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Why does Koheles warn about crookedness that cannot be straightened, since teshuvah can fix any sin? Rashi (רש"י) explains that a parent who commits adultery resulting in a mamzer cannot fully repent, because genuine regret would mean wishing the child didn't exist. This reveals how parent-child bonds can actually impede complete teshuvah when the sin produces consequences we cannot emotionally reject.
This shiur begins with Shlomo HaMelech's statement in Koheles 1:15 about "muvas she'aino yochal leskon" - a crookedness that cannot be straightened. Rabbi Zweig examines Rashi (רש"י)'s interpretation based on the Gemara (גמרא) in Chagigah 9a, which explains this refers to cases like adultery that produces a mamzer (illegitimate child). The question arises: why does the Torah (תורה) state something seemingly obvious - that certain consequences cannot be undone even with teshuvah? Rashi provides a profound psychological insight: the real issue isn't that the mamzer status cannot be removed, but that the parent cannot truly do teshuvah for the adultery. To genuinely regret the sin would mean wishing it never happened, which would mean wishing the child didn't exist. No healthy parent can emotionally sever themselves from their child in this way, making complete repentance nearly impossible.
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Koheles 1:15
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