How could Yaakov use angels to run an errand to Eisav?

(32,4) And Yaakov sent angels before him to Eisav his brother, to the land of Seir, the field of Edom.

The phrase “before him” seems superfluous. It could be that the intention of this phrase is to convey the following:

We have written many times that the messenger must always be subordinate to those who he is serving - both the sender and the one being sent to. This idea is also brought in the Midrash later on in the parsha concerning the posuk “send me away for the dawn has broken”.

Therefore, the fact that Yaakov sent to Eisav angels raises a difficulty, because the angels were certainly superior to Eisav. If so, how could they serve as messengers to Eisav? The answer is that it is true that if the message was for Eisav’s benefit, then the messengers must be inferior to Eisav, since they are being sent for his sake, and so they would be serving him. But actually Yaakov was sending the message for his own sake, for his benefit, and Yaakov was greater than the angels - Chazal teach that Tzaddikim are greater than the ministering angels - and therefore it was fitting that they should serve him.

This is what the posuk means. “And Yaakov sent angels” - and why was he able to send angels, because they were being sent “before him”, for his benefit. Therefore, even though they were being sent to Eisav, his brother, nevertheless he sent angels, because is was fitting for Yaakov to be served by them.

What was Yaakov’s message to Eisav?

(32,5) And he commanded them, saying: Thus you shall say to my lord, to Eisav - "Thus said your servant Yaakov: With Lavan I have sojourned and I delayed until now. And I have acquired oxen and donkeys, flocks and manservants and maidservants; and I am sending to tell to my lord, to find favour in your eyes".

Every time the nations of the world desire to do evil to Klal Yisrael, the result is that Yisrael ultimately benefit. As we see from that which Hashem said to Avrohom “You will surely know that your descendants will be strangers in a land not theirs...and they will afflict them...and afterwards they will go out with great wealth”, that from their slavery resulted great wealth. Here too, Yaakov had lived with Lavan many years, during which time Lavan had endeavoured to do him evil many times. The result was that Yaakov ended up very wealthy. Therefore, since Yaakov knew that Eisav wanted to do him evil, he sent him a message to inform him that anyone who wishes to do to him evil will cause him much good. Therefore, it would be better for him not to continue to do evil towards Yaakov.

This is what our posuk means: “I have lived with Lavan and have delayed until now”, and this has caused me to acquire great wealth - "oxen and donkeys, flocks, manservants and maidservants". Therefore, "I am sending to tell my lord, to find favour in your eyes", that you should not seek any more to harm me, since that will cause me even more good.

Did Yaakov really consider Eisav to be his lord?

(32,5) And he commanded them, saying: Thus you shall say to my lord, to Eisav - "Thus said your servant Yaakov: with Lavan I have sojourned and I delayed until now. And I have acquired oxen and donkeys, flocks and manservants and maidservants; and I am sending to tell to my lord, to find favour in your eyes".

In the posuk when it writes “Thus you shall say to my lord, to Eisav”, the word “to” seems superfluous. But the intention could be that he was warning the angels that they should not make a mistake when they hear Yaakov referring to Eisav as “my lord”, and think that they should really refer to him as such, even not in Eisav’s presence. The truth is that Yaakov did not really consider Eisav as his lord, but in his presence he was forced to flatter him. This is what he was imparting to the angels - thus you shall say to my lord, to Eisav - only to Eisav . In his presence you should refer to him as my lord, but not otherwise.

This also answers a problem in the beginning of the posuk, which says “and he commanded them saying: thus you shall say to my lord, to Eisav“. Chazal teach that the word “tzav” (he commanded) always implies that the person being commanded should be careful and vigilant. But how is this pertinent to what is happening here? Also, the word “saying” appears to be extraneous.

The answer is that the messengers would naturally think that Yaakov's main intention was to tell Eisav about his sojourn with Lavan, and so they would start with the words “thus said your servant Yaakov”, leaving out the beginning of his statement, which was “thus you shall say to my lord, to Eisav”. If so, Yaakov was worried that Eisav would think that Yaakov never referred to himself as Eisav’s servant, and it was just the messengers who were honouring him by saying so. And even if Yaakov had himself said so, he was only flattering Eisav because of fear, and had not said it with any sincerity.

