At the beginning of the portion Vayishlach , the Torah relates how Ya’akov sent emissaries to his brother Esav. He instructed them that, when speaking to Esav, they should refer to Ya’akov as “Esav’s servant” and to Esav as “Ya’akov’s lord.”1 Later on in the portion, we find Ya’akov bowing down seven times before Esav2 ,calling him many times “my lord”3 and referring to himself as “your servant.”4

Ya’akov’s extreme obsequiousness seems hard to fathom. In fact, the Midrash states5 that Ya’akov was punished for sending emissaries to Esav and for calling him “my lord” — his profuse obeisance was considered sinful.

Especially so since G‑d had already told Rivkah that “the older one will serve the younger,”6 and moreover, in Yitzchak’s blessing to Ya’akov, he specifically stated “you shall be a lord over your brother.”

What was the reason for Ya’akov’s servility?

Since the Patriarchs were wholly dedicated to G‑d’s will,7 evil could not have been part of their makeup, and thus, for them to commit gross sins was an impossibility; those actions that appear to be “sins” cannot be construed as such in the simple sense, Heaven forbid.8

The proof that this is indeed so can be derived from this very incident. Although Ya’akov was punished for his actions, we nevertheless learn9 from his behavior that “it is permissible to flatter the wicked … for the sake of peace.” Were Ya’akov’s conduct to have been considered a true sin rather than a mere failing, we would never have derived a lesson from it. What then was the purpose of Ya’akov’s behavior?

Chassidus explains10 that Esav’s spiritual source was loftier than Ya’akov’s; by elevating Esav, Ya’akov was able to draw down an additional measure of spirituality from his brother’s spiritual origin. Ya’akov’s bowing before Esav, calling him “my lord,” etc., was thus primarily directed at Esav’s lofty source rather than at Esav himself.

But the fact remains that Ya’akov was totally subservient before his brother, and was punished for it. How was this befitting Ya’akov’s spiritual quest?

There are two methods by which evil can be vanquished and refined: One is to draw down a great measure of sanctity upon the object one wishes to refine. This has the effect of pushing aside the evil within the object and elevating the rest to holiness.

The second approach involves the descent of the individual, bringing about the purification to the level at which the unrefined object exists. By thus coming into intimate contact with the object, he is able to transform it from evil to good.

Each of these methods has unique advantages. With regard to the person doing the purification, there is obvious merit to drawing down an infusion of holiness, inasmuch as the person himself does not have to undergo a personal descent in order to purify and elevate an object.

For the object involved, however, it is better if the person bringing about its purification actually descends into the object’s realm, for then, rather than having the evil within it simply shunted aside, the object actually becomes holy, and ceases to act as an entity that conceals G‑dliness.

The prime goal of Torah service is to bring peace within the world,11 and true peace comes only when one’s enemy is transformed into a friend. To bring peace “within the world” thus means that one is ready to get “down and dirty,” as it were, clothing oneself in worldly garments in order to transform the material world into a holy entity.

In order for Ya’akov to truly transform his sibling, it was necessary to descend to the level of Esav as he found him. By doing so, he was able to transform Esav so that Esav said: “Let what is yours remain yours,”12 thereby admitting that Ya’akov was entitled to Yitzchak’s blessings, including the blessing of “You shall be a lord over your brother.”

Based on Likkutei Sichos, Vol. XV, pp. 297-301