In early July 2014, the Israeli-Palestinian author, Sayed Kashua, wrote in his popular newspaper column in Ha’aretz newspaper that he was done with Jerusalem, moving to the United States, and never coming back. Despite this emotional piece and his decision to give up and leave Israel, Kashua continued to write his popular weekly column for over three years. He mostly wrote from his new place of dwelling in the Midwest, the metropolitan area of Urbana Champaign, Illinois, a vastly different location than the Jerusalem he left. Using theories of migration and transnational writing, my talk closely examines Kashua’s non-fictional Hebrew and English work during this time. I argue that there is continuous tension between the character Kashua assumes for the Israeli readership and the position he writes from when he aims to reach American audience. Each of these fictional personae relates differently to the move to the US and to the possibility of going back to Israel. Moreover, the Israeli persona continues to write from a minority position whereas the American one, despite best efforts, is associated with white privilege. Finally, the lecture traces the end of Kashua’s dual personae era with his decision to end the weekly column in November 2017.