This essay focuses on a large group of preeminent dissenting intellectual and Orthodox Jewish voices from the start of the twentieth century who were critical of the suitability of Israel as a site of return and who stood in solidarity with Palestinians. It focuses on the victim of Israel’s first political assassination, Jacob Israel de Haan, and raises the then permissible notions of sexuality in Palestine. Since the de Haan’s death in 1924, his journalistic writings, essays, and poems, written over a five-year period in Mandate Palestine, have yet to be published in English or Arabic. The author examines the trajectory of de Haan’s rescinding Zionist attitude as something increasingly common upon arrival in Palestine. De Haan’s work as a litigator uniquely placed him to affect and destabilize the colonial infrastructure in formative Israel, which ultimately led to his murder.