Encountering the ‘Eisavs’ that we face today


The beginning of our parasha, Vayishlach, depicts Ya’akov Avinu’s return to Eretz Yisrael and the preparations he undertook before encountering his estranged brother, Eisav. What thoughts and feelings were racing through his mind as this meeting drew near?

The Torah informs us: “Ya’akov became very frightened and was distressed” (Bereishit 32:8). Rashi notes that Ya’akov’s fear was very powerful, to the extent that “he was frightened lest he be killed.” In the following verse, Ya’akov strategizes and splits his family into two camps, with the hope that at least one group would survive. Once again, Rashi’s midrashically-infused interpretation helps us understand “the story behind the story:” The remaining camp will escape.

“He (Ya’akov) prepared three options: doron, a gift; milchamah, war; and tefilah, prayer. For a doron: ‘So the gift passed on before him’ (32:22). For tefilah: ‘G-d of my father Abraham’ (32:10). For milchamah: ‘The remaining camp will escape’ (32:9).”

This famous gloss contains the essence of Ya’akov’s three-part strategy for confronting Eisav: “doron, tefilah and milchamah.” At first, he sought to propitiate Eisav through gifts of tribute, while simultaneously praying to Hashem in heartfelt and soul-wrenching tefilah. As a last resort, he prepared himself for war should the other two approaches fail to achieve their desired purpose.

Rabbi Isaiah ben Avraham HaLevi Horowitz zatzal (1565-1630), known as the Shlah Hakodesh, has a fascinating approach to applying Ya’akov’s tripartite plan to our modern “Eisavs.” In essence, he reinterprets doron as tzedakah, and milchamah as doing teshuvah, whereas tefilah maintains its normative meaning:

“Just like he [Ya’akov] occupied himself with gifts, prayer, and war, so, too, should we act accordingly with the sons of Eisav … in order to ensure a powerful foundation and the continued existence of Diaspora Jewry. … [In our time,] these three things represent teshuvah, tefilah, and tzedakah. Doron refers to tzedakah; tefilah is understood in the standard manner, and milchamah is teshuvah.”

Moreover, the Shlah Hakodesh views our meritorious actions of teshuvah, tefilah, and tzedakah as key to bringing Mashiach Tzidkanu: “In the time of the Messiah [the Navi] says: ‘And saviors shall ascend Mt. Zion to judge the mountain of Eisav, and the L-rd shall have the kingdom’ (Ovadiah 1:21). The coming of the Messiah is the direct result of the zechuyot that will accrue on behalf of these three actions (that is, teshuvah, tefilah and tzedakah).” 

With Hashem’s help, and the Shlah Hakodesh’s inspiration, may we successfully encounter the “Eisavs” of our time through teshuvah, tefilah, and tzedakah, and may these zechuyot enable us to witness the arrival of Mashiach Tzidkanu soon and in our days. V’chane yihi ratzon.