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Commentary for Genesis 32:4

וַיִּשְׁלַ֨ח יַעֲקֹ֤ב מַלְאָכִים֙ לְפָנָ֔יו אֶל־עֵשָׂ֖ו אָחִ֑יו אַ֥רְצָה שֵׂעִ֖יר שְׂדֵ֥ה אֱדֽוֹם׃

And Jacob sent messengers before him to Esau his brother unto the land of Seir, the field of Edom.

Tiferet Shlomo

Genesis 32:4: "Yaakov sent angels"-- Rashi explains that the word "angel" [in context] means just that: an angel [whereas other commentaries could interpret the word as "messenger"). It's known from the Zohar that every mitzvah creates an angel. The main antagonism to the angelic minister of Eisav is saying the prayer of Shema. This is the meaning of the verse: "the house of Yaakov is fire, the house of Eisav is straw" (Ovadia 1:18) -- "straw" is an acronym is for "kriat shema" [the prayer of Shema]. The Shema directly opposes Eisav. As it says Megaleh Amukot, "so shall say you to my master Esiav" -- "so" refers to recital of Shema. The word "mamish" [used by Rashi in his commentary] stands for "mekabalet malchus shamayim" (accepting the yoke of heaven), referring to the angels emerging from the intent of our Shema. This is the main antagonism to subjugate the angelic minister of Eisav. Eisav also includes the seed of Amalek, and the Torah says that Hashem's name is not complete until Amalek is eradicated. On that day, when the saviors go to the mountain of Zion to judge the mountain of Eisav, dominion will belong to G-d, and on that day Hashem will be one and His Name will be one.
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Rashi on Genesis

וישלח יעקב מלאכים AND JACOB SENT MESSENGERS (Heb. מלאכים angels) — actually angels (Genesis Rabbah 75:4).
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Ramban on Genesis

TO ESAU HIS BROTHER UNTO THE LAND SE’IR. Since the southern part of the Land of Israel adjoins Edom, and Jacob’s father dwelt in the land of the South,4Above, 24:62. he had to pass through Edom or near there. Therefore, he feared lest Esau hear of it, and he took the initiative by sending messengers to him in his country. But the Sages have already taken him to task for this, saying in Bereshith Rabbah:575:2.Like one that taketh a dog by the ears is he that passeth by, and meddleth with a strife not his own.6Proverbs 26:17. The Holy One, blessed be He, said to Jacob, ‘Esau was going his way, and you send him messengers, and say to him, Thus saith thy servant Jacob!7Verse 5 here.
In my opinion this too hints at the fact that we instigated our falling into the hand of Edom [Rome] for the Hasmonean kings during the period of the Second Temple entered into a covenant with the Romans,8In Maccabees, I, 8, it is related how Judah Maccabee sent a delegation to Rome to establish a political alliance with the Romans. and some of them even went to Rome to seek an alliance. This was the cause of their falling into the hands of the Romans. This is mentioned in the words of our Rabbis,9Abodah Zarah 8b. and is well publicized in books.10Ramban is undoubtedly referring to the history book of Josippon, or Joseph ben Gorion, a medieval work regarded as the Hebrew version of Josephus Flavius. It was a popular work with the people of the Middle Ages. See also Ramban on Leviticus 26:16.
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Sforno on Genesis

וישלח יעקב מלאכים, in order to find out Esau’s state of mind concerning him.
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Or HaChaim on Genesis

וישלח, He sent, etc. Why did the Torah say: לפניו, ahead of him, a word which appears to be superfluous? The word אחיו also needs justification. Who did not know that Esau was Jacob's brother? Even the words ארצה שעיר שדה אדום, "to the land of Se-ir the field of Edom," need an explanation. What difference would it make to the angels where Esau was located? Furthermore, why did the Torah use the expression ארצה instead of לארץ? Although Yevamot 13 states that wherever the letter ל is required at the beginning it can be substituted for by the letter ה at the end, this does not explain when the Torah chooses one method rather than another.
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Radak on Genesis

וישלח יעקב מלאכים, even though G’d had assured him of His support twice, he was still afraid of his brother. The reason was that at the time Yaakov had left home Esau had been very angry at him. He was now afraid that due to some sin he might have committed and that he had remained unaware of, he might forfeit G’d’s support. We elaborated on this concept already. In order to find out how Esau felt about him now, he sent some of his mean as emissaries. They were supposed to soften him up if that was necessary.
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Tur HaArokh

