Two camps—from outside Eretz Yisrael... Question: Rashi explained on, “Ascending and descending” (v. 28:12), that the two [groups of angels] were not together. Rather, one ascended and only then the other descended. [Why were both groups together here?] The answer is: Rashi explains at the beginning of Parshas Vayishlach that Yaakov sent actual angels [to Eisov]. Accordingly, it means as follows: Here too, the angels of outside Eretz Yisrael wanted to ascend before the angels of Eretz Yisrael would descend. But Yaakov forced them to stay because he wanted to send them to Eisov. If so, this implies that [the messengers sent by Yaakov] were actual angels.

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.

I have not become an officer or anyone of importance... Otherwise it should simply say, “With Lavan I was delayed.”

Another explanation: The gematria of גרתי... I have kept תרי"ג commandments... Thus, you cannot defeat me. When your father blessed you that “you shall live by your sword” (27:40), that is only “When you have cause to be grieved” (ibid). [I.e., “When the Israelites will transgress the Torah.”] But I kept the whole Torah! Maharshal explains that Rashi is answering the question: Why did Yaakov say, “I have not become an officer...”? For this actually would allow the wicked Eisov to claim, “If the blessings were not fulfilled for you, you surely did not keep the mitzvos! Thus I should fulfill regarding you, ‘When you have cause to be grieved, you will throw off his yoke from your neck.’” Therefore Yaakov told him, “I kept all the 613 mitzvos. Nevertheless, I have not become an officer.”

These are neither from the heavens nor from the earth. Although they are nourished from the earth, they do not actually grow from the earth. Otherwise, [if Yaakov meant as follows, a contradiction arises.] First he said, “I lived as a stranger,” to convey that the blessings were not fulfilled. Then he said ויהי לי שור וחמור, [detailing his many blessings. And he must have meant שור וחמור in plural,] as is customary to refer to many oxen as “ox.” This is obviously so, for he sent Eisov a whole camp as a gift, and would be proven a liar if he meant, “I acquired one ox [and one donkey].” According to Rashi’s other explanation above, Yaakov was saying: “Although I kept the 613 mitzvos, my father’s blessing has not been realized. I have only oxen and donkeys, not the rest of my father’s blessing, which is “from the fat of the land.” Therefore, [since my merits have not been offset by my rewards,] I do not fear you.

To announce that I am coming to you. [Rashi knows this] because if Yaakov was sending [the messengers] to tell him, “I lived as a stranger with Lavan... I acquired oxen and donkeys...” then [the next phrase,] “To find favor in your eyes,” would also refer to this. And that cannot be, for such a message is not a reason to find favor; it is merely [a reason] that Eisov should not hate him. Therefore Rashi explains, “To announce that I am coming to you” to be subservient to you — and through this will I find favor in your eyes. Maharshal writes that Rashi is answering the question: Yaakov said before, “This is what you should say.” Why does he say [again], “To tell my master”? Perforce it means, “To announce that I am coming.” In this way I will find favor, because when people send [messages] to appease someone, they do not come themselves. But I will even come myself! All this is because I am at peace with you.

But he acts towards you as the wicked Eisov... Otherwise, why does it say, “Eisov”? Yaakov had only one brother! Perforce, “Eisov” connotes he who is famous for extreme wickedness. (Re’m) A further explanation: Rashi is answering the question: It should say באנו אל עשו אחיך, like it is written אל עשו אחיו at the beginning of the parshah. Why does it say אל אחיך אל עשו? Maharshal explains [that Rashi is answering the question:] Why does it say אל twice? We need not object: [Accordingly,] why did Yaakov say לאדוני לעשו (v. 4)? For the answer is: There, Yaakov was commanding them to speak with honor. But here, where they are reporting the reply to Yaakov, why did they speak in this fashion? Thus Rashi explains as he does.

ויירא lest he be killed. You might ask: Had Hashem not promised him when he left his father’s house, “And I will bring you back to this land” (28:15)? The Gemara (Berachos 4a, Sanhedrin 98b) answers: [He feared that] sin might cause [the promise not to be fulfilled]. Another answer: The promise was only, “And I will bring you back to this land,” meaning to Eretz Yisrael, but not to his father’s house. See Re’m, R. Noson, Gur Aryeh and Minchas Yaakov.

