This paper argues that the relationship of Palestine's indigenous Jewish communities with Zionism, the Ottoman state and Arab Palestinians has been obscured by the historiography, which has presented a simplistic dichotomy between the Jewish "Old Yishuv" (orthodox and traditional) and the "New Yishuv" (Zionist and modern). The historiography has also misrepresented important distinctions between Sephardic and Ashkenazi Jews, while more recently the romanticized category of the "Arab Jew" does not capture the historical realities for Jews in Palestine. This article seeks to problematise these issues through the memoir of Justice Gad Fromkin, an Ashkenazi Jew who was born in the "Muslim Quarter", educated in Istanbul, appointed by the British to Palestine's Supreme Court and finally dismissed from service by the first Israeli government. The paper will follow the uneasy path of Frumkin from Ottoman integration to Zionist segregation under British rule. Underused by historians outside Israel, Frumkin's memoir proves the rich potential of Jewish and Hebrew published sources to the history of modern Palestine. The memoir provides striking evidence of links between Ashkenazim and Arabs; it shows the ways in which Palestine's indigenous Jewish population - regardless of its sympathies - was swept aside by Zionism and the foundation of Israel; and finally, Frumkin's account of his political attempts to negotiate a "bi-national" state shed new light on the debate which is currently attracting growing attention.