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Why couldn't Eliezer marry his daughter to Yitzchok—and how did he become "blessed" by the end of the story? The Midrash teaches that a slave cannot unite with one who is blessed because a slave's nature is to grasp for his own portion. Eliezer's transformation came when he worked entirely for Yitzchok's shidduch with Rivka despite having his own daughter—demonstrating total selflessness and becoming the very definition of "baruch."
Rabbi Zweig explores one of the most puzzling elements of the story of finding a wife for Yitzchok: why Eliezer, Avrohom's trusted servant, was categorically excluded from the possibility of his daughter marrying Yitzchok. The Midrash Rabbah makes clear that anyone could be considered—Aner, Eshkol, Mamre, even Yishmael—but not Eliezer. Rashi (רש"י) explains this with the principle "ein eved mistavik b'baruch"—a servant cannot unite with one who is blessed. The shiur unpacks what this means and how it was ultimately overcome. The fundamental question is: what is the nature of being an "eved" (slave/servant) that disqualifies one from this union? The answer lies in understanding the original curse of slavery that came upon Canaan. Cham, the father of Canaan and Mitzrayim, sinned because he didn't want his father Noach to have more children—this would reduce his inheritance from a third to a smaller portion. Though the inheritance wasn't yet his, he already had his eye on securing what he felt was coming to him. Canaan was cursed because he approved of his father's actions. The essence of being an "eved," then, is someone whose nature is to grasp at what he perceives as his portion, even when it's not yet rightfully his. The punishment fits perfectly: an eved becomes someone who owns nothing at all—"leis leih migar me'klum"—he himself is owned by his master, and whatever he acquires belongs to his master.
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Bereishis 24 (Parshas Chayei Sarah) - Eliezer's mission to find a wife for Yitzchak
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