Why didn’t Yaakov simply pass Esav by instead of engaging him?
Why did Yaakov send Angels to his brothers rather than humans?
Yaakov sent representatives ahead of him to his brother, Esav, to Edom’s Field toward the land of Seir.
— Bereishis 32:4
The representatives returned to Yaakov and told him: “We came to your brother, Esav, and he’s also heading toward you. He has [a force of] 400 men with him.”
One who grows angry while passing by a quarrel that does not concern him is akin to one who seizes a [sleeping] dog by the ears.
— Mishlei 26:17
Let sleeping dogs lie
— Popular idiom version of passuk in Mishlei
Our Sages (Bereishis Rabbah 75:2) criticized Yaakov for this [sending representatives and gifts to Easv] comparing it to waking a sleeping dog by yanking its ears: The Holy Blessed One said to Yaakov “he [Esav] was going his own way [not considering any hostilities to Yaakov] and you had to send him representatives and remind him [of the old dormant enmity] ‘to my lord Esav. Your humble slave Yaakov says … ’”?
— Ramban Bereishis 32:4
Yaakov remained alone. A man wrestled with him kicking up dust until the darkness lifted
— Bereishis 32:25
… Our Rabbis explained (Bereishis Rabbah 77:3, 78:3) that the wrestling man was the prince (guardian angel) of Esav.
— Rashi Ibid
… Rivkah became pregnant. But the offspring clashed/ scurried inside of her …
— Bereishis 25:21,22
Our Rabbis (Bereishis Rabbah 63:6) interpreted it [the word וַיִתְרוֹצִצו] as an expression of running/ scurrying (רוֹצָה) . When she passed by the entrances of [the] Torah [academies] of Shem and Ever, Yaakov would scurry and struggle to come out; when she passed the entrance of [a temple of] idolatry, Esav would scurry and struggle to come out.
— Rashi Ibid
Question: Isn’t it true that the yetzer hara-the inclination to evil; is not operative in-utero and that it is not within man until man is born … [if so why was Esav drawn to evil before he was even born]? The answer is that while it’s true that man has no yen and desire for evil, as part of his free-will equation, until after he is born; what Esav was doing here [when scurrying towards the temples of idolatry] was qualitatively different. Esav was not yielding to the seductions of his yetzer hara, instead he was magnetically drawn towards his source, nature and species, as it were. For all things are aroused by, and inexorably drawn towards, the source of their intrinsic nature and self-definition.
— Gur Aryeh- supercommentary of the Maharal to Rashi Ibid
It is indeed odd that Yaakov would have awakened the sleeping dog/ giant. At first glance, what could possibly have motivated him to do so is incomprehensible.
According to one approach of the Midrashic sages the representatives that Yaakov dispatched to Esav were heavenly angels. Many commentaries have addressed Yaakov’s “need” for angels. Rav Shmuel Dov Asher-the Biskovitzer Rebbe, maintains that Yaakov was on what, in the contemporary parlance, might be called a mission of kiruv rechokim-bringing those distant from righteousness/ G-d closer. Yaakov was unwilling to stand idly by as his twin brother degenerated deeper and deeper into the hellish depths of evil. He had hoped that the angels would prove equal to the task of discovering and nurturing Esav’s deeply buried goodness until it overwhelmed all his accretions of evil and washed them away in a cleansing wave of teshuvah-repentance. After all, the passuk teaches us that angels are uniquely endowed with the capacity of advocating for deeply flawed individuals who possess as little as one tenth of one percent of decency and goodness: “If one has even a single angel out of a thousand advocating on his behalf by declaring his uprightness, then G-d will be gracious to him and say ‘redeem him from descending into destruction [i.e. the grave] for I havefound atonement/ ransom for him.’” (Iyov 33:23,24)
His interpretation is supported by a fuller, closer reading of the Midrash of “awakening the sleeping, vicious dog.” After citing the passuk in Mishlei the Midrash continues: Shmuel the son of Nachman said “this is comparable to a traveler who awakened the leader of a gang of thieves sleeping at the crossroads and warned him of the imminent dangers [from wild animals]. Instead of thanking the traveler, the gang leader began beating his benefactor. The traveler cried foul ‘you cursed man [is this how you repay me for trying to save your life?]’ The gang leader then said ‘[you deserve it, it’s your own fault] I was slumbering comfortably and you woke me!’”
In this allegory Yaakov is represented by the traveler while Esav’s role is played by the gang leader. Nowhere in this allegory do we find a frightened Yaakov devising strategies and tactics to save himself and/or his family. On the contrary, Yaakov is a selfless do-gooder trying to save the life and limbs of someone else, fast asleep and unaware of the looming, lurking dangers. Yakkov’s good deed did not go unpunished and not only is he forced to struggle with the malicious ingrate Esav but, later, he was forced to contend with his evil guardian angel as well.
While it’s often said that “the path to hell is paved with good intentions” it is still hard to grasp what occurred in this case. Why did Yaakov’s well intentioned plan to save his twin from the wild animals of spiritual ruin go so badly awry? This is especially quizzical in light of the Zohar’s observation that “praiseworthy is he who takes the guilty/sinful by hand [and leads them along the path of repentance and tikkun]”
The Biskovitzer explains that while kiruv is a most praiseworthy endeavor it is wasted upon those whose evil is intrinsic and incorrigible rather than those whose evil is acquired through the incorrect exercise of their free-will. Echoing the Maharal’s clarification for Esav’s in-utero scurrying towards temples of idolatry and, no doubt, paraphrasing earlier sources, the Biskovitzer goes so far as to identify Esav with the primordial serpent who enticed Adam and Chavah into Original Sin. In other words; Esav is not a good kid gone bad, he is just plain bad. He is not one who falls prey to the yetzer hara he IS the yetzer hara. Such evil is incorrigible, dealing with it in any way, even for the noble goal of its rehabilitation, is doomed to failure and to vicious, attacking ingratitude.