This chapter discusses the nexus of Tolstoyan anarcho-pacifism and Jewish tradition in the life and thought of Rabbi Avraham Yehudah Heyn, an orthodox rabbi of prestigious Habad hasidic lineage, who served several communities throughout Europe and in Palestine/Israel. Responding to the infamous Beilis trails, in which the ancient blood libel was revived in Russia, he promoted a hermeneutic of resistance, interpreting Jewish tradition as the foil of the state and of state-sanctioned violence — indeed, all violence. This chapter considers five themes. First, the notion that the essence of Judaism consists in a conviction as to the absolute sanctity of human life. Second, the implications this has for a pacifist vision for human society reminiscent of Tolstoy's but articulated in a distinctively Jewish manner. Third, the way that the idea of human sanctity grounds both Heyn’s socialism and his anarchism, including his approach to building a libertarian Jewish society cognizant of and authentically bound to but not bound by tradition. Fourth, his vision for a morally sound revolution of the heart. Finally, his complex and in some ways contradictory reflections on Zionism.