And Sarah saw the son of Hagar the Egyptian—whom she had borne to Avraham—making merry. And Sarah said to Avraham, "Drive out this handmaid and her son, for the son of this handmaid [is not worthy to] share an inheritance with [anyone who is] my son, [or] with [anyone as righteous as] Yitzchak." But the matter greatly displeased Avraham, concerning his son. And G‑d said to Avraham, "Don't be disturbed about the boy and about your handmaid. Whatever Sarah tells you, listen to her [prophetic] voice, for in Isaac will be called your seed. But also the son of the handmaid I will make into a nation, because he is your seed.

-- Breshis 21:9-13

Classic Questions

What was Yishma'el's bad behavior? (v. 9-10)

Rashi: the word מצחק [lit., "having fun"] is an expression of idolatry, as the verse states [in reference to the golden calf] "they became depraved" (shemos 32:6). Alternatively, it is an expression of adultery, as the verse states [in connection with Potifar's wife], "to deprave me" (below 39:17). Alternatively, it is an expression of murder, as the verse states, "let the boys get up now and kill (וישחקו) before us, etc." (Sam. I 2: 14).

From Sarah's response, "The son of this handmaid [is not worthy] to share an inheritance with [anyone who is] my son" (v. 10), we see that [Yishma'el] used to argue with Yitzchak about their inheritance. He would say, "I am the firstborn, so I should take a double portion!" They would go out to the field, and Yishma'el would take his bow and shoot arrows at Yitzchak, "like one who wearies himself shooting firebrands etc., and says: I'm only joking!" (Prov. 26:18f.).

The Rebbe's Teachings

Yishma'el's Expulsion (v. 9-13)

Rashi cites three opinions regarding Yishma'el's wicked behavior: that he was idolatrous, adulterous and murderous (v. 9-10). On seeing this depravity, Sarah implored Avraham, "Get rid of this handmaid and her son! The son of this handmaid [is not worthy] to share an inheritance with [anyone who is] my son" (v. 10).

Perhaps it could be argued that Yishma'el's primary sin was his claim to the inheritance, i.e., his failure to recognize his proper place as the mere "son of this handmaid." After harboring this resentment for a period of time, it gave rise to the rebellious behavior of murder, etc.

In other words, even though Yishma'el's depraved behavior seems, at first glance, much more serious than his claim to inheritance, the former is in fact the result of the latter. Yishma'el's identity crisis actually caused him to degenerate into evil ways.

Thus, Rashi writes, "He would say, 'I am the firstborn, so I should take a double portion!'" and, as a direct result, "they would go out to the field, and Yishma'el would take his bow and shoot arrows at Yitzchak."

Based on the above, we can understand the difference between Sarah's reaction to Yishma'el's behavior and Avraham's. Yishma'el was Avraham's own son, so it was more difficult for him to perceive that Yitzchak alone was his true heir. In fact, before Yitzchak was born, Avraham had made it clear to G‑d that he would be happy for Yishma'el to be his sole heir, saying, "If only Yishma'el will live [in fear of] You [that would be sufficient!]" (17:18). Consequently, the thought of expelling Yishma'el "disturbed Avraham greatly" (v. 11). Sarah, on the other hand, was not the mother of Yishma'el, so it was easier for her to perceive his true status as an outsider who was unfit to inherit Avraham.

Yishma'el's Teshuvah

Based on the above, we can resolve a problem relating to Yishma'el's teshuvah (repentance):

When Avraham passed away, the Torah relates, "Yitzchak and Yishma'el buried him" (25:9). Rashi notes that Yitzchak's name precedes that of Yishma'el, and comments, "From here we learn that Yishma'el did teshuvah and allowed Yitzchak to go before him."

The Talmud (Bava Basra 16b) and Midrash (Bereishis Rabah 59:7), however, both state explicitly that Yishma'el did teshuvah during Avraham's lifetime. This begs the question: Why does the Torah inform us of Yishma'el's teshuvah only after Avraham already passed away?

Based on our earlier explanation, the answer to this question becomes clear. Since Yishma'el's primary sin (which caused all of his later wicked behavior) was the failure to recognize that he was not Avraham's true heir, it follows that his teshuvah only became apparent when the prospect of inheritance became a reality, after Avraham passed away.

When Yishma'el allowed Yitzchak to go before him, he indicated his concession to the fact that it was Yitzchak who was the true heir, obligated in the burial of his father, and that he, Yishma'el, was a mere handmaid's son.

(Based on Likutei Sichos vol. 15, p. 147ff.)