Therefore, Yaakov instructed them to say to Eisav these exact words, starting with “thus you shall say to my lord, to Eisav”. So that when Eisav hears that he spoke to them these words, this would prove to Eisav that Yaakov referred to him as my lord even not in front of him, and he genuinely thought of Eisav as his lord.

Therefore, "he commanded them" - to be careful with their task, because he knew that it is not normal for messengers to relate the exact words of the sender, only the main content and intention of his words, "saying" - indicating to them that they should start from the following words: “Thus you shall say to my lord, to Eisav”, relating all of his words exactly as he had said them.

Why did Yaakov not send greetings to Eisav until now?

(32,5) And he commanded them, saying: Thus you shall say to my lord, to Eisav - "Thus said your servant Yaakov: with Lavan I have sojourned and I delayed until now. And I have acquired oxen and donkeys, flocks and manservants and maidservants; and I am sending to tell to my lord, to find favour in your eyes".

Another way to explain these posukim is that Yaakov was worried that Eisav might ask why Yaakov had not sent friendly words of greeting until now. But the answer is that when good things happen to a person then it is normal for him to tell his friends and relatives, and to write to those who are farther away. But if he is suffering, he won’t write to them, because why should he cause them distress?

This was his message to Eisav: Do not wonder why I did not send you words of greeting before, because until now "with Lavan I have sojourned", and I was not in a position of power and importance - on the contrary, I was a stranger and very lowly, and I suffered greatly at the hands of Lavan. Therefore, “I delayed until now” and did not write to you to distress you with my suffering. But now "I have acquired oxen and donkeys" - I have become wealthy, and Hashem has began to help me. So, immediately, "I am sending to tell my lord" my good tidings, "to find favour in your eyes".

Why was Yaakov afraid that he might kill Eisav?

(32,8) And Yaakov became very afraid and he was distressed.

In the Midrash it says that “he was afraid” perhaps he would be killed, “and he was distressed” perhaps he would kill. If I overpower him, I will kill him, and if he will overpower me, he will kill me. This is the correct text. The commentaries Yefas Toar and Nezer HaKodesh ask why he was distressed that he might kill Eisav. After all, Eisav was intending to kill him, and the rule is “if one is coming to kill you, you should kill him first”.

In parshas Toldos, regarding Eisav’s selling his birthright to Yaakov, it writes “And Yaakov said: Swear to me as of this day” . Now, there is a halachic problem regarding the buying and selling of something which has not yet come into the world yet, because technically one cannot acquire that which does not yet exist. However, it is brought in the sefer Orach Chaim in the name of the Rivash, who himself brings it in the name of the Ramban and the Rosh, that if a person sells something which does not yet exist, and swears to the purchaser regarding the sale, then the buyer does acquire it. The proof for this is from Yaakov, who demanded that Eisav swear to him, because the birthright - for example, receiving a double portion of the inheritance - does not yet exist. It only comes into existence when Yitchok dies. But the Rivash himself holds that one cannot acquire this way, and rejects the proof, saying that in those days this halachah that one cannot acquire that which does not yet exist was not the law, and the reason why Yaakov demanded an oath was only to make the deal more solid.

But one does not have to reject completely the words of the Ramban and the Rosh, but rather we can say that even if the oath does not itself serve to make the acquisition of something that does not yet exist, nevertheless, it is brought in Shulchan Aruch, Choshen Mishpat, Siman 209 that even so a person must fulfil his oath. However, if he dies before the acquisition takes effect, his children are not required to fulfil the deal.

According to this we can explain that this is the reason why Yaakov wanted Eisav to swear, so that he would obligated to fulfil the deal because of the oath. So that even if he later wanted to break his word, Yitzchok will not let him do so, but rather he would command before he dies to give the double portion to Yaakov since he is now the “firstborn”. This was Yaakov’s intent.

