This paper examines the political awakenings of four prominent Najafi poets, ?Ali al-Sharqi (1890-1964), Ahmad al-Safi al-Najafi (1897-1977), Muhammad Mahdi al-Jawahiri (1899-1997), and Muhammad Salih Bahr al-?Ulum (1909-1984). The paper is based on an intensive reading of archival documents, newspapers, journals, memoirs, and poetry related to the period between the Iranian Constitutional Revolution and the formal termination of the British Mandate. My reading of these sources demonstrates the ways in which formal and informal networks of education and conversation between different generations and different locations contributed to the intellectual and political awakening of each poet. Each of the four poets under consideration in this paper experienced an acute sense of political alienation and social dislocation as a result of their intellectual education. All four experienced the classical education of the Najafi religious academies before ultimately abandoning the clerical vocation in favor of literary and political endeavors. All four had early encounters with modernist thought through their engagement with prominent foreign periodicals like the Egyptian journals al-Muqtataf and al-Hilal and the Lebanese periodical al-?Irfan. All four associated themselves with the anti-colonial political currents of their era and ultimately abandoned the literary and political confines of their native Najaf for the more expansive and enticing atmosphere of the urban metropolis. In sketching the links between these shared intellectual experiences and political journeys, the paper demonstrates how education and intellectual awakening served to exacerbate generational conflict, heighten social tension, and increase political alienation. Discussions of constitutionalism, Darwinism, and Marxism drew these poets, their family members, and their teachers into broader conversation with the politics of modernity that was reshaping the intellectual environment of the Middle East. The experience of British occupation radically transformed the political environment of Iraq, claiming the life of Muhammad Sa?id al-Habbubi, the dominant personality of the Najafi literary salons, and pitting opponents and proponents of collaboration with the British Mandate against one another. These intellectual transformations simultaneously expanded the geographic and ideological worldview of these poets while reinforcing their sense of social isolation and political alienation. My analysis of the critical friction between tradition and modernity in the historical experience of each poet underscores the centrality of education to political awakening.