Who were the Mal'achim that Yaakov sent to Esav?
Rashi: They were the angels that had come to greet him. 1
Targum Onkelos and Targum Yonasan: They were regular emissaries.
See 32:3 and Ba'al ha'Turim there. Oznayim la'Torah - How great is the man who is able to harness angels as messengers - This is in keeping with the Tanchuma, that Tzadikim are greater than angels!
Why did Yaakov send to Esav at all?
Ramban: Because, since Edom was close to the south of Eretz Kena'an, where his father lived, and he would have to pass through it (or close by), he was afraid that Esav would hear of his proximity and attack him. So he sent messengers together with a gift (as a bribe, in order to soften his heart).
Seforno: To know what was in Esav's heart.
Malbim: He sensed from the angels that he is in danger. He sought natural ways to appease Esav, lest he need a miracle.
Ha'amek Davar: He wanted to tell him that he is coming, and he will give to him a gift. However, when Yaakov heard that Esav intends evil, he sent the gift before meeting him. He sent now, after he reached Ever ha'Yarden, which has the sanctity of the Land; 1 for Hashem's promise to return him to "this land" (28:15) was fulfilled, and he was no longer guaranteed protection. Yaakov prayed for protection until he reaches his father's house, but he did not know whether or not Hashem agreed. Harchev Davar - Yaakov now saw that it would have been better to openly leave Lavan than to flee; he thought that likewise, he should not be open with Esav. Hashem removed Yaakov's Chochmah; it would have been better to return covertly to Yitzchak's house (refer to 32:4:4:1).
At what point did Yaakov cross the Yarden, returning from Ever ha'Yarden to Eretz Yisrael proper? Yaakov had just reached Machanayim, which was still on the other side of the Jordan (see Yehoshua 13:26,30; Shmuel II 17:22-24). In this Perek, Yaakov names Penuel and Sukos, which were likewise in Ever ha'Yarden (Yehoshua 13; Shoftim 8). Only much later does Yaakov reach "Shechem, which was in Eretz Kena'an" (33:18). (CS)
Why does the Torah insert the word "Lefanav"?
Because Yaakov sent the messengers ahead of his arrival in Har Se'ir; either to soften Esav before meeting him, 1 or to find out where he stood with him. (EC)
Ohr ha'Chayim: Because angels appeared in front of Yaakov, he felt authorized to use them. Normally, one should not use angels for something that people can do.
Malbim: This is like "v'Es Yehudah Shalach Lefanav" (46:28). The messengers would talk to Esav's heart, that he should accept Yaakov in his land.
Why does the Torah add "Sedeh Edom"?
Malbim: Because at that stage, Esav had not yet conquered the entire land of the Chori who dwelt there, only the area of Sedeh Edom.
Oznayim la'Torah: Refer to 32:4:3.1.3.
Refer to 32:4:151:3.
Ha'amek Davar: Esav's primary residence was in Eretz Yisrael, until Yaakov returned and the land could not sustain both of them. Even so, Esav already acquired land in Se'ir, and it was called Sedeh Edom. Yaakov sent to there to gauge Esav's intent. In his father's land, Esav might hide his hatred due to Kibud Av.
What did Yaakov do to deserve his frightening confrontation with Esav?
Ramban: The Midrash (Bereishis Rabah 75:3) uses the parable of 'grabbing a sleeping dog by its ears!' 1 - Since Esav was not in the least concerned with Yaakov at that moment. Consequently. Yaakov should have by-passed him quietly without announcing himself. 2
R. C. Fogel, citing R. Yechezkel Levenstein: When Yaakov took the Berachos, this caused Esav to scream - and in turn, Esav's descendant Haman caused Mordechai to scream (Esther Rabah 8:1). To avoid this, Yaakov hoped to appease Esav ("Achaperah Fanav" (32:21)), but he failed. Had Yaakov merited more, he would have received the Berachos without causing pain to Esav.
Ramban: 'Ma'aseh Avos Siman l'Banim' - In the time of the second Beis-Hamikdash, it was the Chashmona'i kings who caused their own downfall by initiating a covenant with the Romans - a covenant which the Romans abrogated after 26 years and went on to destroy the second Beis-Hamikdash.
What lessons can we learn from the current episode (Ma'aseh Avos Siman l'Banim)?
Ramban: (a) How Hashem sent an angel to save His servant from his enemy (Esav) who was stronger than he. (b) How Yaakov did not rely on his righteousness, but made the necessary Hishtadlus (via Tefilah, gifts and, as a last resort, battle) to save himself from his brother's clutches. 1
And the onus lies on us to take our cue from Yaakov Avinu when we find ourselves at the mercy of Esav's descendants (in Galus Edom) - Ma'aseh Avos Siman l'Banim.
How will we reconcile this Pasuk, which implies that Esav had already moved to Har Se'ir, with the Pasuk at the end of the Parshah (36:6), which implies that Esav moved only after Yaakov returned to Chevron?
Ramban: Refer to 36:6:151:1 and 36:6:151:2.
Oznayim la'Torah: Esav conquered Har Se'ir while Yaakov was still in Charan, and went there from time to time with his 400 warriors to collect taxes from them, but he himself remained in Chevron, until Yaakov returned home. 1
See Oznayim la'Torah who elaborates on Esav's motives.