However, all this would only work if Eisav was alive when Yitzchok dies - then he would have to fulfil his promise. But if Eisav dies before Yitzchok, his children would not have to fulfil the oath, and they would receive the birthright. For this reason it was impossible for Yaakov to kill Eisav, even though he knew it was permissible to kill his pursuer, because then he would lose the birthright and all its spiritual benefits for all generations, since the deal he had made with Eisav many years before would be nullified. Examine this explanation well - it is very correct.

How could Yaakov be so confident that one camp would escape?

(32,9) And he said: If Eisav comes to one camp and smites it, the remaining camp will escape.

How was it so clear to Yaakov that one camp might be smitten but then the other would then escape? After all, it is possible that both camps would escape or that both would be killed.

Now, Rashi explained in the previous posuk that “he was distressed” perhaps he might kill Eisav, so we see that Yaakov also did not want this to happen. Maybe because, as it says in Proverbs, it is not good for a Tzaddik to punish, or because Yaakov was a Kohen, as is brought in the Midrash, and we hold that a Kohen who kills, even unintentionally, is no longer allowed to bless the priestly blessing, and understandably Yaakov did not want to be disqualified from priestly duties.

Or maybe the reason is like that which the author of the sefer Ma’aseh Hashem wrote, that if Hashem saves a person with a miracle which involves the downfall of the enemy, it is not apparent if it was because of His love for the person that He is saving, or because of His hatred of the enemy. But if Hashem saves him only by defending him and not by causing the downfall of the enemy, then it is clear that is was only because of His love for the person He saved. Here too, Yaakov was worried that he might miraculously kill Eisav, and it would not be apparent for whose sake the miracle had been wrought, and therefore others might say that it was not done for him, to save him, but because of hatred for Eisav.

This also explains the seemingly superfluous word לו (which means to him, or for him) in the expression “he was distressed” - ויצר לו. But according to the above the meaning is that he was distressed about the ‘for him’, that it would not be apparent that the miracle had been wrought for him. Thus there are several possible explanations as to why Yaakov did not wish to kill Eisav.

Now, Chazal have said if a person does something wrong, and somebody else could have protested and stopped him from doing it, but does not protest, it is considered as if he himself had done the wrong thing. Therefore, Yaakov reasoned that if there will be only one camp, and he is part of that camp, then even if someone else will kill Eisav, everyone would still consider it as if Yaakov himself had done the killing, since they were in one group, and Yaakov had not protested against it. And since Yaakov did not want to kill Eisav, either directly or to have the killing ascribed to him, therefore “he divided the people who were with him…into two camps. And he said: If Eisav comes to one of the camps and smites him” - that the camp will smite Eisav, then “the remaining camp will escape” from being associated with that action since they were not one group, and the killing of Eisav would not be ascribed to him.

This solves a problem that the commentaries noted, that the posuk אם יבוא עשו אל המחנה והכהו would appear to mean "if Eisav will come to the camp and smite it", smite the camp. But the problem is that the word for camp is feminine, and the word הכהו means smiting something masculine. But according to the above explanation there is no problem, because the meaning of the posuk is that the camp will smite Eisav, who is of course masculine.

Why was Yaakov afraid that Eisav might harm his wives and children?

(32,10) And Yaakov said: G-d of my father Avrohom and G-d of my father Yitzchok, Hashem, Who said to me: Return to your land and to your birthplace, and I will do good to you. I have become small from all the kindness and from all the truth that you have rendered your servant…Please save me from the hand of my brother, from the hand of Eisav, for I am afraid of him, lest he come and smite me - the mothers and the children.

The explanation and flow of these three posukim is that it was clear to Yaakov that Hashem’s telling him to return home and promising him that He would do good to him, was not due to his personal merit, since if it was due to his merit he would not have been afraid of Eisav, nor would he been afraid for his wives and children. Because even though Eisav had behind him the double merit of Avrohom and Yitzchok, nevertheless they had three, since they also had the merit of Yaakov himself. And so, since their triple merit was greater than Eisav’s two, Yaakov would not have needed to pray for the matter.

