Some two thousand years ago, as the story goes, a rabbi named Yochanan makes the epitome of pragmatic gambles—wagering the entire fate of the Jewish people. In dialogue with the soon-to-be Roman emperor Vespasian, Yochanan acquiesces to the Romans’ destruction of Jerusalem in return for a plot of land in a town called Yavneh. There, after the razing of Jerusalem, Jews will join with their teacher to reenvision a new Judaism—one not based on Temple rites but on real life in exile—laying the groundwork for today’s modern vibrant Judaism. In Rabbi Marc Katz’s novel examination, pragmatism is itself an authentic Jewish strategy for addressing moral questions. The rabbis of the Talmud model the process, demonstrating how to think situationally, weigh competing values, and make hard compromises. Leading rabbis ask, “What will work?” alongside “What is right?” They birth a malleable and nuanced system of law (halakhah) that is faithful to their received tradition and to the people and circumstances before them. By investigating how the rabbis navigate their own ethical challenges—determining truth, upholding compromise, convincing others, keeping peace with neighbors, avoiding infighting, weighing sinning in hopes of promoting a greater good—Yochanan’s Gamble forges a new Jewish path forward for resolving moral conundrums in our day.