Free Will, Teshuvah, and the Three Books of Rosh Hashanah

Rabbi Zweig begins by addressing a fundamental question about the custom of reading specific Torah (תורה) portions on Rosh Hashanah, particularly the story of Yishmael (Hashem (ה׳) pakad es Sarah), questioning how this enhances our understanding of the holiday. He then delves into a complex discussion from the Gemara (גמרא) about divine judgment, examining the apparent contradiction between judging people based on their current state (she'er husha) versus their future trajectory (Hashem sofo). The Maharal's answer - that heavenly courts judge by present state while earthly courts consider future consequences - initially seems counterintuitive. The core of the shiur focuses on the Rambam (רמב"ם)'s placement of the laws of free will (bechira) within Hilchos Teshuvah rather than in Yesodei HaTorah. Rabbi Zweig explains that this reveals a profound insight: teshuvah doesn't just mean we can choose differently going forward (which would belong in foundational principles), but that our past choices don't define our essential identity. We never become what we have chosen to do - we retain the ability to choose differently at any moment.