VaYishlach
Gen. 32:4 – 36:43 

By Rabbi Gary Pokras 

This week’s parasha contains one of the most enigmatic moments in Torah. Jacob, having finally escaped with his family from the manipulation and oppression of his uncle Laban discovers that his twin brother Esau is on his way with four hundred armed men, presumably to extract vengeance for all the harms that Jacob caused him twenty-one years earlier. Given their history, Jacob has reasonable cause to fear for his life. So, he divides his family into separate camps, with the idea that if Esau attacks one, the others could escape. Then night falls, and the real mystery begins: 

“And Jacob was left alone, and a man wrestled with him until the break of dawn.” (Gen. 32:25) 

Who is this strange man? And why do they wrestle through the night? 

The sages argue about the answers, which is to say, we cannot know for sure. It could be that a random stranger just showed up and that they wrestled for no good reason. This answer is discounted by the majority, especially since Jacob refuses to stop until his opponent blesses him. I mean, why would he do that? Another possibility is that Jacob wrestles with God, hence the request for the blessing, and the blessing itself: 

“Your name shall no longer be Jacob, but Israel, for you have striven with beings divine and human and prevailed.” (Gen. 32:29) 

A third possibility is that Jacob wrestled with an angel, a messenger from God. According to Rashi, the angel was Esau’s guardian angel, which suggests that this was a spiritual battle between the two, before they would face each other physically in the morning.  

Finally, a fourth possibility is Jacob wrestled with himself, or rather, with his conscience.  

There is a fascinating Talmudic midrash which shares two opposing views about how Jacob saw this strange man. (Hulin 91a) According to one view, he looked like an idolator; according to the other, like a Torah scholar. Most of the Hassidic masters interpreted this in connection with the idea that Jacob wrestled with Esau’s angel, which they understood as representative of our enemies both physical and spiritual. For example, Rabbi Y.I. Herzog taught: “In our struggles with us, our enemies always use two means, whose aim and goal is the same. The one is brutal force, physical pressure (he appeared to him as an idolator). The other means is … spiritual annihilation,” by example of which he cites the required disputations forced upon us by the church and their scholars at various times in our history. These scholarly disputations were an attempt to prove their superiority over us through the lens of Torah.1 Similarly, Rabbi Avraham of Sochachew suggested these two manifestations describe the two ways that the Evil Inclination seeks to control us, saying: “The first is by openly enticing the person to sin, while the second is by camouflaging the sin and explaining that in reality it is not even a sin at all.”2 These Hassidic teachings feel especially relevant in a moment when we face ever rising antisemitism and uncertainty and they help us to understand (and defend ourselves against) the very real kinds of threats we face: physical, intellectual, emotional, and even spiritual. 

Yet, there is another point of view worth our consideration. Rabbi Amy Scheinerman wonders if, instead of being a manifestation of Esau’s angel, both the idolator and the Torah scholar represent a division within Jacob himself.3 What if we each contain within us the idolator and the Torah scholar, the urge to ignore or break from God and the urge to embrace our spiritual heritage? I think most of us have faced this struggle one time or another, and for many of us, it is ongoing. 

In VaYishlach Jacob overcomes his urge to idolatry and unethical behavior and as a result is transformed from Jacob to Israel. We are his direct descendants. This parasha reminds us that like Jacob, we face struggles both external and internal, and as the children of Israel, we have inherited the strength to prevail.