Yaakov’s Message to Esav
וַיִּשְׁלַח יַעֲקֹב מַלְאָכִים לְפָנָיו אֶל עֵשָׂו אָחִיו
Yaakov sent malachim ahead of him to Esav his brother.
Introduction: The Meaning of the Word “Malach”
The beginning of our parsha relates how Yaakov, after being away for twenty years, sends a message of peace and reconciliation to Esav. The agency he employs to deliver this message is that of “malachim”. We commonly translate the word malach as “angel”, and indeed, Rashi states that Yaakov sent angels to Esav. However, the word malach can also simply mean messenger, referring to a person. Indeed, this is how Onkelos in our verse translates the word “malachim”. Of course, this then raises the question as to why Rashi chose not to translate the word in this seemingly more straightforward way. Interestingly, both of the above explanations are presented in the Midrash Rabbah to our verse.
Understanding Yaakov’s Intentions
Yaakov begins his message to Esav by saying, “עִם לָבָן גַּרְתִּי – I have sojourned with Lavan.” Rashi explains these words as follows:
לא נעשיתי שר וחשוב אלא גר. אינך כדאי לשנוא אותי על ברכת אביך שבירכני "הוי גביר לאחיך" שהרי לא נתקיימה בי
I did not become a dignitary or a notable, but [only] a sojourner. There is [thus] no need for you to hate me over the blessing of your father who blessed me “You shall be a master to your brothers” for it has not been fulfilled in me.
The basis of Rashi’s comment is the fact the word “גַּרְתִּי” denotes a short term stay, whereas Yaakov was at Lavan’s home for twenty years, so that the appropriate term should have been “ישבתי”, denoting a stay of lengthy duration. Therefore, Rashi explains that Yaakov was referring, not to the duration of his stay, but to his lack of prominence there, as he was always regarded as an outsider of no significant standing.
Rashi then proceeds to offer a second explanation:
דבר אחר, "גרתי" בגימטריא תרי"ג, כלומר עם לבן הרשע גרתי ותרי"ג מצוות שמרתי ולא למדתי ממעשיו הרעים
Alternatively, the numerical value of “גרתי” is six hundred and thirteen, as if to say, “I lived with the wicked Lavan, yet I kept the six hundred and thirteen mitzvos, and I did not learn from his evil deeds.”
One cannot help but note the difference in tone between these two interpretations. They seem to be sending almost opposite messages. The first approach sees Yaakov’s words as conciliatory in nature, as if to say, “Please make friends with me,” while the second approach is much more confrontational, saying, “Don’t start up with me!”
One may respond to the above by saying that Yaakov was actually sending a blended or layered message to Esav, as if to say, “What I would like is to make the peace. However if you choose a path of war, then be aware that I have the merit of the six hundred and thirteen mitzvos on my side.” Indeed, in this regard, by alerting Esav to the fact that he was fully prepared for war, Yaakov was thereby further encouraging him to consider taking the more peaceful path.
War, Peace and Gematrias
In truth, however, we need to ask a more basic question:
What is the likelihood that Esav got the gematria?
Of course, it is not inconceivable that Esav would catch that part of Yaakov’s message, however, it is somewhat perplexing that Yaakov would rely on Esav’s gematria powers at a time like this. Esav, we know, was prone to allow anger and emotion to cloud his judgment, surely no more so than upon discovering that Yaakov was alive and well and coming to meet him. This is no time for gematrias!
The matter becomes more baffling still when we consider Yaakov’s words in the next verse, “וַיְהִי לִי שׁוֹר וַחֲמוֹר – I have acquired ox(en) and donkey(s).” Here, too Rashi explains on a straightforward level that Yaakov was demonstrating that he had only achieved success in the area of livestock, as opposed to that of agriculture which was the subject of Yitzchak’s blessing – the “dew of the heavens and the fat of the land.” This, then, was further reason for Esav not to bear resentment over the episode with the blessings. The midrash, however, explains that the “ox” and the “donkey” refer to the personalities of Yosef and Yissachar, citing verses from later on in Chumash which characterize them as such. Through this, too, Yaakov was informing Esav of the people of caliber he had with him. But again we ask, even if Esav was somehow able to decipher the earlier gematria message, when it comes to this midrash, he never had a chance! He is not even aware of Yaakov’s children by their own names, let alone by the beasts to which they may be likened – one in verse at the end of Bereishis which had not yet been said, and the other in the end of Devarim by someone who had not yet even been born!