ויצר לו that he might kill others. [Question: Why did this distress him?] The answer is: Yaakov feared he might kill Eisov, and Yitzchok loved Eisov and considered him a good person. It would pain Yitzchok greatly and bring him to curse Yaakov. (Midrash Tanchuma) An alternative answer: Yaakov surely did not fear killing Eisov, for it says in Sanhedrin 72a: “If someone comes to kill you, kill him first.” Rather, Yaakov feared that he might kill Eisov’s men, who came to kill not Yaakov but Yaakov’s men. Only Eisov came to kill Yaakov. Indeed, Eisov’s men would be attacking Yaakov’s men, and one may save the attacked even by taking the attacker’s life. But if injuring the attacker’s limb would suffice to save the one being attacked, then for killing the attacker [instead of just injuring him] one is liable for the death penalty. Thus, Yaakov feared he might kill them in the confusion of war even where injuring a limb would suffice. Some ask: Why did Yaakov fear being killed? Eisov said, “When the mourning days for my father approach, I will kill my brother Yaakov” (27:41), and Yitzchok was still alive. A further question: Why did Eisov send Elifaz to kill Yaakov [at the time that Yitzchok was alive]? It seems the answer is: When Eisov said he will not kill Yaakov while his father is alive, this applied only if Yaakov was with Yitzchok. But if he was elsewhere, Eisov would kill him. See Minchas Yaakov.

Against his will, because I will do battle with him. I.e., while I will do battle with him, the second camp surely will have time to escape. Maharshal writes that Rashi inferred this because it is not written, “Perhaps the remaining camp will survive,” but, “The remaining camp will survive.” This implies, “Against his will, because I will do battle....” Rashi said all this, based on Scriptural inferences, to support Chazal’s teaching that Yaakov prepared himself for three things. [Rashi says “against his will,” i.e., it surely will be.] This is because the verse cannot mean “perhaps” [the remaining camp will survive]. If so, it would be more logical to gather everyone in one camp to fight Eisov—for maybe they will win due to greater numbers. However if the remaining camp will [surely] survive, against Eisov’s will, it is proper for Yaakov to have divided them into two camps. For it is better to act in a manner that will surely save one camp, even if it places the other camp in greater danger, than to put them in a situation in which they are not sure whether they all will be lost or saved. (Nachalas Yaakov)

He prepared himself for three things. All three are derived from Scripture [see Pesikta D’Rav Kahana 19:3]. And “war” is derived from, “The remaining camp will survive,” showing that this phrase refers to war. Thus Rashi explains it as, “I will do battle with him.”

Return to the Land of your father and to your birthplace, and I will be with you... Yaakov was saying: Since You promised to be with me when I come to the Land of my fathers, if I die on the way, it will turn out that Your promise to me was not fulfilled.

My merits have diminished because of the kindnesses and truth... מכל החסדים means because of the kindnesses. ואת עבדך means, “That you have done with me.” Rashi is explaining that [in this verse,] את means “with.”

Lest from the time You made me the promises, I have become tainted by sin... For the reason of diminished merits alone, Yaakov would not have feared, as there is no death without sin and no suffering without iniquity (Shabbos 55a). Thus Rashi brings also the reason of “tainted by sin.” And for the reason of “tainted by sin” alone, we might think that Yaakov still need not have feared, as his merits would outweigh his sins. Thus Rashi brings also the reason of diminished merits. Due to both of these reasons, Yaakov was frightened.

“Making Your words come true...” Rashi is answering the question: Just because Hashem spoke [true promises], should Yaakov’s merits diminish? For Rashi said above, “My merits have diminished.” [Therefore Rashi explains, “You have kept all the promises.”] And why did Rashi say, “You have kept,” rather than, “You have done,” as the verse says? Because [the fulfillment of] what one says is not called עשייה, but שמירה. I.e., “keeping” it is the same as “doing” it.

The Midrashic explanation is: He placed his staff into the Jordan [River] and the Jordan split. According to this, [Yaakov is saying that] Hashem did him two good deeds: the splitting the Jordan, and the [dividing into] two camps. But according to the simple meaning, there is only one kindness.

“From the hand of my brother who does not act towards me as a brother...” Here too, Rashi deduced this because מיד is written twice. And Yaakov would not use an expression of honor [about Eisov] when speaking to Hashem. (Maharshal)

היטיב**on account of your merits, and איטיב on account of your fathers’ merits.**Although the Torah speaks in the language of man, [thus a double verb need not be expounded,] here it is clear that it is to be expounded. For it should have said היטב תיטב, in second person, like העניק תעניק (Devarim 15:14). This is preferable to Re’m’s explanation, that whenever an exposition can be made it should be made. You might ask: Rashi explained on v. 11 that Yaakov said, “My merits have diminished.” [Why did he pray here on account of his own merits?] The answer is: He surely was not praying here on account of his merits, but on account of his fathers’ merits. That is why Rashi adds, “I will do good on account of your fathers’ merits.”

