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This paper delves into the life and work of Robert Friend (1913-1998), a Communist Jewish American poet, a gay man, and a translator of Hebrew and Yiddish poetry, who lived most of his life in Jerusalem. Born in Brooklyn to Jewish Russian immigrants, Friend's early years at Brooklyn College introduced him to a circle of gay Communist Jewish poets. He later wrote pioneering work in gay-themed poetry, like his first book "Shadow on the Sun" (1941), and translated works of renowned poets such as Rachel Bluwstein, Gabriel Preil, Natan Alterman, and Leah Goldberg, who was also his friend. His time in Israel was marked by his deep humanistic worldview, which led him to form social, sexual, and romantic relationships with Palestinian men during times of social and legal restrictions against homosexuality in Israel and shortly after the occupation of East Jerusalem. The paper argues that Friend's life serves as a crucial case study of a leftist gay Jew who challenged both diasporic and Zionist narratives. Living in Israel but largely in an English-speaking world and maintaining relationships that crossed cultural and national lines, his story offers a nuanced counterpoint to conventional Jewish narratives. Drawing on oral histories, extensive archival research, and a critical examination of Friend's poetry, this paper seeks to resurrect and re-evaluate his neglected legacy, highlighting his role in challenging and diversifying Jewish and queer histories.