All of this requires our attention.
Two Planes of Confrontation
The key to this matter lies in the fact that Yaakov’s confrontation with Esav, as described in the parsha, took place on two levels. There was the physical meeting with Esav himself, but the night beforehand there was also a struggle with Esav’s ministering angel, which was spiritual in nature. The difference between these two struggles lies not only in their form, but also in Yaakov’s approach toward them. It is often true in exile that one must act in a conciliatory way toward Esav, with the goal of appeasing and mollifying him. However, in terms of the spiritual forces that Esav represents, the approach is very different. We do not have as a value the idea of appeasing evil, rather, we seek to confront it, struggle with it and conquer it. Indeed, we see that when Yaakov encountered Esav’s angel, he did not bow down to him, as he later did to Esav, but rather wrestled with him throughout the night.
Once we remind ourselves that Yaakov was preparing for two confrontations, we can appreciate that his opening message was directed toward both aspects of his adversary. This means that his words were invested with two levels of meaning. There was the plain meaning of the words, but they also functioned as “capsules” conveying deeper and more hidden messages, each one intended for its relevant recipient.
· With regards to Esav himself, Yaakov’s message is the plain meaning of his words, which are purely conciliatory in nature. Any deeper or hidden messages – such as gematrias and midrashic allusions – are not for him; in this instance, they literally flew over his head.
· With regards to Esav’s angel, Yaakov sends the message that he is ready to do battle, fortified by his performance of the mitzvos while in Lavan’s house, as well as the prominent spiritual personalities he has with him. For a spiritual entity such as an angel, these messages can be communicated through the medium of allusion, such as gematria and references to concepts that have yet to formally appear in verses in the Chumash.
Indeed, with this in mind, we can go back the word the Torah uses for Yaakov’s messengers – “malachim” – which we noted was the subject of two opinions as to its meaning here: angels or human emissaries. We can now understand that it is possible that the Torah uses this word is because both types were used, each one for its intended recipients:
· For the aspect of the message intended to reach Esav himself, Yaakov was able to send human emissaries.
· For the aspect intended for Esav’s angel, Yaakov used emissaries who were angels themselves – malachim mamash!
 Bereishis 32:4.
 The term מלאך derives from the word מלאכה, and thus refers to any being that is dedicated to performing a specific task (Haksav ve’Hakaballah).
 A beautiful explanation of this matter is provided in the commentary Biurei Maharai by R’ Yisrael Isserlin (author of Responsa Terumas Hadeshen). At the very end of last week’s parsha Yaakov is met by angels, who Rashi explains are the angels of Eretz Yisrael. These, together with the angels of chutz la’aretz make up two camps, as indeed Yaakov proceeds to name the place – “Machanaim”. On the face of it, this would seem to mirror Yaakov’s dream at the beginning of that parsha, in which he saw angels of Eretz Yisrael going up and those of Chutz La’aetz coming down. The difference however, is, that in the earlier case, the two groups of angels simply changed places without coinciding, while in this later case they overlapped. Why would Yaakov need both sets at the same time? From here Rashi learned that although Yaakov was already being escorted by the angels of Eretz Yisrael, he still had need of those of Chutz La’aretz, namely, in order to send them with a message to Esav who was outside Israel in the land of Edom.
 Bereishis Rabbah 75:4.
 The commentators note that Yaakov was not belittling the efficacy of Yitzchak’s blessings in and of themselves, rather, he was noting that they had not been fulfilled through him due to his own unworthiness. Alternatively, he was indicating that the blessing had actually been fulfilled through Esav, who had indeed risen to prominence during those years. Yaakov was saying that since Yitzchak thought it was Esav who was before him and intended the blessings to go to him, he actually ended up being the recipient of the blessings after all, with Yaakov’s attempts to receive them being of no avail. (Malbim)
 Tanchuma Vayishlach sec. 1.
 See Bereishis 49:14 and Devarim 33:17.