This dissertation project focuses on the small island archipelago of Okinawa in Southern Japan. Since the late nineteenth and early twentieth centuries, Okinawans migrated and settled in disparate regions across the Pacific, in North and South America, Polynesia, Micronesia, and Southeast Asia, among others. Beginning in the 1980s, in Okinawa and in the diaspora, there was an increased interest in the history of migration from the Prefecture. This project examines select works of Okinawan literature of the 1990s in relation to the Philippines and Hawai‘i as two diasporic sites. This study focuses on the interconnectedness of these three island locales through the trope of entanglement to describe how Okinawan narratives intersect with discourses of US militarism and settler colonialism in the Pacific during the twentieth century and today. Foregrounding my position as a Filipino American reader—and using an interdisciplinary approach which includes the analysis of literary texts, oral history sources, and fieldwork experiences in the Philippines, Hawai‘i, and Okinawa—I explore the possibilities of reading Okinawan literature as a decolonial practice.