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Why does Rosh Hashanah precede Yom Kippur when teshuvah follows judgment? The shiur develops the principle that Rosh Hashanah is not a tally of past deeds but a chance to forge a new identity through malchus. On Yom Kippur, we ask Hashem (ה׳) to wipe away the damage done by the person we no longer are.
Rabbi Zweig addresses the paradoxical order of the High Holy Days: why does Rosh Hashanah, the day of judgment, precede Yom Kippur, the day of forgiveness? If Hashem (ה׳) offers us the chesed (חסד) of teshuvah and kapparah, wouldn't it make more sense to cleanse the slate first, then judge us afterward? The shiur opens by reframing the entire season of din. Elul, with its theme of "Ani l'dodi v'dodi li," emphasizes relationship over punishment. Rashi (רש"י) explains that this phrase means we ask each other to do for ourselves—Hashem wants us to do for Him not because He needs it, but because it creates a loving relationship. Similarly, He wants us to ask Him for what we need because He wants to be the one to give. The shiur then tackles the central question: on what basis can we ask Hashem for mechilah? If we sinned, we are responsible. Even if we regret our actions and commit to change, how does that wipe away the past? The Gemara (גמרא) warns that anyone who says Hashem is vatran—that He doesn't care—will have his life thrown away. We cannot approach Yom Kippur as if our sins don't matter. So what justifies our request for forgiveness?
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