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

Full Summary

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. Using Rashi (רש"י)'s commentary on Kohelet about wicked people not understanding they harm themselves, Rabbi Zweig illustrates how people often excuse their behavior by saying 'that's just who I am.' This mindset prevents true teshuvah because if someone believes their negative traits define them, they see no point in change - whether they act badly or not, they remain the same person. The Rambam's revolutionary insight is that there are two distinct aspects of teshuvah: fixing the past (requiring viduy, suffering, and Yom Kippur depending on the severity) and creating a new present relationship. The Rambam in Chapter 7 describes how someone can transform overnight from being rejected by Hashem to being embraced, not through fixing past sins but through genuine commitment to future righteousness. This explains the puzzle of three books opened on Rosh Hashanah. Complete tzadikim are immediately sealed for life, complete reshaim for death, but beinonim (intermediate people) remain in a third book until Yom Kippur. The teshuvah required for beinonim isn't the complete fixing of past wrongs but rather a sincere commitment to future improvement. They become 'written for life' without being 'sealed' - receiving another year to grow while their past issues remain to be addressed. Rabbi Zweig connects this to practical relationship advice: when people are in conflict, trying to resolve every past hurt is often impossible. Instead, they should agree to treat each other well for six months, building trust and new positive experiences before attempting to address historical grievances. The reading of Yishmael's story on Rosh Hashanah now makes perfect sense. Despite his past and future problems, at that moment when he was dying of thirst, his cry to Hashem was sincere. God judged him 'basher hu sham' - where he was at that moment - not based on his past crimes or future misdeeds. This exemplifies the Rosh Hashanah judgment: we are evaluated based on our current sincere commitment to improvement, not our ability to undo the past. Rabbi Zweig concludes that Rosh Hashanah preparation shouldn't focus on comprehensive repentance for every past wrong (which belongs to Yom Kippur) but on making genuine resolutions for future behavior. This approach is both more psychologically healthy and more aligned with the holiday's essential character. The absence of viduy (confessional) in Rosh Hashanah prayers supports this interpretation - we're not fixing the past but committing to a better future.