“When a man or woman shall commit any sin that men commit, to do a trespass against the Lord, and that person be guilty; then they shall confess their sin which they have done: and he shall make restitution for this trespass in full.” So reads chapter 5 from the book of Numbers. Repentance is on the Jewish mind these days. The time between Rosh Hashanah and Yom Kippur is called the Ten Days of Teshuva—the Ten Days of Repentance—and during it observant Jews engage in prayer and penitence. What is repentance? How does it operate? What’s actually happening in the mind of the penitent? Daniel Rynhold is dean of the Bernard Revel Graduate School of Jewish Studies and professor of Jewish philosophy at Yeshiva University. He has thought and written much about repentance and sees it as a way to illustrate some of the most interesting contrasts between medieval and modern philosophers. Joining Mosaic editor Jonathan Silver here to discuss the subject, he focuses on three major thinkers, two from within the Jewish tradition and one outside of it. The first is Rabbeinu Yonah, the 13th-century author of the rabbinic work The Gates of Repentance. The second is Joseph B. Soloveitchik, known as the Rav, who was perhaps the central intellectual figure of post-war Modern Orthodoxy. The third is the German philosopher Friedrich Nietzsche, a famous critic of the Enlightenment, of liberalism, and of modernity. The last two are the focus of his book, written with Michael Harris, Nietzsche, Soloveitchik, and Contemporary Jewish Philosophy, published in 2018 by Cambridge University Press. Musical selections in this podcast are drawn from the Quintet for Clarinet and Strings, op. 31a, composed by Paul Ben-Haim and performed by the ARC Ensemble.