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This chapter discusses the life and thought of R. Yaakov Meir Zalkind. His journey led through the elite institutions of Eastern European rabbinic learning, the Western European university, the ferment of London’s East End, and finally to British Mandate Palestine. In these wanderings, R. Zalkind accumulated the ideological material — Zionism, pacifism, communism, and anarchism — with which he progressively constructed his own unique worldview. Both the theoretical content of that view and also how he applied it in his career as an activist, journalist, translator, and communal rabbi are considered. It is argued that in spite of his apparent eclecticism, Zalkind’s fundamental commitments remained consistent and that he drew on various ideologies to defend them.