Aurelio Tolentino (1869–1915) is best remembered as the first nationalist dramatist who was in and out of prison because of his mutinous writings. His five extant novels manifest the sociopolitical struggle of early 20th-century Filipinos from the worldview of a versatile author. Tolentino’s fiction from 1909 to 1914 unveils how the colonized adapted ingrained, rigid, and conventional Spanish influences to the liberal and materialistic scheme imposed by the United States. A sociohistorical approach was used to investigate Tolentino’s narratives, revealing a people with a pliant but firm character brought about by their four centuries of subjugation. The literary method used in the study likewise illuminates the economic and literary struggles of the author as an ex-convict. The novels illustrate how the suppressed survived and yearned for sovereignty from the dual domination that beset the land.