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Why can machshirim for milah be derived to override Shabbos (שבת), but not for tzitzis? Tosfos reveals that mitzvah (מצוה) bo b'averah only applies when the transgression outweighs the mitzvah. Since milah itself overrides Shabbos, any preparatory violations remain valid machshirim, unlike tzitzis where Shabbos violations would negate the entire mitzvah.
This advanced Gemara (גמרא) shiur delves deep into a complex Tosfos on Shabbos (שבת) 130a-b, analyzing when preparatory acts (machshirim) for mitzvos override Shabbos prohibitions. Rabbi Zweig begins by examining Tosfos's fundamental question: why didn't the Gemara ask about shtei halechem (two loaves) when questioning the derivation of tzitzis from milah? The answer reveals a sophisticated understanding of mitzvah (מצוה) bo b'averah (a mitzvah that comes through transgression). The core principle emerges: mitzvah bo b'averah only applies when the transgression is more significant than the mitzvah. When milah is performed, even if preparatory violations of Shabbos occurred, it cannot become mitzvah bo b'averah because milah overrides Shabbos (milah docheh Shabbos). Therefore, any Shabbos violation in service of milah remains a valid machshir, though it may be prohibited without explicit Torah (תורה) permission.
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Shabbos 130a-b
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Why does the Gemara say one Shabbos protects from Amalek while two Shabboses bring redemption? The shiur applies a principle from Kiddushin about repetition changing psychology: the first time doing anything is experimental, but the second demonstrates genuine desire. True Shabbos connection with Hashem requires moving beyond spiritual curiosity to authentic internalization.
