How Does Esav Attack?

Vayi’vaser Yaakov levado vayei’avek ish imo ad alos hashachar (Bereishis 32:25)

After ferrying his family across a stream, Yaakov returned to the other side to retrieve some small pitchers that he had forgotten; there he was confronted by a man who wrestled with him throughout the night. Rashi explains that this was not any ordinary man, but rather Esav’s guardian angel, who came in the guise of a man to fight with Yaakov and unsuccessfully attempted to subdue him.

The Gemara (Chullin 91a) offers two opinions regarding the appearance of this man: One opinion says that Esav’s angel came in the guise of a Torah scholar, while others maintain that he looked like a non-Jew.

The Chasam Sofer explains the deeper logic behind these two opinions by noting that while Yaakov told Esav that he had observed all 613 mitzvos (Rashi 32:5), there were two areas in which he was somewhat weak: the mitzvah of honoring his parents, which Yaakov was unable to perform during the time that he was away from home; and the prohibition against marrying two sisters. Esav’s guardian angel therefore attempted to attack him in these vulnerable spots.

One view says that he appeared in the guise of a Torah scholar, hinting to Yaakov’s deficiency in honoring his parents, since the Gemara (Megillah 16b) teaches that he was not punished for neglecting this mitzvah during the time that he was studying Torah in the yeshivah of Shem and Eiver.

The other opinion maintains that Esav’s guardian angel came to Yaakov looking like a gentile, as a way of implying that he had acted like a non-Jew by marrying Rochel and Leah, as the prohibition against marrying two sisters only applies to Jews.

The Chasam Sofer suggests that these two mitzvos are alluded to in the Torah’s description (32:8) of Yaakov’s response to the news that Esav was heading toward him with 400 men: Vayira Yaakov me’od vayetzer lo — Yaakov became very frightened, and it distressed him. Why are these two different verbs used to express Yaakov’s reaction?

The word vayira hints to the mitzvah of honoring one’s parents, which is expressed by the Torah (Vayikra 19:3) as “ish imo v’aviv tira’u — a man should fear his father and mother”; while the term vayetzer corresponds to the prohibition against marrying two sisters, which is described by the Torah (Vayikra 18:18) as “v’ishah el achosah lo sikach litzor — you shall not marry a woman in addition to her sister, to make them rivals.”

Harav Moshe Aharon Friedman of Yeshivas Mir in Yerushalayim offers a different explanation for the angel appearing to Yaakov as either a Torah scholar or a non-Jew. The Shelah HaKadosh writes that Esav’s guardian angel represents the yetzer hara (evil inclination), which was attempting to assail Yaakov and defeat him. Sometimes, the yetzer hara comes to a person in the guise of a gentile, brazenly trying to entice him to sin. At other times, the evil inclination appears in the form of a Torah scholar, presenting numerous calculations and justifications to “prove” that good is bad and bad is good, in an effort to trick a person into believing that a terrible sin is actually a mitzvah.

The Gemara (Shabbos 75a) discusses the reason for the prohibition against ritually slaughtering an animal on Shabbos. One opinion posits that it is forbidden because it colors the animal, whose hide becomes dyed by the blood. The Baal Shem Tov homiletically explains that because the yetzer hara’s mission is to “slaughter” us, it attempts to do so by painting a distorted picture of reality, confusing our judgment about right and wrong.

Yaakov referenced the angel’s dual nature when he beseeched Hashem (32:12), “Rescue me from the hand of my brother, from the hand of Esav.” As Esav was his only brother, why did Yaakov use two seemingly redundant expressions?

The Beis Halevi explains that Yaakov was worried about two distinct scenarios: He was afraid that Esav may come to assault him in his standard non-Jewish appearance, but he was even more frightened by the possibility that he may look like a brother, acting friendly toward him to win him over to his philosophy and worldview.

Q: Rashi writes (32:5) that Yaakov sent a message to his brother Esav stating that although he had dwelled with the wicked Lavan for 20 years, he had remained steadfast in his faith and had continued to keep all 613 of the commandments. How is this to be understood, as it is physically impossible for any person to observe all of the mitzvos?

A: Harav Aharon Leib Steinman, shlita, rejects the explanation that Yaakov meant that he had studied the laws of all 613 mitzvos, as Rashi writes that he said that he had observed them. Instead, he suggests that because Yaakov’s intention was to fulfill every mitzvah when he would have the opportunity to do so, it was considered as if he kept them all.

Harav Moshe Sternbuch, shlita, notes that Yaakov didn’t say that he fulfilled all of the mitzvos, but rather that he was shomer all of them. Rashi writes (37:11) that this term can be used when a person guards something in the sense that they are waiting and anxiously looking forward to its fulfillment. In this case, Yaakov was guarding the mitzvos through his desire for the opportunity to perform all of them.

Rav Sternbuch adds that at present, we lack the Beis Hamikdash and all of the mitzvos that can only be performed there, but if we yearn for the time when we will have the merit to observe them, it will be considered as if we have already done so.

Originally from Kansas City, Rabbi Ozer Alport graduated from Harvard, learned in Mir Yerushalayim for five years, and now lives in Brooklyn, where he learns in Yeshivas Beis Yosef, is the author of the recently-published sefer Parsha Potpourri, and gives weekly shiurim. To send comments to the author or to receive his Divrei Torah weekly, please email