During the last quarter of the nineteenth century, Gaza – the city and its eponymous region – saw significant shifts. Almost overnight, it turned both into a global commodity frontier, supplying grains to European markets through maritime trade, and into and an inter-imperial frontier, following the British occupation of Egypt. While heavily affecting the lives of peasants, urbanites, and nomads throughout southern Palestine, this dual development also positioned Gaza on the mental map of Jewish geographical horizons. Starting in the 1880s, Jewish immigrants and entrepreneurs, Sephardi and European, Zionist and non-Zionist, sought to benefit from what seemed to be a port city in-the-making as well as from the possibility of future British protection around it. This paper delves into the Jewish past-futures of Gaza, where contending visions of modern urban life, economic development, and imperial subjecthood intersected. The Gazan political and economic borderland allowed the emergence of diverse Jewish realities and imaginaries, which relied upon close acquaintance and cooperation with the Gazan Arab population, the Bedouin tribes of Sinai and local peasants, as well as upon exploiting the frictions between the Ottoman and British imperial interests. Relaying on Ottoman, British and Zionist archival documents, as well as on Gazan histories and memoirs, the paper examines Jewish utopian visions of Gaza and southern Palestine, the haphazard trials for their realizations, and eventually their abandonment, during the early British Mandate period. The paper looks closely at the ties between the Sephardi community of Gaza and Gazan Arab notables and tribal leaders, and at the community’s uneasy dynamic vis-a-vis European Zionist institutions. A historic fossil in eyes of the Zionist establishment, the Sephardi community of Gaza was fully conscious of its advantages as a borderland society and used these to reverse the colonial power structures with their European coreligionists. To demonstrate this social dynamic, the paper analyses cross-border land purchase deals and settlement plans, and the roles of the Arab, Jewish and British parties involved in it. The paper further narrates the story of the Zionist Anglo-Palestine bank, the first to be established in Gaza in 1913, to show how Gaza’s economic prospects were calculated and financialized for purposes of colonization. Finally, the paper discusses Jewish and Arab ruin-dwelling in the war-torn city in the aftermath of the First World War, to examine how Zionist metropolitan dreams and Gazan efforts of reconstruction were shattered as part of a mutual process under British rule.