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And Yaakov sent malachim before him
to his brother Eisav.
Commenting on the word malachim, Rashi notes that Yaakov sent real spiritual angels to greet Eisav. The commentators inform us that with the performance of a mitzvah an angel is created that serves as an advocate for the person who preformed that mitzvah. The Bal Shem Tov notes that the first letters of the first four words in this posuk spell vyamal which is translated as he circumcised. This idea together with the aforementioned Rashi intimates that the angels Yaakov sent were those that were created through the performance of the mitzvah of circumcision. (See On the Eight Day by Rabbi Eliezer Ginsburg, Artscroll, for an elaboration.) We may ask, what significance lay in angels created from circumcision that Yaakov decided to choose them as his representatives in greeting his brother Eisav?
Before we attempt to answer this question we must lay out some background.
First, a basic principle of Judaism is the notion that the Jewish people humble themselves to their elders and forefathers. Indeed, three times a day, we begin the critical section of our prayer by declaring that Hashem is the G-d of Avraham, Yitzchak and Yaakov. It is noteworthy that we have three commandments in which we are obligated to perform actions that express this concept. The commandments are: (1) to honor ones parents, (2) circumcision and (3) to live in Eretz Yisroel. Honoring ones parents is self-understood. Circumcision is unique in that the primary commandment of the performance of circumcision is upon no one other than the father. Only where the father is unable or unavailable to carry out his obligation is this responsibility redirected to another. Circumcision thus forges a bond between the father and son because the son is aware for the remainder of his life that it was his father who was responsible for his circumcision. The third commandment mentioned above was to live in Eretz Yisroel. When we live in Eretz Yisroel we are not living in the land that Hashem gave directly to us. We are living in the land that Hashem gave us through our forefathers, as stated clearly in the Torah (Bereishis 12:7, 26:3-4, 28:13.) Thus, every moment of life in Eretz Yisroel expresses a connection to our forefathers who earned the land that Hashem gave to them and who have in turn bequeathed it to us.
Second, with regard to these three mitzvos, although it is true that at times they are fulfilled only through suffering and hardship, however, only with regard to one is the actual nature of the mitzvah one of suffering. This is the commandment of circumcision. It addition to the obvious pain of the child, the father is apprehensive of subjecting his child to this operation.
Third, the commentators tell us that Yaakov was afraid of Eisav because he realized that Eisav possessed the merit of two great mitzvos that he lacked. They were the mitzvos of honoring ones parents and living in Eretz Yisroel. Yaakov was away from his parents and Eretz Yisroel for twenty-two years and thus lost out on both of these mitzvos for a significant period of time.
Finally, the Midrash tells us that Eisav never had a circumcision. He was born with a severely reddish complexion causing his parent to be concerned that the performance of a circumcision would be life threatening. As he grew older and was proven to be healthy, he skillfully delayed his circumcision until he got away without having one at all.
Now, with all this in mind let us return to our question. Why did Yaakov send angels that were created through the performance of circumcision? The answer is that Yaakov delivered a sharp warning to Eisav with the presence of these particular angels. Yaakov realized that in addition to feeling secure with his physical prowess, Eisav also felt confident that he prevailed over Yaakov on a spiritual level. In contrast to Yaakov, Eisav did after all succeed in fulfilling two of the aforementioned fundamental mitzvos during the last twenty-two years, the mitzvos of honoring ones parents and living in Eretz Yisroel. With these angels Yaakov reminded Esav that he still lacked the third mitzvah of circumcision that he possessed. Although it was only a single mitzvah and thus the minority of the three, its quality is greater. Circumcision forges a bond between the child and parent through pain and suffering. The two mitzvos Esav fulfilled came to him with relative ease. Yaakov was stating that his fundamental connection to his roots even without Eretz Yisroel and kibud av was stronger because it was one that came through pain and suffering. Therefore, the merits of Yaakov would outweigh the merits of Esav.
The message is simple. What counts is quality, not quantity. If a person performs only a few mitzvos with diligence, fervor, perseverance and sacrifice, as Yaakov did, they can truly outweigh many mitzvos that one performs lacking this quality of service as in the case of Eisav.