The Torah

Jacob sent messengers ahead to his brother Esau in the land of Seir, the country of Edom, and instructed them as follows, “Thus you shall say to my lord Esau, ‘Thus says your servant Jacob: I stayed with Laban and remained until now; I have acquired cattle, donkeys, sheep, and male and female slaves; and I send this message to my lord in the hope of gaining your favor.’” The messengers returned to Jacob, saying, “We came to your brother Esau; he himself is coming to meet you, and there are four hundred men with him.” Jacob was greatly frightened; in his anxiety, he divided the people with him, and the flocks and herds and camels, into two camps, thinking, “If Esau comes to the one camp and attacks it, the other camp may yet escape.” Then Jacob said, “O G-d of my father Abraham and G-d of my father Isaac, O L-rd, who said to me, ‘Return to your native land and I will deal bountifully with you’! I am unworthy of all the kindness that You have so steadfastly shown Your servant: with my staff alone I crossed this Jordan, and now I have become two camps. Deliver me, I pray, from the hand of my brother, from the hand of Esau; else, I fear, he may come and strike me down, mothers and children alike. Yet You have said, ‘I will deal bountifully with you and make your offspring as the sands of the sea, which are too numerous to count.’” After spending the night there, he selected from what was at hand these presents for his brother Esau.
(Genesis 32:4-14)

Rashi, Biblical and Talmudic commentator (1040-1105)
In the hope of gaining your favor – I am at peace with you and I seek your friendship.
(Commentary to Genesis 32:6)

The Midrash

Rabbi Yehuda Hanasi instructed Rabbi Efes to write a letter from him to “our master, King Antoninus.” Rabbi Efes wrote, “From Yehudah the Nasi to our master, King Antoninus.” Rabbi Yehuda Hanasi took the letter, read it and tore it up, telling him to write instead, “From your servant Yehuda, to our master, King Antoninus.” Rabbi Efes asked, “Rabbi, why do you ignore your own honor?” Rabbi Yehuda Hanasi replied, “Am I better than my grandfather? Didn’t he say ‘so says your servant Jacob’?”
(Genesis Rabbah 75:6)

Ramban, Biblical and Talmudic commentator (1194-1270)
All that happened to our father with his brother Esau happens to us constantly with Esau’s children. We must adopt the methods of that righteous man, to make the three preparations that he made: prayer, a gift, and escape through war, that is, to flee and take refuge.
(Introduction to Parshas Vayishlach)

Rabbi Isaac Abarbanel, Spanish Biblical commentator (1437-1508)
Just as Jacob prepared himself with prayer, gifts and war, so it will happen to us in all generations, that our efforts to be saved from Esau and his descendents will be, firstly, by prayer and supplication before the G-d of Jacob, with gifts, bribes and presents to him, and with war – to flee and save from his hand.

Rabbi Elazar Azikri, author of Sefer Charedim (1533-1600)
Jacob instructed his servants to say to Esau, “These animals are a gift to you from your servant Jacob, sent to my lord Esau.” This is in line with what the Sages say, that G-d made the Jewish people swear not to rebel against the nations of the world, but rather to bear the exile and show respect to them like a servant to his master, for they are only a whip in the hand of G-d. Therefore, speak to them respectfully and when they demand taxes, do not fight back or speak impudently, but rather pay the tax with respect and honor.
(Sefer Charedim, Parshas Vayishlach)

Rabbi Yehoshua ibn Shu’ib, Spanish preacher (1280-1340)
We, the Jewish people in exile, must follow in the footsteps of Jacob our forefather, bearing our trials and responding to danger by humbling ourselves before the gentiles. We must call them our masters and ourselves their servants. Furthermore, when speaking to them we must minimize our own greatness, just as Jacob our father said, “I have sojourned with Lavan” – I have not become a powerful or wealthy figure. “I have acquired an ox and a donkey” – the blessings of my father, that I would get the dew of heaven and the fats of the earth, were not fulfilled, for oxen and donkeys are neither from heaven nor from earth. And the singular “ox” and “donkey” also minimized Jacob’s wealth (Rashi). This is the humble way we must speak to the gentiles.

Rabbi Yishaya Horowitz, known as the Shelah (1555-1630)
Just as Jacob used prayer, gifts and war, so do we approach Esau’s descendants in our times. Our power is only through our mouth, to pray to G-d in difficult times. But war – to fight with the nations – does not apply to us. Our “war” with them means activism – that Jewish activists must boldly face kings and leaders and work for the good of the Jewish people. Even if the leaders throw them out angrily, they must keep coming back; this is our pillar of existence in exile, until the messiah comes.
(Vayishlach, Amud Hagolah)

In the era of exile we must bear our fate, as the Midrash says on the words “I adjure you,” that we should not rebel; and on the contrary, we must accept it submissively and do as Jacob our father did, presenting gifts to his brother Esau.
(Torah Shebichsav, Parshas Exodus)

Rabbi Moshe Sofer, Rabbi of Bratislava, known as Chasam Sofer (1762-1839)
The story of Jacob and Esau is a lesson for us. Jacob and Esau were twin brothers and equals, yet Jacob humbled himself before Esau so much. He called him “my lord” and bowed before him seven times; his wives, concubines and children all bowed before him too. He begged him to accept his gift, and said, “Seeing your face is like meeting an angel.” He gave him lavish gifts. This teaches the future generations in exile how humble we must be before the nations, with our speech, our displays of honor and our gifts. Because since G-d gave them the power, and placed us in exile among them like foreigners, it is no doubt the will of G-d that we should respect them and honor them and be submissive to them.
(Shir Maon, Parshas Vayishlach)

Rabbi Tovia ben Eliezer, author of Lekach Tov (11th century)
The command to show respect to Esau also applies to future generations. They must not stand up against the wave, for whoever stands up against a wave, the wave sweeps him away; but when one bows to the wave, the wave passes over.

Rabbi Yonasan Eybeshutz, Rav of Hamburg (1690-1764)
The Jewish people can benefit the most from their exile when they accept it humbly and meekly. The Talmud (Yevamos 121a) tells the story of how Rabbi Akiva’s ship sank and he survived by holding onto a piece of wreckage. To each wave that came his way, he bowed his head. The lesson is that if difficult circumstances befall a person, he should bend his head and accept it, and this will allow him to survive.
(Yaaros Devash, v. 1, Drush 3)

Rabbi Yisroel Meir Hakohein, author of Chofetz Chaim (1839-1933)
We must follow in the footsteps of the patriarch Jacob in his encounter with his brother Esau… All that happened between Jacob and Esau happens to us constantly with Esau’s children. We must adopt the methods of the righteous Jacob, to make the three preparations that he made: prayer, a gift, and to save himself through war, which [for us] means to flee to safety. As long as we walked on that well-tread path, G-d saved us from their hands. But since we have strayed from the path and new leaders have arisen who chose new methods, leaving behind our ancestors’ weapons and adopting the methods of our enemies, we have fared worse and worse, and great travails have befalle n us.
(Chofetz Chaim Al Hatorah, Parshas Devarim)

Rabbi Elchonon Wasserman, Rosh Yeshiva of Baranovitch, Poland (1874-1941)
When we speak to the nations of the world, we must beg, not demand. “A soft tongue breaks a bone” (Proverbs 25:15). When our Sages came to Rome to protest a decree, they said, “Are we not children of one father and one mother? Why are we different from all other nations, that you pass harsh decrees against us?” (Rosh Hashanah 19a).
(Article entitled “The Calm Words of the Wise are Heard,” printed in Yalkut Maamarim Umichtavim, pp. 101-102)