Until I have done. Also this verse shows that, “Until I have done that which I have spoken for you,” refers to [what Hashem spoke to] Avraham, as Rashi explained on v. 28:15. Otherwise, the difficulty [remains]: Hashem never said this to Yaakov.

In his possession. There is a question [on the first explanation]: Why does it need to say בידו? [Obviously, he took only from what was his!] Thus Rashi brings the Midrashic explanation that it refers to jewels. But there is a question on this: Why does it not mention [the type of jewel] by name, [as it does with the animals]? Therefore Rashi brings the alternate explanation, about tithes. But this explanation alone does not suffice, because why did it say, “Which comes into his hand”? The non-sacred was already in his hand, [as he made it so by tithing it]. That is why Rashi presents all the explanations. (Maharshal)

Once an animal has become pregnant it does not accept the male. Rashi is saying that it is the nature of an animal to mate as often as enjoyment calls for and free time permits. Since he-goats and rams are free all day, Yaakov gave them ten females each. This enabled them to fulfill their desire and maximize offspring for the owner. And so Yaakov gave each [type of male animal] according to its free time. This raises a question: Although he-goats and rams are free all day, they do not know that their mating with many females benefits the owner. Perhaps one male will fulfill its desire with one female, mating with it repeatedly? To this Rashi answers: “Once an animal has become pregnant...” This forces the male to separate from her and go to a second and a third, etc. Re’m explained differently; the reader may decide. See Kesubos 62a, which says that free time serves as the determining factor. (Nachalas Yaakov)

And their young were with them... Rashi is saying that there were also thirty young ones. Otherwise, why would it include them all in the same number, when the verse is coming to describe how large the gift was? The young are not significant when [included] with their mothers! Perforce, the verse should be rearranged to read: גמלים מניקות שלשים ובניהם.

The Midrashic explanation... one male per female... Accordingly, שלשים is rightly written after בניהם, for it indicates that there were thirty altogether. The numbers of the males and of the females were not stated explicitly because camels are discreet in mating.

And their young were with them... This [first explanation] is saying that there were also thirty young ones. Question: If so, why does it not say שלשים also for the young, like it does for the nursing camels? Thus Rashi brings the Midrashic explanation, that they were thirty altogether. And so that we will not ask, “If so, why does the verse not state the numbers of the males and of the females?” Therefore Rashi explains, “Since it is discreet in mating...” And in fact there were fifteen males and fifteen females. (Maharshal)

A distance of one day or less... [Rashi knows that they were] not immediately ahead of Yaakov, because it is written in v. 22: “The present passed on ahead of him, but he spent the night in the camp.” If they were just a short way from Yaakov, they could have all spent the night together. And they were not more than a day’s distance ahead, because Yaakov gave Eisov the present on the same day [after daybreak], as is evident from the coming verses.

And I will follow behind you. [Rashi knows this] because Yaakov told them to say to Eisov, “And see, he himself is also behind us.” Thus, Yaakov must have said it to them, too: “Pass on ahead of me and I will follow behind you.”

One herd was ahead of the other... Rashi is explaining that they were herd behind herd. [Rashi knows this] because if they were lined up alongside each other, how could they be described [in the coming verses as] first, second and third? They would all be “first.”

To whom is this gift being sent... I.e., the second למי conveys [“to whom”, which is] its primary meaning. But למי אתה does not convey its primary meaning, which would be: “To whom are you bringing it.” [Rashi knows this] because it says afterward, “You should say, ‘They belong to your servant, Yaakov.’” This is answering Eisov’s first question first, as Rashi explains there. But if the first למי conveyed its simple meaning, then it should say afterward, “To my master, Eisov” — for that would be the answer to Eisov’s [first] question.

Referring to Yaakov. [How does Rashi know this? Because] it is written, “He commanded the first one... and to all who followed after....” If so, the last one also said, “He is also behind us” — although there was no [group] behind him. Perforce, it referred to Yaakov. Consequently, all [the groups must have meant] the same. [You might ask: If so,] why does it then say, “You should also say, ‘See, your servant Yaakov is behind us”? [This is repetitious, as] all the servants already said this! The answer is: Yaakov was saying to them as follows. Regarding what I commanded you to say to Eisov — “And see, he is also behind us” — do not say it vaguely, by concealing my name. Rather, say it expressly, like this: “See, your servant Yaakov is behind us.” I.e., mention to him [also my] servility.

