A Parting Gift | Various Rabbis | Beit Midrash

Torah Portion and Tanach
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קטגוריה משנית

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We usually think of Yaakov, in his interaction with Eisav upon his return, to have acted meekly to avoid possible conflict with Eisav. Anything to survive! The gemara (Sota 41b) actually gives two explanations of what Yaakov meant by saying that seeing Eisav was like seeing an angel. One was (false) flattery; the other was a semi-veiled threat: I have handled your angel; I can handle you if need to. Let us explore another example in which Yaakov may have been at once conciliatory and assertive. We start with an apparent contradiction.
Where did Eisav live when Yaakov was on his way home to Chevron? The beginning of the parasha implies he was living in Se’ir, as that is where Yaakov sent the messengers (Bereishit 32:4). As they part, Yaakov also says that he will visit Eisav in Se’ir (ibid. 33:16). Yet, the end of the parasha (ibid. 36: 6-7) seems to say explicitly differently. Eisav took his family and possessions and left the Land of C’na’an because of Yaakov, because there was not enough grazing land for the vast flocks of the two brothers (ibid. 36:6). Thus, until Yaakov settled in C’na’an with his flock, Eisav was in Chevron. The Ramban (ad loc.) posits that before Yaakov’s return, Eisav lived in Chevron with his family and flock, but spent significant time in Se’ir "on business," with a band of 400 armed men to exert his influence on the area. According to the Ramban, he knew that eventually C’na’an would be Yaakov’s, as Yitzchak had told Yaakov (when he knew it was Yaakov - Bereishit 28:4).
From here, let us part ways with the Ramban and suggest the following approach to Yaakov’s strategy. Yaakov sends his "telegram" to Eisav’s Se’ir address, hinting that he knew that Eisav had a stronghold there. He said: "I have been away a long time until now; I have cattle, donkeys, flocks, and male and female servants, and I am sending to you to tell you to find favor in your eyes" (ibid. 32:6). This may be a nice way of saying: Look, you have been with Yitzchak for a long time. I’m ready to take over looking out for him. Realize it is not a good idea for us to be together because of our flocks. Maybe the time has come for you to move full time to Se’ir. (Perhaps, Yaakov wanted to come with a lot of animals particularly for this purpose.) Eisav approaches angrily, and Yaakov sends him many animals as a present. The present is nice, but it won’t solve the problem of lack of grazing land, as the sum total is unchanged. Eisav suggests: Let’s go together. After all, I live in Chevron, and you are coming to Chevron. Yaakov answers: No, I have to go slowly; I will visit you in Se’ir, where you will certainly be living exclusively by the time I get to Chevron. Indeed, Yaakov goes very slowly, and by the time he gets there, Yitzchak alone lives there (see the language of Bereishit 35:27).
If our thesis is correct, we see that Yaakov is willing to be assertive with the powerful Eisav. While Yaakov is willing to show respect to Eisav, when it comes to the values of separating the two families and having Yaakov take over his father’s spiritual legacy and hold on the future Land of Israel, he politely but firmly stands up for his rights.