וישלח יעקב מלאכים לפניו, “Yaakov sent messengers ahead of him.” Their assignment was to walk in front of him. Alternatively, their assignment was to investigate the “face” of Esau, i.e. his attitude toward Yaakov at this time. Although G’d had given Yaakov all kinds of assurances, (some time earlier) he did not rely on his righteousness alone to save him from Esau, but took every prudent precaution to minimize the risk to his family and to himself. Yaakov’s conduct is to serve as a model for his children and future descendants to teach them how to deal with the descendants of Esau. Just as he prayed, offered bribes, and was prepared for battle, so his descendants should employ these three means of insuring their survival also.
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Rabbeinu Bahya

מעין נרפש ומקור משחת צדיק מט לפני רשע אכול דבש הרבות לא-טוב וחקר כבודם כבוד “A righteous man who falters in front of the wicked, is like a murky well and a polluted fountain. It is no good to eat too much honey, nor is it honorable to seek personal glory.”(Proverbs 25, 26-27)
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Siftei Chakhamim

Actual angels. Otherwise, why does it need to say לפניו? The verse is saying that Yaakov sent the messengers [i.e., the angels] who were לפניו. In other words, he sent the ones mentioned before: “And the angels of Elohim met him” (v. 2). (Re’m) Much more has been said regarding this. See Gur Aryeh, R. Noson and Nachalas Yaakov.
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Chizkuni

וישלח יעקב מלאכים, “Yaakov sent out messengers;” the meaning of the word: malachim here is, as understood by both translators into Aramaic, izgedin, runners, messengers; [human beings. Ed.]
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Rashi on Genesis

ארצה שעיר means TO THE LAND OF SEIR — A word that requires a ל as prefix has a ה placed as a suffix (Yevamot 13b).
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Sforno on Genesis

ארצה שעיר שדה אדום, to the region of Seir where he lived. At that time he had not yet conquered the whole Chori, the inhabitants of that land. (compare 36,8)
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Radak on Genesis

ארצה שעיר, he had heard that Esau was there at the time although he had not settled there with his family. At this time he still lived in the land of Canaan. We know from 36,6-9 that Esau migrated to the land of Seir only at that time, after the meeting with Yaakov.
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Tur HaArokh

ארצה שעיר, שדה אדום, “the land Seir, the field of Edom.” Anyone traveling from Charan to the land of Israel travels through the land of Seir. Even though Esau spent most of his time in the land of Canaan, as is clear from Genesis 36,6: “Esau took his wives and went to “a (another) land,” on account of his brother Yaakov,” Yaakov had reason to believe that he would encounter him near his wives, who had come from the land of Seir. Our sages have criticized Yaakov, comparing his conduct to the proverbial “he who grabs the ears of a dog must not be surprised if he gets bitten.” Yaakov’s sending gifts ahead to Esau alerted him to the fact that he was about to approach him. Yaakov’s mistake was repeated during the latter days of the second Jewish commonwealth, when the Romans were invited by a Jewish king Aristobul, descendant of the Maccabees, to conclude an alliance with him. This was the beginning of the collapse of the Jewish commonwealth and of the second Temple, followed by total loss of Jewish independence, such as it had been.
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Rabbeinu Bahya

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Or HaChaim on Genesis

The verse wants to justify the expression "he sent angels." Why did Jacob employ heavenly beings without a pressing need? He could have accomplished the same thing by employing human messengers! The Torah says לפניו, to tell us that since Jacob had already met with these angels and they had obviously come to help him, he was permitted to use them as messengers for a task that human messengers might prove inadequate for. Jacob reasoned that seeing that these messengers would meet an important man such as Esau, he might not consider messengers of a lower order as appropriate to his stature (compare Bereshit Rabbah 75). Esau might not have responded to any other messengers at all. It is also possible that Esau would immediately pounce on Jacob's human messengers as the eagle does when he swoops out of the skies, thus not giving him any warning before attacking him. For all these reasons Jacob was justified in employing celestial beings to act as his messengers. Perhaps he also hoped that when Esau became aware that he, Jacob, had celestial beings do his bidding he would desist from his planned attack on Jacob altogether. The Midrash we quoted above refers to those angels as being garbed in "fiery garments, riding horses of fire, etc."
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Ramban on Genesis

To Eisav his brother in the land of Edom: Since southern Israel is near Edom, and his father (Yitzchok) was living in the south, he (Yaakov) would need to pass through Edom, or close by. Therefore he was afraid the Eisav would hear (that Yaakov was there), and he preemptively sent messengers to his land. Our Rabbis take him to task for this, as it says in (the medrash) Bereishis Rabba, "'He who holds the ears of a dog...' Hashem said to him (Yaakov), 'He was going on his way, and you sent messengers to him saying, so said your servant Yaakov?'" In my opinion, this also hints for us, that we began our downfall into the hands of Edom (when) the kings of the Second Temple Era entered into a covenant with Rome, and some even went to Rome. This was the reason for their downfall.
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Chizkuni

