Why did Yaakov arrange his family - Shefachos and their children, Leah and her children, Rachel and Yosef?
Targum Yonasan: He figured that if Esav would attack the maidservants' children and rape the mothers, he and the other children would attack him.
Peninim mi'Shulchan ha'Gra (2): This is a Siman for the time of Mashi'ach. The Erev Rav will be the leaders, Stam Bnei Yisrael will be after them, and Talmidei Chachamim will be least esteemed. R' Elchanan Wasserman said that this has been fulfilled in our days.
Why does the Torah say "Acharonim" after "Leah vi'Yeladeha"? Rachel and Yosef were in back of them!
Tosfos Yom Tov to Demai 7:3: We see from here that the Torah sometimes refers to something as '"Acharon," even though it is only the middle item. 1
See Torah Temimah, note 'Alef,' who elaborates.
Rashi (to 30:25) writes that Yosef was the Satan (opponent) of Esav. Yaakov should have put him at the front, and not at the back!
Moshav Zekenim (to 31:25): "And the house of Yaakov will be fire, the house of Yosef, a flame [and the house of Esav, straw]" (Ovadyah 1:18). Fire damages only nearby. A flame can damage even from afar.
Above (32:8), it says that Yaakov split into two Machanos. Here we find that they are three groups!
Malbim (to 32:8): Initially, all his children were in one Machaneh. (Now he divided within the Machaneh of his children.)
Ha'amek Davar (to 32:8): Yaakov split into two Machanos when he thought that Esav will come that same day. When he did not come, Yaakov understood that Esav lodged on the road, so also Yaakov lodged and crossed the river. In the morning, after [he had overcome] the angel, he was confident [and re-united his camp].
Why does it say "Leah vi'Yeladeha"? Regarding the other mothers, it says v'Es (Yaldeihen or Yosef)!
Ha'amek Davar: This hints that Dinah was missing, like the Midrash says (refer to 32:23:1:1).
