וַיִּשְׁלַח יַעֲקֹב מַלְאָכִים לְפָנָיו אֶל עֵשָׂו אָחִיו אַרְצָה שֵׂעִיר שְׂדֵה אֱדוֹם.
And Jacob sent messengers before him to Esau his brother unto the land of Seir, the field of Edom. And he commanded them, saying: ‘Thus shall ye say unto my lord Esau: Thus saith thy servant Jacob: I have sojourned with Laban, and stayed until now. And I have oxen, and asses and flocks, and men-servants and maid-servants; and I have sent to tell my lord, that I may find favour in thy sight.’ And the messengers returned to Jacob, saying: ‘We came to thy brother Esau, and moreover he cometh to meet thee, and four hundred men with him.’ Then Jacob was greatly afraid and was distressed. And he divided the people that was with him, and the flocks, and the herds, and the camels, into two camps. And he said: ‘If Esau come to the one camp, and smite it, then the camp which is left shall escape.’
Genesis Rabbah 75, 11
When Jacob called Esau 'my lord,' the Holy One, blessed be He, said to him: 'You have abased yourself and called Esau "my lord" eight times. I will raise up eight kings of his descendants before your descendants,' as it says, And these are the kings that reigned in the land of Edom, before there reigned any king over the children of Israel (Gen. 36:31).
Judah haNasi once directed Rabbi Afes to write a letter in Judah’s name to Emperor Antoninus. Rabbi Afes wrote: “From Judah the Prince to our Sovereign the Emperor Antoninus.” Judah read the letter, tore it up, and wrote: “From your servant Judah to our Sovereign the Emperor Antoninus.” Rabbi Afes remonstrated that Judah treated his honor too lightly. Judah replied that he was not better than his ancestor, who in Genesis 32 sent a message saying: “Thus says your servant Jacob.”
Rabbi Moses ben Nachman (Nachmanides) (Gerona, 1194-1274)
"In my opinion, this detail alludes to the fact that WE WERE THE CAUSE OF OUR OWN DOWNFALL by the hands of the Rome. In the Second Temple period, the Hasmonean kings made a treaty with Rome and some of their representatives even went to Rome and in the end, this was the first step of our falling into their hands. (http://vbm-torah.org/archive/intparsha72/08-72vayishlach.htm)
Midrash Lekach Tov (R. Tuvia ben Eliezer, 1036-1108, Greece and Bulgaria)
Said Rabbi Jonathan: Whoever wishes to placate a king or authority and is not familiar with their ways and tactics should place this chapter (Gen. 32) in front of him and learn from it the arts of appeasement and placation.
For Discussion:
1. What are ways in which the debate over the interpretation of Jacob's appeasement of Esau continues today?
2. What are appropriate criteria in gauging the balance between diplomacy and belligerence?