Why Didn’t Eisav Marry Leah? Upon Yaakov’s return to Eretz Yisrael, when his encounter with Eisav became inevitable, Yaakov sent a message to Eisav saying, “Im Lavan Garti… Vayehi Li Shor Vachamor…;I lived with Lavan and I have accumulated a great deal of assets.” (Vayishlach 32:5-6) What message was Yaakov sending to Eisav with these two seemingly irrelevant details about his life which Eisav already knew? The Ben Ish Chai answers with another question. Everyone knew that Lavan had two daughters and they were supposed to marry Rivka’s two sons. Why, after Yitzchok sent Yaakov to Lavan, did Eisav not also go to take Leah for his wife? The Ben Ish Chai answers that after Yaakov stole the Brachos from Eisav, Eisav said, “Now I know why they call him Yaakov, because he tricked me twice.” From then on before dealing with anyone Eisav checked into his name. Lavan’s name turned out to be a disaster. Lavan backwards is “Naval” or despicable. No one ever went into Lavan’s house and came out safely. He was the Sitra Acher and everything he did came out backwards left to right. Furthermore, Naval is the name of the Malach responsible for poverty, something that Eisav wanted no part of and was terrified of. Yaakov wanted to let Eisav know that his power was beyond the realm of nature. Not only did he come out of Lavan’s house alive, but he also came out with a large family, and he even became very rich. He conquered a place that Eisav feared to tread… and he was prepared to face off against his brother, his nemesis, as well.
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Why Killing Eisav Would Have Been A Disaster Rashi says (Vayishlach 32:8) that the pasuk says twice that Yaakov was afraid(Vayira, Vayeitzer) of his meeting with Eisav because he was afraid of two things. He was afraid that Eisav may kill him, and he was afraid,that he may kill Eisav. Why was he afraid of killing Eisav in self defense? Rav Aryeh Leib Tzintz writes in Milo HaOmer that the whole reason Eisav hated Yaakov was because Yaakov bought the Bechor from him. Yaakov wanted the Bechor for its spiritual reason, namely he wanted to do the avodah in the Bais HaMikdash. The halacha is that a Kohen who has killed someone, even by accident, may not raise his hands for Birchas Kohanim and may certainly not do any avoda in the Bais HaMikdash. Had Yaakov killed Eisav, his 34 years of running from Eisav would have been for naught because he would be disqualified from the avoda anyway, and the Bechor would have been rendered meaningless.
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Dina’s Male Tendencies “Vateitzei Dina Bas Leah Asher Yalda L’Yaakov,” (Vayishlach 34:1). Dina went to check out the new neighborhood and because of this was taken by Sh’chem. Rashi says that the reason the Torah calls her Bas Leah is to say that she acquired this bad middah from her mother who also went out to meet Yaakov after she gave the flowers to Rochel.
The Alshich offers another pshat. He says that Dina was not completely at fault for going out since it was her nature from the womb. Chazal tell us that Dina was a boy in Leah’s womb until Leah davened that she become a girl so that Rochel can have the boy instead of the girl that was in her womb. Because of this Dina had tendencies of a boy, who by nature go out and do not stay in the home.
We see this from the words of the pasuk. Dina was the daughter of Leah from the womb. However, she only became the the daughter of Yaakov upon her birth, since when Leah was originally pregnant with Yaakov’s child, it was not this one.
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Why Yaakov “Broke Down” In Succos Yaakov cautiously returned to Eretz Yisrael, to go back to his parents, wary of Eisav. After the big showdown Yaakov went to Succos where he spent a year and a half, and then another half year in Bais Kel. The Gemara (Megila 17a) says that Yaakov was punished for those two years for not returning to his father. Why, after twenty years, did Yaakov wait another two years on the threshhold of his home, before going to his father?
Rav Chaim Kanievsky in Taama Dikra answers that Yaakov told Eisav that he could not go with him to Sai’ir because the children and cattle walked slowly. Yaakov did, however, tell Eisav that he would make his way there slowly. Had Yaakov turned around and gone home, Eisav would have felt fooled by Yaakov yet again. Therefore, to avoid further confrontation, Yaakov stopped in Succos, pretending to break down. He stayed there for enough time that Eisav would give up on him, realizing that, in fact, the journey is too much for his entourage. Only then did Yaakov finally return home to Yitzchok.
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The Malach Was Ashamed Of His Own Name “Lama Zeh Tishal LShmi,” (Vayishlach 32:30) Yaakov asked the Malach what his name is, but the Malach refused to answer. Why? Rav Shmuel Aharon Yudelevitch answers that immediately prior to this conversation the Malach told Yaakov that he has a new name in honor of his victory over the Malach. If so, surely the Malach had a new name to commemorate this event as well. Yaakov wanted to know what you call a Malach that is defeated by a human. This shame, the Malach did not want to reveal to him.

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