Ki Savo: Wishing Well for Others Through Ayin Tov

Rabbi Zweig explores a fundamental character trait required for Rosh Hashanah preparation: the capacity not to begrudge others their success. He begins with guidance from Rabbi Finkel, mashgiach of Yeshivas Slobodka and mentor to post-Holocaust Torah (תורה) leadership, who taught that the best preparation for the High Holy Days is helping younger students—a practice that seems counterintuitive but contains a profound message about human nature and unity. The shiur focuses on a puzzling teaching from Parshas Ki Savo regarding the laws of shikchah (forgotten sheaves). The Torah states that if a farmer forgets sheaves in his field, he should not return for them, and Hashem (ה׳) will bless him. Rashi (רש"י) quotes the Sifra, saying that if one receives reward even without intention, how much more so with intention. Furthermore, the Sifra derives that if someone loses money and a poor person finds and benefits from it, the original owner receives reward. This teaching appears illogical on multiple levels: How is forgetting something praiseworthy? How can we derive the case of lost money from forgotten sheaves? And how is the forgotten sheaf case "without intention" when the farmer consciously chooses not to retrieve it?