This dissertation analyzes the relationship between property and agrarian republicanism in the Philippines during the US colonial period (1898 - 1941) through the history of land settlement projects in the Philippine frontier, particularly in the southern region of Mindanao. I argue that the American colonial project contributed to the emergence of a market-based vision of republican freedom that remains central to the Philippine postcolonial state while narrowing its anti-colonial and anti-imperial traditions. The history of property and colonialism in the Philippines is often told through a liberal narrative of dispossession wherein “landed elites” (be it Filipino, American, or “foreign”) “dispossess” poor farmers (be it “indio” during the Spanish era, or “Filipino” during the US period). Landed estates in the Central Luzon region have, since the onset of US rule, remained the primary empirical and conceptual locus of analysis. Consequently, a liberal interpretation of the meaning of dispossession has structured modern Philippine nationalist historiography and its postwar political traditions. Why the language of possession structures the definition of Philippine postcolonial freedom remains unasked. I critique the persistence of this liberal narrative of property by looking at the relationship between agrarian republicanism and American empire. Instead of focusing on large, landed estates, I look at attempts to encourage Filipino settlerism in the frontier. US colonial policies on land and labor restricted the development of large-scale plantations worked by “Asiatic” indentured laborers in the Philippines. This, in turn, created the space for an imaginary, propagated by both American and Filipino elites, that the Philippine postcolony should be composed of a republican yeomanry—a property-owning smallholding agrarian citizenry. What this imaginary belies, however, is how the ostensible support for a democratic distribution of land is reconciled with national developmentalist imperatives for securing “national territory” and a modern peasant agriculture. The promise of property in the frontier entailed dispossessive logics that connected the US project of “benevolent assimilation” and the Philippine corporatist project of nation-building. By bridging the intellectual-institutional history of colonial state formation and the political economy of American empire, I present a revisionist account of the Philippine postcolonial state to demonstrate how the US colonial project shaped the meaning of freedom and self-determination in the 20th century.