Why does it say, "to his brother"?
Ohr ha'Chayim #1: Yaakov strove so much for Shalom, lest there be war, and the merit of Esav's fathers will help him.
Ohr ha'Chayim #2: He sent "El Esav Achiv" - Yaakov was unsure if he is [acting like] Esav the hater, or like his brother.
Ohr ha'Chayim #3: The verse hints to three eras of the relation of Yaakov and Esav. (a) Esav Achiv - when they are equal (neither dominates the other), e.g. until the Churban. (Only for a short time, Esav was under Yisrael.) (b) "Artzah Se'ir" - after the Churban, Esav dominates. (c) "Sedeh Edom" - in the future, it will be plowed (Yisrael will inherit it).
QUESTIONS ON RASHI
Rashi writes: "'Mal'achim' - actual angels." Why doesn't Rashi explain this word simply as 'messengers'?
Gur Aryeh #1: In the preceding verse (32:3), Yaakov saw two camps of angels simultaneously; those of Eretz Yisrael as well as those of Chutz la'Aretz. Why didn't the angels of Chutz la'Aretz ascend to Heaven first? 1 It must be because Yaakov would need them, to send them on this mission to Esav. 2
Gur Aryeh #2: Why did the angels of Eretz Yisrael descend already at this point, even before Yaakov arrived there? 3 It must be because Yaakov would need them, to send them on this mission to Esav. 4
Gur Aryeh #3: Why doesn't the verse first tell us the reason for Yaakov's actions (i.e. by saying, 'Yaakov was afraid of his brother Esav, and therefore he sent Mal'achim....')? Rather, our verse is a continuation of the preceding one - 'Yaakov sent some of the angels he had encountered to Esav....'
Refer to 28:12:1.3:1 and 32:3:1.1.
Gur Aryeh: Although they could not ascend first in this case so as not to leave Yaakov unprotected (Gur Aryeh to 32:2); the name 'Machanayim' (two camps) implies that the angels of Chutz la'Aretz remined, and not merely for a short time.
Gur Aryeh: However, these two approaches would imply that Yaakov acted correctly in alerting Esav to his arrival; while the Midrash says otherwise.
Rashi writes: "'Mal'achim' - actual angels." The Midrash derives this from Hagar, to whom five actual angels appeared (16:7-12). Yet the 'Mal'achim' that Moshe sent (Bamidbar 20:14) were human messengers; as were those of Yehoshua (Yehoshua 2:1)?
Mizrachi: We derive that Yaakov sent actual angels from the preceding Pesukim (32:2-3). If we should wonder how this is possible, the Midrash tells us that even Hagar was greeted by angels.
Gur Aryeh: The Avos are the foundation, the initial root of the Jewish People (and hence of Creation). 1 Their needs are not of individuals, but rather of the entire world. 2 Indeed, the angels' designated function is to protect the world, and as such, Yaakov made use of them now, as he returned to Eretz Yisrael. As great as Moshe was, he is not considered one of the Avos. 3
And therefore while even the maidservant of the Avos, Hagar, merited seeing angels, we should not expect to find this in later generations.
Gur Aryeh: See Shemos Rabah (28:1) - When Moshe ascended to Shamayim before receiving the Torah, the angels wished to harm him; until Hashem changed Moshe's countenance, to appear like - Avraham!
Rashi writes (to 32:2) that Yaakov encountered angels of Eretz Yisrael, and he sent [them] to Esav. How could he send them to Sedeh Edom, which is Chutz la'Aretz?
Moshav Zekenim (to 32:5, from Bereishis Rabah 74:17): He sent from both of them. 1
Moshav Zekenim (to 32:5): Se'ir is considered like Eretz Yisrael, for it is one of them three lands that Yisrael will only inherit in the future.
Oznayim la'Torah: At Bris Bein ha'Besarim, Hashem promised Amon, Mo'av and Edom, part of which is called Har Se'ir. The Torah added Sedeh Edom, to teach that it will be called Eretz Yisrael.
Oznayim la'Torah: He sent angels of Eretz Yisrael and of Chutz la'Aretz, for he was unsure where Esav is. Only the angels of his location can fulfill the mission.
Rashi writes: "'Artzah Se'ir' - For any word that requires the prefix Lamed (meaning 'to'), the Torah may use the suffix Hey." If so, why can't we say for 'Reuven went to Shimon,' 'Reuven Halach Shimonah'?
Rashi writes that Yaakov sent angels. Why did he do so?
Ohr ha'Chayim #1: Had he sent people, Esav might have struck them and swiftly come upon Yaakov. Angels would scare Esav and deter him from evil.
Ohr ha'Chayim: Angels could reach Esav immediately and do their mission while Yaakov is still far away.
Tosfos (Shabbos 12b DH she'Ein), Rosh (Berachos 2:2): Angels know people's thoughts. Ma'adanei Yom Tov (on the Rosh) discusses possible source for this, but asks from "Atah Levadcha Yada'ta Es Levav Bnei ha'Adam" (Divrei ha'Yamim II 6:30) and "Akov ha'Lev... Mi Yeida'enu... Ani Hashem Choker Lev!" (Yirmeyahu 17:9,10).
Esav was "Ish Tzayid" (25:27) - a master deceiver (refer to 25:27:151:1).