But Yaakov was certain that Hashem’s promise to him was only in the merit of his fathers, because his merit had already been used up. If so, both he and Eisav had the merit of two, and thus even if he didn’t have to fear, since has was equal to Eisav, nevertheless, he was afraid that Eisav would be able to kill his wives and children. Because even though they also had the merit of two, they were one generation further away from Avrohom and Yitzchok, and so their merit was weaker than that of Eisav.

This is what Yaakov was saying: “the G-d of my father Avrohom and G-d of my father Yitzchok”, only in their merit “Hashem said to me: Return to your land and to your birthplace, and I will do good to you.” But “I have become small from all the kindness and from all the truth that you have rendered your servant” - my merits have already been reduced because of all the kindness that you have done for me. Therefore, because Eisav also has the merit of our fathers, I pray “Deliver me from the hand of my brother, from the hand of Eisav, for I am afraid of him”. And even if, since we are equal in our merits, I don’t have to fear him, still I am afraid “lest he come and smite me”, that is, “the mothers and the children”. The flow of the posukim is now clear.

What argument did Yaakov use to guarantee that Hashem Himself would save him from Eisav?

(32,12) "Please save me from the hand of my brother, from the hand of Eisav, for I am afraid of him, lest he come and smite me - the mother and the children."

The Midrash writes that Yaakov said to Hashem: Master of the World, You wrote in your Torah in Vayikra 22,28, "An ox or sheep, it and its offspring you shall not slaughter in one day". If this wicked one comes and destroys my sons and their mother together, the Sefer Torah which You are destined to give on Mount Sinai, who will read it? Please save me from his hand, that he should not come and smite me, the mother and the children, as it says "Please save me…".

This Midrash is a puzzle - why did it repeat at the end "please save me"? Also, from where did the Midrash learn that Yaakov argued "the Sefer Torah which You are destined to give on Mount Sinai, who will read it"?

But it seems to me that we can explain the Midrash very well, because behold, I quoted earlier the Midrash which Rashi brings on the posuk "and Yaakov became very afraid and distressed" - he was afraid that he might be killed, he was distressed that he might kill others. It seems to me that Yaakov was certain that Hashem would make for him a miracle, but the miracle could be in one of two ways. Either Hashem will change Eisav's heart and mind towards him for the good, from being an enemy to one who loves him, and so not do to him any evil, as in fact happened, or Eisav will remain with his hatred of Yaakov, but Yaakov will prevail over him in battle, and Eisav will fall by his hands. Now, the second way - to kill others - was not pleasing to Yaakov, and therefore it says "he was distressed", and therefore he very much desired that Hashem will change Eisav's heart.

Now, the difference between these two miracles, is that to change a person's heart and to change his will, is something which is very difficult, as the Zohar discusses at length. And the Rav, the author of Maaseh Hashem, wrote, that after all the wonders that Hashem did in Egypt, He commanded them to ask the Egyptians for their gold and silver, in order that they should know that Hashem has the ability to overturn the heart of someone who has freewill. And this was a greater miracle than all the others. If so, it is clear that to change a person's heart is more difficult than all the miracles of Egypt. Therefore, it would seem that this ability is not in the hand of any angel, but rather only in Hashem's hand. Only in His hand are the hearts of people, to direct them to wherever He desires.

But the second type of miracle, that Yaakov would prevail over Eisav in battle, this could be effected by an angel. Like we find with Elisha, who showed his servant chariots of fire and fiery horses, and told him that there are more with us than there is with the enemy, and so they could easily prevail. So too we find with Devorah that she prevailed in battle in a miraculous way, and this was possible with the assistance of an angel.

