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Parashat VaYiShlach begins with Yaakov Avinu’s preparations prior to facing his brother Eisav in the land of Sei’ir. He sends spies who report back that Eisav is heavily armed and appears intent to wage war.  Famously, Yaakov responds by dividing his camp in half, reciting prayers, and sending gifts to his brother.

The night before the confrontation, Yaakov finds himself alone and is attacked by a man who Rashi describes as “שָׂרוֹ שֶׁל עֵשָׂו,” “the angel of Eisav”. As the fight progresses, the angel realizes he cannot overpower him so he grabs Yaakov's hip bone and dislocates it. The Torah then describes that for this reason Jews don’t eat the  גִּ֣יד הַנָּשֶׁ֗ה until this day.  A truly perplexing story. 

Two important questions emerge:  First, why was Yaakov alone?  Secondly, why did the angel wait until Yaakov was alone to attack? Rashi famously explains that Yaakov had left small jars in the camp and went back for them. From here we could learn a beautiful lesson of caring for even the smallest of things. Sforno and Ramban explain that Yaakov was bringing his family over the river in groups in an effort to prepare for his confrontation with Eisav. From here we learn great lessons of Hishtadlut and personal involvement. But neither commentary answer explains why the Mal’ach waited until Yaakov was alone to attack.  

An additional question is posed by Rabbi Aryeh Lebowitz in his weekly Parashah shiur.  If Hashem commands an angel to fight Yaakov, why should Yaakov be able to fight back? The Mal’ach has its shlichus (mission) and the fight should be over before it even starts? How strange that we read that the Mal’ach realizes he can't win so he attempts one final hit on Yaakov. That doesn't sound very angel-on-a-mission-like!  Rather, we must conclude that the mission of the angel was to injure Yaakov because angels can't decide that on their own. 

Rabbi Lebowitz explains that the battle between Yaakov and the Saro Shel Eisav is a paradigm of each person’s general encounter with the Yetzer HaRa. We can learn how to confront the Yetzer HaRa by studying how Yaakov battled the angel, using the principle of Ma'aseh Avot Siman LeBanim. HaKadosh Baruch Hu doesn’t send the Yetzer HaRa to utterly destroy us. If that were the case, human beings wouldn’t stand a chance. The real purpose of sending the Yetzer HaRa is to battle us, to challenge us to make the right decisions.  We earn rewards for standing up to our enemy and it definitely isn't easy. That is why Yaakov is able to fight back, because the job of the Yetzer HaRa is to concede when we show strength.

Returning to our second question, we can now understand why HaShem sent the angel at a time when Yaakov was alone. Rabbi Lebowitz explains that one of the best methods we can use to counter the Yetzer HaRa is a weapon known as “Chevrah”. Social pressure and being part of something bigger has the ability to push people to work harder and not be persuaded by the coaxing thoughts of the Yetzer HaRa.  The Mal’ach knew that Yaakov was at his strongest when surrounded by friends and family so he attempted to surprise him when he was alone and vulnerable.

As it says in Kohelet: “Tovim HaShnayim Min Ha’Echad Asher Yeish Lahem Sachar Tov Ba’Amalam: Ki Im Yipolu Ha’Echad Yakim Et Chaveiro Ve’Ilo Ha’Echad SheYipol Ve’Ein Sheini LaHakimo,” “Two people are better off than one, for they can help each other succeed. If one person falls,the other can reach out and help. But woe is to someone who falls alone with no one else to pick him up” (4:9-10).

May we all surround ourselves with friends who strengthen us in the path of Avodat HaShem.