This paper discusses the political writings, mostly in the form of poetry, of Palestinian intellectual Shafiq Habib. Habib is much less known in wide literary and cultural circles than many of his contemporaries, including such poets as the late Samih al-Qasim and Mahmoud Darwish, and authors such as the late Emile Habiby. Yet Habib himself views them as colleagues and friends, and likens his own literary and political contributions to theirs. He was the object of political and judicial persecution by the Israeli government, yet was eventually cleared of all charges and even awarded a governmental prize for his poetry. In this paper, we discuss his work within the context of Palestinian poetry and literature in general and evaluate his status among Palestinian intellectuals in light of the themes and style of his writings as well as his universalist, Communist world views espoused in his literary work. We argue that his poetry reflects important continuities in Palestinian culture. On the one hand, he locates himself within a poetic genealogy that begins in the medieval past, continues to the Palestinian Nahḍa, the communist literature of the 1950s, and the literature of resistance of the 1960s. At the same time, his poetry reflects the new contexts that came into being in Israel/Palestine during the late 1980s and the 1990s when the first Intifāḍa inspired new ideas about poetry, resistance and tradition and when Palestinian writers had to deal with new forms of oppression by the Israeli regime. We analyse the shifts in his poetry between different temporalities, forms, and genres, paying heed to two moments in his career: his struggle with Israeli censorship during the 1990s and his latest Diwan, Ma ʾamarra al-ʿinab ('How bitter the grapes are').