In our previous two editions of S.A.L.T., we have discussed the theory posited by Rabbi Menachem Leibtag (http://tanach.org/breishit/vayish3.htm) concerning the sequence of events recorded in Parashat Vayishlach. Rabbi Leibtag contended that although the Torah records Yaakov's experiences in Shekhem before his journey to Beit-El, the death of Rachel, and Yaakov's reunion with his father in Chevron, in truth, the story of Shekhem occurred later. Yaakov first traveled to Beit-El, in fulfillment of the vow he had declared when he left Canaan some twenty years earlier. He then proceeded towards Chevron to reunite with his father, and Rachel passed away along the way as she delivered her second son, Binyamin. Only some time later did he return to the area of Shekhem to permanently settle there, and it was then that Dina was abducted.
At least one Midrashic tradition, which is recorded in a number of sources, appears to lend support to Rabbi Leibtag's contention. Targum Yonatan Ben Uziel (to 32:25) and Pirkei De-Rabbi Eliezer (chapter 37) tell that the angel, who assaulted Yaakov before he crossed the Yabok River, demanded that Yaakov donate one-tenth of his sons to God. The angel reminded Yaakov of his promise to donate to God one-tenth of everything God gives him during his sojourn in Aram, and, the angel notes, Yaakov had since begotten twelve sons. Yaakov "tithed" his children by first excluding the four firstborn sons, who were already consecrated by virtue of being firstborns, and then began counting from Shimon, according to age: Shimon, Levi, Yissakhar, Zevulun, Naftali, Asher, Binyamin, and then back to Shimon and Levi. Levi was thus the "tenth" son, and the tribe of Levi was designated for the service of God.
Oddly enough, these Midrashim include Binyamin among the sons of Yaakov, despite the fact that Binyamin is born only later, along Yaakov's route to Chevron. Pirkei De-Rabbi Eliezer mentions that Rachel was pregnant at the time with Binyamin, and he was therefore included with his brothers for the purpose of "tithing" Yaakov's sons. Of course, if Rachel had already conceived with Binyamin as Yaakov and his family made their way back to Canaan, the birth of Binyamin must have transpired shortly thereafter. This seems possible only if we accept Rabbi Leibtag's theory, that Yaakov's journey to Chevron, along which Rachel passed away as she delivered Binyamin, took place earlier, before Yaakov's settlement in Shekhem. (It should be noted that these sources would presumably disagree with the Gemara's comment in Masekhet Megila 17a that Yaakov spent a year and a half in Sukkot before his arrival in Shekhem. Surprisingly, however, Targum Yonatan on 33:17 comments that Yaakov spent one year in Sukkot, which is very difficult to explain if Rachel had been pregnant with Binyamin beforehand.)
Furthermore, the Zohar (vol. 1, p.158b) comments that Yaakov fled from Lavan's home when Rachel conceived with Binyamin. This, too, seemingly compels us to conclude that Binyamin's birth occurred within the first nine months of Yaakov's return to Canaan, which seems difficult to accept if Yaakov first settled in Shekhem before embarking on the journey during which Binyamin was born.