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Why is Rosh Hashanah both a day of terror and joy? The shiur reveals that divine judgment itself is the ultimate chesed (חסד) because God could treat us as property but chooses to relate as King to subjects. This grants us dignity and the right to earn our existence rather than merely receive it as divine welfare.
This shiur presents a revolutionary understanding of Rosh Hashanah that resolves the apparent contradiction between the day being described as one of judgment and terror, yet also characterized as 'Ani L'dodi V'dodi Li' (I am to my beloved and my beloved is to me) and a day of simcha according to the Rambam (רמב"ם). The speaker argues that our natural fear and subsequent denial of Elul and Rosh Hashanah stems from a fundamental misunderstanding of what judgment means in this context. The core insight emerges from a Midrash on the pasuk 'Alah Elokim b'teruah, Hashem (ה׳) b'kol shofar' - God ascends with the shofar blast. Rather than God moving from judgment to mercy as commonly understood, the Midrash reveals that both movements represent ascension through shofar. This teaches that the very act of divine judgment is itself the ultimate chesed (חסד).
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Psalms 47:6 (Alah Elokim b'teruah), various Midrashim on Rosh Hashanah
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May a man who has already fulfilled his shofar obligation blow shofar for a woman on Rosh Hashanah? The Baal Itur forbids it while Rav Yehuda permits it. The shiur develops that the core dispute is not about violating shvus for another's benefit, but whether a man's blowing creates a "tekiah shel mitzvah" that enables the woman to be yotzei.
Why does the Gemara connect Purim to Tisha B'Av using "just like"—here you *decrease* joy, here you *increase* it? The shiur develops that Purim fixes the sin of Achashverosh's feast, where Klal Yisrael's desire to socialize with goyim revealed a physical disconnection from each other. Mishloach Manot and matanos la'evyonim create the physical unity—eating and drinking together—that is the tikkun for sinas chinam and the foundation for Kabbalas HaTorah.
Why is the Haggadah in Aramaic, and what does "haggadah" (which means both storytelling and harsh speech) really mean? The shiur develops that Aramaic represents the ability to see from another's perspective, the foundation of true communication. Pesach night's she'eilah u'teshuvah (question-and-answer) format demands we understand what the listener truly needs to hear—creating unity through genuine dialogue rather than prepared speeches.
Why did Mordecai provoke Haman by refusing to bow, endangering all the Jews? Rabbi Zweig argues Mordecai read history and saw the Jewish people on the brink of spiritual destruction—enjoying Achashverosh's party celebrating Judaism's demise meant they had become self-hating. By provoking a crisis, Mordecai forced Jews to face that assimilation was no refuge and reconnect to their roots.
