The Hebrew word malachim means both “messengers” and “angels” (an angel being a divine messenger). Thus, the verse “Jacob sent malachim to Esau his brother” can be understood as a reference to human messengers as well. Hence Rashi’s clarification that it means “actual angels.”
Chassidic master Rabbi DovBer of Mezeritch sees a deeper meaning in Rashi’s words: Jacob sent the “actuality” of his angels to Esau, but kept their higher spiritual essence with him.
He was afraid that he might be killed, and distressed that he might kill.
He prepared himself in three ways: he sent a gift, he prayed, and he made ready for war.
The meaning of this is that every kindness bestowed by G‑d upon a person should cause him to be exceedingly humble. For a divine kindness is an expression of “His right hand embraces me”—G‑d is literally bringing the person closer to Himself. And the closer a person is to G‑d, the greater the humility this should evoke in him, for since “all before Him is as naught,” the more “before Him” a person is, the more “as naught” does he perceive himself to be.
This is the manner of Jacob. The very opposite is the case in the contrasting realm of kelipah (evil). There, the greater the kindness shown a person, the more he grows in arrogance and self-satisfaction.
(Rabbi Schneur Zalman of Liadi)
And where was Dinah? Jacob had placed her in a chest and locked her in, lest Esau set his eyes on her. For this, Jacob was punished in that Dinah fell into the hands of Shechem, for had he not withheld her from his brother, perhaps she would have brought him back to the proper path.
Said G‑d to Jacob: “You wouldn’t give her in marriage to a circumcised person; behold, she is now possessed by an uncircumcised one. You wouldn’t give her in legitimate wedlock; behold, she is now taken in illegitimate fashion.”
(Rashi; Midrash Rabbah)
He remained for the sake of some small jars he had left behind. Hence [it is learned] that to the righteous, their money is dearer than their body.
(Talmud, Chullin 91a)
This is because the righteous know that their material possessions contain “sparks of holiness” which are redeemed and elevated when the object or resource they inhabit is utilized to fulfill the divine will. The righteous person sees these sparks of divine potential as virtual extensions of his own soul, since he understands that the very fact that Divine Providence has caused them to come into his possession indicates that their redemption is integral to his mission in life.
(The Chassidic Masters)
This was the “prince” of Esau (the angel who embodies the spirit of Esau).
(Midrash Rabbah; Rashi)
Jacob’s struggle with Esau’s angel represents the physical suffering of galut. When the angel of Esau injured Jacob’s hip-joint, he injured his righteous descendants. In the words of the Midrash, “This is the generation of the shmad”—the cruel tortures inflicted by the Romans in Mishnaic times (1st and 2nd century CE) in their effort to eradicate the faith of Israel.
There were other generations in which the same and worse was done to us. We suffered all this and persevered, as alluded to by the verse “Jacob arrived, whole.”
Said Jacob to him: “Are you a thief or a gambler, that you are afraid of the morning?” Said he: “I am an angel, and from the day that I was created, my time to sing praises to G‑d has not come until now.”
(Talmud, Chullin 91b)
[Jacob] prostrated himself to the ground seven times, until he came close to his brother. . . . The maidservants and their children drew near and prostrated themselves. And Leah and her children drew near and prostrated themselves, and after [them], Joseph and Rachel drew near and prostrated themselves (33:3–7)
When Mordechai refused to bow to Haman, they said to him: “You’re going to get us all killed! How dare you go against the decree of the king?”
Said Mordechai: “I am a Jew.”
Said they to him: “Did not [our] forefathers bow to his forefather?”
Replied Mordechai: “I am a descendant of Benjamin, who was in his mother’s womb at that time. Just as my forefather did not bow, so too I shall not kneel nor bow.”
In the Torah, the word vayishakeihu (“and he kissed him”) is dotted on top, implying that this was an exception to the rule. Said Rabbi Yannai: This is to tell us that he did not intend to kiss him, but to bite him. But Jacob’s throat turned to marble and broke the evil one’s teeth.
What was different about this kiss? Our sages debate this. There are those who say that it implies that Esau did not kiss Jacob with all his heart. Rabbi Shimon ben Yochai says: It is a well-known law that Esau hates Jacob. Here, the kiss was an exception in that he did kiss him with all his heart.
Said Rabbi Abbahu: We have searched the whole of Scripture and do not find that Jacob ever went to Esau to the mountain of Seir. Is it then possible that Jacob, the truthful one, should deceive him? [No.] But when will he come to him? In the messianic era, when “the saviors shall ascend Mount Zion to judge the mountain of Esau” (Obadiah 1:21).
For “himself”—for his true self and his true priorities—Jacob constructed a “home”; for “his cattle”—his material possessions and other peripheral elements of his life—he sufficed with a minimal “shed.”
(The Lubavitcher Rebbe)
A chassid of Rabbi Sholom DovBer of Lubavitch (1860–1920) opened a plant for the manufacture of galoshes. Soon his every waking hour and thought was completely occupied in his new and flourishing business.
Said the rebbe to him: “I’ve seen people put their feet into galoshes, but a head in galoshes . . . ?”
