Parshas Vayishlach brings about the long awaited showdown between Yaakov and Esav. After waiting years to confront Yaakov for stealing the brachos, Esav finally got his chance at revenge. When he heard Yaakov was returning to Eretz Yisrael from Charan, he immediately gathered 400 men and began marching towards him. When Yaakov heard that Esav was coming, he began to prepare for the inevitable confrontation. He prepared his camp for battle, he davened to Hashem to protect him, and he arranged a lavish, three-part gift to be sent to Esav.
Together with the gift, he gave his messengers very specific instructions. “וַיְצַו אֶת הָרִאשׁוֹן לֵאמֹר כִּי יִפְגָּשְׁךָ עֵשָׂו אָחִי וִשְׁאֵלְךָ לֵאמֹר לְמִי אַתָּה וְאָנָה תֵלֵךְ וּלְמִי אֵלֶּה לְפָנֶיךָ. וְאָמַרְתָּ לְעַבְדְּךָ לְיַעֲקֹב מִנְחָה הִוא שְׁלוּחָה לַאדֹנִי לְעֵשָׂו וְהִנֵּה גַם הוּא אַחֲרֵינוּ. וַאֲמַרְתֶּם גַּם הִנֵּה עַבְדְּךָ יַעֲקֹב אַחֲרֵינוּ כִּי אָמַר אֲכַפְּרָה פָנָיו בַּמִּנְחָה הַהֹלֶכֶת לְפָנָי וְאַחֲרֵי כֵן אֶרְאֶה פָנָיו אוּלַי יִשָּׂא פָנָי.”“And he commanded the first group saying, ‘When you meet Esav, my brother, and he will ask you, ‘To whom do you belong, where are you going, and for whom are these before you?’ And you will say, ‘(We belong) to your servant, Yaakov, it is a gift to my master, Esav. And, behold, he (Yaakov) is (coming) behind us.’… (And Yaakov commanded the other two groups) And you will say, ‘Behold! Also your servant, Yaakov is behind us…” (Bereishis 32: 18-19, 21).
The Kli Yakar asks: In pesukim 18-19, we are told exactly what Yaakov told his messengers, including the fact that they should tell Esav that he is following behind them. In pasuk 21, we see Yaakov talking to the second and third groups of messengers, but there he only mentions to them to tell Esav that he is following behind them. Without the pasuk saying anything, we would assume that Yaakov told the exact same thing to each group; now that the pasuk does tell us something he told to the later groups, it appears to be the exact same thing he told the first group! Why does the pasuk repeat this command?
Yaakov figured that Esav would ask his messengers three questions: who do you belong to, where are you going, and who is the present for. Therefore, he gave them three answers: we belong to Yaakov, we are going to Esav, and the present is for him. However, Esav was not necessarily going to ask where Yaakov was at the moment, maybe because he figured Yaakov wouldn’t be anywhere near him. Therefore, Yaakov told his messengers to tell Esav that he himself was coming to meet Esav, in order to honor him.
The second and third groups would know that they would need to know the answers to the three questions, otherwise, how would Esav know who this stuff was for! So those answers they would make sure they paid attention to while hearing the instructions given to the first group. However, maybe they would not have to tell him that Yaakov was coming too since it had nothing to do with Esav’s receiving the gift. Therefore, Yaakov had to specifically mention to them to tell Esav that he was coming, more than having to repeat to them the answers to the three questions. So the pasuk is not simply repeating one piece of Yaakov’s message, it’s actually repeating exactly what Yaakov told the last groups (it’s the only thing he actually told them)!
Why was it so important to make sure each group repeated the message? Wouldn’t it be enough if the first group alone gave it over? The answer is Yaakov was afraid that Esav would expect him to be there immediately after the first group. Upon seeing the second group, Esav would question them as to where Yaakov was and they wouldn’t be able to answer because they wouldn’t know Yaakov was heading that way! He would assume Yaakov was lying about the whole thing and wouldn’t accept any of the present, putting Yaakov in a dangerous position. In order to avoid this potentially tragic circumstance, Yaakov impressed this message upon the messengers.
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