So why in the world does Jacob send messengers ahead to Esau? Why does Jacob alert Esau that he is returning? The Midrash ascribes the following blunt words to God, "Esau had gone his way, and you sent for him?"
There is another potentially puzzling feature about Jacob's behavior here as well. When Jacob's messengers return from having spoken with Esau, they report that Esau has set out to greet Jacob with a company of 400 men. Although by habit we assume Esau's mood to be vengeful and his intentions to be hostile, the commentator Rashbam -- Rabbi Shmuel ben Meir, a student and grandson of Rashi -- insists that the Torah's words here do not connote this at all. To the contrary, he points out that the phrase the Torah uses to describe Esau's intention, yotze likrtecha, connotes going out to extend honor to someone. This is clearly the meaning of this phrase when it is used in Exodus, for example, to describe Aaron's going out to greet Moses.
Rashbam's reading actually receives substantial support as the Torah reading continues, and Esau embraces Jacob, and speaks not a harsh word to him at all. Assuming Rashbam's reading for the moment then, we must ask ourselves why it was that Jacob reacted to his messengers' report about Esau and his 400 men with such alarm. "And Jacob became very afraid and distressed," and proceeded to prepare for Esau's attack upon his family (Genesis 32:8). Why did he not accept his messengers' portrayal of Esau's actions?
The answers to both of these questions emerge from a proper understanding of what has happened to Jacob during these last 20 years since he left home. The Jacob we knew in his parents' home was a man who was well intentioned, obedient, and "simple" (someone who generally responded to events rather than initiating them). Yet there were certain moments at which these very qualities led him into ethically compromised positions. In purchasing Esau's birthright, Jacob acted (I am completely willing to grant) in the best interests of his grandfather, Abraham, and the legacy of spiritual greatness that Abraham's heirs were commanded to bear and carry forward. Yet, as the medieval commentator Radak (Rabbi David Kimchi) states, "and nonetheless Jacob was later chastised for this, for he had acted against minhag ha'olam, the accepted norms of appropriate behavior." Similarly, Jacob was a most reluctant participant in his stealth acquisition of the blessing that Isaac had intended for Esau. He entered Isaac's room disguised as Esau only because his mother, Rebecca, commanded him to do so. Reluctant as he was though, he wound up looking into his father's sightless eyes, and declaring, "I am Esau your firstborn." The Jacob who fled his parents' home was a good man who had stumbled into a pair of ethical lapses.
But in the home of his Uncle Laban, Jacob came to raise expectations of himself. Jacob recoiled from this new environment in which deceit was the modus operandi, and honesty was synonymous with naiveté. Seeing and repeatedly falling victim to routine violations of ethical norms, Jacob responded by committing himself to excellence. He would have no tolerance for even the hint of dishonesty in himself and very legitimately saw himself as a model of uprightness and virtue. When Laban later accused Jacob of stealing and making off with his gods, Jacob powerfully and eloquently defended his own character. He reminds Laban that over the course of the 20 long years he served as Laban's shepherd, he consistently accepted financial responsibility, even for losses that are never usually regarded as being the shepherd's fault. "Those beasts which were torn, I never brought to you. I bore the loss of it." Over the course of the 20 long years, even when weather conditions were such that shepherds would ordinarily place their own welfare over that of the sheep, Jacob never ever neglected his solemn commitment. While Laban was repeatedly finagling with Jacob and with his remuneration, Jacob had indeed established himself as a model of impeccable ethical behavior.
Which brings us back to where we began. Jacob, as he approaches Canaan, is not merely approaching a geographical place. He is approaching the beginning of his destiny, the starting point of his career as patriarch. But he realizes that he cannot uphold his hard-won identity as someone who is upright and beyond ethical reproach as long as his record is blemished by his history with Esau.
Jacob did have to notify Esau of his imminent return to Canaan. He needed to notify him. "And I have sent my messengers to you, so that I might find favor in your eyes" (Genesis 32:4).
And as Jacob anticipates the return of his messengers, we can imagine him replaying the episodes of the birthright and the blessing over and over again in his mind's eye, growing ever more filled with regret, as they are so strikingly inconsistent with his current understanding of himself and his principles. It is no wonder then that he reacts with alarm to the report of Esau and the 400 men "coming to greet him." Jacob had already convinced himself that Esau had every right to be angry.
The story, of course, turns out to be one of reconciliation and not hostility. But the overarching lesson of the story is the one that played out in Jacob's mind and soul. The way up in life is to firmly commit ourselves to a self-identity of spiritual and moral excellence, and then to demand that we actually live the self-image we have created. It is true that our past errors will become magnified as a result, and our conscience will not remain silent. But this too is part of the way up.
Yosef Kanefsky is the rabbi of B'nai David-Judea Congregation, a Modern Orthodox congregation in the Pico-Robertson area.