Whole in body, for he was healed of his limp. Whole in wealth, for he sustained no loss as a result of the gift [he dispatched to Esau]. Whole in his Torah, for he forgot nothing of his learning in the house of Laban.
This is one of the three places regarding which the nations of the world cannot accuse Israel and say, “You have stolen them.” The three places are: the Cave of Machpelah, the site of the Holy Temple, and the tomb of Joseph at Shechem. The cave of Machpelah, as it is written (Genesis 23:16): “Abraham weighed to Ephron the silver.” The Temple: “So David gave to Ornan for the place six hundred shekels of gold” (I Chronicles 21:25). And Joseph’s tomb: “[Jacob] bought the piece of land for a hundred kesitah.”
Because of her going out, she is called “the daughter of Leah.” For Leah, too, was an “outgoer,” as it is written, “Leah went out to greet him” (Genesis 30:16). Regarding her it has been said, “Like mother, like daughter.”
Thus it is written, “But a man of wisdom holds his peace” (Proverbs 11:12).
When any one of them entered the city laden with his wares, they said to him, “Come and be circumcised,” and he would reply, “Shechem is marrying her, and Mabgai must be circumcised?!”
Was she then the sister of these two only, and not the sister of all Jacob’s sons? But she is called by their name because they risked their lives for her sake.
Our sages calculate that the younger of the two, Levi, was exactly thirteen years old at the time. The fact that the Torah refers to him as a “man” is thus one of the sources that 13 is the age at which the Jewish male attains the age of manhood and daat (intellectual maturity), rendering him a bar mitzvah, one who is bound by the commandments.
On the face of it, this seems a rather inappropriate context in which to convey the law of bar mitzvah. Simeon and Levi’s act seems the very antithesis of daat. Indeed, Jacob denounced their deed as irrational, irresponsible, and of questionable legitimacy under Torah law. Yet this is the event that the Torah chooses to teach us the age of reason, maturity, responsibility and commitment to the fulfillment of the mitzvot!
But as Simeon and Levi replied to Jacob, the situation that prompted their action did not allow them the luxury of rational consideration of its consequences. The integrity of Israel was at stake, and the brothers of Dinah could give no thought to their own person—not to the jeopardy of their physical lives, nor to the jeopardy of their spiritual selves by the violence and impropriety of their deed. In the end, their instinctive reaction, coming from the deepest place in their souls—deeper than reason, deeper than all self-consideration—was validated. G‑d condoned their deed and came to their assistance.
This is the message which the Torah wishes to convey when establishing the age of reason and the obligation of mitzvot. Rare is the person who is called upon to act as did Simeon and Levi. This is not the norm; indeed, the norm forbids it. But the essence of their deed should permeate our rational lives. Our every mitzvah should be saturated with the self-sacrifice and depth of commitment that motivated the brothers of Dinah.
(The Lubavitcher Rebbe)
They dragged her out. . . . For at first she refused to go with them, saying, “And I, where shall I carry my shame?” (II Samuel 13:13), until Simeon swore that he would marry her.
There are those who say that Job lived in the times of Jacob, and that he married Dinah, the daughter of Jacob.
(Talmud, Bava Batra 15b)
What was Deborah doing with Jacob? Since Rebecca had said to Jacob, “I will send and bring you from there” (Genesis 27:45), she sent Deborah to summon him from Charan, and Deborah died on the road.
What was Jacob’s reason for burying Rachel at the roadside? Jacob foresaw that the exiles from Jerusalem would pass that way. Therefore he buried her there so that she might pray for mercy for them. Thus it is written (Jeremiah 31:15): “A voice is heard in Ramah . . . Rachel weeping for her children . . .”
Whoever maintains that Reuben literally sinned is simply making an error. For the Torah immediately states, “and the sons of Jacob were twelve,” teaching that they were all equally righteous. How, then, do I interpret “He lay with Bilhah, his father’s concubine”? It means that he relocated his father’s bed, for which the Torah faults him as if he had lain with his father’s wife.
(Talmud, Shabbat 55a)
In what way did Reuben violate his father’s bed? When Rachel died, Jacob took his bed, which always had stood in Rachel’s tent, and placed it in Bilhah’s tent. Reuben resented his mother’s humiliation. Said he: “If my mother’s sister was a rival to my mother, shall the handmaid of my mother’s sister be a rival to my mother?” Thereupon he arose and removed Jacob’s bed.
Manasseh the son of Hezekiah examined biblical narratives to prove them worthless. Thus he jeered: Had Moses nothing better to write than “Lotan’s sister was Timna . . . and Timna was a concubine to Eliphaz”?
What, indeed, is the Torah’s purpose in writing, “Lotan’s sister was Timna”?
Timna was a royal princess, as it is written (Genesis 36:29), “Duke Lotan.” Desiring to become a proselyte, she went to Abraham, Isaac and Jacob, but they did not accept her. So she went and became a concubine to Eliphaz the son of Esau, saying, “I would rather be a servant to this people than a mistress of another nation.” From her was descended Amalek, who afflicted Israel. Why so? Because they should not have repulsed her.
(Talmud, Sanhedrin 99b)