Now, the Nezer HaKodesh brings in the name of the Zohar, that somebody who has the power of the Torah is looked after completely by Hashem Himself. But one who does not have the power of the Torah is looked after by an angel. And concerning Yaakov it says that he was "a complete person, sitting in tents", that is, sitting in the Torah Academies of Shem and Ever. If so, presumably he had the power of Torah which would protect him and guarantee that he would be looked after solely by Hashem.

However, this is not so, because before the giving of the Torah he was not commanded in the Mitzvos, and therefore the merit of observing the Torah was not able to protect him. As it says in the gemara in Sotah, "If she has merit her punishment is suspended. The gemara asks: Which merit does she have? If we say the merit of the Torah, is she commanded to learn Torah? So we see that if one is not commanded, then the power of Torah does not protect.

But Hashem had earlier promised Yaakov that He would be with him. However, Yaakov was afraid lest he had fallen from his lofty level, and so would no longer be looked after by Hashem. If so, he would not merit the miracle that Hashem will overturn Eisav's heart, because an angel is unable to do this, and so he could only merit the miracle of vanquishing Eisav in battle. But this would involve killing others, and he did not desire this.

Therefore, Yaakov prefaced his words and requested "save me please" - You, Yourself, Hashem, please be my saviour to save me from my brother, from Eisav, and not by way of an angel. Because even though I do not have the power of Torah, nevertheless, my main fear is that I am afraid of him, lest he come and smite mother and children, and if so the Sefer Torah that You are destined to give, who will read it? My main fear is concern for the future giving of the Torah, and since it relates to the Torah, logic requires that the intervention should be by You specifically. Therefore, save me please from the hand of my brother, from Eisav, to change his heart and mind towards me for the good, and as a result I will not need to kill others.

This then is how the Midrash knew what Yaakov argued before Hashem. It saw that Yaakov did not desire to kill others, and so he needed an argument to guarantee that Hashem Himself will intervene and change Eisav's heart. Thus he said to Hashem: The sefer Torah which You are destined to give to Your children, who will read it if Eisav kills mother and children? And therefore the Midrash concludes, as it says, "Please save me from my brother", that the salvation will be by You, Hashem, and not by an angel, and then the will of Eisav will be overturned from bad to good, and I will not need to kill others. Examine all this carefully, because it is very correct.

Why did Yaakov tithe the animals before he gave them to Eisav as a gift?

(32,15) "And he lodged there on that night, and he took from what came to his hand a gift for his brother Eisav."

In the concluding phrase - "for his brother Eisav" - the words "his brother" seem to be superfluous. But Rashi explained here that he tithed the animals before he took the animals for a gift. According to this, we can explain that since Eisav was his brother he was commanded to take a tithe like Yaakov. Therefore, Yaakov did not want to give to him without first tithing the animals, in order that he will not transgress the sin of "do not out a stumbling block before a blind person".

This is what the posuk is saying: "and he took from what came to his hand", that is, he gave a tithe, and the reason why he gave a tithe is because it was "for his brother Eisav", who was commanded to take tithes like him.

An alternative explanation of this posuk, is that since we hold that if a king seizes a person's produce because he owes the king a debt, the person must first tithe the produce, because he benefits from the seizure since he thereby discharges his debt. But if the produce is seized for no reason, then he is not obligated to tithe it, since the seizure is not to his benefit.

This is what the posuk is saying, that if Eisav had not been his brother, just a bandit or a thief, then Yaakov would not have been obligated to tithe that which he gave him. But Eisav was his brother, and he had also received a blessing from Yitzchok. But in truth Yaakov took everything, as Yitzchok said to Eisav in Bereishis 27,37, "Behold, I made him master over you, and I gave him all his brothers as servants… so for you then, what shall I do, my son?", which implies that Yaakov took everything. If so, he is obligated to pay to Eisav that which he took from his portion, and so it is like the king seizing his produce to pay his debt, and so he is obligated to first take a tithe.

This is what the posuk is saying: "he took from that which came to his hand as a gift", that is, he gave a tithe, like Rashi explained. And the reason was because it was "for his brother Eisav", who took it for the debt that he was owed.