Spanning from the Caribbean and the Atlantic Coast of the continental United States all the way across the Pacific Ocean to Southeast Asia, the American Empire was at its territorial height during the interwar period. This growth led to increased opportunities, redistributing worker populations across the empire. One of the most significant population redistributions was that of the Filipino people. By the 1930s, around 100,000 have migrated across the empire, mainly in Hawaiʻi. At the same time, economic and political upheavals initiated a further redistribution, many to even newer frontiers such as the island of Mindanao. Among those affected included the likes of Hilario Camino Moncado, the leader of a Filipino confraternal organization, and Pablo Manlapit, a beloved unionist and labor rights activist. In both (Asian) American histories and Filipino histories, these two figures have been relegated to the margins. But looking at their movements from a more archipelagic, oceanic perspective disrupts long-held models of migration as unidirectional and dispels both myths of assimilation into America as well as the formation of a unitary Filipino consciousness. Their migrations between parallel peripheries also suggest the importance of Filipino labor in legitimating imperial claims to the hinterlands by exemplifying productivity and the economic value of acquiring such new lands, often at the expense of its indigenous peoples. By undertaking a comparative study of the autobiographies of Moncado and Manlapit, we can see how Filipino migrant laborers navigated their way between imperialism and incipient nationalism by moving within imperial peripheries.