ארצה שעיר, “towards the land of Seir.” This land had originally belonged to “Seir,” but when Esau married Oholivamah, daughter of Ana, he inherited this land courtesy of his wife whose maternal links had been Ana, a daughter of Tzivon as stated in Genesis 36,2. Esau had moved there from the land of Canaan to spend more time with his wives to whom he felt greatly attached. Eventually this land was named after him, i.e. “field of Edom.” This term reminds everyone of Esau’s primary vocation as hunter in the field.
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Radak on Genesis

שדה אדום, a synonym for “the land of Edom.” We have the same synonym also being used for the land of Moav in Ruth 1,1 when Elimelech left the land of Israel to settle in שדה מואב, meaning in ארץ מואב.
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Or HaChaim on Genesis

The reason the Torah mentions the word "his brother," is to emphasize that Jacob despatched the messengers in a spirit of brotherliness and that he accorded Esau the honour due to an older brother. He was afraid of engaging Esau in warfare in case the latter should invoke his father's merits.
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Or HaChaim on Genesis

Another approach is also possible. The Torah emphasizes: אל עשו in order to tell us that on the one hand Esau hated him; on the other hand, the Torah wrote אל אחיו, to tell us that he did not hate him, that he was his brother. The messengers should be guided in their approach to Esau according to the frame of mind they would find him in. Since only celestial beings could divine Esau's frame of mind with any certainty, Jacob had to send celestial messengers to accomplish this task.
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Or HaChaim on Genesis

Still another possibility is that Jacob's strategy was to send messengers to Esau before Esau had a chance to hear about his approach from another source. This is in line with the various Midrashim in which Jacob is criticised severely for not letting sleeping dogs lie, for demeaning himself by repeating so many times "your servant Jacob," etc. He chose to send angels who would not have to exert themselves by excessive travel. To the angels the whole universe appeared no greater than four cubits do to us mortal human beings. When the Torah reports that Jacob sent messengers ahead of him to Esau, the word לפניו, before him, is an allusion that the angels were still literally in his presence although they performed their mission to Esau who was quite a distance away. The reason that the Torah wrote ארצה שעיר instead of לארץ שעיר, is to emphasize that the angels did not actually have to go anywhere. All they had to do was to face in a different direction. The reason that the field is called "Edom" is that they would arrive at Esau's, i.e. the field of Edom, before the latter had a chance to even to get under way towards Jacob.
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Rabbeinu Bahya

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Or HaChaim on Genesis

This verse may also be understood as alluding to three different historical periods during each of which Esau's conduct would be different. One period finds Jacob and Esau in a brotherly relationship. This is alluded to by the words: "to Esau his brother." This period would extend until the destruction of the Holy Temple. Even though there were times prior to that when the Edomites were subjugated by Israel, such periods were relatively brief. During a different period in history, after the destruction of the Holy Temple until the end of the present era (before the advent of the Messiah), Esau would occupy a lofty position on earth and Israel would not even be considered by it as of any importance at all. This is the period which is alluded to here by the words ארצה שעיר, with the vowel patach under the letter א. This vowel underlines the superior position of Esau. The third period is the one we are hoping for when Edom will become an inheritance (for the Jewish people). This period is alluded to by the words שדה אדום, i.e. that Edom will be ploughed over as predicted by the prophet.
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Rabbeinu Bahya

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Rabbeinu Bahya

The sages of the Midrash in Bereshit Rabbah 75,2 take a different view. They describe Yaakov as taking hold of the ears of a dog by getting involved in a struggle which was not his. The last we had heard of Esau was that he pursued his own interests and married another wife to mollify his parents (28,9). According to Bereshit Rabbah 75,5 Yaakov acted very precipitously by sending messengers to Esau and reminding him of his existence, almost provoking him into a confrontation. This is how they interpret the verse in Proverbs we started out with, i.e. that Yaakov unnecessarily muddied the waters. They ascribe an overly obsequious letter from Rabbi Yehudah Hanassi to the governor of Palestine Antoninus as reflecting this lack of backbone displayed here by his ancestor Yaakov. Antoninus reputedly replied to this letter by questioning Rabbi Yehudah Hanassi: “are you then my servant? I wish I would become your servant in the hereafter.” Rabbi Yehudah replied “I am not greater than my ancestor Yaakov; and you are not smaller than your ancestor Esau.” After all, my ancestor Yaakov sent a message to your ancestor Esau in which he addressed him as ‘your servant Yaakov.’” According to an opinion in that Midrash, we learn from here that Royalty must be addressed deferentially.
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