ישמעאל ועשו

1. The Parallel Downfalls of Yishmael and Esav

We begin our study of Hamishi—the fifth aliyah—in Parashat Vayera, focusing on the episode where Yishmael is sent away from Avraham’s house. There is a striking pattern in the Torah: both Avraham and Yitzchak have sons who go astray. For Avraham, it is Yishmael; for Yitzchak, it is Esav. Both sons ultimately take a wicked path, but their stories diverge in significant ways. Notably, while Esav is considered a Yisrael mummer—a Jew who has abandoned his faith—Yishmael is not even considered Jewish at all. Of course, this was before Matan Torah—the giving of the Torah—so the definitions are different, but the distinction remains important.

2. The Sin of Yishmael: Understanding “Mitzachek”

The Torah describes Sarah seeing “the son of the Egyptian woman,” pointedly not naming Yishmael but instead referencing his mother Hagar’s Egyptian background. This hints at certain negative traits he may have inherited or absorbed from her environment. The verse says Sarah saw him mitzachek—playing or mocking—but what does this mean? Rashi brings several interpretations from various verses: mitzachek can refer to murder, idol worship (avodah zarah), or promiscuity (gilui arayot). According to Rashi, Yishmael was guilty of all these transgressions.

3. Inheritance Dispute and Identity Crisis

When Sarah demands that Avraham send Yishmael away, she insists that “this son will not inherit with my son.” Rashi explains that there was an argument about who deserved to inherit Avraham’s legacy. This mirrors the later dispute between Yaakov and Esav over the birthright (bekhorah). Yishmael claimed he was entitled to inherit as the firstborn, even though his mother was Hagar and not Sarah. Before Matan Torah, Hagar had already left idol worship and connected herself to Avraham’s household, so why shouldn’t her son be entitled? The answer lies in Sarah’s insistence that only her son, Yitzchak, should inherit. The Rebbe explains that Yishmael suffered from an identity crisis—he saw himself as belonging in Avraham’s house and as a rightful heir. This sense of entitlement led him down a path of negative behavior. His actions—such as throwing arrows at Yitzchak under the guise of play—stemmed from this unresolved identity issue.

4. The Role of Sarah’s Intuition and Prophecy

Sarah’s clarity stands out in this narrative. While Avraham hesitated due to his paternal love for Yishmael, Sarah saw more clearly what needed to be done. Rashi notes that our matriarchs often possessed greater prophetic insight than even the patriarchs themselves. Hashem affirms this by telling Avraham to listen to whatever Sarah says regarding sending Yishmael away. Sarah recognized that as long as Yishmael remained in the household, he would continue to see himself as an inheritor and perpetuate conflict with Yitzchak. Only by sending him away could she clarify who truly belonged in Avraham’s spiritual legacy.

5. The Teshuvah of Yishmael: When Was It Recognized?

Rashi points out that at Avraham’s burial, the Torah lists “Yitzchak and Yishmael” (with Yitzchak first), even though Yishmael was older. This reversal signals that Yishmael did teshuvah—repentance—and accepted Yitzchak’s precedence as heir. However, if we know from other sources (such as Gemara) that he repented earlier, why does the Torah highlight his repentance only at this moment? According to the Rebbe’s interpretation, it becomes clear: all of Yishmael’s troubles stemmed from his belief that he was an inheritor. Only when Avraham passed away and it came time for inheritance did it become evident that Yishmael accepted his true place—by allowing Yitzchak to go first at the burial.

6. Lessons for Today: Separation and Its Implications

The narrative teaches us about boundaries within spiritual inheritance and community identity. Even though Yishmael eventually did teshuvah, we continue to experience challenges from his descendants—if those claiming descent are indeed truly descended from him—which resonates with ongoing struggles in Eretz Yisrael today. Sarah’s insistence on separation teaches us that sometimes coexistence is not possible when fundamental values are at stake. Attempting to share or compromise on core spiritual inheritance can lead to ongoing conflict rather than peace.

7. Dedication and Communal Announcements

This learning is dedicated for an aliyat neshamah—elevation of soul—for Michael (full name unclear) and Shulamit bat Baruch. May their souls have an elevation through our study together. Everyone is invited after Mairiv—the evening prayer—for a special memorial meal accompanied by Mishnah learning in their memory. Baruch will lead us in Mairiv, followed by this communal gathering for further merit for those we remember today.