What did Yaakov mean when he instructed the messengers to tell Eisav that he was following them?
Ramban: Refer to 32:21:2:3.
Rashbam (to 32:21,23), Hadar Zekenim: Yaakov had actually intended to flee 1 in another direction to avoid meeting Eisav. 2 He said this to trick Eisav into believing that he intended to meet him.
Malbim: Even though Yaakov is not going to Se'ir, and hopes to meet you on the road, he sent the gift [to appease you beforehand].
Hadar Zekenim: Hashem sent the angel to stop him from fleeing. This was a punishment for fleeing Lavan, and not trusting in Hashem's promise. Rashbam (to 32:25) - It was in order to show Yaakov the fulfillment of Hashem's promise, that Eisav will not harm him.
This is why he crossed over the River Yabok at night, with his entire family (32:23); like David ha'Melech, who later crossed the Jordan River in the same region (Shmuel II 17:21-24) in order to escape from Avshalom (Rashbam).
"And you shall say, 'Also, behold, your servant Yaakov is behind us....." Wasn't this stated already in 32:19?
Gur Aryeh: It was repeated here in order to add, "... for he said, I shall appease [Eisav's] countenance, etc." (32:21) - all of which the shepherds were to say to Eisav as well.
What was Yaakov trying to achieve by sending Eisav this gift? What does "Achaperah Fanav" mean?
Rashi #2 (in Ha?azinu Devarim, 32:43) and Targum Yonasan: It means ?I will appease his countenance (him)?. 3
Ramban: After informing Eisav that his servant Ya?akov was following them, he instructed his messengers to tell him that he was sending his honor 'a redemption of the soul' (Kofer Nafsho), in the way that servants enter the presence of the king with gifts, after he has granted them the privilege of a private audience ... .
Seforno: By humiliating himself before Eisav, he hoped to diminish his anger.
As in Yeshayah, 28:18 & 47:1. See Rashi, who elaborates.
Ha'amek Davar: People often give gifts to a master even when they have not sinned; only in the event that they have, the gift is that much larger. Consequently, Ya?akov instructed the messengers to make sure that Eisav realizes that the gift is so large because he wants to appease him! And seeing that he was so humbled would surely fill him with mercy.
Who is the narrator of the phrase, "For he said, 'I shall appease his countenance....'"?
Rashbam, Ibn Ezra: The Torah is telling us what Yaakov was thinking to himself.
Ramban #2, Gur Aryeh (to 32:19), Ha'amek Davar: The shepherds who were escorting the gift were to say all of this to Eisav; 'Yaakov wishes to appease you with this gift, and only then appear before you....'
