Yaakov’s complex, multifaceted approach to the feared confrontation with Esav may be seen as a model of the complex way with which we must deal with all the “Esav’s” we confront, the many different problems, issues and pressing matters that we must address both as individuals and as a people.  

       Rashi, in his commentary to Parashat Vayishlach (32:9), cites the famous comment of the Midrash that as Yaakov anticipated his reunion with his brother, he “prepared himself in three matters: a gift, prayer, and war.”  Yaakov undertook three different measures in preparation for what he feared would be a hostile encounter.  He sent a bribe, recited an impassioned prayer to God, and mobilized for warfare.

            Rav Yuval Cherlow noted that these three measures, in a certain sense, contradict one another.  Prayer in the face of crisis expresses the recognition of God’s power over the situation, and our absolute dependence on His grace, whereas sending bribes and preparing for war reflect a confident sense of self-sufficiency, or at least a recognition of the value and effectiveness of our efforts.  Offering gifts of appeasement to one’s enemy is an act of submission and helplessness, the precise opposite of mobilization for combat, which expresses the firm resolve to stand up for oneself and fight.

            Rav Cherlow then proceeds to explain the significance of Yaakov’s simultaneously employing these three contradictory strategies:

This structure is so characteristic of the Torah that we have: there is nothing which is always correct, except the first two Commandments, which constitute the foundation of everything, the only fixed foundation of Torat Yisrael.  All other topics are complex issues through which many different paths of God’s manifestation are expressed.

Yaakov’s complex, multifaceted approach to the feared confrontation with Esav may be seen as a model of the complex way with which we must deal with all the “Esav’s” we confront, the many different problems, issues and pressing matters that we must address both as individuals and as a people.  There is no single correct strategy or response to a difficult situation.  Often, different and even conflicting approaches must be balanced off one another in order to best deal with a complex issue.  Yaakov’s “triple strategy” should remind us to avoid overly simplistic formulas and solutions to life’s challenges, and to recognize that complex issues usually require a complex approach in searching for an effective solution.