill meet you there.”)
Esav’s guilt is my own interpretation, but I don’t think any murderous intent is evident either. Travelling with your entourage is a symbol of status, it reflects the respect that Esav feels Yakov is entitled to. When the King visits, everyone in the town comes out to greet him, that sort of thing.
As for happiness to see him, I think running to him (perhaps a breach of protocol?) and embracing him and kissing him show love more than murderous intent. And I read shock and happiness in his questions of “who ARE these kids?!?” As if “nephews! I have nephews! These are my family” Yes, it’s my reading, but I think it’s more consistent with the text and the tone of the text than reading in a murderous intent and evil.
I understand the classical commentaries have read in evil here, but I (as a plain reading of the text) don’t. I actually see Esav as a somewhat sympathetic, tragic character. Given no chance by his parents (as least his mother, aware of the prophesy from her pregnancy) from before his birth, he’s kind of dealt a bad hand.
Also, the connection of Esav to modern enemies (Rome, etc.) is simply not borne out as historically accurate. It makes for nice homiletics, but as a simple reading of the text, it’s not there.
When Esav proposes going together, he doesn’t say where. Could he mean together to live in Canaan? It’s only after Yakov rejects him that he goes to Se’ir (because he not allowed to join with Yakov).
I agree that at times Esav is a sympathetic character, such as when he’s begging Yitzchak for a bracha. And I hear your point as to how the plain text could indicate Esav’s good intentions.
I’m still bothered, though, by the 400 men he brought with him (the amount). What you see as an entourage seems just as likely to me as an army troop. Why wouldn’t we assume a sinister motive since the text doesn’t give us any details about these men with him other than conveying that when the malachim reported what they saw to Yaakov, (Esav +400) Yaakov became frightened? Also, if Esav was greeting Yaakov with fanfare, wouldn’t the Torah tell us that? (trumpets, gifts, etc…)
I can’t perfectly explain the number other than to suggest it’s his entire group: as protocol would dictate, he took everyone with him.
Why was Yakov afraid? Maybe that’s Yakov’s own perceived bias? He doesn’t fully trust his brother (and I get that, he was threatened by him). Yakov isn’t necessarily acting irrationally, but that doesn’t mean he’s right.
The text does give us more info, though: Esav runs to Yakov and hugs and kisses him (and doesn’t have to tell his men to “stand down”). Also, when they are separating, Esav offers some men to escort Yakov. To me, that suggests he brought them as an escort, not as an attack, and was offering Yakov to take part. I don’t think military attack is the clear first implication of the men he brings.