The contemporary mobilization of the apartheid-Israel analogy on the part of activists and academics alike obscures the fact that it has a long history of use on the part of Hebrew-speaking writers and intellectuals. Some of the earliest comparative references to apartheid arose from the Hebrew translation and stage adaptation of Alan Paton’s celebrated 1948 novel Cry, the Beloved Country. Departing from the performative focus of Eitan Bar-Yosef who uses blackface in the stage adaptation to reflect on Jewish whiteness in the nascent state of Israel, we analyse critical intellectual responses to the prose translation on the part of figures who were very differently positioned in relation to the hegemonic Zionist ideology of the period. Analysis of the commentary by the socialist Rivka Gurfein, the liberal Ezriel Carlebach, and the revisionist Yohannan Pogrebinsky, allows us to position apartheid as a heuristic device through which to chart debates internal to Israeli politics in the early years of the Zionist state. These help to expose the constitutive ambivalence of Israel as a “colonial post-colony” in Joseph Massad’s reckoning, thus touching on the very self-definition of the Jewish state.