Horav Yaakov Moshe Charlop, zl, explains the imagery of Yaakov Avinu holding onto Eisav’s heel as a metaphor that underscores the concept of limitation and restraint. A vicious dog chained to a stationary place cannot go beyond the pull of his chain. He can bark and growl and attack anything that comes within the parameter of his chain, but that is it. He is locked in place. Veritably, it often appears that Eisav is on top; he is first. Despite Eisav’s precedence in birth order, which grants him certain parameters of strength, Yaakov continues to hold on to his heel. Eisav is the symbol of evil, often associated with negative forces or inclinations and, ultimately, held in check by the forces of good, represented by Yaakov and his descendants. Negative influences have inherent limitations.
Furthermore, we often associate Eisav with the material world, its temptations and pitfalls. He — together with his minions then and now — has done all in his power to impede our spiritual growth, to oppose our spiritual mission in this world. When they could not kill us, they focused on “loving” relationships in order to break down our self-imposed barrier to their “friendship.” Yaakov holding on to Eisav’s heel teaches us that, while negative forces present a threatening challenge to our growth, they are controlled from Above and can only go as far as the “chain” allows them. Perhaps we may expound on this. Among the many metaphors associated with the heel, one that stands out is vulnerability, as in Achilles heel, which represents the one critical weakness in an otherwise strong individual or system. The greatest vulnerability of our enemies is their hatred of us. Animus is an obsession resulting from a person’s inability to accept the truth. Thus, Eisav and his minions despise Yaakov, because Yaakov represents emes, truth, and Eisav represents sheker, falsehood, at its nadir. We have a rule: sinaah mikalkeles es ha’shurah, “Hatred distorts a straight line.” People resort to hatred when they are losing, when they are unable to destroy you. Hatred distorts one’s cognitive ability, preventing him from thinking rationally. In other words, one who is obsessed with hate cannot think cogently. When one is not rational, he makes mistakes and acts foolishly. His decisions are non-sensical, his oral expression is, for the most part, derisive and pathetic. Just like a chained dog, he can only go so far.
We see this play out in Eisav’s insane reaction to Yaakov’s receiving the b’rachos which Eisav felt belonged to him. He screamed and wept, which was not unusual, but then he added a caveat: “As soon as my father dies, I will take out my revenge on Yaakov and kill him.” Did he not understand that, while it is true that if Yaakov were to die, the b’rachah, V’he’vei gvir l’achecha, “Be a lord to your kinsmen,” (ibid 27:29) would not materialize, because the world would no longer belong to two brothers, and Yaakov would not lord over Eisav? If he believed in his father’s ability to bless, however, then he should have realized that he would not succeed in killing Yaakov. Yitzchak’s blessing was destined to achieve fruition, and not one iota of that blessing was in vain If Yitzchak said it would happen, nothing would stop it from achieving fruition. Was Eisav thinking?
Rav Charlop explains that Eisav was completely steeped in materialism. One who rejects matters of the spirit eschews eternity, does not connect with anything of enduring value. Such people flip from one thing to another, to whatever fancies them at the time. It is all about “now.” Since mundane time has no lasting value, every moment is different from the next. What was is no longer, and what will be has no relevance, because this, too, can change and become part of the past. Klal Yisrael clings/connects with Hashem, the Source of nitzchiyus, eternity. Thus, every minute of time has infinite value. All time is connected with — and part of — a continuum. A life connected to the spirit is transformative, thus infusing the mundane and material with enduring value. This is something that Eisav refused to accept. Thus, he, like so many who followed him, was filled with contradictions and hypocrisy. One who refuses to confront the truth ends up hating it. This was his vulnerability.