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This chapter discusses the life and thought of Isaac Nahman Steinberg. The scion of an enlightened rabbinic family, steeped in traditional learning, he went on to study law in Western Europe. Ultimately returning to Russia, he participated in the 1917 Russian revolution and, as a member of the Left-Socialist Revolutionaries assumed — prior to the Bolshevik coup — the position of Commissar of Justice as an openly observant Jew. Recent scholarly interest has alighted on his later leadership of the Territorialist movement, but here focus is placed on his largely anarchistic vision for what Jewish autonomy would look like. The chapter begins by examining his efforts to formulate a concept of Jewish tradition that is both authentic and mutable, such that it is able to inform efforts to synthesize morality and politics. Steinberg’s views on revolution are then addressed, followed by a discussion of his approach to revolutionary violence and his critique of Bolshevik and Tolstoyan camps alike. This is followed by an analysis of his views on the link between socialism and anarchism, the anarchization of the Jewish world, and the idea of the Jews as a vanguard people. Finally, his reflections on Zionism are considered.