This article explores the relations between European Zionists, Sephardim, and Oriental Jews in late Ottoman Palestine by narrating the story of A. Yehudai, a Bulgarian Jewish teacher in the Sephardi community of Gaza in 1913. Reading through Yehudai’s ambitions, deliberations, and frustrations, the article makes two main arguments: First, it challenges the inclusivity often attributed in scholarly literature to the category of “Sephardi,” suggesting that as a practical category used by historical figures, especially in the context of national discourses, it was regarded as much more bounded and rigid. Second, the article points to the period before European Zionist domination over Middle Eastern Jews. Through the case of late Ottoman Gaza, the article shows that Jewish communities in Palestine were essential for institutional Zionist bodies, were aware of their situation, and even used this power structure for their own gain. Taken together, both arguments testify to the fact that communal demarcations are essential for human society in the sense that the crossing of boundaries always entails the delineation of new ones.