He was also angry that he had to resort to all this. [Rashi knows this] because it is written על פניו — similar to על אפו (in his anger) — instead of לפניו. (Gur Aryeh)

Where was Deenah? You might ask: How does Rashi know this? Perhaps Deenah was among the eleven, and one of the sons was missing. The answer is: It is written in v. 43:29, “Hashem be gracious to you, my son.” Yoseif said this to Binyamin. And, as Rashi explains, Yoseif blessed him so because for the other brothers it had already been said (v. 33:5), “The children whom Hashem has graciously granted your servant”. [Yaakov said this to Eisov when they met.] Since Binyomin was not yet born at that time, Yoseif blessed him now with grace. This clearly shows that “his eleven children” were the eleven sons, without Deenah. For otherwise, the question stands: why did Yoseif bless only Binyomin with grace, and not the other son who was missing at the time [that Yaakov met Eisov]?

So that Eisov could not set eyes on her... I.e., for this reason we must say that it was Deenah who was missing, and that Yaakov placed her in a box because of Eisov. For otherwise, why was Yaakov punished through Deenah [i.e., the episode with Shechem]? Perforce, he was punished because he feared Eisov, and Yaakov therefore put her in a box. And this answers the question in the previous entry.

Yaakov was thus punished... You might ask: It is written in v. 35:1, “Arise, go up to Beis Eil,” on which Rashi explains, “Because you lingered on your journey you have been punished and this trouble of your daughter has come to you.” [Does this not imply that Yaakov was not punished for withholding Deenah?] The answer is: Each of thee matters caused [Yaakov’s punishment].

The cattle and movable property. He acted as a bridge... [How does Rashi know he acted as a bridge? The answer is:] Scripture writes [only once] that he “crossed over the ford of the Yabbok.” Otherwise [i.e., if he did not act as a bridge] Scripture should have written that he crossed back to where his wives were, before saying, “He took them....” [Perforce, he merely stretched his arms back over the river.] Another answer is: Rashi deduced this because it is written, “He took them and crossed them,” instead of simply saying, “He crossed them.” Perforce, he acted as a bridge.

He had forgotten some small jars and he returned for them. [Rashi knows this] because he had already brought over all the important utensils, as it is written, “He brought over all that he possessed.” It does not mean literally jars, as all unimportant utensils are called פכים. Much has been said on this in Gur Aryeh and R. Noson, but Rashi explained it this way in Chulin 91a. (Kitzur Mizrachi)

Our Sages have explained that this was Eisov’s guardian angel. Rashi proves this on, “If I have found favor in your eyes... like seeing the face of a Godly being” (33:10). Maharshal writes: You might ask: What caused Rashi make the forced explanation that ויאבק is of Aramaic origin, instead of saying like Menachem did? The answer is: It is because our Sages say that this was Eisov’s guardian angel. [And it says in Chulin 91a that according to the view that they kicked up dust,] they raised dust until the Throne of Glory. But Eisov’s guardian angel, [could not reach such a lofty level].

Concede to me the blessings with which my father blessed me... You might ask: Perhaps Yaakov requested that he actually bless him? The answer is: The angel replied, “No longer will your name be spoken of as Yaakov.” How did this answer [Yaakov’s request]? Perforce, the angel’s answer means as Rashi explains: “It will no longer be said that the blessings came to you through deceit and trickery.” This implies that Yaakov had requested for a concession to the blessings, and the angel replied accordingly. (Re’m)

God will reveal Himself to you in Beis Eil, and change your name... I.e., the angel did not change Yaakov’s name here. Rather, he told Yaakov that Hashem will change his name in the future, and he said that he will interpret the change [of his name] that Hashem will make as applying to the blessings.

We do not have a set name. Our names keep changing... I.e., he was not angry when Yaakov asked this. [And how does Rashi know?] Because the angel asked Yaakov the same question.

Those hours that the sun prematurely set ... it prematurely rose for him. Rashi is answering the question: Even if we say that the sun shone for him [to heal him], did it shine only “for him”?

He was limping when the sun rose. Rashi is saying he was limping when the sun began to rise, but he was cured right afterward.