In Parashat VaYishlach, Yaakov completes his trek from Charan to Eretz Yisrael, the same one his grandfather Avraham had taken over a century earlier. By Avraham, we are told he had been accompanied by “HaNefesh Asher Asu BeCharan,” “The souls whom they [he and Sarah] made in Charan” (BeReishit 12:5), which Chazal interpret to mean those individuals whom they had been MiKareiv, spiritually brought closer to service of God; Yaakov appears to lack such a following. In fact, throughout Parashat VaYishlach, Chazal criticize Yaakov for failing to capitalize on several opportunities to do Kiruv. Rav Matis Blum brings three such examples.
When Yaakov meets his brother Eisav, he is described as being with his eleven children. Chazal point out that his daughter Dinah is not counted because Yaakov had hidden her in a box to prevent Eisav from seeing her beauty and marrying her. Chazal claim that this was inappropriate— Dinah could have positively influenced the evil Eisav towards a more righteous path. Furthermore, this week’s Parashah mentions Timna, the concubine of Eisav’s son Elifaz. A Midrash describes Timna as a princess who wants to convert to Judaism, but is rejected by Avraham, Yitzchak, and Yaakov. She, therefore, turns to Elifaz and becomes his concubine. As punishment to the Jews for not accepting her, Hashem causes her to give birth to Amaleik, the hater of the Jewish people. Additionally, another Midrash states that Dinah becomes pregnant from her incident with Shechem and gives birth to a daughter named Osnat. To hide the promiscuity, Yaakov sends her away to the spiritual wasteland of Egypt, instead of attempting to raise the child in a proper Jewish home.
Interestingly, his son Yosef appears to inherit this challenge to embrace opportunities for Kiruv. Chazal point out in next week’s Parashah, VaYeishev, that Yosef made an extra effort to treat the maidservants’ children—those of Bilhah and Zilpah— with warmth and compassion, rather than isolate and degrade them as did Leah’s sons. In doing so, Yosef clearly displays an active interest in those who lie somewhat removed from Bnei Yisrael but sincerely wish to become part of the larger nation, rather than repel willing converts like Timna, as his father did.
Additionally, while in Egypt, Yosef marries the previously scorned Osnat, returning her to Judaism. And by Eisav? Yosef could not overcome this hurdle; instead he inherited the position of the leading figure in the perpetual battle between Yaakov and Eisav, as the Navi Ovadyah states, “VeHayah Beit Yaakov Eish UVeit Yosef Lehavah UVeit Eisav LeKash VeDaleku Vahem VaAchalum,” “And the house of Yaakov will be fire, and the house of Yosef, flame, and the house of Eisav, straw; they will light them and consume them” (Ovadyah 1:18).