What did Yaakov mean when he instructed the messengers to tell Esav 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 Esav. 2 He said this to trick Esav 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 Esav 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 [Esav's] countenance, etc." (32:21) - all of which the shepherds were to say to Esav as well.
What was Yaakov trying to achieve by sending Esav this gift? What does "Achaperah Fanav" mean?
Rashi and Targum Onkelos: Yaakov wanted to negate Esav's anger, as he explicitly stated 1 when he said "Achaperah Fanav." 2
Targum Yonasan: Yaakov's plan was to appease Esav, before meeting him face-to-face.
Ramban #2: After informing Esav that his servant Yaakov was following them, he instructed his messengers to tell Esav 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....
Ha'amek Davar: People often give gifts to a master even when they did not sin and do not seek to excuse themselves; if they seek to excuse themselves, the gift is larger. Make sure Esav realize that the gift is so big because I want to appease him! Surely, seeing that I am so humbled will 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 Esav; 'Yaakov wishes to appease you with this gift, and only then appear before you....'
