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Rashi (רש"י) praises Rivka for rising above her wicked family, yet her prayers for children went unanswered while Yitzchok's were accepted—because he was a tzaddik ben tzaddik. The shiur resolves this tension by exploring how low self-esteem or deficiency can drive chesed (חסד) and religious accomplishment, but only actions rooted in healthy self-worth reflect true character. The Torah (תורה)'s emphasis on the beauty of the imahos signals they had no void to fill—their kindness was genuine.
The shiur opens with an apparent contradiction in Rashi (רש"י)'s commentary on Parshas Toldos. Rashi praises Rivka for becoming righteous despite being the daughter and sister of wicked people—a tremendous accomplishment. Yet immediately afterward, when both Yitzchok and Rivka pray for children, the Torah (תורה) states that Hashem (ה׳) answered *him*, not her. Rashi explains that the prayer of a tzaddik ben tzaddik (the son of a righteous person) is superior to that of a tzaddik ben rasha (the child of a wicked person). This seems to undermine the earlier praise: if Rivka's righteousness despite her background is so remarkable, shouldn't her prayers be *more* effective, not less? Rabbi Zweig brings a parallel halachic dispute to frame the question. The Magen Avrohom (Orach Chaim 53) rules that a tzaddik ben tzaddik is preferable as a shaliach tzibbur because his prayers are more readily accepted, citing the Gemara (גמרא) in Yevamos. The Taz disagrees, arguing that a ba'al teshuvah—someone who has overcome a background of wickedness—is greater, and therefore his prayers should be more effective. How does the Taz understand the Gemara's conclusion that a tzaddik ben tzaddik's prayers are superior?
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Bereishis 25:21 (Parshas Toldos)
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How could Avrohom keep the entire Torah before it was given, including rabbinical laws? The key insight is that mitzvos represent eternal spiritual realities, not just historical commemorations, so Avrohom could access these truths through his genuine search. His entire 172-year journey—even his early idolatry—retroactively became service of God once he reached ultimate truth.